Document:

exv10w2

 

EXHIBIT 10.2

Execution Copy

Registration Rights Agreement

          This Registration Rights Agreement (the “Agreement”) is made and entered
into as of September 1, 2006, by and among American Oil & Gas, Inc., a Nevada corporation (the
“Company”), and the investors listed on the signature pages to this Agreement (the
“Stockholders”).

          In order to induce the Stockholders to purchase shares of common stock of the Company, par
value $0.001 per share, from Sunstone Oil and Gas, LLC, an Oklahoma company (“Sunstone”),
which shares are to be issued to Sunstone pursuant to that certain Purchase and Sale Agreement
dated September 1, 2006 between the Company and Sunstone (the “Purchase Agreement”), the
Company has agreed to provide the registration rights set forth in this Agreement. The execution
of this Agreement is a condition to the closing under the Purchase Agreement. The terms “herein,”
“hereof,” “hereto,” “hereinafter” and similar terms, as used in this Agreement, shall in each case
refer to this Agreement as a whole and not to any particular section, paragraph, sentence or other
subdivision of this Agreement.

          The Company agrees with the Stockholders (i) for their benefit and (ii) for the benefit of the
beneficial owners from time to time of the Registrable Securities (as defined herein) (each of the
foregoing a “Holder” and, together, the “Holders”), as follows:

     1. Definitions. As used in this Agreement, the following terms shall have the
following meanings:

     (a) “Affiliate” means, with respect to any specified person, an “affiliate,” as
defined in Rule 144, of such person.

     (b) “Business Day” means each day on which the American Stock Exchange is open
for trading.

     (c) “Claim” has the meaning set forth in Section 8(m) hereof.

     (d) “Common Stock” means the 2,050,000 shares of common stock, par value $0.001
per share, of the Company issued pursuant to the Purchase Agreement, and any additional shares of common stock, par value $0.001 per share, of the Company issued pursuant to this
Agreement.

     (e) “Effectiveness Deadline Date” has the meaning set forth in Section 2(a)
hereof.

     (f) “Effectiveness Period” means a period that terminates when there are no
Registrable Securities outstanding or, with respect to a Holder, the date on which such

 

 

Holder may sell Registrable Securities held by it pursuant to Rule 144(k) under the
Securities Act

     (g) “Exchange Act” means the Securities Exchange Act of 1934, as amended, and
the rules and regulations of the SEC promulgated thereunder.

     (h) “Form S-3” means Form S-3 under the Securities Act.

     (i) “Holder” has the meaning set forth in the preamble hereto.

     (j) “Holder Information” has the meaning set forth in Section 5(b) hereof.

     (k) “Indemnified Party” has the meaning set forth in Section 5(c) hereof.

     (l) “Indemnifying Party” has the meaning set forth in Section 5(c) hereof.

     (m) “Initial Shelf Registration Statement” has the meaning set forth in Section
2(a) hereof.

     (n) “Material Event” has the meaning set forth in Section 3(i) hereof.

     (o) “Proceeding” has the meaning set forth in Section 5(c) hereof.

     (p) “Prospectus” means the prospectus included in any Shelf Registration
Statement (including, without limitation, a prospectus that discloses information previously
omitted from a prospectus filed as part of an effective registration statement in reliance
upon Rule 415 under the Securities Act), as amended or supplemented by any amendment or
prospectus supplement, including post-effective amendments and any prospectus filed with
respect to any Shelf Registration Statement pursuant to Rule 424 under the Securities Act,
and all materials incorporated by reference or deemed to be incorporated by reference in
such Prospectus.

     (q) “Purchase Agreement” has the meaning set forth in the preamble hereof.

     (r) “Registrable Securities” means the Common Stock, and any securities issued
with respect thereto by reason of or in connection with any stock dividend, stock split or
similar event, until, in the case of any such security, the earliest of:

     (i) the date on which such security has been effectively registered under the
Securities Act and sold pursuant to a Registration Statement relating thereto; or

     (ii) the date on which such security has been publicly sold pursuant to Rule
144 or any successor provision thereto.

     (s) “Registration Expenses” has the meaning set forth in Section 4 hereof.

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     (t) “Registration Statement” means any registration statement, under the
Securities Act, of the Company that covers any of the Registrable Securities pursuant to
this Agreement, including the Prospectus, amendments and supplements to such registration
statement, including post-effective amendments, all exhibits and all materials incorporated
by reference or deemed to be incorporated by reference in such registration statement,
Prospectus, amendment or supplement.

     (u) “Rule 144” means Rule 144 under the Securities Act, as such Rule may be
amended from time to time, or any similar rule or regulation hereafter adopted by the SEC.

     (v) “SEC” means the Securities and Exchange Commission.

     (w) “Securities Act” means the Securities Act of 1933, as amended, and the
rules and regulations promulgated by the SEC thereunder.

     (x) “Shelf Registration Statement” means the Initial Shelf Registration
Statement and any Subsequent Shelf Registration Statement.

     (y) “Subsequent Shelf Registration Statement” has the meaning set forth in
Section 2(b) hereof.

     2. Shelf Registration.

     (a) The Company shall prepare and file, or cause to be prepared and filed, with the SEC
as soon as practicable a Registration Statement (the “Initial Shelf Registration
Statement”) for an offering to be made on a delayed or continuous basis pursuant to Rule
415 under the Securities Act registering the resale from time to time by the Holders thereof
of any and all of the Registrable Securities. The Initial Shelf Registration Statement
shall be filed as a post-effective amendment to the Company’s Registration Statement on Form
S-3 (Registration No. 333-120987) or, with the agreement of the Holders, on a new Form S-3
or another appropriate form and shall provide for the registration of such Registrable
Securities for resale by such Holders in accordance with any reasonable method of
distribution elected by such Holders. The Company shall use its commercially reasonable
efforts to (i) cause the Initial Shelf Registration Statement to become effective under the
Securities Act as promptly as practicable but in any event by the date (the
“Effectiveness Deadline Date”) that is one hundred twenty (120) days after the date
hereof and (ii) keep the Initial Shelf Registration Statement (or any Subsequent Shelf
Registration Statement) continuously effective under the Securities Act until the expiration
of the Effectiveness Period. At the time the Initial Shelf Registration Statement becomes
effective under the Securities Act, the Company shall have named each Holder as a selling
securityholder in the Initial Shelf Registration Statement and the related Prospectus in
such a manner as to permit such Holder to deliver such Prospectus to purchasers of
Registrable Securities in accordance with applicable law.

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     (b) If any Shelf Registration Statement ceases to be effective under the Securities Act
for any reason at any time during the Effectiveness Period, the Company shall use its
commercially reasonable efforts to promptly cause such Shelf Registration Statement to
become effective under the Securities Act (including obtaining the prompt withdrawal of any
order suspending the effectiveness of such Shelf Registration Statement), and in any event,
subject to Section 3(i)(B), shall within fifteen (15) days of such cessation of
effectiveness, (i) amend such Shelf Registration Statement in a manner reasonably expected
to obtain the withdrawal of any order suspending the effectiveness of such Shelf
Registration Statement or (ii) file an additional Registration Statement (a “Subsequent
Shelf Registration Statement”) for an offering to be made on a delayed or continuous
basis pursuant to Rule 415 of the Securities Act registering the resale from time to time by
Holders thereof of all securities that are Registrable Securities as of the time of such
filing. If a Subsequent Shelf Registration Statement is filed, the Company shall use its
commercially reasonable efforts to (A) cause such Subsequent Shelf Registration Statement to
become effective under the Securities Act as promptly as practicable after such filing, but
in no event later than the date that is thirty (30) days after the date such Subsequent
Shelf Registration Statement is required by this Section 2(b) to be filed with the SEC and
(B) keep such Subsequent Shelf Registration Statement (or another Subsequent Shelf
Registration Statement) continuously effective until the end of the Effectiveness Period.
Any such Subsequent Shelf Registration Statement shall be on Form S-3 or, with the Agreement
of the Holders, another appropriate form and shall provide for the registration of such
Registrable Securities for resale by such Holders in accordance with any reasonable method
of distribution elected by the Holders.

     (c) The Company shall supplement and amend any Shelf Registration Statement if required
by the rules, regulations or instructions applicable to the registration form used by the
Company for such Shelf Registration Statement, if required by the Securities Act or as
reasonably requested by any Holder.

     (d) The parties hereto agree that the Holders of Registrable Securities will suffer
damages, and that it would not be feasible to ascertain the extent of such damages with
precision, if: the Initial Shelf Registration Statement has not become effective under the
Securities act on or prior to the Effectiveness Deadline Date. In such event, the Company
shall, on or before the seventh (7th) day after the Effectiveness Deadline Date,
pay to each Holder, by wire transfer of immediately available funds to an account designated
by such Holder, an amount equal to ten cents ($0.10) in respect of each Registrable Security
then held by such Holder.

     3. Registration Procedures. In connection with the registration obligations of the
Company under this Agreement, the Company shall:

     (a) Prepare and file with the SEC a Shelf Registration Statement or Shelf Registration
Statements on Form S-3 or, with the agreement of the Holders, any other appropriate form
under the Securities Act available for the sale of the Registrable Securities by the Holders
thereof in accordance with the intended method or methods of

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distribution thereof, and use its commercially reasonable efforts to cause each such
Shelf Registration Statement to become effective under the Securities Act and remain
effective under the Securities Act as provided herein; provided, that, before filing
any Shelf Registration Statement or Prospectus or any amendments or supplements thereto with
the SEC, the Company shall furnish to the Holders and counsel for the Holders copies of all
such documents proposed to be filed and reflect in each such document when so filed with the
SEC such comments as the Holders or such counsel reasonably shall propose within three (3)
Business Days of the delivery of such copies to the Holders and such counsel.

     (b) Prepare and file with the SEC such amendments and post-effective amendments to each
Shelf Registration Statement as may be necessary to keep such Shelf Registration Statement
or Subsequent Shelf Registration Statement continuously effective until the expiration of
the Effectiveness Period; cause the related Prospectus to be supplemented by any required
Prospectus supplement and, as so supplemented, to be filed with the SEC pursuant to Rule 424
(or any similar provisions then in force) under the Securities Act; and comply with the
provisions of the Securities Act applicable to it with respect to the disposition of all
securities covered by each Shelf Registration Statement during the Effectiveness Period in
accordance with the intended methods of disposition by the sellers thereof set forth in such
Shelf Registration Statement as so amended or such Prospectus as so supplemented.

     (c) As promptly as practicable, give notice to the Holders and counsel for the Holders:

     (i) when any Prospectus, Prospectus supplement, Shelf Registration Statement or
post-effective amendment to a Shelf Registration Statement has been filed with the
SEC and, with respect to a Shelf Registration Statement or any post-effective
amendment, when the same has become effective under the Securities Act,

     (ii) of any request, following the effectiveness of a Shelf Registration
Statement under the Securities Act, by the SEC or any other governmental authority
for amendments or supplements to such Shelf Registration Statement or the related
Prospectus or for additional information,

     (iii) of the issuance by the SEC or any other governmental authority of any
stop order suspending the effectiveness of any Shelf Registration Statement or the
initiation or threatening of any proceedings for that purpose,

     (iv) of the receipt by the Company or its legal counsel of any notification
with respect to the suspension of the qualification or exemption from qualification
of any of the Registrable Securities for sale in any jurisdiction or the initiation
or threatening of any proceeding for such purpose,

     (v) after the effective date of any Shelf Registration Statement filed

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with the SEC pursuant to this Agreement, of the occurrence of (but not the
nature of or details concerning) a Material Event, and

     (vi) of the determination by the Company that a post-effective amendment to a
Shelf Registration Statement or a Subsequent Shelf Registration Statement will be
filed with the SEC, which notice may, at the discretion of the Company (or as
required pursuant to Section 3(i)), state that it constitutes a Suspension Notice,
in which event the provisions of Section 3(i) shall apply.

     (d) Use its best efforts to (i) prevent the issuance of, and, if issued, to obtain the
withdrawal of, any order suspending the effectiveness of a Shelf Registration Statement and
(ii) obtain the lifting of any suspension of the qualification (or exemption from
qualification) of any of the Registrable Securities for sale in any jurisdiction in which
they have been qualified for sale, in either case at the earliest possible moment, and
provide prompt notice to each Holder, and counsel for the Holders, of the withdrawal or
lifting of any such order or suspension.

     (e) If requested by the Holders, as promptly as practicable incorporate in a Prospectus
supplement or a post-effective amendment to a Shelf Registration Statement such information
as the Holder or counsel for the Holders shall determine to be required to be included
therein by applicable law and make any required filings of such Prospectus supplement or
such post-effective amendment; provided, however, that the Company shall not
be required to take any actions under this Section 3(e) that, in the written opinion of
counsel for the Company, are not in compliance with applicable law.

     (f) As promptly as practicable, furnish to each Holder and counsel for the Holders,
without charge, at least one (1) conformed copy of each Shelf Registration Statement and
each amendment thereto, including financial statements but excluding schedules, all
documents incorporated or deemed to be incorporated therein by reference and all exhibits
(unless requested in writing to the Company by such Holder or such counsel).

     (g) During the Effectiveness Period, deliver to each Holder and, counsel for the
Holders, in connection with any sale of Registrable Securities pursuant to a Shelf
Registration Statement, without charge, as many copies of the Prospectus or Prospectuses
relating to such Registrable Securities (including each preliminary prospectus) and any
amendment or supplement thereto as such Holder may reasonably request; and the Company
hereby consents (except during such periods that a Suspension Notice is outstanding and has
not been revoked) to the use of such Prospectus and each amendment or supplement thereto by
each Holder, in connection with any offering and sale of the Registrable Securities covered
by such Prospectus or any amendment or supplement thereto in the manner set forth therein.

     (h) Prior to any public offering of the Registrable Securities pursuant to a Shelf
Registration Statement, use its best efforts to register or qualify or cooperate with the
Holders in connection with the registration or qualification (or exemption from such

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registration or qualification) of such Registrable Securities for offer and sale under
the securities or Blue Sky laws of such jurisdictions within the United States as any Holder
reasonably requests in writing; use its best efforts to keep each such registration or
qualification (or exemption therefrom) effective during the Effectiveness Period in
connection with such Holder’s offer and sale of Registrable Securities pursuant to such
registration or qualification (or exemption therefrom) and do any and all other acts or
things reasonably necessary or advisable to enable the disposition in such jurisdictions of
such Registrable Securities in the manner set forth in the relevant Shelf Registration
Statement and the related Prospectus; provided, however, that the Company
will not be required to qualify generally to do business in any jurisdiction where it is not
then so qualified.

     (i) Upon: (A) the occurrence or existence of any pending corporate development (a
“Material Event”) that, in the reasonable discretion of the Company, makes it
appropriate to suspend the availability of any Shelf Registration Statement and the related
Prospectus; (B) the issuance by the SEC of a stop order suspending the effectiveness of any
Shelf Registration Statement or the initiation of proceedings with respect to any Shelf
Registration Statement under Section 8(d) or 8(e) of the Securities Act; or (C) the
occurrence of any event or the existence of any fact as a result of which any Shelf
Registration Statement shall contain any untrue statement of a material fact or omit to
state any material fact required to be stated therein or necessary to make the statements
therein not misleading, or any Prospectus shall contain any untrue statement of a material
fact or omit to state any material fact necessary in order to make the statements therein,
in the light of the circumstances under which they were made, not misleading,

     (i) in the case of clause (A) or (C) above, as promptly as practicable, prepare
and file, if necessary pursuant to applicable law, a post-effective amendment to
such Shelf Registration Statement or a supplement to such Prospectus or any document
incorporated therein by reference or file any other required document that would be
incorporated by reference into such Shelf Registration Statement and Prospectus so
that such Shelf Registration Statement does not contain any untrue statement of a
material fact or omit to state any material fact required to be stated therein or
necessary to make the statements therein not misleading, and so that such Prospectus
does not contain any untrue statement of a material fact or omit to state any
material fact necessary in order to make the statements therein, in the light of the
circumstances under which they were made, not misleading, as thereafter delivered to
the purchasers of the Registrable Securities being sold thereunder, and, in the case
of a post-effective amendment to a Shelf Registration Statement, use its best
efforts to cause it to become effective under the Securities Act as promptly as
practicable, and

     (ii) give notice to the Holders and counsel for the Holders that the
availability of the Shelf Registration Statement is suspended (a “Suspension
Notice”).

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The Company will use its commercially reasonable efforts to ensure that the use of the
Prospectus may be resumed as promptly as is practicable and, in any event, so that the
period during which the availability of the Shelf Registration Statement and any Prospectus
is suspended pursuant to this Section 3(i) does not exceed thirty (30) days in the aggregate
in any three (3) month period or sixty (60) days in the aggregate in any twelve (12) month
period.

     (j) Make available for inspection during normal business hours by representatives for
the Holders and any underwriters participating in any disposition pursuant to any Shelf
Registration Statement and any broker-dealers, attorneys and accountants retained by such
Holders or any such underwriters, all relevant financial and other records and pertinent
corporate documents and properties of the Company and its subsidiaries, and cause the
appropriate officers, directors and employees of the Company and its subsidiaries to make
available for inspection during normal business hours all relevant information reasonably
requested by such representatives for the Holders, or any such underwriters, broker-dealers,
attorneys or accountants in connection with such disposition, in each case as is customary
for similar “due diligence” examinations; provided, however, that such
persons shall, at the Company’s request, first agree in writing with the Company that any
information that is reasonably and in good faith designated by the Company in writing as
confidential at the time of delivery of such information shall be kept confidential by such
persons and shall be used solely for the purposes of exercising rights under this Agreement,
unless (i) disclosure of such information is required by court or administrative order or is
necessary to respond to inquiries of governmental or regulatory authorities, (ii) disclosure
of such information is required by law (including any disclosure requirements pursuant to
federal securities laws in connection with the filing of any Shelf Registration Statement or
the use of any Prospectus referred to in this Agreement) or necessary to defend or prosecute
a claim brought against or by any such persons (e.g., to establish a “due diligence”
defense), (iii) such information becomes generally available to the public other than as a
result of a disclosure or failure to safeguard by any such person or (iv) such information
becomes available to any such person from a source other than the Company and such source is
not bound by a confidentiality agreement or is not otherwise under a duty of trust to the
Company; provided further, that the foregoing inspection and information
gathering shall, to the greatest extent possible, be coordinated on behalf of all the
Holders and the other parties entitled thereto by counsel for the Holders in connection with
Shelf Registration Statements.

     (k) Comply with all applicable rules and regulations of the SEC; and make generally
available to its securityholders earnings statements satisfying the provisions of Section
11(a) of the Securities Act and Rule 158 thereunder (or any similar rule promulgated under
the Securities Act), which statements shall cover a period of twelve (12) months commencing
on the first day of the first fiscal quarter of the Company commencing after the effective
date of each Shelf Registration Statement (within the meaning of Rule 158(c) under the
Securities Act), and which statements shall be so made generally available to the Company’s
securityholders no later than seventy-five (75) days after the end of each fiscal year of
the Company.

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     (l) Cooperate with each Holder to facilitate the timely preparation and delivery of
certificates representing Registrable Securities to be sold pursuant to a Shelf Registration
Statement, which certificates shall not bear any restrictive legends, and cause such
Registrable Securities to be registered in such names as such Holder may request in writing.

     (m) Cooperate and assist in any filings required to be made with the National
Association of Securities Dealers, Inc.

     (n) Use its best efforts (including without limitation, seeking to cure in the
Company’s listing application any deficiencies listed by the exchange) to qualify for and
list and include all Registrable Securities on the American Stock Exchange.

     (o) Take all actions and enter into such customary agreements as are necessary, or
reasonably requested by the Holders, in order to expedite or facilitate disposition of such
Registrable Securities.

     4. Registration Expenses. The Company shall bear all fees and expenses incurred in
connection with the performance by the Company of its obligations under Section 2 and Section 3 of
this Agreement whether or not any of the Shelf Registration Statements are filed or declared
effective under the Securities Act. Such fees and expenses (“Registration Expenses”) shall
include, without limitation, (i) all registration and filing fees and expenses (including, without
limitation, fees and expenses with respect to compliance with federal securities laws and state
securities or Blue Sky laws, (ii) all printing expenses (including, without limitation, expenses of
printing certificates for Registrable Securities), (iii) all duplication and mailing expenses
relating to copies of any Shelf Registration Statement or Prospectus delivered to any Holders
hereunder, (iv) all fees and disbursements of counsel for the Company, (v) all fees and
disbursements of the registrar and transfer agent for the Common Stock, and (vi) Securities Act
liability insurance obtained by the Company. In addition, the Company shall pay the internal
expenses of the Company (including, without limitation, all salaries and expenses of officers and
employees performing legal or accounting duties), the expense of any annual audit or quarterly
review, the fees and expenses incurred in connection with the listing by the Company of the
Registrable Securities on any securities exchange or quotation system on which similar securities
of the Company are then listed and the fees and expenses of any person, including, without
limitation, special experts, retained by the Company. The Company shall not be responsible to pay
any brokerage fees and commissions incurred by the Holders in connection with their sale of
Registrable Securities.

     5. Indemnification, Contribution.

     (a) The Company agrees to indemnify, defend and hold harmless (i) each Holder, (ii)
each person (a “Controlling Person”), if any, who controls any Holder within the
meaning of Section 15 of the Securities Act or Section 20 of the Exchange Act and (iii) the
respective officers, directors, partners, members, employees, representatives and agents of
each Holder or any Controlling Person (each, an “Indemnified Party”), from

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and against any loss, damage, expense, liability, claim or any actions in respect
thereof (including the reasonable cost of investigation) which such Indemnified Party may
incur or become subject to under the Securities Act, the Exchange Act or otherwise, insofar
as such loss, damage, expense, liability, claim or action arises out of or is based upon any
untrue statement or alleged untrue statement of a material fact contained in any Shelf
Registration Statement or Prospectus or any free writing prospectus, including any document
incorporated by reference therein, or in any amendment or supplement thereto or in any
preliminary prospectus, or arises out of or is based upon any omission or alleged omission
to state a material fact required to be stated in any Shelf Registration Statement or in any
amendment or supplement thereto or necessary to make the statements therein not misleading,
or arises out of or is based upon any omission or alleged omission to state a material fact
necessary in order to make the statements made in any Prospectus or any free writing
prospectus or in any amendment or supplement thereto or in any preliminary prospectus, in
the light of the circumstances under which such statements were made, not misleading, and
the Company shall reimburse, as incurred, the Indemnified Parties for any legal or other
expenses reasonably incurred by them in connection with investigating or defending any such
loss, damage, expense, liability, claim or action in respect thereof; provided,
however, that the Company shall not be required to provide any indemnification
pursuant to this Section 5(a) in any such case insofar as any such loss, damage, expense,
liability, claim or action arises out of or is based upon any untrue statement or omission
or alleged untrue statement or omission of a material fact contained in, or omitted from,
and in conformity with information furnished in writing by or on behalf of a Holder to the
Company expressly for use in, any Shelf Registration Statement or any Prospectus;
provided, further, however, that this indemnity agreement will be in
addition to any liability which the Company may otherwise have to such Indemnified Party.

     (b) Each Holder, severally and not jointly, agrees to indemnify, defend and hold
harmless (i) the Company, (ii) its directors, officers, employees and (iii) any person who
controls the Company within the meaning of Section 15 of the Securities Act or Section 20 of
the Exchange Act (each, a “Company Indemnified Party”) from and against any loss,
damage, expense, liability, claim or any actions in respect thereof (including the
reasonable cost of investigation) which such Company Indemnified Party may incur or become
subject to under the Securities Act, the Exchange Act or otherwise, insofar as such loss,
damage, expense, liability, claim or action arises out of or is based upon any untrue
statement or alleged untrue statement of a material fact contained in, and in conformity
with information (the “Holder Information”) furnished in writing by or on behalf of
such Holder to the Company expressly for use in, any Shelf Registration Statement or
Prospectus, or arises out of or is based upon any omission or alleged omission to state a
material fact in connection with such Holder Information required to be stated in any Shelf
Registration Statement or Prospectus or necessary to make such Holder Information, in light
of the circumstances under which such statements were made, not misleading; and, subject to
the limitation set forth in the immediately preceding clause, each Holder shall reimburse,
as incurred, the Company for any legal or other expenses reasonably incurred by the Company
or any such controlling person in connection with investigating or defending any loss,
damage, expense, liability, claim or

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action in respect thereof. This indemnity agreement will be in addition to any
liability which such Holder may otherwise have to the Company or any of its controlling
persons. In no event shall the liability of any selling Holder of Registrable Securities
hereunder be greater in amount than the dollar amount of the proceeds received by such
Holder upon the sale, pursuant to the Shelf Registration Statement, of the Registrable
Securities giving rise to such indemnification obligation.

     (c) If any action, suit or proceeding (each, a “Proceeding”) is brought against
any person in respect of which indemnity may be sought pursuant to either Section 5(a) or
Section 5(b), such person (the “Indemnified Party”) shall promptly notify the person
against whom such indemnity may be sought (the “Indemnifying Party”) in writing of
the institution of such Proceeding and the Indemnifying Party shall assume the defense of
such Proceeding; provided, however, that the omission to so notify such
Indemnifying Party shall not relieve such Indemnifying Party from any liability which it may
have to such Indemnified Party or otherwise. Such Indemnified Party shall have the right to
employ its own counsel in any such case, but the fees and expenses of such counsel shall be
at the expense of such Indemnified Party unless the employment of such counsel shall have
been authorized in writing by such Indemnifying Party in connection with the defense of such
Proceeding or such Indemnifying Party shall not have employed counsel to have charge of the
defense of such Proceeding within thirty (30) days of the receipt of notice thereof or such
Indemnified Party shall have reasonably concluded upon the written advice of counsel that
there may be one or more defenses available to it that are different from, additional to or
in conflict with those available to such Indemnifying Party (in which case such Indemnifying
Party shall not have the right to direct that portion of the defense of such Proceeding on
behalf of the Indemnified Party, but such Indemnifying Party may employ counsel and
participate in the defense thereof but the fees and expenses of such counsel shall be at the
expense of such Indemnifying Party), in any of which events such reasonable fees and
expenses shall be borne by such Indemnifying Party and paid as incurred (it being
understood, however, that such Indemnifying Party shall not be liable for the expenses of
more than one separate counsel in any one Proceeding or series of related Proceedings
together with reasonably necessary local counsel representing the Indemnified Parties who
are parties to such action). An Indemnifying Party shall not be liable for any settlement
of such Proceeding effected without the written consent of such Indemnifying Party, but if
settled with the written consent of such Indemnifying Party, such Indemnifying Party agrees
to indemnify and hold harmless an Indemnified Party from and against any loss or liability
by reason of such settlement. Notwithstanding the foregoing sentence, if at any time an
Indemnified Party shall have requested an Indemnifying Party to reimburse such Indemnified
Party for fees and expenses of counsel as contemplated by the second sentence of this
paragraph, then such Indemnifying Party agrees that it shall be liable for any settlement of
any Proceeding effected without its written consent if (i) such settlement is entered into
more than sixty (60) Business Days after receipt by such Indemnifying Party of the aforesaid
request, (ii) such Indemnifying Party shall not have fully reimbursed such Indemnified Party
in accordance with such request prior to the date of such settlement and (iii) such
Indemnified Party shall have given such Indemnifying Party at least thirty (30) days’ prior
notice of its intention to settle. No Indemnifying Party shall, without the prior

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written consent of any Indemnified Party, effect any settlement of any pending or
threatened Proceeding in respect of which such Indemnified Party is or could have been a
party and indemnity could have been sought hereunder by such Indemnified Party, unless such
settlement includes an unconditional release of such Indemnified Party from all liability on
claims that are the subject matter of such Proceeding and does not include an admission of
fault or culpability or a failure to act by or on behalf of such Indemnified Party.

     (d) If the indemnification provided for in this Section 5 is unavailable to an
Indemnified Party under Section 5(a) or Section 5(b), or insufficient to hold such
Indemnified Party harmless, in respect of any losses, damages, expenses, liabilities, claims
or actions referred to therein, then each applicable Indemnifying Party, in lieu of
indemnifying such Indemnified Party, shall contribute to the amount paid or payable by such
Indemnified Party as a result of such losses, damages, expenses, liabilities, claims or
actions (i) in such proportion as is appropriate to reflect the relative fault of the
Company, on the one hand, and of the Holders, on the other hand, in connection with the
statements or omissions which resulted in such losses, damages, expenses, liabilities,
claims or actions, as well as any other relevant equitable considerations. The relative
fault of the Company, on the one hand, and of the Holders, on the other hand, shall be
determined by reference to, among other things, whether the untrue statement or alleged
untrue statement of a material fact or omission or alleged omission relates to information
supplied by the Company or by the Holders and the parties’ relative intent, knowledge,
access to information and opportunity to correct or prevent such statement or omission. The
amount paid or payable by a party as a result of the losses, damages, expenses, liabilities,
claims and actions referred to above shall be deemed to include any reasonable legal or
other fees or expenses reasonably incurred by such party in connection with investigating or
defending any Proceeding.

     (e) The Company and the Holders agree that it would not be just and equitable if
contribution pursuant to this Section 5 were determined by pro rata allocation or by any
other method of allocation which does not take account of the equitable considerations
referred to in Section 5(d) above. Notwithstanding the provisions of this Section 5, no
Holder shall be required to contribute any amount in excess of the amount by which the total
price at which the Registrable Securities giving rise to such contribution obligation and
sold by such Holder were offered to the public exceeds the amount of any damages which it
has otherwise been required to pay by reason of such untrue or alleged untrue statement or
omission or alleged omission. No person guilty of fraudulent misrepresentation (within the
meaning of Section 11(f) of the Securities Act) shall be entitled to contribution from any
person who was not guilty of such fraudulent misrepresentation. The Holders’ respective
obligations to contribute pursuant to this Section 5 are several in proportion to the
respective amount of Registrable Securities they have sold pursuant to a Shelf Registration
Statement, and not joint. The remedies provided for in this Section 5 are not exclusive and
shall not limit any rights or remedies which may otherwise be available to any indemnified
party at law or in equity.

     (f) The indemnity and contribution provisions contained in this Section 5

- 12 -

 

shall remain operative and in full force and effect regardless of (i) any termination
of this Agreement, (ii) any investigation made by or on behalf of any Holder or any person
controlling any Holder, or the Company, or the Company’s officers or directors or any person
controlling the Company and (iii) the sale of any Registrable Security by any Holder.

     6. Information Requirements.

     (a) The Company covenants that, if at any time before the end of the Effectiveness
Period it is not subject to the reporting requirements of the Exchange Act, it will
cooperate with any Holder of Registrable Securities and take such further action as any
Holder of Registrable Securities may reasonably request in writing (including, without
limitation, making such representations as any such Holder may reasonably request), all to
the extent required from time to time to enable such Holder to sell Registrable Securities
without registration under the Securities Act within the limitations of the exemptions
provided by Rule 144, Rule 144A, Regulation S and Regulation D under the Securities Act and
customarily taken in connection with sales pursuant to such exemptions. Upon the written
request of any Holder, the Company shall deliver to such Holder a written statement as to
whether the Company has complied with the reporting requirements of the Exchange Act, unless
such a statement has been included in the Company’s most recent report filed with the SEC
pursuant to Section 13 or Section 15(d) of Exchange Act.

     (b) The Company shall use commercially reasonable efforts to file the reports required
to be filed by it under the Exchange Act and to comply with all other requirements set forth
in the instructions to Form S-3 in order to allow the Company to be eligible to file
registration statements on Form S-3.

     7. Obligations of the Holders

     (a) Within ten (10) Business Days of the Company’s request to a Holder therefore, such
Holder, if it wishes to include its Registrable Securities in a Registration Statement,
shall furnish in writing to the Company answers to the questions on the Investor
Questionnaire in the form attached hereto as Exhibit “A” and such Holder will notify the
Company promptly of any change in any of such information not less than five (5) Business
Days prior to any attempted or actual distribution of Registrable Securities under a
Registration Statement.

     (b) Each Holder, by its acceptance of the Registrable Securities agrees to cooperate
with the Company as reasonably requested by the Company in connection with the preparation
and filing of a Registration Statement hereunder, unless such Investor has notified the
Company in writing of its election to exclude all of its Registrable Securities from such
Registration Statement.

     (c) Each Holder agrees that, upon receipt of any Suspension Notice from the Company in
accordance with Section 3(i) hereof, such Holder will immediately

- 13 -

 

discontinue disposition of Registrable Securities pursuant to the Registration
Statement covering such Registrable Securities until (i) the Holder’s receipt of the copies
of the supplemented or amended prospectus filed with the SEC (and notice from the Company
that any related post-effective amendment is declared effective, which notice shall be
promptly provided by the Company) or (ii) or such Holder is advised in writing by the
Company that the Prospectus may be used.

     8. Miscellaneous.

     (a) Remedies. The Company acknowledges and agrees that any failure by the
Company to comply with its obligations under this Agreement may result in material
irreparable injury to the Holders for which there is no adequate remedy at law, that it will
not be possible to measure damages for such injuries precisely and that, in the event of any
such failure, any Holder may obtain such relief as may be required to specifically enforce
the Company’s obligations under this Agreement. The Company further agrees to waive the
defense in any action for specific performance that a remedy at law would be adequate.

     (b) No Conflicting Agreements. The Company is not, as of the date hereof, a
party to, nor shall it, on or after the date of this Agreement, enter into, any agreement
with respect to the Company’s securities that conflicts with the rights granted to the
Holders in this Agreement. The Company represents and warrants that the rights granted to
the Holders hereunder do not in any way conflict with the rights granted to the holders of
the Company’s securities under any other agreements. The Company will not take any action
with respect to the Registrable Securities which would adversely affect the ability of any
of the Holders to include such Registrable Securities in a registration undertaken pursuant
to this Agreement.

     (c) Amendments and Waivers. The provisions of this Agreement, including the
provisions of this sentence, may not be amended, modified or supplemented, and waivers or
consents to departures from the provisions hereof may not be given, unless the Company has
obtained the written consent of the Holders holding a majority of the Registrable
Securities. Notwithstanding the foregoing, a waiver or consent to depart from the
provisions hereof with respect to a matter that relates exclusively to the rights of Holders
of Registrable Securities whose securities are being sold pursuant to a Shelf Registration
Statement and that does not directly or indirectly affect the rights of other Holders of
Registrable Securities may be given by the Holders holding a majority of the Registrable
Securities being sold pursuant to such Shelf Registration Statement.

     (d) Notices. All notices and other communications provided for or permitted
hereunder shall be made in writing by hand delivery, by telecopier, by courier guaranteeing
overnight delivery or by first-class mail, return receipt requested, and shall be deemed
given (A) when made, if made by hand delivery, (B) upon confirmation, if made by telecopier,
(C) one (1) Business Day after being deposited with such courier, if made by overnight
courier or (D) on the date indicated on the notice of receipt, if made by first-class mail,
to the parties as follows:

- 14 -

 

     (i) if to a Holder, at the most current address given by such Holder to the
Company in a Notice and Questionnaire or any amendment thereto;

     (ii) if to the Company, to:

American Oil & Gas, Inc.

1050 Seventeenth Street, Suite 2400

Denver, CO 80265

Attention: Pat O’Brien, Chief Executive Officer

Facsimile No.: (303) 595-0709

     (iii) if to a Holder, to the Holder at the most recent address for such Holder
given by the transfer agent and registrar of the common stock, par value $0.001 per
share, of the Company:

or to such other address as such person may have furnished to the other persons identified
in this Section 8(d) in writing in accordance herewith.

     (e) Third Party Beneficiaries. The Holders shall be third party beneficiaries
to the agreements made hereunder between the Company, on the one hand, and the Stockholders,
on the other hand, and shall have the right to enforce such agreements directly to the
extent they may deem such enforcement necessary or advisable to protect their rights or the
rights of Holders hereunder.

     (f) Successors and Assigns. Any person who purchases any Registrable Security
from any Holder shall be deemed, for purposes of this Agreement, to be an assignee of such
Holder. This Agreement shall inure to the benefit of and be binding upon the respective
successors and assigns of each of the parties hereto and shall inure to the benefit of and
be binding upon each Holder of any Registrable Security.

     (g) Counterparts. This Agreement may be executed in any number of counterparts
and by the parties hereto in separate counterparts, each of which when so executed shall be
deemed to be original and all of which taken together shall constitute one and the same
agreement.

     (h) Headings. The headings in this Agreement are for convenience of reference
only and shall not limit or otherwise affect the meaning hereof.

     (i) Governing Law. THIS AGREEMENT SHALL BE GOVERNED BY, AND CONSTRUED IN
ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK, WITHOUT REGARD TO CONFLICTS OF LAWS
PRINCIPLES THEREOF.

     (j) Severability. If any term, provision, covenant or restriction of this
Agreement is held to be invalid, illegal, void or unenforceable, the remainder of the

- 15 -

 

terms, provisions, covenants and restrictions set forth herein shall remain in full
force and effect and shall in no way be affected, impaired or invalidated thereby, and the
parties hereto shall use commercially reasonable efforts to find and employ an alternative
means to achieve the same or substantially the same result as that contemplated by such
term, provision, covenant or restriction, it being intended that all of the rights and
privileges of the parties shall be enforceable to the fullest extent permitted by law.

     (k) Entire Agreement. This Agreement is intended by the parties hereto as a
final expression of their agreement and is intended to be a complete and exclusive statement
of the agreement and understanding of the parties hereto in respect of the subject matter
contained herein and the registration rights granted by the Company with respect to the
Registrable Securities. This Agreement supersedes all prior agreements and undertakings
among the parties with respect to such registration rights.

     (l) Termination. This Agreement and the obligations of the parties hereunder
shall terminate upon the end of the Effectiveness Period, except for any liabilities or
obligations under Section 2(d) incurred prior to the end of the Effective Period and any
limitations or obligations under Section 4 or Section 5 hereof, all of which liabilities and
obligations shall remain in effect in accordance with the terms of this Agreement.

     (m) Submission to Jurisdiction. Except as set forth below, no claim,
counterclaim or dispute of any kind or nature whatsoever arising out of or in any way
relating to this Agreement (“Claim”) may be commenced, prosecuted or continued in
any court other than the courts of the State of New York located in the City and County of
New York or in the United States District Court for the Southern District of New York, which
courts shall have jurisdiction over the adjudication of such matters, and the Company hereby
consents to the jurisdiction of such courts and personal service with respect thereto. The
Company hereby consents to personal jurisdiction, service and venue in any court in which
any Claim arising out of or in any way relating to this Agreement is brought by any third
party against any Holder. THE COMPANY HEREBY WAIVES ALL RIGHTS TO TRIAL BY JURY IN ANY
PROCEEDING (WHETHER BASED UPON CONTRACT, TORT OR OTHERWISE) IN ANY WAY ARISING OUT OF OR
RELATING TO THIS AGREEMENT. The Company agrees that a final judgment in any such Proceeding
brought in any such court shall be conclusive and binding upon the Company and may be
enforced in any other courts in the jurisdiction of which the Company is or may be subject,
by suit upon such judgment.

[The Remainder of This Page Intentionally Left Blank; Signature Page Follows]

- 16 -

 

          In Witness Whereof, the parties have executed this Agreement as of the date first
written above.

	 	 	 	 	 
	 	Very truly yours,

American Oil & Gas, Inc.

 	 
	 	By:  	

/s/ Andrew P. Calerich
 	 
	 	 	Name:  	Andrew P. Calerich 	 
	 	 	Title:  	President 	 

 

 

	 	 	 	 	 

Investors:

Accepted and agreed to as of the date

first above written, on behalf of itself

and the Holders (as defined herein):

Edison Sources Ltd.

By: State Street Research and Management Company

	 	 	 	 	 
	By:

	 	/s/ Dan Rice
	 	 
	 

	 	 	 	 
	 

	 	Name: Dan Rice	 	 
	 

	 	Title: Managing Director	 	 

Raytheon Master Pension Trust 

By: State Street Research and Management Company

	 	 	 	 	 
	By:

	 	/s/ Dan Rice
	 	 
	 

	 	 	 	 
	 

	 	Name: Dan Rice	 	 
	 

	 	Title: Managing Director	 	 

Raytheon Combined DB/DC Master Trust

By: State Street Research and Management Company

	 	 	 	 	 
	By:

	 	/s/ Dan Rice
	 	 
	 

	 	 	 	 
	 

	 	Name: Dan Rice	 	 
	 

	 	Title: Managing Director	 	 

SSR Energy and Natural Resources Hedge Fund LLC 

By: State Street Research and Management Company

	 	 	 	 	 
	By:

	 	/s/ Dan Rice
	 	 
	 

	 	 	 	 
	 

	 	Name: Dan Rice	 	 
	 

	 	Title: Managing Director	 	 

 

 

Exhibit “A”

Investor Questionnaire

AMERICAN OIL & GAS, INC.

Questionnaire for Selling Stockholders

	 	 	 	 	 
	Name (please print):
	 	 	 	 
	 

	 	 

	 	 

     Please complete, sign and return this Questionnaire before September 14, 2006. If you have
questions about this Questionnaire or are unsure about what information is requested by a
particular question, please call Andy Calerich at (303) 991-0173. When this Questionnaire is
completed, please retain one copy for your personal files and return one signed copy to:

Andy Calerich

American Oil & Gas, Inc.

1050 Seventeenth Street, Suite 2400

Denver, CO 80265

Fax (303) 595-0709

Phone: (303) 991-0173

With a copy to:

Robert M. Bearman

Patton Boggs LLP

1660 Lincoln Street, Suite 1900

Denver, Colorado 80264

Fax (303) 894-9239

Phone (303) 894-6169

     The information you supply in response to this Questionnaire will be used by American Oil &
Gas, Inc. (the “Corporation”) to assure the accuracy of certain data to be included in a
Registration Statement (the “Registration Statement) which is to be filed with the U.S. Securities
and Exchange Commission (the “SEC”) and which registers the sale by you of certain securities
issued by the Corporation. Please exercise great care in completing this Questionnaire. Under
certain circumstances, selling securityholders are subject to personal liability if the
Registration Statement misrepresents a material fact or omits a material fact. The information
requested is for your protection and that of the Corporation, and will be used to assure that
related information in the Registration Statement is correct.

     Your signature at the end of this Questionnaire will constitute your consent to use the
information contained in your answers in the Registration Statement.

GLOSSARY

An “Affiliate” of the Corporation is any person, corporation, partnership, association or other
business or professional entity that directly, or indirectly through one or more intermediaries,
controls, or is controlled by, or is under common control with the Corporation.

 

 

A “Beneficial Owner” of a security is any person who, directly or indirectly, through any contract,
arrangement, understanding, relationship or otherwise has or shares: (a) voting power (which
includes the power to vote or to direct the voting of such security), or (b) investment power
(which includes the power to dispose or to direct the disposition of such security). A person is
deemed to be the beneficial owner of the security if he has the right to acquire beneficial
ownership of such security at any time within 60 days, including but not limited to any right to
acquire (x) through the exercise of any option, warrant or right, (y) through the conversion of a
security, or (z) pursuant to the power to revoke a trust, discretionary account or similar
arrangement.

The above definition is very broad and may include, for example, securities held in the name of any
relative living in a person’s home. The final determination of beneficial ownership of the
securities is, of course, a question to be determined in light of the facts of each particular
case. Thus, while a person may include security holdings of members of his family or others, he
may, nonetheless, disclaim beneficial ownership of such securities. If a person does so disclaim,
he should give his details as to the number of such securities and the basis upon which he
disclaims beneficial ownership of such securities.

If you receive or are entitled to receive the benefits from shares that are not owned of record,
i.e., shares held for your benefit in the name of anyone else (your spouse or any member of your
family, an estate or trust, a partnership in which you are a member, a brokerage firm, etc.), such
shares are beneficially owned by you.

Shares held of record by another should also be listed as beneficially owned by you if you have the
power to invest or reinvest title to such shares in yourself at once or at some future time. The
number of shares as to which you have such power, the authority pursuant to which and the manner in
which your power may be exercised, and your relationship with the person who at present holds such
shares should be clearly indicated.

It is the position of the SEC that shares held by persons with whom you have certain specified
relationships shall be deemed to be beneficially owned by you. As a result, securities held by
your wife, or by a minor child, or by any other relative of you or your wife living in your
household, in which you believe you have no beneficial interest should be included in part Question
2, and you should indicate in Question 2 that you disclaim beneficial ownership.

“Immediate Family” includes your spouse, parents, children, siblings, mothers and fathers-in-law,
sons and daughters-in-law, and brothers and sisters-in-law.

Information is “material” if there is a substantial likelihood that a reasonable stockholder would
consider the information important in deciding how to vote. In addition, there are certain
specific requirements as to information concerning material transactions that are reported pursuant
to this Questionnaire, and certain exceptions for transactions that might otherwise be deemed
material. It is suggested that guidance of counsel be sought in the event of any questions in this
area.

“Restricted Shares” means the shares of common stock or other securities of the Corporation that
are Registrable Securities as defined in the Registration Rights Agreement dated as of September
     , 2006 among the Corporation and the Investors listed on the signature pages thereto.

*****

 

 

	1.	 	Ownership of the Corporation’s Securities
	 
	 	 	Please provide the following information:

	 	 	 	 	 	 	 	 	 
	 	 	(i)	 	Full legal name of Selling Stockholder:	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	(ii)	 	Full legal name of registered holder (if different from Selling Stockholder):	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 

	 	 	 	 	 	 	 	 	 
	 	 	(iii)	 	Address for notices to Selling Stockholder:	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 
	 

	 	 	 	Telephone:	 	 	 	 
	 

	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 

	 	 	 	Fax:	 	 	 	 
	 

	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 

	 	 	 	Contact Person:	 	 	 	 
	 

	 	 	 	 	 	 	 	 

(a) Please list the number of shares of common stock of the Corporation you were the
“beneficial owner” of as of the current date. If such stock is not owned of record by you
(e.g. in the name of a family member, in “street” name, and partnership name, etc.), please
indicate the name of the record owner and the number of shares held by such record owner.
Please use the last row of the table to report any securities which you have the right to
acquire within sixty days from options, warrants, rights, conversion privilege or similar
obligations. Please see the definition of “beneficial ownership” in the glossary.

	 	 	 
	Type of Ownership	 	Number of Shares
	 
	Common stock registered in your name
	 	 
	 

	 	 
	 
	 	 
	Common stock registered in “immediate family’s” name (see Glossary)
	 	 
	 

	 	 
	 
	 	 
	Common stock held as trustee of a trust
	 	 
	 

	 	 
	 
	 	 
	Common stock held by a brokerage firm or other nominee (street name)
	 	 
	 

	 	 
	 
	 	 
	Common stock held in other forms (explain)
	 	 
	 

	 	 

 

 

(b) Please identify below the number of shares of common stock of the Corporation
you listed in response to (a) above that are Restricted Securities as of the current date.
If any such Registrable Securities are not owned of record by you (e.g. in the name of a
family member, in “street” name, and partnership name, etc.), please indicate the name of
the record owner and the number of shares of Registrable Securities held by such record
owner.

	 	 	 
	Type of Ownership	 	Number of Restricted Securities
	 
	Restricted Securities registered in your name
	 	 
	 

	 	 
	 
	 	 
	Restricted Securities registered in “immediate 

family’s” name (see Glossary)
	 	 
	 

	 	 
	 
	 	 
	Restricted Securities held as trustee of a trust
	 	 
	 

	 	 
	 
	 	 
	Restricted Securities held by a brokerage firm 

or other nominee (street name)
	 	 
	 

	 	 
	 
	 	 
	Restricted Securities held in other forms

(explain)
	 	 
	 

	 	 

(c) Do you wish to disclaim beneficial ownership of any of the securities reported
in response to 1(a) or 1(b) above? ___yes ___no.

     If the answer is “Yes,” please briefly state your reason(s) for disclaiming beneficial
ownership and furnish the following information with respect to the person or persons who
should be shown as the “beneficial owner” (see Appendix) of the securities in question.

	 	 	 	 	 
	 	 	 	 	Number or Amount and
	Name of Actual	 	Relationship of	 	Class of Securities
	Beneficial Owner	 	Beneficial Owner to You	 	Beneficially Owned
	 
	 

	 	 
	 	 
	 
	 	 	 	 
	 

	 	 
	 	 
	 
	 	 	 	 
	 

	 	 
	 	 
	 
	 	 	 	 
	 

	 	 
	 	 

(d) Do you own any other securities of the Corporation not described in item 1 above, e.g.,
debentures, bonds, notes? If so please describe.

 

 

	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	(e) If you share with any other “person” voting power or investment power over any of
the securities listed above in response to Question 1 above, please describe the
arrangement, indicating the person and the amount of securities involved.
	 
	 	 	 	 

	 
	 	 	 	 

	 
	 	 	 	 

The undersigned agrees to promptly notify the Corporation of any inaccuracies or changes in the
information provided in this Questionnaire that may occur subsequent to the date hereof.

The undersigned hereby acknowledges that he or she understands the purposes for which the foregoing
information was obtained, and represents and warrants that the information supplied in this
Questionnaire is true and complete.

	 	 	 	 	 	 	 	 	 
	Printed Name of Entity:
	 	 	 	 	 	 	 	 
	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	By:
	 	 	 	 	 	 	 	 
	 	 	 	 	 
	 	 	(Signature)	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	Printed Name:	 	 	 	 
	 

	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 

	 	Title:	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	Date:exv10w1

 

Exhibit 10.1

WINTRUST FINANCIAL CORPORATION

as Company

INDENTURE

Dated as of September 1, 2006

LASALLE BANK NATIONAL ASSOCIATION

As Trustee

JUNIOR SUBORDINATED DEBT SECURITIES

Due September 15, 2036

(8) Wintrust Financial Corporation

 

 

TABLE OF CONTENTS

	 	 	 	 	 	 	 
	 	 	 	 	Page
	 
	 	 	 	 	 	 
	ARTICLE I

	DEFINITIONS

	SECTION 1.01.

	 	Definitions
	 	 	1	 
	 
	 	 	 	 	 	 
	ARTICLE II

	DEBT SECURITIES

	SECTION 2.01.

	 	Authentication and Dating
	 	 	8	 
	SECTION 2.02.

	 	Form of Trustee’s Certificate of Authentication
	 	 	9	 
	SECTION 2.03.

	 	Form and Denomination of Debt Securities
	 	 	9	 
	SECTION 2.04.

	 	Execution of Debt Securities
	 	 	10	 
	SECTION 2.05.

	 	Exchange and Registration of Transfer of Debt Securities
	 	 	10	 
	SECTION 2.06.

	 	Mutilated, Destroyed, Lost or Stolen Debt Securities
	 	 	13	 
	SECTION 2.07.

	 	Temporary Debt Securities
	 	 	14	 
	SECTION 2.08.

	 	Payment of Interest
	 	 	14	 
	SECTION 2.09.

	 	Cancellation of Debt Securities Paid, etc
	 	 	16	 
	SECTION 2.10.

	 	Computation of Interest
	 	 	16	 
	SECTION 2.11.

	 	Extension of Interest Payment Period
	 	 	18	 
	SECTION 2.12.

	 	CUSIP Numbers
	 	 	19	 
	SECTION 2.13.

	 	Income Tax Certification
	 	 	19	 
	SECTION 2.14.

	 	Global Debentures
	 	 	19	 
	 
	 	 	 	 	 	 
	ARTICLE III

	PARTICULAR COVENANTS OF THE COMPANY

	SECTION 3.01.

	 	Payment of Principal, Premium and Interest; Agreed
Treatment of the Debt Securities
	 	 	21	 
	SECTION 3.02.

	 	Offices for Notices and Payments, etc
	 	 	22	 
	SECTION 3.03.

	 	Appointments to Fill Vacancies in Trustee’s Office
	 	 	23	 
	SECTION 3.04.

	 	Provision as to Paying Agent
	 	 	23	 
	SECTION 3.05.

	 	Certificate to Trustee
	 	 	24	 
	SECTION 3.06.

	 	Additional Interest
	 	 	24	 
	SECTION 3.07.

	 	Compliance with Consolidation Provisions
	 	 	24	 
	SECTION 3.08.

	 	Limitation on Dividends
	 	 	24	 
	SECTION 3.09.

	 	Covenants as to the Trust
	 	 	25	 

-i-

 

TABLE OF CONTENTS
(CONTINUED)

	 	 	 	 	 	 	 
	 	 	 	 	Page
	ARTICLE IV

	LISTS AND REPORTS BY THE COMPANY AND THE TRUSTEE

	SECTION 4.01.

	 	Securityholders’ Lists
	 	 	26	 
	SECTION 4.02.

	 	Preservation and Disclosure of Lists
	 	 	26	 
	 
	 	 	 	 	 	 
	ARTICLE V

	REMEDIES OF THE TRUSTEE AND SECURITYHOLDERS UPON AN EVENT OF DEFAULT

	SECTION 5.01.

	 	Events of Default
	 	 	27	 
	SECTION 5.02.

	 	Payment of Debt Securities on Default; Suit Therefor
	 	 	30	 
	SECTION 5.03.

	 	Application of Moneys Collected by Trustee
	 	 	31	 
	SECTION 5.04.

	 	Proceedings by Securityholders
	 	 	31	 
	SECTION 5.05.

	 	Proceedings by Trustee
	 	 	32	 
	SECTION 5.06.

	 	Remedies Cumulative and Continuing
	 	 	32	 
	SECTION 5.07.

	 	Direction of Proceedings and Waiver of Defaults by Majority
of Securityholders
	 	 	32	 
	SECTION 5.08.

	 	Notice of Defaults
	 	 	33	 
	SECTION 5.09.

	 	Undertaking to Pay Costs
	 	 	34	 
	 
	 	 	 	 	 	 
	ARTICLE VI

	CONCERNING THE TRUSTEE

	SECTION 6.01.

	 	Duties and Responsibilities of Trustee
	 	 	34	 
	SECTION 6.02.

	 	Reliance on Documents, Opinions, etc
	 	 	35	 
	SECTION 6.03.

	 	No Responsibility for Recitals, etc
	 	 	36	 
	SECTION 6.04.

	 	Trustee, Authenticating Agent, Paying Agents, Transfer Agents or

Registrar May Own Debt Securities
	 	 	37	 
	SECTION 6.05.

	 	Moneys to be Held in Trust
	 	 	37	 
	SECTION 6.06.

	 	Compensation and Expenses of Trustee
	 	 	37	 
	SECTION 6.07.

	 	Officers’ Certificate as Evidence
	 	 	38	 
	SECTION 6.08.

	 	Eligibility of Trustee
	 	 	38	 
	SECTION 6.09.

	 	Resignation or Removal of Trustee, Calculation
Agent, Paying Agent or Debt Security Registrar
	 	 	39	 
	SECTION 6.10.

	 	Acceptance by Successor
	 	 	40	 
	SECTION 6.11.

	 	Succession by Merger, etc
	 	 	41	 

-ii-

 

TABLE OF CONTENTS
(CONTINUED)

	 	 	 	 	 	 	 
	 	 	 	 	Page
	SECTION 6.12.

	 	Authenticating Agents
	 	 	41	 
	 
	 	 	 	 	 	 
	ARTICLE VII

	CONCERNING THE SECURITYHOLDERS

	SECTION 7.01.

	 	Action by Securityholders
	 	 	43	 
	SECTION 7.02.

	 	Proof of Execution by Securityholders
	 	 	43	 
	SECTION 7.03.

	 	Who Are Deemed Absolute Owners
	 	 	44	 
	SECTION 7.04.

	 	Debt Securities Owned by Company Deemed Not Outstanding
	 	 	44	 
	SECTION 7.05.

	 	Revocation of Consents; Future Securityholders Bound
	 	 	44	 
	 
	 	 	 	 	 	 
	ARTICLE VIII

	SECURITYHOLDERS’ MEETINGS

	SECTION 8.01.

	 	Purposes of Meetings
	 	 	45	 
	SECTION 8.02.

	 	Call of Meetings by Trustee
	 	 	45	 
	SECTION 8.03.

	 	Call of Meetings by Company or Securityholders
	 	 	45	 
	SECTION 8.04.

	 	Qualifications for Voting
	 	 	46	 
	SECTION 8.05.

	 	Regulations
	 	 	46	 
	SECTION 8.06.

	 	Voting
	 	 	46	 
	SECTION 8.07.

	 	Quorum; Actions
	 	 	47	 
	SECTION 8.08.

	 	Written Consent Without a Meeting
	 	 	48	 
	 
	 	 	 	 	 	 
	ARTICLE IX

	SUPPLEMENTAL INDENTURES

	SECTION 9.01.

	 	Supplemental Indentures without Consent of Securityholders
	 	 	48	 
	SECTION 9.02.

	 	Supplemental Indentures with Consent of Securityholders
	 	 	49	 
	SECTION 9.03.

	 	Effect of Supplemental Indentures
	 	 	50	 
	SECTION 9.04.

	 	Notation on Debt Securities
	 	 	51	 
	SECTION 9.05.

	 	Evidence of Compliance of Supplemental Indenture to be furnished to Trustee
	 	 	51	 
	 
	 	 	 	 	 	 
	ARTICLE X

	REDEMPTION OF SECURITIES

	SECTION 10.01.

	 	Optional Redemption
	 	 	51	 
	SECTION 10.02.

	 	Special Event Redemption
	 	 	51	 
	SECTION 10.03.

	 	Notice of Redemption; Selection of Debt Securities
	 	 	52	 

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TABLE OF CONTENTS
(CONTINUED)

	 	 	 	 	 	 	 
	 	 	 	 	Page
	SECTION 10.04.

	 	Payment of Debt Securities Called for Redemption
	 	 	52	 
	 
	 	 	 	 	 	 
	ARTICLE XI

	CONSOLIDATION, MERGER, SALE, CONVEYANCE AND LEASE

	SECTION 11.01.

	 	Company May Consolidate, etc., on Certain Terms
	 	 	53	 
	SECTION 11.02.

	 	Successor Entity to be Substituted
	 	 	54	 
	SECTION 11.03.

	 	Opinion of Counsel to be Given to Trustee
	 	 	54	 
	 
	 	 	 	 	 	 
	ARTICLE XII

	SATISFACTION AND DISCHARGE OF INDENTURE

	SECTION 12.01.

	 	Discharge of Indenture
	 	 	55	 
	SECTION 12.02.

	 	Deposited Moneys to be Held in Trust by Trustee
	 	 	55	 
	SECTION 12.03.

	 	Paying Agent to Repay Moneys Held
	 	 	56	 
	SECTION 12.04.

	 	Return of Unclaimed Moneys
	 	 	56	 
	 
	 	 	 	 	 	 
	ARTICLE XIII

	IMMUNITY OF INCORPORATORS, STOCKHOLDERS, OFFICERS AND DIRECTORS

	SECTION 13.01.

	 	Indenture and Debt Securities Solely Corporate Obligations
	 	 	56	 
	 
	 	 	 	 	 	 
	ARTICLE XIV

	MISCELLANEOUS PROVISIONS

	SECTION 14.01.

	 	Successors
	 	 	56	 
	SECTION 14.02.

	 	Official Acts by Successor Entity
	 	 	57	 
	SECTION 14.03.

	 	Surrender of Company Powers
	 	 	57	 
	SECTION 14.04.

	 	Addresses for Notices, etc
	 	 	57	 
	SECTION 14.05.

	 	Governing Law
	 	 	57	 
	SECTION 14.06.

	 	Evidence of Compliance with Conditions Precedent
	 	 	57	 
	SECTION 14.07.

	 	Non-Business Days
	 	 	58	 
	SECTION 14.08.

	 	Table of Contents, Headings, etc
	 	 	58	 
	SECTION 14.09.

	 	Execution in Counterparts
	 	 	58	 
	SECTION 14.10.

	 	Severability
	 	 	58	 
	SECTION 14.11.

	 	Assignment
	 	 	59	 
	SECTION 14.12.

	 	Acknowledgment of Rights
	 	 	59	 
	 
	 	 	 	 	 	 
	ARTICLE XV

	SUBORDINATION OF DEBT SECURITIES

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TABLE OF CONTENTS
(CONTINUED)

	 	 	 	 	 	 	 
	 	 	 	 	Page
	SECTION 15.01.

	 	Agreement to Subordinate
	 	 	59	 
	SECTION 15.02.

	 	Default on Senior Indebtedness
	 	 	60	 
	SECTION 15.03.

	 	Liquidation; Dissolution; Bankruptcy
	 	 	60	 
	SECTION 15.04.

	 	Subrogation
	 	 	61	 
	SECTION 15.05.

	 	Trustee to Effectuate Subordination
	 	 	62	 
	SECTION 15.06.

	 	Notice by the Company
	 	 	62	 
	SECTION 15.07.

	 	Rights of the Trustee, Holders of Senior Indebtedness
	 	 	63	 
	SECTION 15.08.

	 	Subordination May Not Be Impaired
	 	 	63	 
	 
	 	 	 	 	 	 
	EXHIBITS
	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	EXHIBIT A

	 	FORM OF DEBT SECURITY	 	 	 	 

-v-

 

          THIS INDENTURE, dated as of September 1, 2006, between Wintrust Financial Corporation, an
Illinois company (hereinafter sometimes called the “Company”), and LaSalle Bank National
Association as trustee (hereinafter sometimes called the “Trustee”).

WITNESSETH:

          WHEREAS, for its lawful corporate purposes, the Company has duly authorized the issuance of
its Junior Subordinated Debt Securities due September 15, 2036 (the “Debt Securities”) under this
Indenture and to provide, among other things, for the execution and authentication, delivery and
administration thereof, the Company has duly authorized the execution of this Indenture.

          NOW, THEREFORE, in consideration of the premises, and the purchase of the Debt Securities by
the holders thereof, the Company covenants and agrees with the Trustee for the equal and
proportionate benefit of the respective holders from time to time of the Debt Securities as
follows:

ARTICLE I

DEFINITIONS

     SECTION 1.01. Definitions.

          The terms defined in this Section 1.01 (except as herein otherwise expressly provided or
unless the context otherwise requires) for all purposes of this Indenture and of any indenture
supplemental hereto shall have the respective meanings specified in this Section 1.01. All
accounting terms used herein and not expressly defined shall have the meanings assigned to such
terms in accordance with generally accepted accounting principles and the term “generally accepted
accounting principles” means such accounting principles as are generally accepted in the United
States at the time of any computation. The words “herein,” “hereof” and “hereunder” and other words
of similar import refer to this Indenture as a whole and not to any particular Article, Section or
other subdivision.

          “Additional Interest” shall have the meaning set forth in Section 3.06.

          “Additional Provisions” shall have the meaning set forth in Section 15.01.

          “Authenticating Agent” means any agent or agents of the Trustee which at the time shall be
appointed and acting pursuant to Section 6.12.

          “Bankruptcy Law” means Title 11, U.S. Code, or any similar federal or state law for the relief
of debtors.

          “Board of Directors” means the board of directors or the executive committee or any other duly
authorized designated officers of the Company.

 

 

          “Board Resolution” means a copy of a resolution certified by the Secretary or an Assistant
Secretary of the Company to have been duly adopted by the Board of Directors and to be in full
force and effect on the date of such certification and delivered to the Trustee.

          “Business Day” means any day other than a Saturday, Sunday or any other day on which banking
institutions in Wilmington, Delaware, New York City or the city of the Principal Office of the
Trustee or the Company are permitted or required by any applicable law or executive order to close.

          “Calculation Agent” means the Person identified as “Trustee” in the first paragraph hereof
with respect to the Debt Securities and the Institutional Trustee with respect to the Trust
Securities.

          “Capital Securities” means undivided beneficial interests in the assets of the Trust which are
designated as “TP Securities” and rank pari passu with Common Securities issued by the Trust;
provided, however, that if an Event of Default (as defined in the Declaration) has occurred and is
continuing, the rights of holders of such Common Securities to payment in respect of distributions
and payments upon liquidation, redemption and otherwise are subordinated to the rights of holders
of such Capital Securities.

          “Capital Securities Guarantee” means the guarantee agreement that the Company will enter into
with LaSalle Bank National Association or other Persons that operates directly or indirectly for
the benefit of holders of Capital Securities of the Trust.

          “Capital Treatment Event” means, if the Company is organized and existing under the laws of
the United States or any state thereof or the District of Columbia, the receipt by the Company and
the Trust of an Opinion of Counsel experienced in such matters to the effect that, as a result of
(a) any amendment to, or change in, the laws, rules or regulations of the United States or any
political subdivision thereof or therein, or any rules, guidelines or policies of any applicable
regulatory authority for the Company or (b) any official or administrative pronouncement or action
or decision interpreting or applying such laws, rules or regulations, which amendment or change is
effective or which pronouncement, action or decision is announced on or after the date of original
issuance of the Debt Securities, there is more than an insubstantial risk that, within 90 days of
the receipt of such opinion, the aggregate Liquidation Amount of the Capital Securities will not be
eligible to be treated by the Company as “Tier 1 Capital” (or the then equivalent thereof) for
purposes of the capital adequacy guidelines of the Federal Reserve or OTS, as applicable (or any
successor regulatory authority with jurisdiction over bank or financial holding companies), as then
in effect and applicable to the Company (or if the Company is not a financial holding company, such
guidelines applied to the Company as if the Company were subject to such guidelines); provided,
however, that the inability of the Company to treat all or any portion of the aggregate Liquidation
Amount of the Capital Securities as Tier 1 Capital shall not constitute the basis for a Capital
Treatment Event, if such inability results from the Company having cumulative preferred stock,
minority interests in consolidated subsidiaries, or any other class of security or interest which
the Federal Reserve or OTS, as applicable, may now or hereafter accord Tier 1 Capital treatment in
excess of the
amount which may now or hereafter qualify for treatment as Tier 1 Capital under applicable
capital adequacy guidelines; provided further, however, that the distribution of the Debt

-2-

 

Securities in connection with the liquidation of the Trust by the Company shall not in and of
itself constitute a Capital Treatment Event unless such liquidation shall have occurred in
connection with a Tax Event or an Investment Company Event.

          “Certificate” means a certificate signed by any one of the principal executive officer, the
principal financial officer or the principal accounting officer of the Company.

          “Common Securities” means undivided beneficial interests in the assets of the Trust which are
designated as “Common Securities” and rank pari passu with Capital Securities issued by the Trust;
provided, however, that if an Event of Default (as defined in the Declaration) has occurred and is
continuing, the rights of holders of such Common Securities to payment in respect of distributions
and payments upon liquidation, redemption and otherwise are subordinated to the rights of holders
of such Capital Securities.

          “Company” means Wintrust Financial Corporation, a financial holding company incorporated in
Illinois, and, subject to the provisions of Article XI, shall include its successors and assigns.

          “Debt Security” or “Debt Securities” has the meaning stated in the first recital of this
Indenture.

          “Debt Security Register” has the meaning specified in Section 2.05.

          “Debt Security Registrar” has the meaning specified in Section 2.05.

          “Declaration” means the Amended and Restated Declaration of Trust of the Trust dated as of
September 1, 2006, as amended or supplemented from time to time.

          “Default” means any event, act or condition that with notice or lapse of time, or both, would
constitute an Event of Default.

          “Defaulted Interest” has the meaning set forth in Section 2.08.

          “Deferred Interest” has the meaning set forth in Section 2.11.

          “Depositary” means an organization registered as a clearing agency under the Exchange Act that
is designated as Depositary by the Company or any successor thereto. DTC will be the initial
Depositary.

          “Depositary Participant” means a broker, dealer, bank, other financial institution or other
Person for whom from time to time the Depositary effects book-entry transfers and pledges of
securities deposited with the Depositary.

          “DTC” means The Depository Trust Company, a New York corporation.

          “Event of Default” means any event specified in Section 5.01, which has continued for the
period of time, if any, and after the giving of the notice, if any, therein designated.

-3-

 

          “Exchange Act” means the Securities Exchange Act of 1934, as amended from time to time, or any
successor legislation.

          “Extension Period” has the meaning set forth in Section 2.11.

          “Federal Reserve” means the Board of Governors of the Federal Reserve System.

          “Fixed Rate” means a per annum rate of interest, equal to 6.836% commencing September 1, 2006.

          “Fixed Rate Period” has the meaning assigned to it in Section 2.10(a).

          “Global Debenture” means a security that evidences all or part of the Debt Securities, the
ownership and transfers of which shall be made through book entries by a Depositary.

          “Indenture” means this instrument as originally executed or, if amended or supplemented as
herein provided, as so amended or supplemented, or both.

          “Initial Purchaser” means the initial purchaser of the Capital Securities.

          “Institutional Trustee” has the meaning set forth in the Declaration.

          “Interest Payment Date” means March 15, June 15, September 15 and December 15 of each year,
commencing on December 15, 2006, during the term of this Indenture.

          “Interest Payment Period” means the period from and including an Interest Payment Date, or in
the case of the first Interest Payment Period, the original date of issuance of the Debt
Securities, to, but excluding, the next succeeding Interest Payment Date or, in the case of the
last Interest Payment Period, the Redemption Date, Special Redemption Date or Maturity Date, as the
case may be.

          “Interest Rate” means the Fixed Rate and Variable Rate, as applicable.

          “Investment Company Event” means the receipt by the Company and the Trust of an Opinion of
Counsel experienced in such matters to the effect that, as a result of a change in law or
regulation or written change in interpretation or application of law or regulation by any
legislative body, court, governmental agency or regulatory authority, there is more than an
insubstantial risk that the Trust is or, within 90 days of the date of such opinion will be,
considered an “investment company” that is required to be registered under the Investment Company
Act of 1940, as amended, which change or prospective change becomes effective or would become
effective, as the case may be, on or after the date of the original issuance of the Debt
Securities.

          “LIBOR” means the London Interbank Offered Rate for U.S. Dollar deposits in Europe as
determined by the Calculation Agent according to Section 2.10(b).

          “LIBOR Banking Day” has the meaning set forth in Section 2.10(b)(1).

-4-

 

          “LIBOR Business Day” has the meaning set forth in Section 2.10(b)(1).

          “LIBOR Determination Date” has the meaning set forth in Section 2.10(b).

          “Liquidation Amount” means the liquidation amount of $1,000 per Trust Security.

          “Maturity Date” means September 15, 2036.

          “Notice” has the meaning set forth in Section 2.11.

          “Officers’ Certificate” means a certificate signed by the Chairman of the Board, the Vice
Chairman, the President or any Vice President, and by the Chief Financial Officer, the Treasurer,
an Assistant Treasurer, the Comptroller, an Assistant Comptroller, the Secretary or an Assistant
Secretary of the Company, and delivered to the Trustee. Each such certificate shall include the
statements provided for in Section 14.06 if and to the extent required by the provisions of such
Section.

          “Opinion of Counsel” means an opinion in writing signed by legal counsel, who may be an
employee of or counsel to the Company, or may be other counsel reasonably satisfactory to the
Trustee. Each such opinion shall include the statements provided for in Section 14.06 if and to the
extent required by the provisions of such Section.

          “OTS” means the Office of Thrift Supervision and any successor federal agency that is
primarily responsible for regulating the activities of savings and loan holding companies.

          “Outstanding” means, when used with reference to Debt Securities, subject to the provisions of
Section 7.04, as of any particular time, all Debt Securities authenticated and delivered by the
Trustee or the Authenticating Agent under this Indenture, except

          (a) Debt Securities theretofore canceled by the Trustee or the Authenticating Agent or
delivered to the Trustee for cancellation;

          (b) Debt Securities, or portions thereof, for the payment or redemption of which moneys in the
necessary amount shall have been deposited in trust with the Trustee or with any Paying Agent
(other than the Company) or shall have been set aside and segregated in trust by the Company (if
the Company shall act as its own Paying Agent); provided, that, if such Debt Securities, or
portions thereof, are to be redeemed prior to maturity thereof, notice of such redemption shall
have been given as provided in Articles X and XIV or provision satisfactory to the Trustee shall
have been made for giving such notice; and

          (c) Debt Securities paid pursuant to Section 2.06 or in lieu of or in substitution for which
other Debt Securities shall have been authenticated and delivered pursuant to the terms of Section
2.06 unless proof satisfactory to the Company and the Trustee is presented that any such Debt
Securities are held by bona fide holders in due course.

          “Paying Agent” has the meaning set forth in Section 3.04(e).

-5-

 

          “Person” means any individual, corporation, limited liability company, partnership, joint
venture, association, joint-stock company, trust, unincorporated organization or government or any
agency or political subdivision thereof.

          “Placement Agent” means Cohen Bros. & Company.

          “Predecessor Security” of any particular Debt Security means every previous Debt Security
evidencing all or a portion of the same debt as that evidenced by such particular Debt Security;
and, for the purposes of this definition, any Debt Security authenticated and delivered under
Section 2.06 in lieu of a lost, destroyed or stolen Debt Security shall be deemed to evidence the
same debt as the lost, destroyed or stolen Debt Security.

          “Principal Office of the Trustee” means the office of the Trustee, at which at any particular
time its corporate trust business shall be principally administered, which at all times shall be
located within the United States and at the time of the execution of this Indenture shall be 135 S.
LaSalle Street, Suite 1511, Chicago, Illinois 60603, Attention: CDO Trust Services Group – Wintrust
Capital Trust IX.

          “Redemption Date” has the meaning set forth in Section 10.01.

          “Redemption Price” means 100% of the principal amount of the Debt Securities being redeemed
plus accrued and unpaid interest on such Debt Securities to the Redemption Date.

          “Responsible Officer” means, with respect to the Trustee, any officer within the CDO Trust
Services Group in the Principal Office of the Trustee with direct responsibility for the
administration of the Indenture, including any vice-president, any assistant vice-president, any
secretary, any assistant secretary, the treasurer, any assistant treasurer, any trust officer or
other officer of the Principal Office of the Trustee customarily performing functions similar to
those performed by any of the above designated officers and also means, with respect to a
particular corporate trust matter, any other officer to whom such matter is referred because of
that officer’s knowledge of and familiarity with the particular subject.

          “Securities Act” means the Securities Act of 1933, as amended from time to time, or any
successor legislation.

          “Securityholder,” “holder of Debt Securities” or other similar terms, means any Person in
whose name at the time a particular Debt Security is registered on the Debt Security Register.

          “Senior Indebtedness” means, with respect to the Company, (i) the principal, premium, if any,
and interest in respect of (A) indebtedness of the Company for money borrowed and (B) indebtedness
evidenced by securities, debentures, notes, bonds or other similar instruments issued by the
Company; (ii) all capital lease obligations of the Company; (iii) all obligations of the Company
issued or assumed as the deferred purchase price of property, all conditional sale obligations of
the Company and all obligations of the Company under any title retention agreement (but excluding
trade accounts payable arising in the ordinary course of business); (iv) all obligations of the
Company for the reimbursement of any letter of credit, any

-6-

 

banker’s acceptance, any security
purchase facility, any repurchase agreement or similar arrangement, any interest rate swap, any
other hedging arrangement, any obligation under options or any similar credit or other transaction;
(v) all obligations of the type referred to in clauses (i) through (iv) above of other Persons for
the payment of which the Company is responsible or liable as obligor, guarantor or otherwise; and
(vi) all obligations of the type referred to in clauses (i) through (v) above of other Persons
secured by any lien on any property or asset of the Company (whether or not such obligation is
assumed by the Company), whether incurred on or prior to the date of this Indenture or thereafter
incurred, unless, with the prior approval of the Federal Reserve if not otherwise generally
approved, it is provided in the instrument creating or evidencing the same or pursuant to which the
same is outstanding, that such obligations are not superior or are pari passu in right of payment
to the Debt Securities; provided, however, that Senior Indebtedness shall not include (A) any debt
securities issued to any trust other than the Trust (or a trustee of such trust) that is a
financing vehicle of the Company (a “financing entity”), in connection with the issuance by such
financing entity of equity or other securities in transactions substantially similar in structure
to the transactions
contemplated hereunder and in the Declaration, (B) any guarantees of the Company in respect of
the equity or other securities of any financing entity referred to in clause (A) above or (C) any
other instruments classified as subordinated or pari passu to the Debt Securities by the Federal
Reserve from time to time hereafter.

          “Special Event” means any of a Tax Event, an Investment Company Event or a Capital Treatment
Event.

          “Special Redemption Date” has the meaning set forth in Section 10.02.

          “Special Redemption Price” means 100% of the principal amount of the Debt Securities being
redeemed plus accrued and unpaid interest on such Debt Securities to the Special Redemption Date.

          “Subsidiary” means, with respect to any Person, (i) any corporation, at least a majority of
the outstanding voting stock of which is owned, directly or indirectly, by such Person or by one or
more of its Subsidiaries, or by such Person and one or more of its Subsidiaries, (ii) any general
partnership, joint venture or similar entity, at least a majority of the outstanding partnership or
similar interests of which shall at the time be owned by such Person, or by one or more of its
Subsidiaries, or by such Person and one or more of its Subsidiaries, and (iii) any limited
partnership of which such Person or any of its Subsidiaries is a general partner. For the purposes
of this definition, “voting stock” means shares, interests, participations or other equivalents in
the equity interest (however designated) in such Person having ordinary voting power for the
election of a majority of the directors (or the equivalent) of such Person, other than shares,
interests, participations or other equivalents having such power only by reason of the occurrence
of a contingency.

          “Tax Event” means the receipt by the Company and the Trust of an Opinion of Counsel
experienced in such matters to the effect that, as a result of any amendment to or change
(including any announced prospective change) in the laws or any regulations thereunder of the
United States or any political subdivision or taxing authority thereof or therein, or as a result
of any official administrative pronouncement (including any private letter ruling, technical advice

-7-

 

memorandum, regulatory procedure, notice or announcement (an “Administrative Action”)) or judicial
decision interpreting or applying such laws or regulations, regardless of whether such
Administrative Action or judicial decision is issued to or in connection with a proceeding
involving the Company or the Trust and whether or not subject to review or appeal, which amendment,
clarification, change, Administrative Action or decision is enacted, promulgated or announced, in
each case on or after the date of original issuance of the Debt Securities, there is more than an
insubstantial risk that: (i) the Trust is, or will be within 90 days of the date of such opinion,
subject to United States federal income tax with respect to income received or accrued on the Debt
Securities; (ii) if the Company is organized and existing under the laws of the United States or
any state thereof or the District of Columbia, interest payable by the Company on the Debt
Securities is not, or within 90 days of the date of such opinion, will not be, deductible by the
Company, in whole or in part, for United States federal income tax purposes; or (iii) the Trust is,
or will be within 90 days of the date of such opinion, subject to or otherwise required to pay, or
required to withhold from distributions
to holders of Trust Securities, more than a de minimis amount of other taxes (including
withholding taxes), duties, assessments or other governmental charges.

          “Trust” means Wintrust Capital Trust IX, the Delaware statutory trust, or any other similar
trust created for the purpose of issuing Capital Securities in connection with the issuance of Debt
Securities under this Indenture, of which the Company is the sponsor.

          “Trust Indenture Act” means the Trust Indenture Act of 1939, as amended from time-to-time, or
any successor legislation.

          “Trust Securities” means Common Securities and Capital Securities of Wintrust Capital Trust
IX.

          “Trustee” means the Person identified as “Trustee” in the first paragraph hereof, and, subject
to the provisions of Article VI hereof, shall also include its successors and assigns as Trustee
hereunder.

          “United States” means the United States of America and the District of Columbia.

          “U.S. Person” has the meaning given to United States Person as set forth in Section
7701(a)(30) of the Internal Revenue Code of 1986, as amended.

          “Variable Rate” means a per annum rate of interest, equal to LIBOR plus 6.836%, as determined
on the LIBOR Determination Date preceding each Interest Payment Date, reset quarterly, commencing
upon expiration of the Fixed Rate Period.

ARTICLE II

DEBT SECURITIES

     SECTION 2.01. Authentication and Dating.

          Upon the execution and delivery of this Indenture, or from time to time thereafter, Debt
Securities in an aggregate principal amount not in excess of $51,547,000 may be executed

-8-

 

and delivered by the Company to the Trustee for authentication, and the Trustee shall thereupon
authenticate and make available for delivery said Debt Securities to or upon the written order of
the Company, signed by its Chairman of the Board of Directors, Vice Chairman, President or Chief
Financial Officer or one of its Vice Presidents, without any further action by the Company
hereunder. In authenticating such Debt Securities, and accepting the additional responsibilities
under this Indenture in relation to such Debt Securities, the Trustee shall be entitled to receive,
and (subject to Section 6.01) shall be fully protected in relying upon a copy of any Board
Resolution or Board Resolutions relating thereto and, if applicable, an appropriate record of any
action taken pursuant to such resolution, in each case certified by the Secretary or an Assistant
Secretary or other officers with appropriate delegated authority of the Company as the case may be.

          The Trustee shall have the right to decline to authenticate and deliver any Debt Securities
under this Section if the Trustee, being advised by counsel, determines that such action may not
lawfully be taken or if a Responsible Officer of the Trustee in good faith shall determine that
such action would expose the Trustee to personal liability to existing Securityholders. The
Trustee shall also be entitled to receive an opinion of counsel to the effect that (1) all
conditions precedent to the execution, delivery and authentication of the Securities have been
complied with; (2) the Securities are not required to be registered under the Securities Act; and
(3) the Indenture is not required to be qualified under the Trust Indenture Act.

          The definitive Debt Securities shall be typed, printed, lithographed or engraved on steel
engraved borders or may be produced in any other manner, all as determined by the officers
executing such Debt Securities, as evidenced by their execution of such Debt Securities.

     SECTION 2.02. Form of Trustee’s Certificate of Authentication.

          The Trustee’s certificate of authentication on all Debt Securities shall be in substantially
the following form:

          This represents Debt Securities referred to in the within-mentioned Indenture.

          LaSalle Bank National Association, not in its individual capacity but solely as Trustee

	 	 	 	 	 	 	 
	 

	 	By	 	 	 	 
	 

	 	 	 	 

Authorized Signatory
	 	 

     SECTION 2.03. Form and Denomination of Debt Securities.

          The Debt Securities shall be substantially in the form of Exhibit A hereto. The Debt
Securities shall be in registered, certificated form without coupons and in minimum denominations
of $100,000 and any multiple of $1,000 in excess thereof. The Debt Securities shall be numbered,
lettered, or otherwise distinguished in such manner or in accordance with such plans as the
officers executing the same may determine with the approval of the Trustee as evidenced by the
execution and authentication thereof.

-9-

 

     SECTION 2.04. Execution of Debt Securities.

          The Debt Securities shall be signed in the name and on behalf of the Company by the manual or
facsimile signature of any of its Chairman of the Board of Directors, Vice Chairman, President or
Chief Financial Officer or one of its Executive Vice Presidents, Senior Vice Presidents or Vice
Presidents, under its corporate seal (if legally required), which may be affixed thereto or
printed, engraved or otherwise reproduced thereon, by facsimile or otherwise, and which need not be
attested. Only such Debt Securities as shall bear thereon a certificate of authentication
substantially in the form herein before recited, executed by the Trustee or the Authenticating
Agent by the manual signature of an authorized officer, shall be entitled to the benefits of this
Indenture or be valid or obligatory for any purpose. Such certificate by the Trustee or the
Authenticating Agent upon any Debt Security executed by the Company shall be
conclusive evidence that the Debt Security so authenticated has been duly authenticated and
delivered hereunder and that the Securityholder is entitled to the benefits of this Indenture.

          In case any officer of the Company who shall have signed any of the Debt Securities shall
cease to be such officer before the Debt Securities so signed shall have been authenticated and
delivered by the Trustee or the Authenticating Agent, or disposed of by the Company, such Debt
Securities nevertheless may be authenticated and delivered or disposed of as though the Person who
signed such Debt Securities had not ceased to be such officer of the Company; and any Debt Security
may be signed on behalf of the Company by such Persons as, at the actual date of the execution of
such Debt Security, shall be the proper officers of the Company, although at the date of the
execution of this Indenture any such person was not such an officer.

          Every Debt Security shall be dated the date of its authentication.

     SECTION 2.05. Exchange and Registration of Transfer of Debt Securities.

          The Trustee, in its capacity as “Debt Security Registrar”, shall cause to be kept, at the
office or agency maintained for the purpose of registration of transfer and for exchange as
provided in Section 3.02, a register (the “Debt Security Register”) for the Debt Securities issued
hereunder in which, subject to such reasonable regulations as it may prescribe, the Debt Security
Registrar shall provide for the registration and transfer of all Debt Securities as provided in
this Article II. Such register shall be in written form or in any other form capable of being
converted into written form within a reasonable time.

          Debt Securities to be exchanged may be surrendered at the Principal Office of the Trustee or
at any office or agency to be maintained by the Company for such purpose as provided in Section
3.02, and the Company shall execute, the Company or the Trustee shall register and the Trustee or
the Authenticating Agent shall authenticate and make available for delivery in exchange therefor
the Debt Security or Debt Securities which the Securityholder making the exchange shall be entitled
to receive. Upon due presentment for registration of transfer of any Debt Security at the Principal
Office of the Trustee or at any office or agency of the Company maintained for such purpose as
provided in Section 3.02, the Company shall execute, the Company or the Trustee shall register and
the Trustee or the Authenticating Agent shall authenticate and make available for delivery in the
name of the transferee or transferees a

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new Debt Security for a like aggregate principal amount.
Registration or registration of transfer of any Debt Security by the Trustee or by any agent of the
Company appointed pursuant to Section 3.02, and delivery of such Debt Security, shall be deemed to
complete the registration or registration of transfer of such Debt Security.

          All Debt Securities presented for registration of transfer or for exchange or payment shall
(if so required by the Company or the Trustee or the Authenticating Agent) be duly endorsed by, or
be accompanied by, a written instrument or instruments of transfer in form satisfactory to the
Company and either the Trustee or the Authenticating Agent duly executed by, the Securityholder or
such Securityholder’s attorney duly authorized in writing.

          Neither the Trustee nor the Debt Security Registrar shall be responsible for ascertaining
whether any transfer hereunder complies with the registration provisions of or any exemptions from
the Securities Act (under and as defined in the Declaration), applicable state securities laws or
the applicable laws of any other jurisdiction, ERISA, the United States Internal Revenue Code of
1986, as amended, or the Investment Company Act (under and as defined in the Declaration).

          No service charge shall be made for any exchange or registration of transfer of Debt
Securities, but the Company or the Trustee may require payment of a sum sufficient to cover any
tax, fee or other governmental charge that may be imposed in connection therewith.

          The Company or the Trustee shall not be required to exchange or register a transfer of any
Debt Security for a period of 15 days immediately preceding the date of selection of Debt
Securities for redemption.

          Notwithstanding the foregoing, Debt Securities may not be transferred except in compliance
with the restricted securities legend set forth below, unless otherwise determined by the Company
in accordance with applicable law, which legend shall be placed on each Debt Security:

          THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE
“SECURITIES ACT”), OR ANY STATE SECURITIES LAWS OR ANY OTHER APPLICABLE SECURITIES LAWS. NEITHER
THIS SECURITY NOR ANY INTEREST OR PARTICIPATION HEREIN MAY BE REOFFERED, SOLD, ASSIGNED,
TRANSFERRED, PLEDGED, ENCUMBERED OR OTHERWISE DISPOSED OF IN THE ABSENCE OF SUCH REGISTRATION OR
UNLESS SUCH TRANSACTION IS EXEMPT FROM, OR NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE
SECURITIES ACT. THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF AGREES TO OFFER, SELL OR
OTHERWISE TRANSFER SUCH SECURITY ONLY (A) TO THE COMPANY, (B) PURSUANT TO RULE 144A UNDER THE
SECURITIES ACT (“RULE 144A”), TO A PERSON THE HOLDER REASONABLY BELIEVES IS A “QUALIFIED
INSTITUTIONAL BUYER” AS DEFINED IN RULE 144A THAT PURCHASES FOR ITS OWN ACCOUNT OR FOR THE ACCOUNT
OF A QUALIFIED INSTITUTIONAL BUYER TO WHOM NOTICE IS GIVEN THAT THE TRANSFER IS BEING MADE IN
RELIANCE ON RULE 144A, (C) TO A “NON U.S. PERSON” IN AN “OFFSHORE TRANSACTION” PURSUANT TO
REGULATION S

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UNDER THE SECURITIES ACT, (D) PURSUANT TO AN EXEMPTION FROM THE REGISTRATION
REQUIREMENTS OF THE SECURITIES ACT TO AN “ACCREDITED INVESTOR” WITHIN THE MEANING OF SUBPARAGRAPH
(a) (1), (2), (3) OR (7) OF RULE 501 UNDER THE SECURITIES ACT THAT IS ACQUIRING THE SECURITY FOR
ITS OWN ACCOUNT, OR FOR THE ACCOUNT OF SUCH AN “ACCREDITED INVESTOR,” FOR INVESTMENT PURPOSES AND
NOT WITH A VIEW TO, OR FOR OFFER OR SALE IN CONNECTION WITH, ANY DISTRIBUTION IN VIOLATION OF THE
SECURITIES ACT, OR (E) PURSUANT TO ANOTHER AVAILABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS
OF THE SECURITIES ACT, SUBJECT TO THE COMPANY’S RIGHT PRIOR TO ANY SUCH OFFER, SALE OR TRANSFER
PURSUANT TO CLAUSES (D) OR (E) TO REQUIRE THE DELIVERY OF AN OPINION
OF COUNSEL, CERTIFICATION AND/OR OTHER INFORMATION SATISFACTORY TO IT IN ACCORDANCE WITH THE
INDENTURE, A COPY OF WHICH MAY BE OBTAINED FROM THE COMPANY. THE HOLDER OF THIS SECURITY BY ITS
ACCEPTANCE HEREOF AGREES THAT IT WILL COMPLY WITH THE FOREGOING RESTRICTIONS.

          THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF AGREES, REPRESENTS AND WARRANTS THAT IT
WILL NOT ENGAGE IN HEDGING TRANSACTIONS INVOLVING THIS SECURITY UNLESS SUCH TRANSACTIONS ARE IN
COMPLIANCE WITH THE SECURITIES ACT OR AN APPLICABLE EXEMPTION THEREFROM.

          THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF ALSO AGREES, REPRESENTS AND WARRANTS THAT
IT IS NOT AN EMPLOYEE BENEFIT, INDIVIDUAL RETIREMENT ACCOUNT OR OTHER PLAN OR ARRANGEMENT SUBJECT
TO TITLE I OF THE EMPLOYEE RETIREMENT INCOME SECURITY ACT OF 1974, AS AMENDED (“ERISA”), OR SECTION
4975 OF THE INTERNAL REVENUE CODE OF 1986, AS AMENDED (THE “CODE”), (EACH A “PLAN”), OR AN ENTITY
WHOSE UNDERLYING ASSETS INCLUDE “PLAN ASSETS” BY REASON OF ANY PLAN’S INVESTMENT IN THE ENTITY AND
NO PERSON INVESTING “PLAN ASSETS” OF ANY PLAN MAY ACQUIRE OR HOLD THIS SECURITY OR ANY INTEREST
THEREIN, UNLESS SUCH PURCHASER OR HOLDER IS ELIGIBLE FOR THE EXEMPTIVE RELIEF AVAILABLE UNDER U.S.
DEPARTMENT OF LABOR PROHIBITED TRANSACTION CLASS EXEMPTION 96-23, 95-60, 91-38, 90-1 OR 84-14 OR
ANOTHER APPLICABLE EXEMPTION OR ITS PURCHASE AND HOLDING OF THIS SECURITY IS NOT PROHIBITED BY
SECTION 406 OF ERISA OR SECTION 4975 OF THE CODE WITH RESPECT TO SUCH PURCHASE OR HOLDING. ANY
PURCHASER OR HOLDER OF THIS SECURITY OR ANY INTEREST THEREIN WILL BE DEEMED TO HAVE REPRESENTED BY
ITS PURCHASE AND HOLDING THEREOF THAT EITHER (i) IT IS NOT AN EMPLOYEE BENEFIT PLAN WITHIN THE
MEANING OF SECTION 3(3) OF ERISA, OR A PLAN TO WHICH SECTION 4975 OF THE CODE IS APPLICABLE, A
TRUSTEE OR OTHER PERSON ACTING ON BEHALF OF AN EMPLOYEE BENEFIT PLAN OR PLAN, OR ANY OTHER PERSON
OR ENTITY USING THE ASSETS OF ANY EMPLOYEE BENEFIT PLAN OR PLAN TO FINANCE SUCH PURCHASE, OR (ii)
SUCH PURCHASE WILL NOT RESULT IN A PROHIBITED TRANSACTION UNDER SECTION

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406 OF ERISA OR SECTION
4975 OF THE CODE FOR WHICH THERE IS NO APPLICABLE STATUTORY OR ADMINISTRATIVE EXEMPTION.

          IN CONNECTION WITH ANY TRANSFER, THE HOLDER OF THIS SECURITY WILL DELIVER TO THE COMPANY AND
TRUSTEE SUCH CERTIFICATES AND OTHER INFORMATION AS MAY BE REQUIRED BY THE INDENTURE TO CONFIRM THAT
THE TRANSFER COMPLIES WITH THE FOREGOING RESTRICTIONS.

          THIS SECURITY WILL BE ISSUED AND MAY BE TRANSFERRED ONLY IN BLOCKS HAVING A PRINCIPAL AMOUNT
OF NOT LESS THAN $100,000 AND MULTIPLES OF $1,000 IN EXCESS THEREOF. ANY ATTEMPTED TRANSFER OF THIS
SECURITY IN A BLOCK HAVING A PRINCIPAL AMOUNT OF LESS THAN $100,000
SHALL BE DEEMED TO BE VOID AND OF NO LEGAL EFFECT WHATSOEVER. ANY SUCH PURPORTED TRANSFEREE
SHALL BE DEEMED NOT TO BE THE HOLDER OF THIS SECURITY FOR ANY PURPOSE, INCLUDING, BUT NOT LIMITED
TO, THE RECEIPT OF DISTRIBUTIONS ON THIS SECURITY, AND SUCH PURPORTED TRANSFEREE SHALL BE DEEMED TO
HAVE NO INTEREST WHATSOEVER IN THIS SECURITY.

          THIS OBLIGATION IS NOT A DEPOSIT AND IS NOT INSURED BY THE UNITED STATES OR ANY AGENCY OR FUND
OF THE UNITED STATES, INCLUDING THE FEDERAL DEPOSIT INSURANCE CORPORATION. THIS OBLIGATION IS
SUBORDINATED TO THE CLAIMS OF DEPOSITORS AND THE CLAIMS OF GENERAL AND SECURED CREDITORS OF THE
COMPANY, IS INELIGIBLE AS COLLATERAL FOR A LOAN BY THE COMPANY OR ANY OF ITS SUBSIDIARIES AND IS
NOT SECURED.

     SECTION 2.06. Mutilated, Destroyed, Lost or Stolen Debt Securities.

          In case any Debt Security shall become mutilated or be destroyed, lost or stolen, the Company
shall execute, and upon its written request the Trustee shall authenticate and deliver, a new Debt
Security bearing a number not contemporaneously outstanding, in exchange and substitution for the
mutilated Debt Security, or in lieu of and in substitution for the Debt Security so destroyed, lost
or stolen. In every case the applicant for a substituted Debt Security shall furnish to the Company
and the Trustee such security or indemnity as may be required by them to save each of them
harmless, and, in every case of destruction, loss or theft, the applicant shall also furnish to the
Company and the Trustee evidence to their satisfaction of the destruction, loss or theft of such
Debt Security and of the ownership thereof.

          The Trustee may authenticate any such substituted Debt Security and deliver the same upon the
written request or authorization of any officer of the Company. Upon the issuance of any
substituted Debt Security, the Company may require the payment of a sum sufficient to cover any tax
or other governmental charge that may be imposed in relation thereto and any other expenses
connected therewith. In case any Debt Security which has matured or is about to mature or has been
called for redemption in full shall become mutilated or be destroyed, lost or stolen, the Company
may, instead of issuing a substitute Debt Security, pay or authorize the payment of the same
(without surrender thereof except in the case of a mutilated Debt Security)

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if the applicant for
such payment shall furnish to the Company and the Trustee such security or indemnity as may be
required by them to save each of them harmless and, in case of destruction, loss or theft, evidence
satisfactory to the Company and to the Trustee of the destruction, loss or theft of such Security
and of the ownership thereof.

          Every substituted Debt Security issued pursuant to the provisions of this Section 2.06 by
virtue of the fact that any such Debt Security is destroyed, lost or stolen shall constitute an
additional contractual obligation of the Company, whether or not the destroyed, lost or stolen Debt
Security shall be found at any time, and shall be entitled to all the benefits of this Indenture
equally and proportionately with any and all other Debt Securities duly issued hereunder. All Debt
Securities shall be held and owned upon the express condition that, to the extent permitted by
applicable law, the foregoing provisions are exclusive with respect to the replacement or
payment of mutilated, destroyed, lost or stolen Debt Securities and shall preclude any and all
other rights or remedies notwithstanding any law or statute existing or hereafter enacted to the
contrary with respect to the replacement or payment of negotiable instruments or other securities
without their surrender.

     SECTION 2.07. Temporary Debt Securities.

          Pending the preparation of definitive Debt Securities, the Company may execute and the Trustee
shall authenticate and make available for delivery temporary Debt Securities that are typed,
printed or lithographed. Temporary Debt Securities shall be issuable in any authorized
denomination, and substantially in the form of the definitive Debt Securities but with such
omissions, insertions and variations as may be appropriate for temporary Debt Securities, all as
may be determined by the Company. Every such temporary Debt Security shall be executed by the
Company and be authenticated by the Trustee upon the same conditions and in substantially the same
manner, and with the same effect, as the definitive Debt Securities. Without unreasonable delay,
the Company will execute and deliver to the Trustee or the Authenticating Agent definitive Debt
Securities and thereupon any or all temporary Debt Securities may be surrendered in exchange
therefor, at the Principal Office of the Trustee or at any office or agency maintained by the
Company for such purpose as provided in Section 3.02, and the Trustee or the Authenticating Agent
shall authenticate and make available for delivery in exchange for such temporary Debt Securities a
like aggregate principal amount of such definitive Debt Securities. Such exchange shall be made by
the Company at its own expense and without any charge therefor except that in case of any such
exchange involving a registration of transfer the Company may require payment of a sum sufficient
to cover any tax, fee or other governmental charge that may be imposed in relation thereto. Until
so exchanged, the temporary Debt Securities shall in all respects be entitled to the same benefits
under this Indenture as definitive Debt Securities authenticated and delivered hereunder.

     SECTION 2.08. Payment of Interest.

          During the Fixed Rate Period, each Debt Security will bear interest at the Fixed Rate.
Thereafter, each Debt Security will bear interest at the then applicable Interest Rate from and
including each Interest Payment Date or, in the case of the first Interest Payment Period, the
original date of issuance of such Debt Security to, but excluding, the next succeeding Interest
Payment Date or, in the case of the last Interest Payment Period, the Redemption Date, Special

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Redemption Date or Maturity Date, as applicable, on the principal thereof, on any overdue principal
and (to the extent that payment of such interest is enforceable under applicable law) on Deferred
Interest and on any overdue installment of interest (including Defaulted Interest), payable
(subject to the provisions of Article XII) on each Interest Payment Date commencing on December 15,
2006. Interest and any Deferred Interest on any Debt Security that is payable, and is punctually
paid or duly provided for by the Company, on any Interest Payment Date shall be paid to the Person
in whose name said Debt Security (or one or more Predecessor Securities) is registered at the close
of business on the regular record date for such interest installment, except that interest and any
Deferred Interest payable on the Maturity Date, the Redemption Date (to the extent redeemed) or the
Special Redemption Date shall be paid to the Person to whom principal is paid. In the event that
any Debt Security or portion thereof is called for redemption and the redemption date is subsequent
to a regular record date with respect to any Interest Payment Date
and either on or prior to such Interest Payment Date, interest on such Debt Security will be
paid upon presentation and surrender of such Debt Security.

          Any interest on any Debt Security, other than Deferred Interest, that is payable, but is not
punctually paid or duly provided for by the Company, on any Interest Payment Date (herein called
“Defaulted Interest”) shall forthwith cease to be payable to the registered Securityholder on the
relevant regular record date by virtue of having been such Securityholder, and such Defaulted
Interest shall be paid by the Company to the Persons in whose names such Debt Securities (or their
respective Predecessor Securities) are registered at the close of business on a special record date
for the payment of such Defaulted Interest, which shall be fixed in the following manner: the
Company shall notify the Trustee in writing of the amount of Defaulted Interest proposed to be paid
on each such Debt Security and the date of the proposed payment, and at the same time the Company
shall deposit with the Trustee an amount of money equal to the aggregate amount proposed to be paid
in respect of such Defaulted Interest or shall make arrangements reasonably satisfactory to the
Trustee for such deposit prior to the date of the proposed payment, such money when deposited to be
held in trust for the benefit of the Persons entitled to such Defaulted Interest as in this clause
provided. Thereupon the Trustee shall fix a special record date for the payment of such Defaulted
Interest which shall not be more than fifteen nor less than ten days prior to the date of the
proposed payment and not less than ten days after the receipt by the Trustee of the notice of the
proposed payment. The Trustee shall promptly notify the Company of such special record date and, in
the name and at the expense of the Company, shall cause notice of the proposed payment of such
Defaulted Interest and the special record date therefor to be mailed, first class postage prepaid,
to each Securityholder at his or her address as it appears in the Debt Security Register, not less
than ten days prior to such special record date. Notice of the proposed payment of such Defaulted
Interest and the special record date therefor having been mailed as aforesaid, such Defaulted
Interest shall be paid to the Persons in whose names such Debt Securities (or their respective
Predecessor Securities) are registered on such special record date and thereafter the Company shall
have no further payment obligation in respect of the Defaulted Interest.

          Any interest scheduled to become payable on an Interest Payment Date occurring during an
Extension Period shall not be Defaulted Interest and shall be payable on such other date as may be
specified in the terms of such Debt Securities.

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          The term “regular record date” as used in this Indenture shall mean the fifteenth day prior to
the applicable Interest Payment Date whether or not such date is a Business Day.

          Subject to the foregoing provisions of this Section, each Debt Security delivered under this
Indenture upon registration of transfer of or in exchange for or in lieu of any other Debt Security
shall carry the rights to interest accrued and unpaid, and to accrue, that were carried by such
other Debt Security.

     SECTION 2.09. Cancellation of Debt Securities Paid, etc.

          All Debt Securities surrendered for the purpose of payment, redemption, exchange or
registration of transfer, shall, if surrendered to the Company or any Paying Agent, be surrendered
to the Trustee and promptly canceled by it, or, if surrendered to the Trustee, shall
be promptly canceled by it, and no Debt Securities shall be issued in lieu thereof except as
expressly permitted by any of the provisions of this Indenture. The Trustee shall dispose of all
canceled Debt Securities in accordance with its customary practices, unless the Company otherwise
directs the Trustee in writing, in which case the Trustee shall dispose of such Debt Securities as
directed by the Company. If the Company shall acquire any of the Debt Securities, however, such
acquisition shall not operate as a redemption or satisfaction of the indebtedness represented by
such Debt Securities unless and until the same are surrendered to the Trustee for cancellation.

     SECTION 2.10. Computation of Interest.

          (a) From September 1, 2006 until September 15, 2011 (the “Fixed Rate Period”), the interest
shall be computed on the basis of a 360-day year of twelve 30-day months and the amount payable for
any partial period shall be computed on the basis of the number of days elapsed in a 360-day year
of twelve 30-day months. Upon expiration of the Fixed Rate Period, the amount of interest payable
for any Interest Payment Period will be computed on the basis of a 360-day year and the actual
number of days elapsed in the relevant interest period; provided, however, that
upon the occurrence of a Special Event Redemption pursuant to Section 10.02 the amounts payable
pursuant to this Indenture shall be calculated as set forth in the definition of Special Redemption
Price.

          (b) Upon expiration of the Fixed Rate Period, LIBOR, for any Interest Payment Period, shall be
determined by the Calculation Agent in accordance with the following provisions:

     (1) On the second LIBOR Business Day (provided, that on such day commercial
banks are open for business (including dealings in foreign currency deposits) in
London (a “LIBOR Banking Day”), and otherwise the next preceding LIBOR Business Day
that is also a LIBOR Banking Day) prior to March 15, June 15, September 15 and
December 15 (or, with respect to the first Interest Payment Period upon expiration
of the Fixed Rate Period, on September 15, 2011) (each such day, a “LIBOR
Determination Date” for the following Interest Payment Period), the Calculation
Agent shall obtain the rate for three-month U.S. Dollar deposits in Europe, which
appears on Telerate Page 3750 (as defined in the

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International Swaps and Derivatives
Association, Inc. 2000 Interest Rate and Currency Exchange Definitions) or such
other page as may replace such Telerate Page 3750 on the Moneyline Telerate, Inc.
service (or such other service or services as may be nominated by the British
Banker’s Association as the information vendor for the purpose of displaying London
Interbank offered rates for U.S. dollar deposits), as of 11:00 a.m. (London time) on
such LIBOR Determination Date, and the rate so obtained shall be LIBOR for such
Interest Payment Period. “LIBOR Business Day” means any day that is not a Saturday,
Sunday or other day on which commercial banking institutions in The City of New York
or Chicago, Illinois are authorized or obligated by law or executive order to be
closed. If such rate is superseded on Telerate Page 3750 by a corrected rate before
12:00 noon (London time) on the same LIBOR Determination Date,
the corrected rate as so substituted will be LIBOR for that Interest Payment Period.

     (2) If, on any LIBOR Determination Date, such rate does not appear on Telerate
Page 3750 or such other page as may replace such Telerate Page 3750 on the Moneyline
Telerate, Inc. service (or such other service or services as may be nominated by the
British Banker’s Association as the information vendor for the purpose of displaying
London Interbank offered rates for U.S. dollar deposits), the Calculation Agent
shall determine the arithmetic mean of the offered quotations of the Reference Banks
(as defined below) to leading banks in the London Interbank market for three-month
U.S. Dollar deposits in Europe (in an amount determined by the Calculation Agent) by
reference to requests for quotations as of approximately 11:00 a.m. (London time) on
the LIBOR Determination Date made by the Calculation Agent to the Reference Banks.
If, on any LIBOR Determination Date, at least two of the Reference Banks provide
such quotations, LIBOR shall equal the arithmetic mean of such quotations. If, on
any LIBOR Determination Date, only one or none of the Reference Banks provide such a
quotation, LIBOR shall be deemed to be the arithmetic mean of the offered quotations
that at least two leading banks in the City of New York (as selected by the
Calculation Agent) are quoting on the relevant LIBOR Determination Date for
three-month U.S. Dollar deposits in Europe at approximately 11:00 a.m. (London time)
(in an amount determined by the Calculation Agent). As used herein, “Reference
Banks” means four major banks in the London Interbank market selected by the
Calculation Agent.

     (3) If the Calculation Agent is required but is unable to determine a rate in
accordance with at least one of the procedures provided above, LIBOR for the
applicable Interest Payment Period shall be LIBOR in effect for the immediately
preceding Interest Payment Period.

          (c) All percentages resulting from any calculations on the Debt Securities will be rounded, if
necessary, to the nearest one hundred-thousandth of a percentage point, with five one-millionths of
a percentage point rounded upward (e.g., 9.876545% (or .09876545)
being rounded to 9.87655% (or .0987655)), and all dollar amounts used in or resulting from such calculation will be rounded to
the nearest cent (with one-half cent being rounded upward).

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          (d) As soon as practicable following each LIBOR Determination Date, but in no event later than
the 30th day following such LIBOR Determination Date, the Calculation Agent shall notify, in
writing, the Company, the Institutional Trustee and the Paying Agent of the applicable Variable
Rate in effect for the related Interest Payment Period. The Calculation Agent shall, upon the
request of any Securityholder, provide the Variable Rate then in effect. All calculations made by
the Calculation Agent in the absence of manifest error shall be conclusive for all purposes and
binding on the Company and the Securityholders. Any error in a calculation of the Variable Rate by
the Calculation Agent may be corrected at any time by the delivery of a notice of such corrected
Variable Rate as provided above. The Paying Agent shall be entitled to rely on information
received from the Calculation Agent or the Company as to the Variable Rate. The Company shall, from
time to time, provide any necessary information to the Paying Agent
relating to any original issue discount and interest on the Debt Securities that is included
in any payment and reportable for taxable income calculation purposes. Failure to notify the
Company, the Institutional Trustee or the Paying Agent of the applicable Variable Rate shall not
affect the obligation of the Company to make payment on Debentures at such Variable Rate; provided,
however, that the Company shall not be in default if it shall tender corrected payment, based on
the notice of the corrected Variable Rate, within 10 days of the Company’s receipt of such notice.

     SECTION 2.11. Extension of Interest Payment Period.

          So long as no Event of Default pursuant to paragraphs (c), (e), (f) or (g) of Section 5.01 of
this Indenture has occurred and is continuing, the Company shall have the right under this
Indenture, from time to time and without causing an Event of Default, to defer payments of interest
on the Debt Securities by extending the interest distribution period on the Debt Securities at any
time and from time to time during the term of the Debt Securities, for up to twenty consecutive
quarterly periods (each such extended interest distribution period, an “Extension Period”), during
which Extension Period no interest shall be due and payable (except any Additional Interest that
may be due and payable). No Extension Period may end on a date other than an Interest Payment Date.
During any Extension Period, interest will continue to accrue on the Debt Securities, and interest
on such accrued interest (such accrued interest and interest thereon referred to herein as
“Deferred Interest”) will accrue at an annual rate equal to the Interest Rate applicable during
such Extension Period, compounded quarterly from the date such Deferred Interest would have been
payable were it not for the Extension Period, to the extent permitted by law. No interest or
Deferred Interest shall be due and payable during an Extension Period, except at the end thereof.
At the end of any such Extension Period the Company shall pay all Deferred Interest then accrued
and unpaid on the Debt Securities; provided, however, that no Extension Period may
extend beyond the Maturity Date, Redemption Date (to the extent redeemed) or Special Redemption
Date; and provided further, however, that during any such Extension Period,
the Company shall be subject to the restrictions set forth in Section 3.08 of this Indenture. Prior
to the termination of any Extension Period, the Company may further extend such period,
provided, that such period together with all such previous and further consecutive
extensions thereof shall not exceed twenty consecutive quarterly periods, or extend beyond the
Maturity Date, Redemption Date (to the extent redeemed) or Special Redemption Date. Upon the
termination of any Extension Period and upon the payment of all Deferred Interest, the Company may
commence a new Extension Period, subject to the foregoing requirements. No interest or Deferred
Interest shall be due and payable during an Extension Period, except at the end thereof,

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but Deferred Interest shall accrue upon each installment of interest that would otherwise have been due
and payable during such Extension Period until such installment is paid. The Company must give the
Trustee notice of its election to begin any Extension Period or extend an Extension Period
(“Notice”) not later than the related regular record date for the relevant Interest Payment Date.
The Notice shall describe, in reasonable detail, why the Company has elected to begin an Extension
Period. The Notice shall acknowledge and affirm the Company’s understanding that it is prohibited
from issuing dividends and other distributions during the Extension Period. Upon receipt of the
Notice, the Placement Agent shall have the right, at its sole discretion, to disclose the name of
the Company, the fact that the Company has elected to begin an Extension Period and other
information that such Placement Agent, at its sole discretion, deems relevant to the
Company’s election to begin an Extension Period. The Trustee shall give notice of the
Company’s election to begin a new Extension Period to the Securityholders.

     SECTION 2.12. CUSIP Numbers.

          The Company in issuing the Debt Securities may use a “CUSIP” number (if then generally in
use), and, if so, the Trustee shall use a “CUSIP” number in notices of redemption as a convenience
to Securityholders; provided, that any such notice may state that no representation is made
as to the correctness of such number either as printed on the Debt Securities or as contained in
any notice of a redemption and that reliance may be placed only on the other identification numbers
printed on the Debt Securities, and any such redemption shall not be affected by any defect in or
omission of such numbers. The Company will promptly notify the Trustee in writing of any change in
the CUSIP number.

     SECTION 2.13. Income Tax Certification. 

          As a condition to the payment of any principal of or interest on the Debt Securities without
the imposition of withholding tax, the Trustee shall require the previous delivery of properly
completed and signed applicable U.S. federal income tax certifications (generally, an Internal
Revenue Service Form W-9 (or applicable successor form) in the case of a person that is a “United
States person” within the meaning of Section 7701 (a)(30) of the Code (under and as defined in the
Declaration) or an Internal Revenue Service Form W-8 (or applicable successor form) in the case of
a person that is not a “United States person” within the meaning of Section 7701(a)(30) of the
Code, and any other certification acceptable to it to enable the Trustee or any Paying Agent to
determine their respective duties and liabilities with respect to any taxes or other charges that
they may be required to pay, deduct or withhold in respect of such Debt Securities.

     SECTION 2.14. Global Debentures.

          (a) Upon the election of the holder of Outstanding Debt Securities, which election need not be
in writing, the Debt Securities owned by such holder shall be issued in the form of one or more
Global Debentures registered in the name of the Depositary or its nominee. Each Global Debenture
issued under this Indenture shall be registered in the name of the Depositary designated by the
Company for such Global Debenture or a nominee thereof and delivered to such Depositary or a
nominee thereof or custodian therefor, and each such Global Debenture shall constitute a single
Debt Security for all purposes of this Indenture.

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          (b) Notwithstanding any other provision in this Indenture, no Global Debenture may be
exchanged in whole or in part for Debt Securities registered, and no transfer of a Global Debenture
in whole or in part may be registered, in the name of any Person other than the Depositary for such
Global Debenture or a nominee thereof unless (i) such Depositary advises the Trustee and the
Company in writing that such Depositary is no longer willing or able to properly discharge its
responsibilities as Depositary with respect to such Global Debenture, and no qualified successor is
appointed by the Company within ninety (90) days of receipt by the Company of such notice, (ii)
such Depositary ceases to be a clearing agency registered under the Exchange Act and no successor
is appointed by the Company within ninety (90) days after
obtaining knowledge of such event, (iii) the Company executes and delivers to the Trustee a
company order stating that the Company elects to terminate the book-entry system through the
Depositary or (iv) an Event of Default shall have occurred and be continuing. Upon the occurrence
of any event specified in clause (i), (ii), (iii) or (iv) above, the Trustee shall notify the
Depositary and instruct the Depositary to notify all owners of beneficial interests in such Global
Debenture of the occurrence of such event and of the availability of Debt Securities to such owners
of beneficial interests requesting the same. Upon the issuance of such Debt Securities and the
registration in the Debt Security Register of such Debt Securities in the names of such owners of
the beneficial interests therein, the Trustee shall recognize such owners of beneficial interests
as holders thereof.

          (c) If any Global Debenture is to be exchanged for other Debt Securities or canceled in part,
or if another Debt Security is to be exchanged in whole or in part for a beneficial interest in any
Global Debenture, then either (i) such Global Debenture shall be so surrendered for exchange or
cancellation as provided in this Article II or (ii) the principal amount thereof shall be
reduced or increased by an amount equal to the portion thereof to be so exchanged or canceled, or
equal to the principal amount of such other Debt Security to be so exchanged for a beneficial
interest therein, as the case may be, by means of an appropriate adjustment made on the records of
the Debt Security Registrar, whereupon the Trustee, in accordance with the applicable depository
procedures, shall instruct the Depositary or its authorized representative to make a corresponding
adjustment to its records. Upon any such surrender or adjustment of a Global Debenture by the
Depositary, accompanied by registration instructions, the Company shall execute and the Trustee
shall authenticate and deliver any Debt Securities issuable in exchange for such Global Debenture
(or any portion thereof) in accordance with the instructions of the Depositary. The Trustee shall
not be liable for any delay in delivery of such instructions and may conclusively rely on, and
shall be fully protected in relying on, such instructions.

          (d) Every Debt Security authenticated and delivered upon registration of transfer of, or in
exchange for or in lieu of, a Global Debenture or any portion thereof shall be authenticated and
delivered in the form of, and shall be, a Global Debenture, unless such Debt Security is registered
in the name of a Person other than the Depositary for such Global Debenture or a nominee thereof.

          (e) Debt Securities distributed to holders of Book-Entry Capital Securities (as defined in the
Trust Agreement) upon the dissolution of the Trust shall be distributed in the form of one or more
Global Debentures registered in the name of a Depositary or its nominee, and deposited with the
Debt Security Registrar, as custodian for such Depositary, or with such

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Depositary, for credit by
the Depositary to the respective accounts of the beneficial owners of the Debt Securities
represented thereby (or such other accounts as they may direct). Debt Securities distributed to
holders of Capital Securities other than Book-Entry Capital Securities upon the dissolution of the
Trust shall not be issued in the form of a Global Debenture or any other form intended to
facilitate book-entry trading in beneficial interests in such Debt Securities.

          (f) The Depositary or its nominee, as the registered owner of a Global Debenture, shall be the
holder of such Global Debenture for all purposes under this Indenture and the Debt Securities, and
owners of beneficial interests in a Global Debenture shall hold such
interests pursuant to the Applicable Depository Procedures. Accordingly, any such owner’s
beneficial interest in a Global Debenture shall be shown only on, and the transfer of such interest
shall be effected only through, records maintained by the Depositary or its nominee or its
Depositary Participants. The Debt Security Registrar and the Trustee shall be entitled to deal
with the Depositary for all purposes of this Indenture relating to a Global Debenture (including
the payment of principal and interest thereon and the giving of instructions or directions by
owners of beneficial interests therein and the giving of notices) as the sole holder of the Debt
Security and shall have no obligations to the owners of beneficial interests therein. Neither the
Trustee nor the Debt Security Registrar shall have any liability in respect of any transfers
affected by the Depositary.

          (g) The rights of owners of beneficial interests in a Global Debenture shall be exercised only
through the Depositary and shall be limited to those established by law and agreements between such
owners and the Depositary and/or its Depositary Participants.

          (h) No holder of any beneficial interest in any Global Debenture held on its behalf by a
Depositary shall have any rights under this Indenture with respect to such Global Debenture, and
such Depositary may be treated by the Company, the Trustee and any agent of the Company or the
Trustee as the owner of such Global Debenture for all purposes whatsoever. None of the Company,
the Trustee nor any agent of the Company or the Trustee will have any responsibility or liability
for any aspect of the records relating to or payments made on account of beneficial ownership
interests of a Global Debenture or maintaining, supervising or reviewing any records relating to
such beneficial ownership interests. Notwithstanding the foregoing, nothing herein shall prevent
the Company, the Trustee or any agent of the Company or the Trustee from giving effect to any
written certification, proxy or other authorization furnished by a Depositary or impair, as between
a Depositary and such holders of beneficial interests, the operation of customary practices
governing the exercise of the rights of the Depositary (or its nominee) as holder of any Debt
Security.

ARTICLE III

PARTICULAR COVENANTS OF THE COMPANY

     SECTION 3.01. Payment of Principal, Premium and Interest; Agreed Treatment of the Debt
Securities.

          (a) The Company covenants and agrees that it will duly and punctually pay or cause to be paid
all payments due on the Debt Securities at the place, at the respective times and

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in the manner
provided in this Indenture and the Debt Securities. At the option of the Company, each installment
of interest on the Debt Securities may be paid (i) by mailing checks for such interest payable to
the order of the Securityholders entitled thereto as they appear on the Debt Security Register or
(ii) by wire transfer to any account with a banking institution located in the United States
designated by such Securityholders to the Paying Agent no later than the related record date.
Notwithstanding anything to the contrary contained in this Indenture or any Debt Security, if the
Trust or the Trustee of the Trust is the holder of any Debt Security, then all payments in respect
of such Debt Security shall be made by the Company in immediately available funds when due.

          (b) The Company will treat the Debt Securities as indebtedness, and the interest payable in
respect of such Debt Securities as interest, for all U.S. federal income tax purposes. As a
condition to the payment of any principal of or interest on any Debt Security without the
imposition of withholding tax, the Company shall require the previous delivery of properly
completed and signed applicable U.S. federal income tax certifications (generally, an Internal
Revenue Service Form W-9 (or applicable successor form) in the case of a Person that is a U.S.
Person or an Internal Revenue Service Form W-8 (or applicable successor form) in the case of a
Person that is not a U.S. Person and any other certification acceptable to it to enable the Company
and the Trustee to determine their respective duties and liabilities with respect to any taxes or
other charges that they may be required to pay or withhold in respect of such Debt Security or the
holder of such Debt Security under any present or future law or regulation of the United States or
any political subdivision thereof or taxing authority therein or to comply with any reporting or
other requirements under any such law or regulation.

          (c) As of the date of this Indenture, the Company represents that it has no intention to
exercise its right under Section 2.11 to defer payments of interest on the Debt Securities by
commencing an Extension Period.

     SECTION 3.02. Offices for Notices and Payments, etc.

          So long as any of the Debt Securities remain outstanding, the Company will maintain an office
or agency where the Debt Securities may be presented for payment, an office or agency where the
Debt Securities may be presented for registration of transfer and for exchange as provided in this
Indenture and an office or agency where notices and demands to or upon the Company in respect of
the Debt Securities or of this Indenture may be served. The Company hereby appoints the Trustee at
LaSalle Bank National Association, 135 South LaSalle Street, Suite 1511, Chicago, Illinois 60603,
Attention: CDO Trust Services Group – Wintrust Capital Trust IX as such office or agency. In case
the Company shall fail to maintain any such office or shall fail to give such notice of the
location or of any change in the location thereof, presentations and demands may be made and
notices may be served at the Principal Office of the Trustee.

          In addition to any such office or agency, the Company may from time to time designate one or
more other offices or agencies where the Debt Securities may be presented for registration of
transfer and for exchange in the manner provided in this Indenture, and the Company may from time
to time rescind such designation, as the Company may deem desirable or expedient; provided,
however, that no such designation or rescission shall in any manner

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relieve the Company of
its obligation to maintain any such office or agency for the purposes above mentioned. The Company
will give to the Trustee prompt written notice of any such designation or rescission thereof.

     SECTION 3.03. Appointments to Fill Vacancies in Trustee’s Office.

          The Company, whenever necessary to avoid or fill a vacancy in the office of Trustee, will
appoint, in the manner provided in Section 6.09, a Trustee, so that there shall at all times be a
Trustee hereunder.

     SECTION 3.04. Provision as to Paying Agent.

          (a) If the Company shall appoint a Paying Agent other than the Trustee, it will cause such
Paying Agent to execute and deliver to the Trustee an instrument in which such agent shall agree
with the Trustee, subject to the provision of this Section 3.04:

     (1) that it will hold all sums held by it as such agent for the payment of all
payments due on the Debt Securities (whether such sums have been paid to it by the
Company or by any other obligor on the Debt Securities) in trust for the benefit of
the Securityholders;

     (2) that it will give the Trustee prompt written notice of any failure by the
Company (or by any other obligor on the Debt Securities) to make any payment on the
Debt Securities when the same shall be due and payable; and

     (3) that it will, at any time during the continuance of any Event of Default,
upon the written request of the Trustee, forthwith pay to the Trustee all sums so
held in trust by such Paying Agent.

          (b) If the Company shall act as its own Paying Agent, it will, on or before each due date of
the payments due on the Debt Securities, set aside, segregate and hold in trust for the benefit of
the Securityholders a sum sufficient to pay such payments so becoming due and will notify the
Trustee in writing of any failure to take such action and of any failure by the Company (or by any
other obligor under the Debt Securities) to make any payment on the Debt Securities when the same
shall become due and payable.

          Whenever the Company shall have one or more Paying Agents for the Debt Securities, it will, on
or prior to each due date of the payments on the Debt Securities, deposit with a Paying Agent a sum
sufficient to pay all payments so becoming due, such sum to be held in trust for the benefit of the
Persons entitled thereto and (unless such Paying Agent is the Trustee) the Company shall promptly
notify the Trustee in writing of its action or failure to act.

          (c) Anything in this Section 3.04 to the contrary notwithstanding, the Company may, at any
time, for the purpose of obtaining a satisfaction and discharge with respect to the Debt
Securities, or for any other reason, pay, or direct any Paying Agent to pay to the Trustee all sums
held in trust by the Company or any such Paying Agent, such sums to be held by the Trustee upon the
same terms and conditions herein contained.

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          (d) Anything in this Section 3.04 to the contrary notwithstanding, the agreement to hold sums
in trust as provided in this Section 3.04 is subject to Sections 12.03 and 12.04.

          (e) The Company hereby initially appoints the Trustee to act as Paying Agent (the “Paying
Agent”).

     SECTION 3.05. Certificate to Trustee.

          The Company will deliver to the Trustee on or before 120 days after the end of each fiscal
year, so long as Debt Securities are outstanding hereunder, a Certificate stating that in the
course of the performance by the signers of their duties as officers of the Company they would
normally have knowledge of any default by the Company in the performance of any covenants of the
Company contained herein, stating whether or not they have knowledge of any such default and, if
so, specifying each such default of which the signers have knowledge and the nature thereof.

     SECTION 3.06. Additional Interest.

          If and for so long as the Trust is the holder of all Debt Securities and is subject to or
otherwise required to pay, or is required to withhold from distributions to holders of Trust
Securities, any additional taxes (including withholding taxes), duties, assessments or other
governmental charges as a result of a Tax Event, the Company will pay such additional amounts (the
“Additional Interest”) on the Debt Securities as shall be required so that the net amounts received
and retained by the Trust for distribution to holders of Trust Securities after paying all taxes
(including withholding taxes), duties, assessments or other governmental charges will be equal to
the amounts the Trust would have received and retained for distribution to holders of Trust
Securities after paying all taxes (including withholding taxes on distributions to holders of Trust
Securities), duties, assessments or other governmental charges if no such additional taxes, duties,
assessments or other governmental charges had been imposed. Whenever in this Indenture or the Debt
Securities there is a reference in any context to the payment of principal of or premium, if any,
or interest on the Debt Securities, such mention shall be deemed to include mention of payments of
the Additional Interest provided for in this paragraph to the extent that, in such context,
Additional Interest is, was or would be payable in respect thereof pursuant to the provisions of
this paragraph and express mention of the payment of Additional Interest (if applicable) in any
provisions hereof shall not be construed as excluding Additional Interest in those provisions
hereof where such express mention is not made; provided, however, that,
notwithstanding anything to the contrary contained in this Indenture or any Debt Security, the
deferral of the payment of interest during an Extension Period pursuant to Section 2.11 shall not
defer the payment of any Additional Interest that may be due and payable.

     SECTION 3.07. Compliance with Consolidation Provisions.

          The Company will not, while any of the Debt Securities remain outstanding, consolidate with,
or merge into any other Person, or merge into itself, or sell, convey, transfer or otherwise
dispose of all or substantially all of its property or capital stock to any other Person unless the
provisions of Article XI hereof are complied with.

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     SECTION 3.08. Limitation on Dividends.

          If Debt Securities are initially issued to the Trust or a trustee of such Trust in connection
with the issuance of Trust Securities by the Trust (regardless of whether Debt Securities continue
to be held by such Trust) and (i) there shall have occurred and be continuing an Event of Default,
(ii) the Company shall be in default with respect to its payment of any
obligations under the Capital Securities Guarantee or (iii) the Company shall have given
notice of its election to defer payments of interest on the Debt Securities by extending the
interest distribution period as provided herein and such period, or any extension thereof, shall
have commenced and be continuing, then the Company may not (A) declare or pay any dividends or
distributions on, or redeem, purchase, acquire, or make a liquidation payment with respect to, any
of the Company’s capital stock or (B) make any payment of principal of or interest or premium, if
any, on or repay, repurchase or redeem any debt securities of the Company that rank pari passu in
all respects with or junior in interest to the Debt Securities or (C) make any payment under any
guarantees of the Company that rank pari passu in all respects with or junior in interest to the
Capital Securities Guarantee (other than (a) repurchases, redemptions or other acquisitions of
shares of capital stock of the Company (I) in connection with any employment contract, benefit plan
or other similar arrangement with or for the benefit of one or more employees, officers, directors
or consultants, (II) in connection with a dividend reinvestment or stockholder stock purchase plan
or (III) in connection with the issuance of capital stock of the Company (or securities convertible
into or exercisable for such capital stock), as consideration in an acquisition transaction entered
into prior to the occurrence of (i), (ii) or (iii) above, (b) as a result of any exchange,
reclassification, combination or conversion of any class or series of the Company’s capital stock
(or any capital stock of a subsidiary of the Company) for any class or series of the Company’s
capital stock or of any class or series of the Company’s indebtedness for any class or series of
the Company’s capital stock, (c) the purchase of fractional interests in shares of the Company’s
capital stock pursuant to the conversion or exchange provisions of such capital stock or the
security being converted or exchanged, (d) any declaration of a dividend in connection with any
stockholder’s rights plan, or the issuance of rights, stock or other property under any
stockholder’s rights plan, or the redemption or repurchase of rights pursuant thereto, or (e) any
dividend in the form of stock, warrants, options or other rights where the dividend stock or the
stock issuable upon exercise of such warrants, options or other rights is the same stock as that on
which the dividend is being paid or ranks pari passu with or junior to such stock).

     SECTION 3.09. Covenants as to the Trust.

          For so long as such Trust Securities remain outstanding, the Company shall maintain 100%
ownership of the Common Securities; provided, however, that any permitted successor
of the Company under this Indenture that is a U.S. Person may succeed to the Company’s ownership of
such Common Securities. The Company, as owner of the Common Securities, shall use commercially
reasonable efforts to cause the Trust (a) to remain a statutory trust, except in connection with a
distribution of Debt Securities to the holders of Trust Securities in liquidation of the Trust, the
redemption of all of the Trust Securities or certain mergers, consolidations or amalgamations, each
as permitted by the Declaration, (b) to otherwise continue to be classified as a grantor trust for
United States federal income tax purposes and (c) to cause each holder of Trust Securities to be
treated as owning an undivided beneficial interest in the Debt Securities.

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ARTICLE IV

LISTS AND REPORTS BY THE COMPANY AND THE TRUSTEE

     SECTION 4.01. Securityholders’ Lists.

          The Company covenants and agrees that it will furnish or cause to be furnished to the Trustee:

          (a) on each regular record date for an Interest Payment Date, a list, in such form as the
Trustee may reasonably require, of the names and addresses of the Securityholders as of such record
date; and

          (b) at such other times as the Trustee may request in writing, within 30 days after the
receipt by the Company of any such request, a list of similar form and content as of a date not
more than 15 days prior to the time such list is furnished;

except that no such lists need be furnished under this Section 4.01 so long as the Trustee is in
possession thereof by reason of its acting as Debt Security Registrar.

     SECTION 4.02. Preservation and Disclosure of Lists.

          (a) The Trustee shall preserve, in as current a form as is reasonably practicable, all
information as to the names and addresses of the Securityholders (1) contained in the most recent
list furnished to it as provided in Section 4.01 or (2) received by it in the capacity of Debt
Security Registrar (if so acting) hereunder. The Trustee may destroy any list furnished to it as
provided in Section 4.01 upon receipt of a new list so furnished.

          (b) In case three or more Securityholders (hereinafter referred to as “applicants”) apply in
writing to the Trustee and furnish to the Trustee reasonable proof that each such applicant has
owned a Debt Security for a period of at least six months preceding the date of such application,
and such application states that the applicants desire to communicate with other Securityholders
with respect to their rights under this Indenture or under such Debt Securities and is accompanied
by a copy of the form of proxy or other communication which such applicants propose to transmit,
then the Trustee shall within five Business Days after the receipt of such application, at the
election of the Company, either:

     (1) afford such applicants access to the information preserved at the time by
the Trustee in accordance with the provisions of subsection (a) of this Section
4.02, or

     (2) inform such applicants as to the approximate number of Securityholders
whose names and addresses appear in the information preserved at the time by the
Trustee in accordance with the provisions of subsection (a) of this Section 4.02,
and as to the approximate cost of mailing to such Securityholders the form of proxy
or other communication, if any, specified in such application.

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          If the Company shall elect not to afford such applicants access to such information, the
Trustee shall, upon the written request of such applicants, mail to each Securityholder of Debt
Securities whose name and address appear in the information preserved at the time by the Trustee in
accordance with the provisions of subsection (a) of this Section 4.02 a copy of the form of proxy
or other communication which is specified in such request with reasonable promptness after a tender
to the Trustee of the material to be mailed and of payment, or provision for the payment, of the
reasonable expenses of mailing, unless within five days after such tender, the Trustee shall mail
to such applicants, and file with the Securities and Exchange Commission, if permitted or required
by applicable law, together with a copy of the material to be mailed, a written statement of the
Company to the effect that such mailing would be contrary to the best interests of the holders of
all Debt Securities, as the case may be, or would be in violation of applicable law. Such written
statement shall specify the basis of such opinion. If said Commission, as permitted or required by
applicable law, after opportunity for a hearing upon the objections specified in the written
statement so filed, shall enter an order refusing to sustain any of such objections or if, after
the entry of an order sustaining one or more of such objections, said Commission shall find, after
notice and opportunity for hearing, that all the objections so sustained have been met and shall
enter an order so declaring, the Trustee shall mail copies of such material to all such
Securityholders with reasonable promptness after the entry of such order and the renewal of such
tender; otherwise the Trustee shall be relieved of any obligation or duty to such applicants
respecting their application.

          (c) Each and every Securityholder, by receiving and holding the same, agrees with the Company
and the Trustee that neither the Company nor the Trustee nor any Paying Agent shall be held
accountable by reason of the disclosure of any such information as to the names and addresses of
the Securityholders in accordance with the provisions of subsection (b) of this Section 4.02,
regardless of the source from which such information was derived, and that the Trustee shall not be
held accountable by reason of mailing any material pursuant to a request made under said subsection
(b).

ARTICLE V

REMEDIES OF THE TRUSTEE AND SECURITYHOLDERS UPON AN EVENT OF DEFAULT

     SECTION 5.01. Events of Default.

          The following events shall be “Events of Default” with respect to Debt Securities:

          (a) the Company defaults in the payment of any interest upon any Debt Security when it becomes
due and payable (unless the Company has elected and may defer interest payments pursuant to Section
2.11), and continuance of such default for a period of 30 days; for the avoidance of doubt, an
extension of any interest distribution period by the Company in accordance with Section 2.11 of
this Indenture shall not constitute a default under this clause 5.01(a); or

          (b) the Company defaults in the payment of all or any part of the principal of (or premium, if
any, on) any Debt Securities as and when the same shall become due and payable

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either at maturity, upon redemption, by declaration of acceleration pursuant to Section 5.01
of this Indenture or otherwise; or

          (c) the Company defaults in the payment of any interest upon any Debt Security when it becomes
due and payable following the nonpayment of any such interest for 20 or more consecutive quarterly
periods; or

          (d) the Company defaults in the performance of, or breaches, any of its covenants or
agreements in Sections 3.06, 3.07, 3.08 or 3.09 of this Indenture (other than a covenant or
agreement a default in whose performance or whose breach is elsewhere in this Section specifically
dealt with), and continuance of such default or breach for a period of 30 days after there has been
given, by registered or certified mail, to the Company by the Trustee or to the Company and the
Trustee by the holders of not less than 25% in aggregate principal amount of the outstanding Debt
Securities, a written notice specifying such default or breach and requiring it to be remedied and
stating that such notice is a “Notice of Default” hereunder; or

          (e) a court having jurisdiction in the premises shall enter a decree or order for relief in
respect of the Company in an involuntary case under any applicable bankruptcy, insolvency or other
similar law now or hereafter in effect, or appoints a receiver, liquidator, assignee, custodian,
trustee, sequestrator (or similar official) of the Company or for any substantial part of its
property, or orders the winding-up or liquidation of its affairs and such decree or order shall
remain unstayed and in effect for a period of 90 consecutive days; or

          (f) the Company shall commence a voluntary case under any applicable bankruptcy, insolvency or
other similar law now or hereafter in effect, shall consent to the entry of an order for relief in
an involuntary case under any such law, or shall consent to the appointment of or taking possession
by a receiver, liquidator, assignee, trustee, custodian, sequestrator (or other similar official)
of the Company or of any substantial part of its property, or shall make any general assignment for
the benefit of creditors, or shall fail generally to pay its debts as they become due; or

          (g) the Trust shall have voluntarily or involuntarily liquidated, dissolved, wound-up its
business or otherwise terminated its existence except in connection with (1) the distribution of
the Debt Securities to holders of the Trust Securities in liquidation of their interests in the
Trust, (2) the redemption of all of the outstanding Trust Securities or (3) certain mergers,
consolidations or amalgamations, each as permitted by the Declaration.

          If an Event of Default specified under clause (c) of this Section 5.01 occurs and is
continuing with respect to the Debt Securities, then, and in each and every such case, unless the
principal of the Debt Securities shall have already become due and payable, either the Trustee or
the holders of not less than 25% in aggregate principal amount of the Debt Securities then
outstanding hereunder, by notice in writing to the Company (and to the Trustee if given by
Securityholders), may declare the entire principal of the Debt Securities and any premium and
interest accrued, but unpaid, thereon, if any, to be due and payable immediately, and upon any such
declaration the same shall become immediately due and payable. If an Event of Default specified
under clause (e), (f) or (g) of this Section 5.01 occurs, then, in each and every such

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case, the entire principal amount of the Debt Securities and any premium and interest accrued,
but unpaid, thereon shall ipso facto become immediately due and payable without further action.
Notwithstanding anything to the contrary in this Section 5.01, if at any time during the period in
which this Indenture remains in force and effect, the Company ceases or elects to cease to be
subject to the supervision and regulations of the Federal Reserve, OTS, OCC or similar regulatory
authority overseeing bank, thrift, savings and loan or financial holding companies or similar
institutions requiring specifications for the treatment of capital similar in nature to the capital
adequacy guidelines under the Federal Reserve rules and regulations, then the first sentence of
this paragraph shall be deemed to include clauses (a), (b) and (d) under this Section 5.01 as an
Event of Default resulting in an acceleration of payment of the Debt Securities to the same extent
as provided herein for clause (c).

          With respect to clause (d) of this Section 5.01, the Company agrees that in the event of a
breach by the Company of its covenants or agreements mentioned therein, any remedy at law or in
damages may prove inadequate and therefore the Company agrees that the Trustee shall be entitled to
injunctive relief against the Company in the event of any breach or threatened breach by the
Company, in addition to any other relief (including damages) available to the Trustee under this
Indenture or under law.

          The foregoing provisions, however, are subject to the condition that if, at any time after the
principal of the Debt Securities shall have been so declared due and payable, and before any
judgment or decree for the payment of the moneys due shall have been obtained or entered as
hereinafter provided, (i) the Company shall pay or shall deposit with the Trustee a sum sufficient
to pay all matured installments of interest upon all the Debt Securities and all payments on the
Debt Securities which shall have become due otherwise than by acceleration (with interest upon all
such payments and Deferred Interest, to the extent permitted by law) and such amount as shall be
sufficient to cover reasonable compensation to the Trustee and each predecessor Trustee, their
respective agents, attorneys and counsel, and all other amounts due to the Trustee pursuant to
Section 6.06, if any, and (ii) all Events of Default under this Indenture, other than the
non-payment of the payments on Debt Securities which shall have become due by acceleration, shall
have been cured, waived or otherwise remedied as provided herein, and in each and every such case
the holders of a majority in aggregate principal amount of the Debt Securities then outstanding, by
written notice to the Company and to the Trustee, may waive all defaults and rescind and annul such
declaration and its consequences, but no such waiver or rescission and annulment shall extend to or
shall affect any subsequent default or shall impair any right consequent thereon; provided,
however, that if the Debt Securities are held by the Trust or a trustee of the Trust, such waiver
or rescission and annulment shall not be effective until the holders of a majority in aggregate
liquidation amount of the outstanding Capital Securities of the Trust shall have consented to such
waiver or rescission and annulment.

          In case the Trustee shall have proceeded to enforce any right under this Indenture and such
proceedings shall have been discontinued or abandoned because of such rescission or annulment or
for any other reason or shall have been determined adversely to the Trustee, then and in every such
case the Company, the Trustee and the Securityholders shall be restored respectively to their
several positions and rights hereunder, and all rights, remedies and powers

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of the Company, the Trustee and the Securityholders shall continue as though no such
proceeding had been taken.

     SECTION 5.02. Payment of Debt Securities on Default; Suit Therefor.

          The Company covenants that upon the occurrence of an Event of Default pursuant to paragraphs
(c), (e), (f) or (g) of Section 5.01, and upon demand of the Trustee, the Company will pay to the
Trustee, for the benefit of the Securityholders, the whole amount that then shall have become due
and payable on all Debt Securities including Deferred Interest accrued on the Debt Securities; and,
in addition thereto, such further amount as shall be sufficient to cover the costs and expenses of
collection, including a reasonable compensation to the Trustee, its agents, attorneys and counsel,
and any other amounts due to the Trustee under Section 6.06. In case the Company shall fail
forthwith to pay such amounts upon such demand, the Trustee, in its own name and as trustee of an
express trust, shall be entitled and empowered to institute any actions or proceedings at law or in
equity for the collection of the sums so due and unpaid, and may prosecute any such action or
proceeding to judgment or final decree, and may enforce any such judgment or final decree against
the Company or any other obligor on such Debt Securities and collect in the manner provided by law
out of the property of the Company or any other obligor on such Debt Securities wherever situated
the moneys adjudged or decreed to be payable.

          In case there shall be pending proceedings for the bankruptcy or for the reorganization of the
Company or any other obligor on the Debt Securities under Bankruptcy Law, or in case a receiver or
trustee shall have been appointed for the property of the Company or such other obligor, or in the
case of any other similar judicial proceedings relative to the Company or other obligor upon the
Debt Securities, or to the creditors or property of the Company or such other obligor, the Trustee,
irrespective of whether the principal of the Debt Securities shall then be due and payable as
therein expressed or by declaration of acceleration or otherwise and irrespective of whether the
Trustee shall have made any demand pursuant to the provisions of this Section 5.02, shall be
entitled and empowered, by intervention in such proceedings or otherwise, to file and prove a claim
or claims for the whole amount of principal and interest owing and unpaid in respect of the Debt
Securities and, in case of any judicial proceedings, to file such proofs of claim and other papers
or documents as may be necessary or advisable in order to have the claims of the Trustee (including
any claim for reasonable compensation to the Trustee and each predecessor Trustee, and their
respective agents, attorneys and counsel, and for reimbursement of all other amounts due to the
Trustee under Section 6.06) and of the Securityholders allowed in such judicial proceedings
relative to the Company or any other obligor on the Debt Securities, or to the creditors or
property of the Company or such other obligor, unless prohibited by applicable law and regulations,
to vote on behalf of the Securityholders in any election of a trustee or a standby trustee in
arrangement, reorganization, liquidation or other bankruptcy or insolvency proceedings or Person
performing similar functions in comparable proceedings, and to collect and receive any moneys or
other property payable or deliverable on any such claims, and to distribute the same after the
deduction of its charges and expenses; and any receiver, assignee or trustee in bankruptcy or
reorganization is hereby authorized by each of the Securityholders to make such payments to the
Trustee, and, in the event that the Trustee shall consent to the making of such payments directly
to the Securityholders, to pay to the Trustee such amounts as shall be sufficient to cover
reasonable

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compensation to the Trustee, each predecessor Trustee and their respective agents, attorneys
and counsel, and all other amounts due to the Trustee under Section 6.06.

          Nothing herein contained shall be construed to authorize the Trustee to authorize or consent
to or accept or adopt on behalf of any Securityholder any plan of reorganization, arrangement,
adjustment or composition affecting the Debt Securities or the rights of any holder thereof or to
authorize the Trustee to vote in respect of the claim of any Securityholder in any such proceeding.

          All rights of action and of asserting claims under this Indenture, or under any of the Debt
Securities, may be enforced by the Trustee without the possession of any of the Debt Securities, or
the production thereof at any trial or other proceeding relative thereto, and any such suit or
proceeding instituted by the Trustee shall be brought in its own name as trustee of an express
trust, and any recovery of judgment shall be for the ratable benefit of the Securityholders.

          In any proceedings brought by the Trustee (and also any proceedings involving the
interpretation of any provision of this Indenture to which the Trustee shall be a party) the
Trustee shall be held to represent all the Securityholders, and it shall not be necessary to make
any Securityholders parties to any such proceedings.

     SECTION 5.03. Application of Moneys Collected by Trustee.

          Any moneys collected by the Trustee shall be applied in the following order, at the date or
dates specified pursuant hereto for the distribution of such moneys, upon presentation of the
several Debt Securities in respect of which moneys have been collected, and stamping thereon the
payment, if only partially paid, and upon surrender thereof if fully paid:

          First: To the payment of costs and expenses incurred by, and reasonable fees of, the Trustee,
its agents, attorneys and counsel, and of all other amounts due to the Trustee under Section 6.06;

          Second: To the payment of all Senior Indebtedness of the Company if and to the extent required
by Article XV;

          Third: To the payment of the amounts then due and unpaid upon Debt Securities, in respect of
which or for the benefit of which money has been collected, ratably, without preference or priority
of any kind, according to the amounts due on such Debt Securities; and

          Fourth: The balance, if any, to the Company.

     SECTION 5.04. Proceedings by Securityholders.

          No Securityholder shall have any right to institute any suit, action or proceeding for any
remedy hereunder, unless such Securityholder previously shall have given to the Trustee written
notice of an Event of Default with respect to the Debt Securities and unless the holders of not
less than 25% in aggregate principal amount of the Debt Securities then outstanding shall have
given the Trustee a written request to institute such action, suit or proceeding and shall have

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offered to the Trustee such reasonable indemnity as it may require against the costs, expenses
and liabilities to be incurred thereby, and the Trustee for 60 days after its receipt of such
notice, request and offer of indemnity shall have failed to institute any such action, suit or
proceeding; provided, that no Securityholder shall have any right to prejudice the rights
of any other Securityholder, obtain priority or preference over any other such Securityholder or
enforce any right under this Indenture except in the manner herein provided and for the equal,
ratable and common benefit of all Securityholders.

          Notwithstanding any other provisions in this Indenture, however, the right of any
Securityholder to receive payment of the principal of, premium, if any, and interest on such Debt
Security when due, or to institute suit for the enforcement of any such payment, shall not be
impaired or affected without the consent of such Securityholder. For the protection and enforcement
of the provisions of this Section, each and every Securityholder and the Trustee shall be entitled
to such relief as can be given either at law or in equity.

     SECTION 5.05. Proceedings by Trustee.

          In case of an Event of Default hereunder the Trustee may in its discretion proceed to protect
and enforce the rights vested in it by this Indenture by such appropriate judicial proceedings as
the Trustee shall deem most effectual to protect and enforce any of such rights, either by suit in
equity or by action at law or by proceeding in bankruptcy or otherwise, whether for the specific
enforcement of any covenant or agreement contained in this Indenture or in aid of the exercise of
any power granted in this Indenture, or to enforce any other legal or equitable right vested in the
Trustee by this Indenture or by law.

     SECTION 5.06. Remedies Cumulative and Continuing.

          Except as otherwise provided in Section 2.06, all powers and remedies given by this Article V
to the Trustee or to the Securityholders shall, to the extent permitted by law, be deemed
cumulative and not exclusive of any other powers and remedies available to the Trustee or the
Securityholders, by judicial proceedings or otherwise, to enforce the performance or observance of
the covenants and agreements contained in this Indenture or otherwise established with respect to
the Debt Securities, and no delay or omission of the Trustee or of any Securityholder to exercise
any right or power accruing upon any Event of Default occurring and continuing as aforesaid shall
impair any such right or power, or shall be construed to be a waiver of any such default or an
acquiescence therein; and, subject to the provisions of Section 5.04, every power and remedy given
by this Article V or by law to the Trustee or to the Securityholders may be exercised from time to
time, and as often as shall be deemed expedient, by the Trustee or by the Securityholders.

     SECTION 5.07. Direction of Proceedings and Waiver of Defaults by Majority of
Securityholders.

          The holders of a majority in aggregate principal amount of the Debt Securities affected
(voting as one class) at the time outstanding and, if the Debt Securities are held by the Trust or
a trustee of the Trust, the holders of a majority in aggregate liquidation amount of the
outstanding Capital Securities of the Trust shall have the right to direct the time, method and

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place of conducting any proceeding for any remedy available to the Trustee, or exercising any
trust or power conferred on the Trustee with respect to such Debt Securities; provided,
however, that if the Debt Securities are held by the Trust or a trustee of the Trust, such
time, method and place or such exercise, as the case may be, may not be so directed until the
holders of a majority in aggregate liquidation amount of the outstanding Capital Securities of the
Trust shall have directed such time, method and place or such exercise, as the case may be;
provided, further, that (subject to the provisions of Section 6.01) the Trustee shall have the
right to decline to follow any such direction if the Trustee being advised by counsel shall
determine that the action so directed would be unjustly prejudicial to the holders not taking part
in such direction or if the Trustee being advised by counsel determines that the action or
proceeding so directed may not lawfully be taken or if a Responsible Officer of the Trustee shall
determine that the action or proceedings so directed would involve the Trustee in personal
liability. Prior to any declaration of acceleration, or ipso facto acceleration, of the maturity of
the Debt Securities, the holders of a majority in aggregate principal amount of the Debt Securities
at the time outstanding may on behalf of the holders of all of the Debt Securities waive (or modify
any previously granted waiver of) any past default or Event of Default and its consequences, except
a default (a) in the payment of principal of, premium, if any, or interest on any of the Debt
Securities, (b) in respect of covenants or provisions hereof which cannot be modified or amended
without the consent of the holder of each Debt Security affected, or (c) in respect of the
covenants contained in Section 3.09; provided, however, that if the Debt Securities
are held by the Trust or a trustee of the Trust, such waiver or modification to such waiver shall
not be effective until the holders of a majority in Liquidation Amount of the Trust Securities of
the Trust shall have consented to such waiver or modification to such waiver; provided,
further, that if the consent of the holder of each outstanding Debt Security is required,
such waiver or modification to such waiver shall not be effective until each holder of the
outstanding Capital Securities of the Trust shall have consented to such waiver or modification to
such waiver. Upon any such waiver or modification to such waiver, the Default or Event of Default
covered thereby shall be deemed to be cured for all purposes of this Indenture and the Company, the
Trustee and the Securityholders shall be restored to their former positions and rights hereunder,
respectively; but no such waiver or modification to such waiver shall extend to any subsequent or
other Default or Event of Default or impair any right consequent thereon. Whenever any Default or
Event of Default hereunder shall have been waived as permitted by this Section 5.07, said Default
or Event of Default shall for all purposes of the Debt Securities and this Indenture be deemed to
have been cured and to be not continuing.

     SECTION 5.08. Notice of Defaults.

          The Trustee shall, within 90 days after a Responsible Officer of the Trustee shall have actual
knowledge or received written notice of the occurrence of a Default with respect to the Debt
Securities, mail to all Securityholders, as the names and addresses of such Securityholders appear
upon the Debt Security Register, notice of all Defaults with respect to the Debt Securities
actually known to the Trustee, unless such defaults shall have been cured before the giving of such
notice (the term “defaults” for the purpose of this Section 5.08 being hereby defined to be the
events specified in subsections (a), (b), (c), (d), (e), (f) and (g) of Section 5.01, not including
periods of grace, if any, provided for therein); provided, that, except in the case of
default in the payment of the principal of, premium, if any, or interest on any of the Debt
Securities, the Trustee shall be protected in withholding such notice if and so long as a

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Responsible Officer of the Trustee in good faith determines that the withholding of such
notice is in the interests of the Securityholders.

     SECTION 5.09. Undertaking to Pay Costs.

          All parties to this Indenture agree, and each Securityholder by such Securityholder’s
acceptance thereof shall be deemed to have agreed, that any court may in its discretion require, in
any suit for the enforcement of any right or remedy under this Indenture, or in any suit against
the Trustee for any action taken or omitted by it as Trustee, the filing by any party litigant in
such suit of an undertaking to pay the costs of such suit, and that such court may in its
discretion assess reasonable costs, including reasonable attorneys’ fees and expenses, against any
party litigant in such suit, having due regard to the merits and good faith of the claims or
defenses made by such party litigant; but the provisions of this Section 5.09 shall not apply to
any suit instituted by the Trustee, to any suit instituted by any Securityholder, or group of
Securityholders, holding in the aggregate more than 10% in principal amount of the Debt Securities
(or, if such Debt Securities are held by the Trust or a trustee of the Trust, more than 10% in
liquidation amount of the outstanding Capital Securities), to any suit instituted by any
Securityholder for the enforcement of the payment of the principal of (or premium, if any) or
interest on any Debt Security against the Company on or after the same shall have become due and
payable, or to any suit instituted in accordance with Section 14.12.

ARTICLE VI

CONCERNING THE TRUSTEE

     SECTION 6.01. Duties and Responsibilities of Trustee.

          With respect to the holders of Debt Securities issued hereunder, the Trustee, prior to the
occurrence of an Event of Default with respect to the Debt Securities and after the curing or
waiving of all Events of Default which may have occurred, with respect to the Debt Securities,
undertakes to perform such duties and only such duties as are specifically set forth in this
Indenture. In case an Event of Default with respect to the Debt Securities has occurred (which has
not been cured or waived), the Trustee shall exercise such of the rights and powers vested in it by
this Indenture, and use the same degree of care and skill in their exercise, as a prudent person
would exercise or use under the circumstances in the conduct of such person’s own affairs.

          No provision of this Indenture shall be construed to relieve the Trustee from liability for
its own negligent action, its own negligent failure to act or its own willful misconduct, except
that:

          (a) prior to the occurrence of an Event of Default with respect to the Debt Securities and
after the curing or waiving of all Events of Default which may have occurred

     (1) the duties and obligations of the Trustee with respect to the Debt
Securities shall be determined solely by the express provisions of this Indenture,
and the Trustee shall not be liable except for the performance of such duties and
obligations with respect to the Debt Securities as are specifically set forth in
this

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Indenture, and no implied covenants or obligations shall be read into this
Indenture against the Trustee; and

     (2) in the absence of bad faith on the part of the Trustee, the Trustee may
conclusively rely, as to the truth of the statements and the correctness of the
opinions expressed therein, upon any certificates or opinions furnished to the
Trustee and conforming to the requirements of this Indenture; but, in the case of
any such certificates or opinions which by any provision hereof are specifically
required to be furnished to the Trustee, the Trustee shall be under a duty to
examine the same to determine whether or not they conform on their face to the
requirements of this Indenture;

          (b) the Trustee shall not be liable for any error of judgment made in good faith by a
Responsible Officer or Officers of the Trustee, unless it shall be proved that the Trustee was
negligent in ascertaining the pertinent facts;

          (c) the Trustee shall not be liable with respect to any action taken or omitted to be taken by
it in good faith, in accordance with the direction of the Securityholders pursuant to Section 5.07,
relating to the time, method and place of conducting any proceeding for any remedy available to the
Trustee, or exercising any trust or power conferred upon the Trustee, under this Indenture;

          (d) the Trustee shall not be charged with knowledge of any Default or Event of Default with
respect to the Debt Securities unless either (1) a Responsible Officer shall have actual knowledge
of such Default or Event of Default or (2) written notice of such Default or Event of Default shall
have been given to the Trustee by the Company or any other obligor on the Debt Securities or by any
Securityholder, except with respect to an Event of Default pursuant to Sections 5.01(a), 5.01(b) or
5.01(c) hereof (other than an Event of Default resulting from the default in the payment of
Additional Interest or premium, if any, if the Trustee does not have actual knowledge or written
notice that such payment is due and payable), of which the Trustee shall be deemed to have
knowledge; and

          (e) in the absence of bad faith on the part of the Trustee, the Trustee may seek and rely on
reasonable instructions from the Company.

          None of the provisions contained in this Indenture shall require the Trustee to expend or risk
its own funds or otherwise incur personal financial liability in the performance of any of its
duties or in the exercise of any of its rights or powers.

     SECTION 6.02. Reliance on Documents, Opinions, etc.

          Except as otherwise provided in Section 6.01:

          (a) the Trustee may conclusively rely and shall be fully protected in acting or refraining
from acting upon any resolution, certificate, statement, instrument, opinion, report, notice,
request, consent, order, bond, note, debenture or other paper or document believed by it in good
faith to be genuine and to have been signed or presented by the proper party or parties;

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          (b) any request, direction, order or demand of the Company mentioned herein shall be
sufficiently evidenced by an Officers’ Certificate (unless other evidence in respect thereof be
herein specifically prescribed); and any Board Resolution may be evidenced to the Trustee by a copy
thereof certified by the Secretary or an Assistant Secretary of the Company;

          (c) the Trustee may consult with counsel of its selection and any advice or Opinion of Counsel
shall be full and complete authorization and protection in respect of any action taken, suffered or
omitted by it hereunder in good faith and in accordance with such advice or Opinion of Counsel;

          (d) the Trustee shall be under no obligation to exercise any of the rights or powers vested in
it by this Indenture at the request, order or direction of any of the Securityholders, pursuant to
the provisions of this Indenture, unless such Securityholders shall have offered to the Trustee
reasonable security or indemnity against the costs, expenses and liabilities which may be incurred
therein or thereby;

          (e) the Trustee shall not be liable for any action taken or omitted by it in good faith and
reasonably believed by it to be authorized or within the discretion or rights or powers conferred
upon it by this Indenture; nothing contained herein shall, however, relieve the Trustee of the
obligation, upon the occurrence of an Event of Default with respect to the Debt Securities (that
has not been cured or waived) to exercise with respect to the Debt Securities such of the rights
and powers vested in it by this Indenture, and to use the same degree of care and skill in their
exercise, as a prudent person would exercise or use under the circumstances in the conduct of such
person’s own affairs;

          (f) the Trustee shall not be bound to make any investigation into the facts or matters stated
in any resolution, certificate, statement, instrument, opinion, report, notice, request, consent,
order, approval, bond, debenture, coupon or other paper or document, unless requested in writing to
do so by the holders of not less than a majority in aggregate principal amount of the outstanding
Debt Securities affected thereby; provided, however, that if the payment within a
reasonable time to the Trustee of the costs, expenses or liabilities likely to be incurred by it in
the making of such investigation is, in the opinion of the Trustee, not reasonably assured to the
Trustee by the security afforded to it by the terms of this Indenture, the Trustee may require
reasonable indemnity against such expense or liability as a condition to so proceeding; and

          (g) the Trustee may execute any of the trusts or powers hereunder or perform any duties
hereunder either directly or by or through agents (including any Authenticating Agent) or
attorneys, and the Trustee shall not be responsible for any misconduct or negligence on the part of
any such agent or attorney appointed by it with due care.

     SECTION 6.03. No Responsibility for Recitals, etc.

          The recitals contained herein and in the Debt Securities (except in the certificate of
authentication of the Trustee or the Authenticating Agent) shall be taken as the statements of the
Company and the Trustee and the Authenticating Agent assume no responsibility for the correctness
of the same. The Trustee and the Authenticating Agent make no representations as to

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the validity or sufficiency of this Indenture or of the Debt Securities. The Trustee and the
Authenticating Agent shall not be accountable for the use or application by the Company of any Debt
Securities or the proceeds of any Debt Securities authenticated and delivered by the Trustee or the
Authenticating Agent in conformity with the provisions of this Indenture.

     SECTION 6.04. Trustee, Authenticating Agent, Paying Agents, Transfer Agents or Registrar
May Own Debt Securities.

          The Trustee or any Authenticating Agent or any Paying Agent or any transfer agent or any Debt
Security Registrar, in its individual or any other capacity, may become the owner or pledgee of
Debt Securities with the same rights it would have if it were not Trustee, Authenticating Agent,
Paying Agent, transfer agent or Debt Security Registrar.

     SECTION 6.05. Moneys to be Held in Trust.

          Subject to the provisions of Section 12.04, all moneys received by the Trustee or any Paying
Agent shall, until used or applied as herein provided, be held in trust for the purpose for which
they were received, but need not be segregated from other funds except to the extent required by
law. The Trustee and any Paying Agent shall be under no liability for interest on any money
received by it hereunder except as otherwise agreed in writing with the Company. So long as no
Event of Default shall have occurred and be continuing, all interest allowed on any such moneys, if
any, shall be paid from time to time to the Company upon the written order of the Company, signed
by the Chairman of the Board of Directors, the President, the Chief Operating Officer, a Vice
President, the Treasurer or an Assistant Treasurer of the Company.

     SECTION 6.06. Compensation and Expenses of Trustee.

          Other than as provided in the Fee Agreement of even date herewith between Cohen Bros. &
Company, the Trustee and the Company, the Company covenants and agrees to pay to the Trustee from
time to time, and the Trustee shall be entitled to, such compensation as shall be agreed to in
writing between the Company and the Trustee (which shall not be limited by any provision of law in
regard to the compensation of a trustee of an express trust), and the Company will pay or reimburse
the Trustee upon its written request for all documented reasonable expenses, disbursements and
advances incurred or made by the Trustee in accordance with any of the provisions of this Indenture
(including the reasonable compensation and the reasonable expenses and disbursements of its counsel
and of all Persons not regularly in its employ) except any such expense, disbursement or advance
that arises from its negligence, willful misconduct or bad faith. The Company also covenants to
indemnify each of the Trustee (including in its individual capacity) and any predecessor Trustee
(and its officers, agents, directors and employees) for, and to hold it harmless against, any and
all loss, damage, claim, liability or expense including taxes (other than taxes based on the income
of the Trustee), except to the extent such loss, damage, claim, liability or expense results from
the negligence, willful misconduct or bad faith of such indemnitee, arising out of or in connection
with the acceptance or administration of this Trust, including the costs and expenses of defending
itself against any claim or liability in the premises. The obligations of the Company under this
Section 6.06 to compensate and indemnify the Trustee and to pay or reimburse the Trustee for
documented expenses, disbursements and advances shall constitute additional indebtedness hereunder.
Such

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additional indebtedness shall be secured by (and the Company hereby grants and pledges to the
Trustee) a lien prior to that of the Debt Securities upon all property and funds held or collected
by the Trustee as such, except funds held in trust for the benefit of the holders of particular
Debt Securities.

          Without prejudice to any other rights available to the Trustee under applicable law, when the
Trustee incurs expenses or renders services in connection with an Event of Default specified in
subsections (e), (f) or (g) of Section 5.01, the expenses (including the reasonable charges and
expenses of its counsel) and the compensation for the services are intended to constitute expenses
of administration under any applicable federal or state bankruptcy, insolvency or other similar
law.

          The provisions of this Section shall survive the resignation or removal of the Trustee and the
defeasance or other termination of this Indenture.

          Notwithstanding anything in this Indenture or any Debt Security to the contrary, the Trustee
shall have no obligation whatsoever to advance funds to pay any principal of or interest on or
other amounts with respect to the Debt Securities or otherwise advance funds to or on behalf of the
Company.

     SECTION 6.07. Officers’ Certificate as Evidence.

          Except as otherwise provided in Sections 6.01 and 6.02, whenever in the administration of the
provisions of this Indenture the Trustee shall deem it necessary or desirable that a matter be
proved or established prior to taking or omitting any action hereunder, such matter (unless other
evidence in respect thereof be herein specifically prescribed) may, in the absence of negligence,
willful misconduct or bad faith on the part of the Trustee, be deemed to be conclusively proved and
established by an Officers’ Certificate delivered to the Trustee, and such certificate, in the
absence of negligence, willful misconduct or bad faith on the part of the Trustee, shall be full
warrant to the Trustee for any action taken or omitted by it under the provisions of this Indenture
upon the faith thereof.

     SECTION 6.08. Eligibility of Trustee.

          The Trustee hereunder shall at all times be a U.S. Person that is a banking corporation or
national banking association organized and doing business under the laws of the United States of
America or any state thereof or of the District of Columbia and authorized under such laws to
exercise corporate trust powers, having a combined capital and surplus of at least fifty million
U.S. dollars ($50,000,000) and subject to supervision or examination by federal, state, or District
of Columbia authority. If such corporation or national banking association publishes reports of
condition at least annually, pursuant to law or to the requirements of the aforesaid supervising or
examining authority, then for the purposes of this Section 6.08 the combined capital and surplus of
such corporation or national banking association shall be deemed to be its combined capital and
surplus as set forth in its most recent records of condition so published.

          The Company may not, nor may any Person directly or indirectly controlling, controlled by, or
under common control with the Company, serve as Trustee, notwithstanding

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that such corporation or national banking association shall be otherwise eligible and
qualified under this Article.

          In case at any time the Trustee shall cease to be eligible in accordance with the provisions
of this Section 6.08, the Trustee shall resign immediately in the manner and with the effect
specified in Section 6.09.

          If the Trustee has or shall acquire any “conflicting interest” within the meaning of § 310(b)
of the Trust Indenture Act, the Trustee shall either eliminate such interest or resign, to the
extent and in the manner provided by, and subject to this Indenture.

     SECTION 6.09. Resignation or Removal of Trustee, Calculation Agent, Paying Agent or Debt
Security Registrar.

          (a) The Trustee, or any trustee or trustees hereafter appointed, the Calculation Agent, the
Paying Agent and any Debt Security Registrar may at any time resign by giving written notice of
such resignation to the Company and by mailing notice thereof, at the Company’s expense, to the
Securityholders at their addresses as they shall appear on the Debt Security Register. Upon
receiving such notice of resignation, the Company shall promptly appoint a successor or successors
by written instrument, in duplicate, executed by order of its Board of Directors, one copy of which
instrument shall be delivered to the resigning party and one copy to the successor. If no successor
shall have been so appointed and have accepted appointment within 30 days after the mailing of such
notice of resignation to the affected Securityholders, the resigning party may petition any court
of competent jurisdiction for the appointment of a successor, or any Securityholder who has been a
bona fide holder of a Debt Security or Debt Securities for at least six months may, subject to the
provisions of Section 5.09, on behalf of himself or herself and all others similarly situated,
petition any such court for the appointment of a successor. Such court may thereupon, after such
notice, if any, as it may deem proper and prescribe, appoint a successor.

          (b) In case at any time any of the following shall occur:

     (1) the Trustee shall fail to comply with the provisions of the last paragraph
of Section 6.08 after written request therefor by the Company or by any
Securityholder who has been a bona fide holder of a Debt Security or Debt Securities
for at least six months,

     (2) the Trustee shall cease to be eligible in accordance with the provisions of
Section 6.08 and shall fail to resign after written request therefor by the Company
or by any such Securityholder, or

     (3) the Trustee shall become incapable of acting, or shall be adjudged bankrupt
or insolvent, or a receiver of the Trustee or of its property shall be appointed, or
any public officer shall take charge or control of the Trustee or of its property or
affairs for the purpose of rehabilitation, conservation or liquidation,

     then, in any such case, the Company may remove the Trustee and appoint a successor Trustee by
written instrument, in duplicate, executed by order of the Board of Directors, one

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copy of which instrument shall be delivered to the Trustee so removed and one copy to the
successor Trustee, or, subject to the provisions of Section 5.09, if no successor Trustee shall
have been so appointed and have accepted appointment within 30 days of the occurrence of any of
(1), (2) or (3) above, any Securityholder who has been a bona fide holder of a Debt Security or
Debt Securities for at least six months may, on behalf of himself or herself and all others
similarly situated, petition any court of competent jurisdiction for the removal of the Trustee and
the appointment of a successor Trustee. Such court may thereupon, after such notice, if any, as it
may deem proper and prescribe, remove the Trustee and appoint a successor Trustee.

          (c) Upon prior written notice to the Company and the Trustee, the holders of a majority in
aggregate principal amount of the Debt Securities at the time outstanding may at any time remove
the Trustee and nominate a successor Trustee, which shall be deemed appointed as successor Trustee
unless within ten Business Days after such nomination the Company objects thereto, in which case or
in the case of a failure by such Securityholders to nominate a successor Trustee, the Trustee so
removed or any Securityholder, upon the terms and conditions and otherwise as in subsection (a) of
this Section 6.09 provided, may petition any court of competent jurisdiction for an appointment of
a successor.

          (d) Any resignation or removal of the Trustee, the Calculation Agent, the Paying Agent and any
Debt Security Registrar and appointment of a successor pursuant to any of the provisions of this
Section 6.09 shall become effective upon acceptance of appointment by the successor as provided in
Section 6.10.

     SECTION 6.10. Acceptance by Successor.

          Any successor Trustee, Calculation Agent, Paying Agent or Debt Security Registrar appointed as
provided in Section 6.09 shall execute, acknowledge and deliver to the Company and to its
predecessor an instrument accepting such appointment hereunder, and thereupon the resignation or
removal of the retiring party shall become effective and such successor, without any further act,
deed or conveyance, shall become vested with all the rights, powers, duties and obligations with
respect to the Debt Securities of its predecessor hereunder, with like effect as if originally
named herein; but, nevertheless, on the written request of the Company or of the successor, the
party ceasing to act shall, upon payment of the amounts then due it pursuant to the provisions of
Section 6.06, execute and deliver an instrument transferring to such successor all the rights and
powers of the party so ceasing to act and shall duly assign, transfer and deliver to such successor
all property and money held by such retiring party hereunder. Upon reasonable request of any such
successor, the Company shall execute any and all instruments in writing for more fully and
certainly vesting in and confirming to such successor all such rights and powers. Any party ceasing
to act shall, nevertheless, retain a lien upon all property or funds held or collected to secure
any amounts then due it pursuant to the provisions of Section 6.06.

          If a successor Trustee is appointed, the Company, the retiring Trustee and the successor
Trustee shall execute and deliver an indenture supplemental hereto which shall contain such
provisions as shall be deemed necessary or desirable to confirm that all the rights, powers, trusts
and duties of the retiring Trustee with respect to the Debt Securities as to which the predecessor
Trustee is not retiring shall continue to be vested in the predecessor Trustee, and

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shall add to or change any of the provisions of this Indenture as shall be necessary to
provide for or facilitate the administration of the Trust hereunder by more than one Trustee, it
being understood that nothing herein or in such supplemental indenture shall constitute such
Trustees co-trustees of the same trust and that each such Trustee shall be Trustee of a trust or
trusts hereunder separate and apart from any trust or trusts hereunder administered by any other
such Trustee.

          No successor Trustee shall accept appointment as provided in this Section 6.10 unless at the
time of such acceptance such successor Trustee shall be eligible and qualified under the provisions
of Section 6.08.

          In no event shall a retiring Trustee, Calculation Agent, Paying Agent or Debt Security
Registrar be liable for the acts or omissions of any successor hereunder.

          Upon acceptance of appointment by a successor Trustee, Calculation Agent, Paying Agent or Debt
Security Registrar as provided in this Section 6.10, the Company shall mail notice of the
succession to the Securityholders at their addresses as they shall appear on the Debt Security
Register. If the Company fails to mail such notice within ten Business Days after the acceptance of
appointment by the successor, the successor shall cause such notice to be mailed at the expense of
the Company.

     SECTION 6.11. Succession by Merger, etc.

          Any Person into which the Trustee may be merged or converted or with which it may be
consolidated, or any Person resulting from any merger, conversion or consolidation to which the
Trustee shall be a party, or any Person succeeding to all or substantially all of the corporate
trust business of the Trustee, shall be the successor of the Trustee hereunder without the
execution or filing of any paper or any further act on the part of any of the parties hereto;
provided, that such Person shall be otherwise eligible and qualified under this Article.

          In case at the time such successor to the Trustee shall succeed to the trusts created by this
Indenture any of the Debt Securities shall have been authenticated but not delivered, any such
successor to the Trustee may adopt the certificate of authentication of any predecessor Trustee,
and deliver such Debt Securities so authenticated; and in case at that time any of the Debt
Securities shall not have been authenticated, any successor to the Trustee may authenticate such
Debt Securities either in the name of any predecessor hereunder or in the name of the successor
Trustee; and in all such cases such certificates shall have the full force which it is anywhere in
the Debt Securities or in this Indenture provided that the certificate of the Trustee shall have;
provided, however, that the right to adopt the certificate of authentication of any
predecessor Trustee or authenticate Debt Securities in the name of any predecessor Trustee shall
apply only to its successor or successors by merger, conversion or consolidation.

     SECTION 6.12. Authenticating Agents.

          There may be one or more Authenticating Agents appointed by the Trustee upon the request of
the Company with power to act on its behalf and subject to its direction in the authentication and
delivery of Debt Securities issued upon exchange or registration of transfer thereof as fully to
all intents and purposes as though any such Authenticating Agent had been

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expressly authorized to authenticate and deliver Debt Securities; provided, that the Trustee
shall have no liability to the Company for any acts or omissions of the Authenticating Agent with
respect to the authentication and delivery of Debt Securities. Any such Authenticating Agent shall
at all times be a Person organized and doing business under the laws of the United States or of any
state or territory thereof or of the District of Columbia authorized under such laws to act as
Authenticating Agent, having a combined capital and surplus of at least $50,000,000 and being
subject to supervision or examination by federal, state, territorial or District of Columbia
authority. If such Person publishes reports of condition at least annually pursuant to law or the
requirements of such authority, then for the purposes of this Section 6.12 the combined capital and
surplus of such Person shall be deemed to be its combined capital and surplus as set forth in its
most recent report of condition so published. If at any time an Authenticating Agent shall cease to
be eligible in accordance with the provisions of this Section, it shall resign immediately in the
manner and with the effect herein specified in this Section.

          Any Person into which any Authenticating Agent may be merged or converted or with which it may
be consolidated, or any Person resulting from any merger, consolidation or conversion to which any
Authenticating Agent shall be a party, or any Person succeeding to all or substantially all of the
corporate trust business of any Authenticating Agent, shall be the successor of such Authenticating
Agent hereunder, if such successor Person is otherwise eligible under this Section 6.12 without the
execution or filing of any paper or any further act on the part of the parties hereto or such
Authenticating Agent.

          Any Authenticating Agent may at any time resign by giving written notice of resignation to the
Trustee and to the Company. The Trustee may at any time terminate the agency of any Authenticating
Agent with respect to the Debt Securities by giving written notice of termination to such
Authenticating Agent and to the Company. Upon receiving such a notice of resignation or upon such a
termination, or in case at any time any Authenticating Agent shall cease to be eligible under this
Section 6.12, the Trustee may, and upon the request of the Company shall, promptly appoint a
successor Authenticating Agent eligible under this Section 6.12, shall give written notice of such
appointment to the Company and shall mail notice of such appointment to all Securityholders as the
names and addresses of such Securityholders appear on the Debt Security Register. Any successor
Authenticating Agent upon acceptance of its appointment hereunder shall become vested with all
rights, powers, duties and responsibilities with respect to the Debt Securities of its predecessor
hereunder, with like effect as if originally named as Authenticating Agent herein.

          Other than as provided in the Fee Agreement of even date herewith between Cohen Bros. &
Company, the Company and the Trustee, the Company agrees to pay to any Authenticating Agent from
time to time reasonable compensation for its services. Any Authenticating Agent shall have no
responsibility or liability for any action taken by it as such in accordance with the directions of
the Trustee and shall receive such reasonable indemnity as it may require against the costs,
expenses and liabilities incurred in furtherance of its duties under this Section 6.12.

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ARTICLE VII

CONCERNING THE SECURITYHOLDERS

     SECTION 7.01. Action by Securityholders.

          Whenever in this Indenture it is provided that the holders of a specified percentage in
aggregate principal amount of the Debt Securities or aggregate Liquidation Amount of the Capital
Securities may take any action (including the making of any demand or request, the giving of any
notice, consent or waiver or the taking of any other action), the fact that at the time of taking
any such action the holders of such specified percentage have joined therein may be evidenced (a)
by any instrument or any number of instruments of similar tenor executed by such Securityholders or
holders of Capital Securities, as the case may be, in person or by agent or proxy appointed in
writing, or (b) by the record of such Securityholders voting in favor thereof at any meeting of
such Securityholders duly called and held in accordance with the provisions of Article VIII or of
such holders of Capital Securities duly called and held in accordance with the provisions of the
Declaration, or (c) by a combination of such instrument or instruments and any such record of such
a meeting of such Securityholders or holders of Capital Securities, as the case may be, or (d) by
any other method the Trustee deems satisfactory.

          If the Company shall solicit from the Securityholders any request, demand, authorization,
direction, notice, consent, waiver or other action or revocation of the same, the Company may, at
its option, as evidenced by an Officers’ Certificate, fix in advance a record date for such Debt
Securities for the determination of Securityholders entitled to give such request, demand,
authorization, direction, notice, consent, waiver or other action or revocation of the same, but
the Company shall have no obligation to do so. If such a record date is fixed, such request,
demand, authorization, direction, notice, consent, waiver or other action or revocation of the same
may be given before or after the record date, but only the Securityholders of record at the close
of business on the record date shall be deemed to be Securityholders for the purposes of
determining whether holders of the requisite proportion of outstanding Debt Securities have
authorized or agreed or consented to such request, demand, authorization, direction, notice,
consent, waiver or other action or revocation of the same, and for that purpose the outstanding
Debt Securities shall be computed as of the record date; provided, however, that no
such authorization, agreement or consent by such Securityholders on the record date shall be deemed
effective unless it shall become effective pursuant to the provisions of this Indenture not later
than six months after the record date.

     SECTION 7.02. Proof of Execution by Securityholders.

          Subject to the provisions of Sections 6.01, 6.02 and 8.05, proof of the execution of any
instrument by a Securityholder or such Securityholder’s agent or proxy shall be sufficient if made
in accordance with such reasonable rules and regulations as may be prescribed by the Trustee or in
such manner as shall be satisfactory to the Trustee. The ownership of Debt Securities shall be
proved by the Debt Security Register or by a certificate of the Debt Security Registrar. The
Trustee may require such additional proof of any matter referred to in this Section as it shall
deem necessary.

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          The record of any Securityholders’ meeting shall be proved in the manner provided in Section
8.06.

     SECTION 7.03. Who Are Deemed Absolute Owners.

          Prior to due presentment for registration of transfer of any Debt Security, the Company, the
Trustee, any Authenticating Agent, any Paying Agent, any transfer agent and any Debt Security
Registrar may deem the Person in whose name such Debt Security shall be registered upon the Debt
Security Register to be, and may treat such Person as, the absolute owner of such Debt Security
(whether or not such Debt Security shall be overdue) for the purpose of receiving payment of or on
account of the principal of, premium, if any, and interest on such Debt Security and for all other
purposes; and neither the Company nor the Trustee nor any Authenticating Agent nor any Paying Agent
nor any transfer agent nor any Debt Security Registrar shall be affected by any notice to the
contrary. All such payments so made to any Securityholder for the time being or upon such
Securityholder’s order shall be valid, and, to the extent of the sum or sums so paid, effectual to
satisfy and discharge the liability for moneys payable upon any such Debt Security.

     SECTION 7.04. Debt Securities Owned by Company Deemed Not Outstanding.

          In determining whether the holders of the requisite aggregate principal amount of Debt
Securities have concurred in any direction, consent or waiver under this Indenture, Debt Securities
which are owned by the Company or any other obligor on the Debt Securities or by any Person
directly or indirectly controlling or controlled by or under direct or indirect common control with
the Company (other than the Trust) or any other obligor on the Debt Securities shall be disregarded
and deemed not to be outstanding for the purpose of any such determination; provided, that
for the purposes of determining whether the Trustee shall be protected in relying on any such
direction, consent or waiver, only Debt Securities which a Responsible Officer of the Trustee
actually knows are so owned shall be so disregarded. Debt Securities so owned which have been
pledged in good faith may be regarded as outstanding for the purposes of this Section 7.04 if the
pledgee shall establish to the satisfaction of the Trustee the pledgee’s right to vote such Debt
Securities and that the pledgee is not the Company or any such other obligor or Person directly or
indirectly controlling or controlled by or under direct or indirect common control with the Company
or any such other obligor. In the case of a dispute as to such right, any decision by the Trustee
taken upon the advice of counsel shall be full protection to the Trustee.

     SECTION 7.05. Revocation of Consents; Future Securityholders Bound.

          At any time prior to (but not after) the evidencing to the Trustee, as provided in Section
7.01, of the taking of any action by the holders of the percentage in aggregate principal amount of
the Debt Securities specified in this Indenture in connection with such action, any Securityholder
(in cases where no record date has been set pursuant to Section 7.01) or any holder as of an
applicable record date (in cases where a record date has been set pursuant to Section 7.01) of a
Debt Security (or any Debt Security issued in whole or in part in exchange or substitution
therefor) the serial number of which is shown by the evidence to be included in the Debt Securities
the holders of which have consented to such action may, by filing written notice with the Trustee
at the Principal Office of the Trustee and upon proof of holding as provided in

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Section 7.02, revoke such action so far as concerns such Debt Security (or so far as concerns
the principal amount represented by any exchanged or substituted Debt Security). Except as
aforesaid any such action taken by the holder of any Debt Security shall be conclusive and binding
upon such Securityholder and upon all future holders and owners of such Debt Security, and of any
Debt Security issued in exchange or substitution therefor or on registration of transfer thereof,
irrespective of whether or not any notation in regard thereto is made upon such Debt Security or
any Debt Security issued in exchange or substitution therefor.

ARTICLE VIII

SECURITYHOLDERS’ MEETINGS

     SECTION 8.01. Purposes of Meetings.

          A meeting of Securityholders may be called at any time and from time to time pursuant to the
provisions of this Article VIII for any of the following purposes:

          (a) to give any notice to the Company or to the Trustee, or to give any directions to the
Trustee, or to consent to the waiving of any default hereunder and its consequences, or to take any
other action authorized to be taken by Securityholders pursuant to any of the provisions of Article
V;

          (b) to remove the Trustee and nominate a successor trustee pursuant to the provisions of
Article VI;

          (c) to consent to the execution of an indenture or indentures supplemental hereto pursuant to
the provisions of Section 9.02; or

          (d) to take any other action authorized to be taken by or on behalf of the holders of any
specified aggregate principal amount of such Debt Securities under any other provision of this
Indenture or under applicable law.

     SECTION 8.02. Call of Meetings by Trustee.

          The Trustee may at any time call a meeting of Securityholders to take any action specified in
Section 8.01, to be held at such time and at such place in Chicago, Illinois as the Trustee shall
determine. Notice of every meeting of the Securityholders, setting forth the time and the place of
such meeting and in general terms the action proposed to be taken at such meeting, shall be mailed
to Securityholders affected at their addresses as they shall appear on the Debt Securities
Register. Such notice shall be mailed not less than 20 nor more than 180 days prior to the date
fixed for the meeting.

     SECTION 8.03. Call of Meetings by Company or Securityholders.

          In case at any time the Company pursuant to a Board Resolution, or the holders of at least 10%
in aggregate principal amount of the Debt Securities, as the case may be, then outstanding, shall
have requested the Trustee to call a meeting of Securityholders, by written request setting forth
in reasonable detail the action proposed to be taken at the meeting, and the

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Trustee shall not have mailed the notice of such meeting within 20 days after receipt of such
request, then the Company or such Securityholders may determine the time and the place in for such
meeting and may call such meeting to take any action authorized in Section 8.01, by mailing notice
thereof as provided in Section 8.02.

     SECTION 8.04. Qualifications for Voting.

          To be entitled to vote at any meeting of Securityholders a Person shall be (a) a holder of one
or more Debt Securities with respect to which the meeting is being held or (b) a Person appointed
by an instrument in writing as proxy by a holder of one or more such Debt Securities. The only
Persons who shall be entitled to be present or to speak at any meeting of Securityholders shall be
the Persons entitled to vote at such meeting and their counsel and any representatives of the
Trustee and its counsel and any representatives of the Company and its counsel.

     SECTION 8.05. Regulations.

          Notwithstanding any other provisions of this Indenture, the Trustee may make such reasonable
regulations as it may deem advisable for any meeting of Securityholders, in regard to proof of the
holding of Debt Securities and of the appointment of proxies, and in regard to the appointment and
duties of inspectors of votes, the submission and examination of proxies, certificates and other
evidence of the right to vote, and such other matters concerning the conduct of the meeting as it
shall deem appropriate.

          The Trustee shall, by an instrument in writing, appoint a temporary chairman of the meeting,
unless the meeting shall have been called by the Company or by Securityholders as provided in
Section 8.03, in which case the Company or the Securityholders calling the meeting, as the case may
be, shall in like manner appoint a temporary chairman. A permanent chairman and a permanent
secretary of the meeting shall be elected by majority vote at the meeting.

          Subject to the provisions of Section 7.04, at any meeting each Securityholder with respect to
which such meeting is being held or proxy therefor shall be entitled to one vote for each $1,000
principal amount of Debt Securities held or represented by such Securityholder; provided,
however, that no vote shall be cast or counted at any meeting in respect of any Debt
Security challenged as not outstanding and ruled by the chairman of the meeting to be not
outstanding. The chairman of the meeting shall have no right to vote other than by virtue of Debt
Securities held by such chairman or instruments in writing as aforesaid duly designating such
chairman as the Person to vote on behalf of other Securityholders. Any meeting of Securityholders
duly called pursuant to the provisions of Section 8.02 or 8.03 may be adjourned from time to time
by a majority of those present, whether or not constituting a quorum, and the meeting may be held
as so adjourned without further notice.

     SECTION 8.06. Voting.

          The vote upon any resolution submitted to any meeting of Securityholders with respect to which
such meeting is being held shall be by written ballots on which shall be subscribed the signatures
of such Securityholders or of their representatives by proxy and the serial number or numbers of
the Debt Securities held or represented by them. The permanent

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chairman of the meeting shall appoint two inspectors of votes who shall count all votes cast
at the meeting for or against any resolution and who shall make and file with the secretary of the
meeting their verified written reports in triplicate of all votes cast at the meeting. A record in
duplicate of the proceedings of each meeting of Securityholders shall be prepared by the secretary
of the meeting and there shall be attached to said record the original reports of the inspectors of
votes on any vote by ballot taken thereat and affidavits by one or more Persons having knowledge of
the facts setting forth a copy of the notice of the meeting and showing that said notice was mailed
as provided in Section 8.02. The record shall show the serial numbers of the Debt Securities voting
in favor of or against any resolution. The record shall be signed and verified by the affidavits of
the permanent chairman and secretary of the meeting and one of the duplicates shall be delivered to
the Company and the other to the Trustee to be preserved by the Trustee, the latter to have
attached thereto the ballots voted at the meeting. Any record so signed and verified shall be
conclusive evidence of the matters therein stated.

     SECTION 8.07. Quorum; Actions.

          The Persons entitled to vote a majority in outstanding principal amount of the Debt Securities
shall constitute a quorum for a meeting of Securityholders; provided, however, that
if any action is to be taken at such meeting with respect to a consent, waiver, request, demand,
notice, authorization, direction or other action which may be given by the holders of not less than
a specified percentage in outstanding principal amount of the Debt Securities, the Persons holding
or representing such specified percentage in outstanding principal amount of the Debt Securities
will constitute a quorum. In the absence of a quorum within 30 minutes of the time appointed for
any such meeting, the meeting shall, if convened at the request of Securityholders, be dissolved.
In any other case the meeting may be adjourned for a period of not less than 10 days as determined
by the permanent chairman of the meeting prior to the adjournment of such meeting. In the absence
of a quorum at any such adjourned meeting, such adjourned meeting may be further adjourned for a
period of not less than 10 days as determined by the permanent chairman of the meeting prior to the
adjournment of such adjourned meeting. Notice of the reconvening of any adjourned meeting shall be
given as provided in Section 8.02, except that such notice need be given only once not less than
five days prior to the date on which the meeting is scheduled to be reconvened. Notice of the
reconvening of an adjourned meeting shall state expressly the percentage, as provided above, of the
outstanding principal amount of the Debt Securities which shall constitute a quorum.

          Except as limited by the proviso in the first paragraph of Section 9.02, any resolution
presented to a meeting or adjourned meeting duly reconvened at which a quorum is present as
aforesaid may be adopted by the affirmative vote of the holders of not less than a majority in
outstanding principal amount of the Debt Securities; provided, however, that,
except as limited by the proviso in the first paragraph of Section 9.02, any resolution with
respect to any consent, waiver, request, demand, notice, authorization, direction or other action
that this Indenture expressly provides may be given by the holders of not less than a specified
percentage in outstanding principal amount of the Debt Securities may be adopted at a meeting or an
adjourned meeting duly reconvened and at which a quorum is present as aforesaid only by the
affirmative vote of the holders of not less than such specified percentage in outstanding principal
amount of the Debt Securities.

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          Any resolution passed or decision taken at any meeting of Securityholders duly held in
accordance with this Section shall be binding on all the Securityholders, whether or not present or
represented at the meeting.

     SECTION 8.08. Written Consent Without a Meeting.

          Whenever under this Indenture, Securityholders are required or permitted to take any action by
vote, such action may be taken without a meeting on written consent, setting forth the action so
taken, signed by the Securityholders of all outstanding Debt Securities entitled to vote thereon.
No consent shall be effective to take the action referred to therein unless, within sixty days of
the earliest dated consent delivered in the manner required by this paragraph to the Trustee,
written consents signed by a sufficient number of Securityholders to take action are delivered to
the Trustee at its Principal Office. Delivery made to the Trustee at its Principal Office, shall
be by hand or by certificated or registered mail, return receipt requested. Written consent thus
given by the Securityholders of such number of Debt Securities as is required hereunder, shall have
the same effect as a valid vote of Securityholders of such number of Debt Securities.

ARTICLE IX

SUPPLEMENTAL INDENTURES

     SECTION 9.01. Supplemental Indentures without Consent of Securityholders.

          The Company, when authorized by a Board Resolution, and the Trustee may from time to time and
at any time enter into an indenture or indentures supplemental hereto, without the consent of the
Securityholders, for one or more of the following purposes:

          (a) to evidence the succession of another Person to the Company, or successive successions,
and the assumption by the successor Person of the covenants, agreements and obligations of the
Company, pursuant to Article XI hereof;

          (b) to add to the covenants of the Company such further covenants, restrictions or conditions
for the protection of the Securityholders as the Board of Directors shall consider to be for the
protection of the Securityholders, and to make the occurrence, or the occurrence and continuance,
of a Default in any of such additional covenants, restrictions or conditions a Default or an Event
of Default permitting the enforcement of all or any of the several remedies provided in this
Indenture as herein set forth; provided, however, that in respect of any such
additional covenant, restriction or condition such supplemental indenture may provide for a
particular period of grace after default (which period may be shorter or longer than that allowed
in the case of other defaults) or may provide for an immediate enforcement upon such default or may
limit the remedies available to the Trustee upon such default;

          (c) to cure any ambiguity or to correct or supplement any provision contained herein or in any
supplemental indenture which may be defective or inconsistent with any other provision contained
herein or in any supplemental indenture, or to make or amend such other provisions in regard to
matters or questions arising under this Indenture; provided, that any such action shall not
adversely affect the interests of the Securityholders;

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          (d) to add to, delete from, or revise the terms of Debt Securities, including, without
limitation, any terms relating to the issuance, exchange, registration or transfer of Debt
Securities, including to provide for transfer procedures and restrictions substantially similar to
those applicable to the Capital Securities, as required by Section 2.05 (for purposes of assuring
that no registration of Debt Securities is required under the Securities Act of 1933, as amended);
provided, that any such action shall not adversely affect the interests of the holders of the Debt
Securities then outstanding (it being understood, for purposes of this proviso, that transfer
restrictions on Debt Securities substantially similar to those applicable to Capital Securities
shall not be deemed to adversely affect the Securityholders);

          (e) to evidence and provide for the acceptance of appointment hereunder by a successor Trustee
with respect to the Debt Securities and to add to or change any of the provisions of this Indenture
as shall be necessary to provide for or facilitate the administration of the trusts hereunder by
more than one Trustee, pursuant to the requirements of Section 6.10;

          (f) to make any change (other than as elsewhere provided in this paragraph) that does not
adversely affect the rights of any Securityholder in any material respect; or

          (g) to provide for the issuance of and establish the form and terms and conditions of the Debt
Securities, to establish the form of any certifications required to be furnished pursuant to the
terms of this Indenture or the Debt Securities, or to add to the rights of the Securityholders.

          The Trustee is hereby authorized to join with the Company in the execution of any such
supplemental indenture, to make any further appropriate agreements and stipulations which may be
therein contained and to accept the conveyance, transfer and assignment of any property thereunder,
but the Trustee shall not be obligated to, but may in its discretion, enter into any such
supplemental indenture which affects the Trustee’s own rights, duties or immunities under this
Indenture or otherwise.

          Any supplemental indenture authorized by the provisions of this Section 9.01 may be executed
by the Company and the Trustee without the consent of the Securityholders at the time outstanding,
notwithstanding any of the provisions of Section 9.02.

     SECTION 9.02. Supplemental Indentures with Consent of Securityholders.

          With the consent (evidenced as provided in Section 7.01) of the holders of not less than a
majority in aggregate principal amount of the Debt Securities at the time outstanding affected by
such supplemental indenture, the Company, when authorized by a Board Resolution, and the Trustee
may from time to time and at any time enter into an indenture or indentures supplemental hereto
(which shall conform to the provisions of the Trust Indenture Act, then in effect, applicable to
indentures qualified thereunder) for the purpose of adding any provisions to or changing in any
manner or eliminating any of the provisions of this Indenture or of any supplemental indenture or
of modifying in any manner the rights of the Securityholders; provided, however,
that no such supplemental indenture shall without such consent of the holders of each Debt Security
then outstanding and affected thereby (i) change the Maturity Date of any Debt Security, or reduce
the principal amount thereof or any premium thereon, or reduce

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the rate (or manner of calculation of the rate) or extend the time of payment of interest
thereon, or reduce (other than as a result of the maturity or earlier redemption of any such Debt
Security in accordance with the terms of this Indenture and such Debt Security) or increase the
aggregate principal amount of Debt Securities then outstanding, or change any of the redemption
provisions, or make the principal thereof or any interest or premium thereon payable in any coin or
currency other than United States Dollars, or impair or affect the right of any Securityholder to
institute suit for payment thereof or impair the right of repayment, if any, at the option of the
Securityholder, or (ii) reduce the aforesaid percentage of Debt Securities the holders of which are
required to consent to any such supplemental indenture; and provided, further, that
if the Debt Securities are held by the Trust or a trustee of such trust, such supplemental
indenture shall not be effective until the holders of a majority in Liquidation Amount of the
outstanding Capital Securities shall have consented to such supplemental indenture;
provided, further, that if the consent of the Securityholder of each outstanding
Debt Security is required, such supplemental indenture shall not be effective until each holder of
the outstanding Capital Securities shall have consented to such supplemental indenture.

          Upon the request of the Company accompanied by a Board Resolution authorizing the execution of
any such supplemental indenture, and upon the filing with the Trustee of evidence of the consent of
Securityholders (and holders of Capital Securities, if required) as aforesaid, the Trustee shall
join with the Company in the execution of such supplemental indenture unless such supplemental
indenture affects the Trustee’s own rights, duties or immunities under this Indenture or otherwise,
in which case the Trustee may in its discretion, but shall not be obligated to, enter into such
supplemental indenture.

          Promptly after the execution by the Company and the Trustee of any supplemental indenture
pursuant to the provisions of this Section, the Trustee shall transmit by mail, first class postage
prepaid, a notice, prepared by the Company, setting forth in general terms the substance of such
supplemental indenture, to the Securityholders as their names and addresses appear upon the Debt
Security Register. Any failure of the Trustee to mail such notice, or any defect therein, shall
not, however, in any way impair or affect the validity of any such supplemental indenture.

          It shall not be necessary for the consent of the Securityholders under this Section 9.02 to
approve the particular form of any proposed supplemental indenture, but it shall be sufficient if
such consent shall approve the substance thereof.

     SECTION 9.03. Effect of Supplemental Indentures.

          Upon the execution of any supplemental indenture pursuant to the provisions of this Article
IX, this Indenture shall be and be deemed to be modified and amended in accordance therewith and
the respective rights, limitations of rights, obligations, duties and immunities under this
Indenture of the Trustee, the Company and the Securityholders shall thereafter be determined,
exercised and enforced hereunder subject in all respects to such modifications and amendments and
all the terms and conditions of any such supplemental indenture shall be and be deemed to be part
of the terms and conditions of this Indenture for any and all purposes.

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     SECTION 9.04. Notation on Debt Securities.

          Debt Securities authenticated and delivered after the execution of any supplemental indenture
pursuant to the provisions of this Article IX may bear a notation as to any matter provided for in
such supplemental indenture. If the Company or the Trustee shall so determine, new Debt Securities
so modified as to conform, in the opinion of the Board of Directors of the Company, to any
modification of this Indenture contained in any such supplemental indenture may be prepared and
executed by the Company, authenticated by the Trustee or the Authenticating Agent and delivered in
exchange for the Debt Securities then outstanding.

     SECTION 9.05. Evidence of Compliance of Supplemental Indenture to be furnished to
Trustee.

          The Trustee, subject to the provisions of Sections 6.01 and 6.02, shall, in addition to the
documents required by Section 14.06, receive an Officers’ Certificate and an Opinion of Counsel as
conclusive evidence that any supplemental indenture executed pursuant hereto complies with the
requirements of this Article IX. The Trustee shall receive an Opinion of Counsel as conclusive
evidence that any supplemental indenture executed pursuant to this Article IX is authorized or
permitted by, and conforms to, the terms of this Article IX and that it is proper for the Trustee
under the provisions of this Article IX to join in the execution thereof.

ARTICLE X

REDEMPTION OF SECURITIES

     SECTION 10.01. Optional Redemption.

          At any time the Company shall have the right, subject to the receipt by the Company of prior
approval from any regulatory authority with jurisdiction over the Company if such approval is then
required under applicable capital guidelines or policies of such regulatory authority, to redeem
the Debt Securities, in whole or (provided that all accrued and unpaid interest has been paid on
all Debt Securities for all Interest Payment Periods terminating on or prior to such date) from
time to time in part, on any March 15, June 15, September 15 or December 15 on or after September
15, 2011 (the “Redemption Date”), at the Redemption Price.

     SECTION 10.02. Special Event Redemption.

          If a Special Event shall occur and be continuing, the Company shall have the right, subject to
the receipt by the Company of prior approval from any regulatory authority with jurisdiction over
the Company if such approval is then required under applicable capital guidelines or policies of
such regulatory authority, to redeem the Debt Securities, in whole or in part, at any time within
90 days following the occurrence of such Special Event (the “Special Redemption Date”), at the
Special Redemption Price.

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     SECTION 10.03. Notice of Redemption; Selection of Debt Securities.

          In case the Company shall desire to exercise the right to redeem all, or, as the case may be,
any part of the Debt Securities, it shall fix a date for redemption and shall mail, or cause the
Trustee to mail (at the expense of the Company) a notice of such redemption at least 30 and not
more than 60 days prior to the date fixed for redemption to the Securityholders so to be redeemed
as a whole or in part at their last addresses as the same appear on the Debt Security Register.
Such mailing shall be by first class mail. The notice if mailed in the manner herein provided shall
be conclusively presumed to have been duly given, whether or not the Securityholder receives such
notice. In any case, failure to give such notice by mail or any defect in the notice to the holder
of any Debt Security designated for redemption as a whole or in part shall not affect the validity
of the proceedings for the redemption of any other Debt Security.

          Each such notice of redemption shall specify the CUSIP number, if any, of the Debt Securities
to be redeemed, the date fixed for redemption, the redemption price (or manner of calculation of
the price) at which Debt Securities are to be redeemed, the place or places of payment, that
payment will be made upon presentation and surrender of such Debt Securities, that interest accrued
to the date fixed for redemption will be paid as specified in said notice, and that on and after
said date interest thereon or on the portions thereof to be redeemed will cease to accrue. If less
than all the Debt Securities are to be redeemed the notice of redemption shall specify the numbers
of the Debt Securities to be redeemed. In case the Debt Securities are to be redeemed in part only,
the notice of redemption shall state the portion of the principal amount thereof to be redeemed and
shall state that on and after the date fixed for redemption, upon surrender of such Debt Security,
a new Debt Security or Debt Securities in principal amount equal to the unredeemed portion thereof
will be issued.

          On the Business Day prior to the Redemption Date or the Special Redemption Date specified in
the notice of redemption given as provided in this Section, the Company will deposit with the
Trustee or with one or more Paying Agents an amount of money sufficient to redeem on the redemption
date all the Debt Securities so called for redemption at the appropriate redemption price, together
with unpaid interest accrued to such date.

          The Company will give the Trustee notice not less than 45 nor more than 60 days prior to the
Redemption Date as to the Redemption Price at which the Debt Securities are to be redeemed and the
aggregate principal amount of Debt Securities to be redeemed and the Trustee shall select, in such
manner as in its sole discretion it shall deem appropriate and fair, the Debt Securities or
portions thereof (in integral multiples of $1,000) to be redeemed.

     SECTION 10.04. Payment of Debt Securities Called for Redemption.

          If notice of redemption has been given as provided in Section 10.03, the Debt Securities or
portions of Debt Securities with respect to which such notice has been given shall become due and
payable on the Redemption Date or the Special Redemption Date (as the case may be) and at the place
or places stated in such notice at the applicable redemption price, together with interest accrued
to the date fixed for redemption, and on and after said Redemption Date or the Special Redemption
Date (unless the Company shall default in the payment of such Debt Securities at the redemption
price, together with unpaid interest accrued thereon to said

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date) interest on the Debt Securities or portions of Debt Securities so called for redemption
shall cease to accrue. On presentation and surrender of such Debt Securities at a place of payment
specified in said notice, such Debt Securities or the specified portions thereof shall be paid and
redeemed by the Company at the applicable redemption price, together with unpaid interest accrued
thereon to the Redemption Date or the Special Redemption Date (as the case may be).

          Upon presentation of any Debt Security redeemed in part only, the Company shall execute and
the Trustee shall authenticate and make available for delivery to the holder thereof, at the
expense of the Company, a new Debt Security or Debt Securities of authorized denominations in
principal amount equal to the unredeemed portion of the Debt Security so presented.

ARTICLE XI

CONSOLIDATION, MERGER, SALE, CONVEYANCE AND LEASE

     SECTION 11.01. Company May Consolidate, etc., on Certain Terms.

          Nothing contained in this Indenture or in the Debt Securities shall prevent any consolidation
or merger of the Company with or into any other corporation or corporations (whether or not
affiliated with the Company) or successive consolidations or mergers in which the Company or its
successor or successors shall be a party or parties, or shall prevent any sale, conveyance,
transfer or other disposition of all or substantially all of the property or capital stock of the
Company or its successor or successors to any other corporation (whether or not affiliated with the
Company, or its successor or successors) authorized to acquire and operate the same;
provided, however, that the Company hereby covenants and agrees that, (i) upon any
such consolidation, merger (where the Company is not the surviving corporation), sale, conveyance,
transfer or other disposition, the successor entity shall be a corporation organized and existing
under the laws of the United States or any state thereof or the District of Columbia (unless such
corporation has (1) agreed to make all payments due in respect of the Debt Securities or, if
outstanding, the Capital Securities and Capital Securities Guarantee without withholding or
deduction for, or on account of, any taxes, duties, assessments or other governmental charges under
the laws or regulations of the jurisdiction of organization or residence (for tax purposes) of such
corporation or any political subdivision or taxing authority thereof or therein unless required by
applicable law, in which case such corporation shall have agreed to pay such additional amounts as
shall be required so that the net amounts received and retained by the Securityholders or holders
of Capital Securities, as the case may be, after payment of all taxes (including withholding
taxes), duties, assessments or other governmental charges, will be equal to the amounts that such
Securityholders or holders of Capital Securities would have received and retained had no such taxes
(including withholding taxes), duties, assessments or other governmental charges been imposed, (2)
irrevocably and unconditionally consented and submitted to the jurisdiction of any United States
federal court or New York state court, in each case located in The City of New York, Borough of
Manhattan, in respect of any action, suit or proceeding against it arising out of or in connection
with this Indenture, the Debt Securities, the Capital Securities Guarantee or the Declaration and
irrevocably and unconditionally waived, to the fullest extent permitted by law, any objection to
the laying of venue in any such court or that any such action, suit or proceeding has been brought
in an inconvenient forum and (3)

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irrevocably appointed an agent in The City of New York for service of process in any action,
suit or proceeding referred to in clause (2) above) and such corporation expressly assumes all of
the obligations of the Company under the Debt Securities, this Indenture, the Capital Securities
Guarantee and the Declaration and (ii) after giving effect to any such consolidation, merger, sale,
conveyance, transfer or other disposition, no Default or Event of Default shall have occurred and
be continuing.

     SECTION 11.02. Successor Entity to be Substituted.

          In case of any such consolidation, merger, sale, conveyance, transfer or other disposition
contemplated in Section 11.01 and upon the assumption by the successor entity, by supplemental
indenture, executed and delivered to the Trustee and reasonably satisfactory in form to the
Trustee, of the due and punctual payment of the principal of and premium, if any, and interest on
all of the Debt Securities and the due and punctual performance and observance of all of the
covenants and conditions of this Indenture to be performed or observed by the Company, such
successor entity shall succeed to and be substituted for the Company, with the same effect as if it
had been named herein as the Company, and thereupon the predecessor entity shall be relieved of any
further liability or obligation hereunder or upon the Debt Securities. Such successor entity
thereupon may cause to be signed, and may issue either in its own name or in the name of the
Company, any or all of the Debt Securities issuable hereunder which theretofore shall not have been
signed by the Company and delivered to the Trustee or the Authenticating Agent; and, upon the order
of such successor entity instead of the Company and subject to all the terms, conditions and
limitations in this Indenture prescribed, the Trustee or the Authenticating Agent shall
authenticate and deliver any Debt Securities which previously shall have been signed and delivered
by the officers of the Company, to the Trustee or the Authenticating Agent for authentication, and
any Debt Securities which such successor entity thereafter shall cause to be signed and delivered
to the Trustee or the Authenticating Agent for that purpose. All the Debt Securities so issued
shall in all respects have the same legal rank and benefit under this Indenture as the Debt
Securities theretofore or thereafter issued in accordance with the terms of this Indenture as
though all of such Debt Securities had been issued at the date of the execution hereof.

     SECTION 11.03. Opinion of Counsel to be Given to Trustee.

          The Trustee, subject to the provisions of Sections 6.01 and 6.02, shall receive, in addition
to the Opinion of Counsel required by Section 9.05, an Opinion of Counsel as conclusive evidence
that any consolidation, merger, sale, conveyance, transfer or other disposition, and any
assumption, permitted or required by the terms of this Article XI complies with the provisions of
this Article XI.

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ARTICLE XII

SATISFACTION AND DISCHARGE OF INDENTURE

     SECTION 12.01. Discharge of Indenture.

          When (a) the Company shall deliver to the Trustee for cancellation all Debt Securities
theretofore authenticated (other than any Debt Securities which shall have been destroyed, lost or
stolen and which shall have been replaced or paid as provided in Section 2.06) and not theretofore
canceled, or (b) all the Debt Securities not theretofore canceled or delivered to the Trustee for
cancellation shall have become due and payable, or are by their terms to become due and payable
within one year or are to be called for redemption within one year under arrangements satisfactory
to the Trustee for the giving of notice of redemption, and the Company shall deposit with the
Trustee, in trust, funds, which shall be immediately due and payable, sufficient to pay at maturity
or upon redemption all of the Debt Securities (other than any Debt Securities which shall have been
destroyed, lost or stolen and which shall have been replaced or paid as provided in Section 2.06)
not theretofore canceled or delivered to the Trustee for cancellation, including principal and
premium, if any, and interest due or to become due to such date of maturity or redemption date, as
the case may be, but excluding, however, the amount of any moneys for the payment of principal of,
and premium, if any, or interest on the Debt Securities (1) theretofore repaid to the Company in
accordance with the provisions of Section 12.04, or (2) paid to any state or to the District of
Columbia pursuant to its unclaimed property or similar laws, and if in the case of either clause
(a) or clause (b) the Company shall also pay or cause to be paid all other sums payable hereunder
by the Company, then this Indenture shall cease to be of further effect except for the provisions
of Sections 2.05, 2.06, 3.01, 3.02, 3.04, 6.06, 6.09 and 12.04 hereof, which shall survive until
such Debt Securities shall mature or are redeemed, as the case may be, and are paid in full.
Thereafter, Sections 6.06, 6.09 and 12.04 shall survive, and the Trustee, on demand of the Company
accompanied by an Officers’ Certificate and an Opinion of Counsel, each stating that all conditions
precedent herein provided for relating to the satisfaction and discharge of this Indenture have
been complied with, and at the cost and expense of the Company, shall execute proper instruments
acknowledging satisfaction of and discharging this Indenture, the Company, however, hereby agreeing
to reimburse the Trustee for any costs or expenses thereafter reasonably and properly incurred by
the Trustee in connection with this Indenture or the Debt Securities.

     SECTION 12.02. Deposited Moneys to be Held in Trust by Trustee.

          Subject to the provisions of Section 12.04, all moneys deposited with the Trustee pursuant to
Section 12.01 shall be held in trust and applied by it to the payment, either directly or through
any Paying Agent (including the Company if acting as its own Paying Agent), to the holders of the
particular Debt Securities for the payment of which such moneys have been deposited with the
Trustee, of all sums due and to become due thereon for principal, and premium, if any, and
interest.

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     SECTION 12.03. Paying Agent to Repay Moneys Held.

          Upon the satisfaction and discharge of this Indenture, all moneys then held by any Paying
Agent of the Debt Securities (other than the Trustee) shall, upon demand of the Company, be repaid
to the Company or paid to the Trustee, and thereupon such Paying Agent shall be released from all
further liability with respect to such moneys.

     SECTION 12.04. Return of Unclaimed Moneys.

          Any moneys deposited with or paid to the Trustee or any Paying Agent for payment of the
principal of, and premium, if any, or interest on Debt Securities and not applied but remaining
unclaimed by the Securityholders for two years after the date upon which the principal of, and
premium, if any, or interest on such Debt Securities, as the case may be, shall have become due and
payable, shall be repaid to the Company by the Trustee or such Paying Agent on written demand; and
the holder of any of the Debt Securities shall thereafter look only to the Company for any payment
which such Securityholder may be entitled to collect and all liability of the Trustee or such
Paying Agent with respect to such moneys shall thereupon cease.

ARTICLE XIII

IMMUNITY OF INCORPORATORS, STOCKHOLDERS, OFFICERS AND DIRECTORS

     SECTION 13.01. Indenture and Debt Securities Solely Corporate Obligations.

          No recourse for the payment of the principal of or premium, if any, or interest on any Debt
Security, or for any claim based thereon or otherwise in respect thereof, and no recourse under or
upon any obligation, covenant or agreement of the Company in this Indenture or in any supplemental
indenture, or in any such Debt Security, or because of the creation of any indebtedness represented
thereby, shall be had against any incorporator, stockholder, officer, director, employee or agent,
as such, past, present or future, of the Company or of any predecessor or successor corporation of
the Company, either directly or through the Company or any successor corporation of the Company,
whether by virtue of any constitution, statute or rule of law, or by the enforcement of any
assessment or penalty or otherwise; it being expressly understood that all such liability is hereby
expressly waived and released as a condition of, and as a consideration for, the execution of this
Indenture and the issue of the Debt Securities.

ARTICLE XIV

MISCELLANEOUS PROVISIONS

     SECTION 14.01. Successors.

          All the covenants, stipulations, promises and agreements of the Company contained in this
Indenture shall bind its successors and assigns whether so expressed or not.

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     SECTION 14.02. Official Acts by Successor Entity.

          Any act or proceeding by any provision of this Indenture authorized or required to be done or
performed by any board, committee or officer of the Company shall and may be done and performed
with like force and effect by the like board, committee, officer or other authorized Person of any
entity that shall at the time be the lawful successor of the Company.

     SECTION 14.03. Surrender of Company Powers.

          The Company by instrument in writing executed by authority of 2/3 (two-thirds) of its Board of
Directors and delivered to the Trustee may surrender any of the powers reserved to the Company and
thereupon such power so surrendered shall terminate both as to the Company and as to any permitted
successor.

     SECTION 14.04. Addresses for Notices, etc.

          Any notice or demand which by any provision of this Indenture is required or permitted to be
given or served by the Trustee or by the Securityholders on the Company may be given or served in
writing, duly signed by the party giving such notice, and shall be delivered by facsimile (which
shall be followed by notice delivered or mailed by first class mail) or mailed by first class mail
to the Company at:

Wintrust Financial Corporation

727 North Bank Lane

Lake Forest, IL 60045

Attention: David A. Dykstra

     Any notice, direction, request or demand by any Securityholder or the Company to or upon the
Trustee shall be deemed to have been sufficiently given or made, for all purposes, if given or made
in writing at the office of LaSalle Bank National Association at:

135 South LaSalle Street, Suite 1511

Chicago, Illinois 60603

Attn: CDO Trust Services Group – Wintrust Capital Trust IX

     SECTION 14.05. Governing Law.

          This Indenture and the Debt Securities shall each be governed by, and construed in accordance
with, the laws of the State of New York, without regard to conflict of laws principles of said
State other than Section 5-1401 of the New York General Obligations Law.

     SECTION 14.06. Evidence of Compliance with Conditions Precedent.

          Upon any application or demand by the Company to the Trustee to take any action under any of
the provisions of this Indenture, the Company shall furnish to the Trustee an Officers’ Certificate
stating that in the opinion of the signers all conditions precedent, if any, provided for in this
Indenture relating to the proposed action have been complied with and an Opinion of Counsel stating
that, in the opinion of such counsel, all such conditions precedent

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have been complied with (except that no such Opinion of Counsel is required to be furnished to
the Trustee in connection with the authentication and issuance of Debt Securities issued on the
date of this Indenture).

          Each certificate or opinion provided for in this Indenture and delivered to the Trustee with
respect to compliance with a condition or covenant provided for in this Indenture (except
certificates delivered pursuant to Section 3.05) shall include (a) a statement that the person
making such certificate or opinion has read such covenant or condition and the definitions relating
thereto; (b) a brief statement as to the nature and scope of the examination or investigation upon
which the statements or opinions contained in such certificate or opinion are based; (c) a
statement that, in the opinion of such person, he or she has made such examination or investigation
as is necessary to enable him or her to express an informed opinion as to whether or not such
covenant or condition has been complied with; and (d) a statement as to whether or not, in the
opinion of such person, such condition or covenant has been complied with.

     SECTION 14.07. Non-Business Days.

          Notwithstanding anything to the contrary contained herein, if any Interest Payment Date, other
than on the Maturity Date, any Redemption Date or the Special Redemption Date, falls on a day that
is not a Business Day, then any interest payable will be paid on, and such Interest Payment Date
will be moved to, the next succeeding Business Day, and additional interest will accrue for each
day that such payment is delayed as a result thereof. If the Maturity Date, Redemption Date or
Special Redemption Date falls on a day that is not a Business Day, then the principal, premium, if
any, and/or interest payable on such date will be paid on the next succeeding Business Day, and no
additional interest will accrue (except that, if such Business Day falls in the next calendar year,
such payment will be made on the immediately preceding Business Day).

     SECTION 14.08. Table of Contents, Headings, etc.

          The table of contents and the titles and headings of the articles and sections of this
Indenture have been inserted for convenience of reference only, are not to be considered a part
hereof, and shall in no way modify or restrict any of the terms or provisions hereof.

     SECTION 14.09. Execution in Counterparts.

          This Indenture may be executed in any number of counterparts, each of which shall be an
original, but such counterparts shall together constitute but one and the same instrument.

     SECTION 14.10. Severability.

          In case any one or more of the provisions contained in this Indenture or in the Debt
Securities shall for any reason be held to be invalid, illegal or unenforceable in any respect,
such invalidity, illegality or unenforceability shall not affect any other provisions of this
Indenture or of such Debt Securities, but this Indenture and such Debt Securities shall be
construed as if such invalid or illegal or unenforceable provision had never been contained herein
or therein.

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     SECTION 14.11. Assignment.

          Subject to Article XI, the Company will have the right at all times to assign any of its
rights or obligations under this Indenture and the Debt Securities to a direct or indirect wholly
owned Subsidiary of the Company; provided, however, that, in the event of any such
assignment, the Company will remain liable for all such obligations. Subject to the foregoing, this
Indenture is binding upon and inures to the benefit of the parties hereto and their respective
successors and assigns. This Indenture may not otherwise be assigned by the parties thereto.

     SECTION 14.12. Acknowledgment of Rights.

          The Company acknowledges that, with respect to any Debt Securities held by the Trust or the
Institutional Trustee of the Trust, if the Institutional Trustee of the Trust fails to enforce its
rights under this Indenture as the Securityholder held as the assets of the Trust after the holders
of a majority in Liquidation Amount of the Capital Securities of the Trust have so directed in
writing such Institutional Trustee, a holder of record of such Capital Securities may to the
fullest extent permitted by law institute legal proceedings directly against the Company to enforce
such Institutional Trustee’s rights under this Indenture without first instituting any legal
proceedings against such Institutional Trustee or any other Person. Notwithstanding the foregoing,
if an Event of Default has occurred and is continuing and such event is attributable to the failure
of the Company to pay interest (or premium, if any) or principal on the Debt Securities on the date
such interest (or premium, if any) or principal is otherwise due and payable (or in the case of
redemption, on the redemption date), the Company acknowledges that a holder of record of Capital
Securities of the Trust may directly institute a proceeding against the Company for enforcement of
payment to such holder directly of the principal of (or premium, if any) or interest on the Debt
Securities having an aggregate principal amount equal to the aggregate Liquidation Amount of the
Capital Securities of such holder on or after the respective due date specified in the Debt
Securities.

ARTICLE XV

SUBORDINATION OF DEBT SECURITIES

     SECTION 15.01. Agreement to Subordinate.

          The Company covenants and agrees, and each holder of Debt Securities issued hereunder and
under any supplemental indenture (the “Additional Provisions”) by such Securityholder’s acceptance
thereof likewise covenants and agrees, that all Debt Securities shall be issued subject to the
provisions of this Article XV; and each Securityholder, whether upon original issue or upon
transfer or assignment thereof, accepts and agrees to be bound by such provisions.

          The payment by the Company of the payments due on all Debt Securities issued hereunder and
under any Additional Provisions shall, to the extent and in the manner hereinafter set forth, be
subordinated and junior in right of payment to the prior payment in full of all Senior Indebtedness
of the Company, whether outstanding at the date of this Indenture or thereafter incurred.

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          No provision of this Article XV shall prevent the occurrence of any Default or Event of
Default hereunder.

     SECTION 15.02. Default on Senior Indebtedness.

          In the event and during the continuation of any default by the Company in the payment of
principal, premium, interest or any other payment due on any Senior Indebtedness of the Company
following any applicable grace period, or in the event that the maturity of any Senior Indebtedness
of the Company has been accelerated because of a default, and such acceleration has not been
rescinded or canceled and such Senior Indebtedness has not been paid in full, then, in either case,
no payment shall be made by the Company with respect to the payments due on the Debt Securities.

          In the event that, notwithstanding the foregoing, any payment shall be received by the Trustee
when such payment is prohibited by the preceding paragraph of this Section 15.02, such payment
shall, subject to Section 15.06, be held in trust for the benefit of, and shall be paid over or
delivered to, the holders of Senior Indebtedness or their respective representatives, or to the
trustee or trustees under any indenture pursuant to which any of such Senior Indebtedness may have
been issued, as their respective interests may appear, but only to the extent that the holders of
the Senior Indebtedness (or their representative or representatives or a trustee) notify the
Trustee in writing within 90 days of such payment of the amounts then due and owing on the Senior
Indebtedness and only the amounts specified in such notice to the Trustee shall be paid to the
holders of Senior Indebtedness.

     SECTION 15.03. Liquidation; Dissolution; Bankruptcy.

          Upon any payment by the Company or distribution of assets of the Company of any kind or
character, whether in cash, property or securities, to creditors upon any dissolution or winding-up
or liquidation or reorganization of the Company, whether voluntary or involuntary or in bankruptcy,
insolvency, receivership or other proceedings, all amounts due upon all Senior Indebtedness of the
Company shall first be paid in full, or payment thereof provided for in money in accordance with
its terms, before any payment is made by the Company on the Debt Securities; and upon any such
dissolution or winding-up or liquidation or reorganization, any payment by the Company, or
distribution of assets of the Company of any kind or character, whether in cash, property or
securities, to which the Securityholders or the Trustee would be entitled to receive from the
Company, except for the provisions of this Article XV, shall be paid by the Company, or by any
receiver, trustee in bankruptcy, liquidating trustee, agent or other Person making such payment or
distribution, or by the Securityholders or by the Trustee under this Indenture if received by them
or it, directly to the holders of Senior Indebtedness of the Company (pro rata to such holders on
the basis of the respective amounts of Senior Indebtedness held by such holders, as calculated by
the Company) or their representative or representatives, or to the trustee or trustees under any
indenture pursuant to which any instruments evidencing such Senior Indebtedness may have been
issued, as their respective interests may appear, to the extent necessary to pay such Senior
Indebtedness in full, in money or money’s worth, after giving effect to any concurrent payment or
distribution to or for the holders of such Senior Indebtedness, before any payment or distribution
is made to the Securityholders.

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          In the event that, notwithstanding the foregoing, any payment or distribution of assets of the
Company of any kind or character, whether in cash, property or securities, prohibited by the
foregoing, shall be received by the Trustee before all Senior Indebtedness of the Company is paid
in full, or provision is made for such payment in money in accordance with its terms, such payment
or distribution shall be held in trust for the benefit of and shall be paid over or delivered to
the holders of such Senior Indebtedness or their representative or representatives, or to the
trustee or trustees under any indenture pursuant to which any instruments evidencing such Senior
Indebtedness may have been issued, as their respective interests may appear, as calculated by the
Company, for application to the payment of all Senior Indebtedness of the Company remaining unpaid
to the extent necessary to pay such Senior Indebtedness in full in money in accordance with its
terms, after giving effect to any concurrent payment or distribution to or for the benefit of the
holders of such Senior Indebtedness.

          For purposes of this Article XV, the words “cash, property or securities” shall not be deemed
to include shares of stock of the Company as reorganized or readjusted, or securities of the
Company or any other corporation provided for by a plan of reorganization or readjustment, the
payment of which is subordinated at least to the extent provided in this Article XV with respect to
the Debt Securities to the payment of all Senior Indebtedness of the Company, that may at the time
be outstanding, provided, that (a) such Senior Indebtedness is assumed by the new
corporation, if any, resulting from any such reorganization or readjustment, and (b) the rights of
the holders of such Senior Indebtedness are not, without the consent of such holders, altered by
such reorganization or readjustment. The consolidation of the Company with, or the merger of the
Company into, another corporation or the liquidation or dissolution of the Company following the
conveyance, transfer or other disposition of its property as an entirety, or substantially as an
entirety, to another corporation upon the terms and conditions provided for in Article XI of this
Indenture shall not be deemed a dissolution, winding-up, liquidation or reorganization for the
purposes of this Section 15.03 if such other corporation shall, as a part of such consolidation,
merger, conveyance or transfer, comply with the conditions stated in Article XI of this Indenture.
Nothing in Section 15.02 or in this Section 15.03 shall apply to claims of, or payments to, the
Trustee under or pursuant to Section 6.06 of this Indenture.

     SECTION 15.04. Subrogation.

          Subject to the payment in full of all Senior Indebtedness of the Company, the Securityholders
shall be subrogated to the rights of the holders of such Senior Indebtedness to receive payments or
distributions of cash, property or securities of the Company applicable to such Senior Indebtedness
until all payments due on the Debt Securities shall be paid in full; and, for the purposes of such
subrogation, no payments or distributions to the holders of such Senior Indebtedness of any cash,
property or securities to which the Securityholders or the Trustee would be entitled except for the
provisions of this Article XV, and no payment over pursuant to the provisions of this Article XV to
or for the benefit of the holders of such Senior Indebtedness by Securityholders or the Trustee,
shall, as between the Company, its creditors other than holders of Senior Indebtedness of the
Company, and the Securityholders be deemed to be a payment or distribution by the Company to or on
account of such Senior Indebtedness. It is understood that the provisions of this Article XV are
and are intended solely for the purposes of defining the relative rights of the Securityholders, on
the one hand, and the holders of such Senior Indebtedness, on the other hand.

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          Nothing contained in this Article XV or elsewhere in this Indenture, any Additional Provisions
or in the Debt Securities is intended to or shall impair, as between the Company, its creditors
other than the holders of Senior Indebtedness of the Company, and the Securityholders, the
obligation of the Company, which is absolute and unconditional, to pay to the Securityholders all
payments on the Debt Securities as and when the same shall become due and payable in accordance
with their terms, or is intended to or shall affect the relative rights of the Securityholders and
creditors of the Company, other than the holders of Senior Indebtedness of the Company, nor shall
anything herein or therein prevent the Trustee or the holder of any Debt Security from exercising
all remedies otherwise permitted by applicable law upon default under this Indenture, subject to
the rights, if any, under this Article XV of the holders of such Senior Indebtedness in respect of
cash, property or securities of the Company received upon the exercise of any such remedy.

          Upon any payment or distribution of assets of the Company referred to in this Article XV, the
Trustee, subject to the provisions of Article VI of this Indenture, and the Securityholders shall
be entitled to conclusively rely upon any order or decree made by any court of competent
jurisdiction in which such dissolution, winding-up, liquidation or reorganization proceedings are
pending, or a certificate of the receiver, trustee in bankruptcy, liquidation trustee, agent or
other Person making such payment or distribution, delivered to the Trustee or to the
Securityholders, for the purposes of ascertaining the Persons entitled to participate in such
distribution, the holders of Senior Indebtedness and other indebtedness of the Company, the amount
thereof or payable thereon, the amount or amounts paid or distributed thereon and all other facts
pertinent thereto or to this Article XV.

     SECTION 15.05. Trustee to Effectuate Subordination.

          Each Securityholder by such Securityholder’s acceptance thereof authorizes and directs the
Trustee on such Securityholder’s behalf to take such action as may be necessary or appropriate to
effectuate the subordination provided in this Article XV and appoints the Trustee such
Securityholder’s attorney-in-fact for any and all such purposes.

     SECTION 15.06. Notice by the Company.

          The Company shall give prompt written notice to a Responsible Officer of the Trustee at the
Principal Office of the Trustee of any fact known to the Company that would prohibit the making of
any payment of moneys to or by the Trustee in respect of the Debt Securities pursuant to the
provisions of this Article XV. Notwithstanding the provisions of this Article XV or any other
provision of this Indenture or any Additional Provisions, the Trustee shall not be charged with
knowledge of the existence of any facts that would prohibit the making of any payment of moneys to
or by the Trustee in respect of the Debt Securities pursuant to the provisions of this Article XV,
unless and until a Responsible Officer of the Trustee at the Principal Office of the Trustee shall
have received written notice thereof from the Company or a holder or holders of Senior Indebtedness
or from any trustee therefor; and before the receipt of any such written notice, the Trustee,
subject to the provisions of Article VI of this Indenture, shall be entitled in all respects to
assume that no such facts exist; provided, however, that if the Trustee shall not
have received the notice provided for in this Section 15.06 at least two Business Days prior to the
date upon which by the terms hereof any money may become payable for any

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purpose (including, without limitation, the payment of the principal of (or premium, if any)
or interest on any Debt Security), then, anything herein contained to the contrary notwithstanding,
the Trustee shall have full power and authority to receive such money and to apply the same to the
purposes for which they were received, and shall not be affected by any notice to the contrary that
may be received by it within two Business Days prior to such date.

          The Trustee, subject to the provisions of Article VI of this Indenture, shall be entitled to
conclusively rely on the delivery to it of a written notice by a Person representing himself or
herself to be a holder of Senior Indebtedness of the Company (or a trustee or representative on
behalf of such holder) to establish that such notice has been given by a holder of such Senior
Indebtedness or a trustee or representative on behalf of any such holder or holders. In the event
that the Trustee determines in good faith that further evidence is required with respect to the
right of any Person as a holder of such Senior Indebtedness to participate in any payment or
distribution pursuant to this Article XV, the Trustee may request such Person to furnish evidence
to the reasonable satisfaction of the Trustee as to the amount of such Senior Indebtedness held by
such Person, the extent to which such Person is entitled to participate in such payment or
distribution and any other facts pertinent to the rights of such Person under this Article XV, and,
if such evidence is not furnished, the Trustee may defer any payment to such Person pending
judicial determination as to the right of such Person to receive such payment.

     SECTION 15.07. Rights of the Trustee, Holders of Senior Indebtedness.

          The Trustee in its individual capacity shall be entitled to all the rights set forth in this
Article XV in respect of any Senior Indebtedness at any time held by it, to the same extent as any
other holder of Senior Indebtedness, and nothing in this Indenture or any Additional Provisions
shall deprive the Trustee of any of its rights as such holder.

          With respect to the holders of Senior Indebtedness of the Company, the Trustee undertakes to
perform or to observe only such of its covenants and obligations as are specifically set forth in
this Article XV, and no implied covenants or obligations with respect to the holders of such Senior
Indebtedness shall be read into this Indenture or any Additional Provisions against the Trustee.
The Trustee shall not owe or be deemed to owe any fiduciary duty to the holders of such Senior
Indebtedness and, subject to the provisions of Article VI of this Indenture, the Trustee shall not
be liable to any holder of such Senior Indebtedness if it shall pay over or deliver to
Securityholders, the Company or any other Person money or assets to which any holder of such Senior
Indebtedness shall be entitled by virtue of this Article XV or otherwise.

          Nothing in this Article XV shall apply to claims of, or payments to, the Trustee under or
pursuant to Section 6.06.

     SECTION 15.08. Subordination May Not Be Impaired.

          No right of any present or future holder of any Senior Indebtedness of the Company to enforce
subordination as herein provided shall at any time in any way be prejudiced or impaired by any act
or failure to act on the part of the Company, or by any act or failure to act, in good faith, by
any such holder, or by any noncompliance by the Company, with the terms,

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provisions and covenants of this Indenture, regardless of any knowledge thereof that any such
holder may have or otherwise be charged with.

          Without in any way limiting the generality of the foregoing paragraph, the holders of Senior
Indebtedness of the Company may, at any time and from time to time, without the consent of or
notice to the Trustee or the Securityholders, without incurring responsibility to the
Securityholders and without impairing or releasing the subordination provided in this Article XV or
the obligations hereunder of the Securityholders to the holders of such Senior Indebtedness, do any
one or more of the following: (a) change the manner, place or terms of payment or extend the time
of payment of, or renew or alter, such Senior Indebtedness, or otherwise amend or supplement in any
manner such Senior Indebtedness or any instrument evidencing the same or any agreement under which
such Senior Indebtedness is outstanding; (b) sell, exchange, release or otherwise deal with any
property pledged, mortgaged or otherwise securing such Senior Indebtedness; (c) release any Person
liable in any manner for the collection of such Senior Indebtedness; and (d) exercise or refrain
from exercising any rights against the Company, and any other Person.

          LaSalle Bank National Association, in its capacity as Trustee, hereby accepts the trusts in
this Indenture declared and provided, upon the terms and conditions herein above set forth.

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          IN WITNESS WHEREOF, the parties hereto have caused this Indenture to be duly executed by their
respective officers thereunto duly authorized, as of the day and year first above written.

	 	 	 	 	 
	 	Wintrust Financial Corporation

 	 
	 	By:  	/s/ David A. Dykstra
 	 
	 	 	Name:  	David A. Dykstra 	 
	 	 	Title:  	Senior Executive Vice President and Chief
Operating Officer 	 
	 
	 	LaSalle Bank National Association, as Trustee

 	 
	 	By:  	/s/ Michael Oliver
 	 
	 	 	Name:  	Michael Oliver 	 
	 	 	Title:  	Assistant Vice President 	 
	 

(8) Wintrust Financial Corporation

 

 

EXHIBIT A

FORM OF JUNIOR SUBORDINATED DEBT SECURITY

DUE 2036

[FORM OF FACE OF SECURITY]

     THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE
“SECURITIES ACT”), OR ANY STATE SECURITIES LAWS OR ANY OTHER APPLICABLE SECURITIES LAWS. NEITHER
THIS SECURITY NOR ANY INTEREST OR PARTICIPATION HEREIN MAY BE REOFFERED, SOLD, ASSIGNED,
TRANSFERRED, PLEDGED, ENCUMBERED OR OTHERWISE DISPOSED OF IN THE ABSENCE OF SUCH REGISTRATION OR
UNLESS SUCH TRANSACTION IS EXEMPT FROM, OR NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE
SECURITIES ACT. THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF AGREES TO OFFER, SELL OR
OTHERWISE TRANSFER SUCH SECURITY ONLY (A) TO THE COMPANY, (B) PURSUANT TO RULE 144A UNDER THE
SECURITIES ACT (“RULE 144A”), TO A PERSON THE HOLDER REASONABLY BELIEVES IS A “QUALIFIED
INSTITUTIONAL BUYER” AS DEFINED IN RULE 144A THAT PURCHASES FOR ITS OWN ACCOUNT OR FOR THE ACCOUNT
OF A QUALIFIED INSTITUTIONAL BUYER TO WHOM NOTICE IS GIVEN THAT THE TRANSFER IS BEING MADE IN
RELIANCE ON RULE 144A, (C) TO A “NON U.S. PERSON” IN AN “OFFSHORE TRANSACTION” PURSUANT TO
REGULATION S UNDER THE SECURITIES ACT, (D) PURSUANT TO AN EXEMPTION FROM THE REGISTRATION
REQUIREMENTS OF THE SECURITIES ACT TO AN “ACCREDITED INVESTOR” WITHIN THE MEANING OF SUBPARAGRAPH
(a) (1), (2), (3) OR (7) OF RULE 501 UNDER THE SECURITIES ACT THAT IS ACQUIRING THE SECURITY FOR
ITS OWN ACCOUNT, OR FOR THE ACCOUNT OF SUCH AN “ACCREDITED INVESTOR,” FOR INVESTMENT PURPOSES AND
NOT WITH A VIEW TO, OR FOR OFFER OR SALE IN CONNECTION WITH, ANY DISTRIBUTION IN VIOLATION OF THE
SECURITIES ACT, OR (E) PURSUANT TO ANOTHER AVAILABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS
OF THE SECURITIES ACT, SUBJECT TO THE COMPANY’S RIGHT PRIOR TO ANY SUCH OFFER, SALE OR TRANSFER
PURSUANT TO CLAUSES (D) OR (E) TO REQUIRE THE DELIVERY OF AN OPINION OF COUNSEL, CERTIFICATION
AND/OR OTHER INFORMATION SATISFACTORY TO IT IN ACCORDANCE WITH THE INDENTURE, A COPY OF WHICH MAY
BE OBTAINED FROM THE COMPANY. THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF AGREES THAT IT
WILL COMPLY WITH THE FOREGOING RESTRICTIONS.

     THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF AGREES, REPRESENTS AND WARRANTS THAT IT
WILL NOT ENGAGE IN HEDGING TRANSACTIONS INVOLVING THIS SECURITY UNLESS SUCH TRANSACTIONS ARE IN
COMPLIANCE WITH THE SECURITIES ACT OR AN APPLICABLE EXEMPTION THEREFROM.

A-1

 

     THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF ALSO AGREES, REPRESENTS AND WARRANTS THAT
IT IS NOT AN EMPLOYEE BENEFIT, INDIVIDUAL RETIREMENT ACCOUNT OR OTHER PLAN OR ARRANGEMENT SUBJECT
TO TITLE I OF THE EMPLOYEE RETIREMENT INCOME SECURITY ACT OF 1974, AS AMENDED (“ERISA”), OR SECTION
4975 OF THE INTERNAL REVENUE CODE OF 1986, AS AMENDED (THE “CODE”), (EACH A “PLAN”), OR AN ENTITY
WHOSE UNDERLYING ASSETS INCLUDE “PLAN ASSETS” BY REASON OF ANY PLAN’S INVESTMENT IN THE ENTITY AND
NO PERSON INVESTING “PLAN ASSETS” OF ANY PLAN MAY ACQUIRE OR HOLD THIS SECURITY OR ANY INTEREST
THEREIN, UNLESS SUCH PURCHASER OR HOLDER IS ELIGIBLE FOR THE EXEMPTIVE RELIEF AVAILABLE UNDER U.S.
DEPARTMENT OF LABOR PROHIBITED TRANSACTION CLASS EXEMPTION 96-23, 95-60, 91-38, 90-1 OR 84-14 OR
ANOTHER APPLICABLE EXEMPTION OR ITS PURCHASE AND HOLDING OF THIS SECURITY IS NOT PROHIBITED BY
SECTION 406 OF ERISA OR SECTION 4975 OF THE CODE WITH RESPECT TO SUCH PURCHASE OR HOLDING. ANY
PURCHASER OR HOLDER OF THIS SECURITY OR ANY INTEREST THEREIN WILL BE DEEMED TO HAVE REPRESENTED BY
ITS PURCHASE AND HOLDING THEREOF THAT EITHER (i) IT IS NOT AN EMPLOYEE BENEFIT PLAN WITHIN THE
MEANING OF SECTION 3(3) OF ERISA, OR A PLAN TO WHICH SECTION 4975 OF THE CODE IS APPLICABLE, A
TRUSTEE OR OTHER PERSON ACTING ON BEHALF OF AN EMPLOYEE BENEFIT PLAN OR PLAN, OR ANY OTHER PERSON
OR ENTITY USING THE ASSETS OF ANY EMPLOYEE BENEFIT PLAN OR PLAN TO FINANCE SUCH PURCHASE, OR (ii)
SUCH PURCHASE WILL NOT RESULT IN A PROHIBITED TRANSACTION UNDER SECTION 406 OF ERISA OR SECTION
4975 OF THE CODE FOR WHICH THERE IS NO APPLICABLE STATUTORY OR ADMINISTRATIVE EXEMPTION.

     IN CONNECTION WITH ANY TRANSFER, THE HOLDER OF THIS SECURITY WILL DELIVER TO THE COMPANY AND
TRUSTEE SUCH CERTIFICATES AND OTHER INFORMATION AS MAY BE REQUIRED BY THE INDENTURE TO CONFIRM THAT
THE TRANSFER COMPLIES WITH THE FOREGOING RESTRICTIONS.

     THIS SECURITY WILL BE ISSUED AND MAY BE TRANSFERRED ONLY IN BLOCKS HAVING A PRINCIPAL AMOUNT
OF NOT LESS THAN $100,000 AND MULTIPLES OF $1,000 IN EXCESS THEREOF. ANY ATTEMPTED TRANSFER OF THIS
SECURITY IN A BLOCK HAVING A PRINCIPAL AMOUNT OF LESS THAN $100,000 SHALL BE DEEMED TO BE VOID AND
OF NO LEGAL EFFECT WHATSOEVER. ANY SUCH PURPORTED TRANSFEREE SHALL BE DEEMED NOT TO BE THE HOLDER
OF THIS SECURITY FOR ANY PURPOSE, INCLUDING, BUT NOT LIMITED TO, THE RECEIPT OF DISTRIBUTIONS ON
THIS SECURITY, AND SUCH PURPORTED TRANSFEREE SHALL BE DEEMED TO HAVE NO INTEREST WHATSOEVER IN THIS
SECURITY.

     THIS OBLIGATION IS NOT A DEPOSIT AND IS NOT INSURED BY THE UNITED STATES OR ANY AGENCY OR FUND
OF THE UNITED STATES, INCLUDING THE FEDERAL DEPOSIT INSURANCE CORPORATION. THIS OBLIGATION IS
SUBORDINATED TO THE CLAIMS OF DEPOSITORS AND THE CLAIMS OF GENERAL AND SECURED CREDITORS OF THE
COMPANY, IS INELIGIBLE AS COLLATERAL

A-2

 

FOR A LOAN BY THE COMPANY OR ANY OF ITS SUBSIDIARIES AND IS NOT SECURED.

A-3

 

Form of Junior Subordinated Debt Security due 2036

of

Wintrust Financial Corporation

     Wintrust Financial Corporation, a financial holding company incorporated in Illinois (the
“Company”), for value received promises to pay to LaSalle Bank National Association, not in its
individual capacity but solely as Institutional Trustee for Wintrust Capital Trust IX, a Delaware
statutory trust (the “Securityholder”), or registered assigns, the principal sum of Fifty One
Million Five Hundred Forty Seven Thousand Dollars on September 15, 2036 and to pay interest on said
principal sum from September 1, 2006, or from the most recent interest payment date (each such
date, an “Interest Payment Date”) to which interest has been paid or duly provided for, quarterly
(subject to deferral as set forth herein) in arrears on March 15, June 15, September 15 and
December 15 of each year commencing December 15, 2006, at the rate of 6.836% (the “Fixed Rate”) per
annum until September 15, 2011 (the “Fixed Rate Period”) and thereafter at a variable per annum
rate equal to LIBOR (as defined in the Indenture) plus 1.63% (the “Variable Rate” and together with
the Fixed Rate, the “Interest Rate”) (provided, however, that the Interest Rate for any Interest
Payment Period may not exceed the highest rate permitted by New York law, as the same may be
modified by United States law of general applicability) until the principal hereof shall have
become due and payable, and on any overdue principal and (without duplication and to the extent
that payment of such interest is enforceable under applicable law) on any overdue installment of
interest at an annual rate equal to the Interest Rate in effect for each such Extension Period
compounded quarterly. The amount of interest payable on any Interest Payment Date shall be computed
during the Fixed Rate Period on the basis of a 360-day year of twelve 30-day months and the amount
payable for any partial period shall be computed on the basis of the number of days elapsed in a
360-day year of twelve 30-day months, and thereafter on the basis of a 360-day year and the actual
number of days elapsed in the relevant interest period. Notwithstanding anything to the contrary
contained herein, if any Interest Payment Date, other than on the Maturity Date, any Redemption
Date (to the extent redeemed) or the Special Redemption Date, falls on a day that is not a Business
Day, then any interest payable will be paid on, and such Interest Payment Date will be moved to,
the next succeeding Business Day, and no additional interest will accrue for each day that such
payment is delayed as a result thereof. If the Maturity Date, Redemption Date or Special
Redemption Date falls on a day that is not a Business Day, then the principal, premium, if any,
and/or interest payable on such date will be paid on the next succeeding Business Day, and no
additional interest will accrue (except that, if such Business Day falls in the next calendar year,
such payment will be made on the immediately preceding Business Day). The interest installment so
payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided
in the Indenture, be paid to the Person in whose name this Debt Security (or one or more
Predecessor Securities, as defined in said Indenture) is registered at the close of business on the
regular record date for such interest installment, except that interest and any Deferred Interest
payable on the Maturity Date shall be paid to the Person to whom principal is paid. Any such
interest installment not punctually paid or duly provided for shall forthwith cease to be payable
to the registered Securityholders on such regular record date and may be paid to the Person in
whose name this Debt Security (or one or more Predecessor Debt Securities) is registered at the
close of business on a special record date to be fixed by the Trustee for the payment of such
defaulted

A-4

 

interest, notice whereof shall be given to the registered Securityholders not less than 10
days prior to such special record date, all as more fully provided in the Indenture. The principal
of and interest on this Debt Security shall be payable at the office or agency of the Trustee (or
other Paying Agent appointed by the Company) maintained for that purpose in any coin or currency of
the United States of America that at the time of payment is legal tender for payment of public and
private debts; provided, however, that payment of interest may be made at the
option of the Company by check mailed to the registered Securityholder at such address as shall
appear in the Debt Security Register or by wire transfer of immediately available funds to an
account appropriately designated by the holder hereof. Notwithstanding the foregoing, so long as
the holder of this Debt Security is the Institutional Trustee, payment of the principal of and
premium, if any, and interest on this Debt Security shall be made in immediately available funds
when due at such place and to such account as may be designated by the Institutional Trustee. All
payments in respect of this Debt Security shall be payable in any coin or currency of the United
States of America that at the time of payment is legal tender for payment of public and private
debts.

     Upon submission of Notice (as defined in the Indenture) and so long as no Event of Default
pursuant to paragraphs (c), (e), (f) or (g) of Section 5.01 of the Indenture has occurred and is
continuing, the Company shall have the right under the Indenture, from time to time and without
causing an Event of Default, to defer payments of interest on the Debt Securities by extending the
interest distribution period on the Debt Securities at any time and from time to time during the
term of the Debt Securities, for up to 20 consecutive quarterly periods (each such extended
interest distribution period, an “Extension Period”), during which Extension Period no interest
shall be due and payable (except any Additional Interest that may be due and payable). During any
Extension Period, interest will continue to accrue on the Debt Securities, and interest on such
accrued interest (such accrued interest and interest thereon referred to herein as “Deferred
Interest”) will accrue at an annual rate equal to the Interest Rate applicable during such
Extension Period, compounded quarterly from the date such Deferred Interest would have been payable
were it not for the Extension Period, to the extent permitted by law. No Extension Period may end
on a date other than an Interest Payment Date. At the end of any such Extension Period the Company
shall pay all Deferred Interest then accrued and unpaid on the Debt Securities; provided,
however, that no Extension Period may extend beyond the Maturity Date, Redemption Date (to
the extent redeemed) or Special Redemption Date; and provided, further, however,
during any such Extension Period, the Company may not (i) declare or pay any dividends or
distributions on, or redeem, purchase, acquire, or make a liquidation payment with respect to, any
of the Company’s capital stock or (ii) make any payment of principal of or premium, if any, or
interest on or repay, repurchase or redeem any debt securities of the Company that rank pari passu
in all respects with or junior in interest to the Debt Securities or (iii) make any payment under
any guarantees of the Company that rank in all respects pari passu with or junior in respect to the
Capital Securities Guarantee (other than (a) repurchases, redemptions or other acquisitions of
shares of capital stock of the Company (A) in connection with any employment contract, benefit plan
or other similar arrangement with or for the benefit of one or more employees, officers, directors
or consultants, (B) in connection with a dividend reinvestment or stockholder stock purchase plan
or (C) in connection with the issuance of capital stock of the Company (or securities convertible
into or exercisable for such capital stock), as consideration in an acquisition transaction entered
into prior to the applicable Extension Period, (b) as a result of any exchange, reclassification,
combination or conversion of any class or series of the

A-5

 

Company’s capital stock (or any capital stock of a subsidiary of the Company) for any class or
series of the Company’s capital stock or of any class or series of the Company’s indebtedness for
any class or series of the Company’s capital stock, (c) the purchase of fractional interests in
shares of the Company’s capital stock pursuant to the conversion or exchange provisions of such
capital stock or the security being converted or exchanged, (d) any declaration of a dividend in
connection with any stockholder’s rights plan, or the issuance of rights, stock or other property
under any stockholder’s rights plan, or the redemption or repurchase of rights pursuant thereto, or
(e) any dividend in the form of stock, warrants, options or other rights where the dividend stock
or the stock issuable upon exercise of such warrants, options or other rights is the same stock as
that on which the dividend is being paid or ranks pari passu with or junior to such stock). Prior
to the termination of any Extension Period, the Company may further extend such Extension Period;
provided, that no Extension Period (including all previous and further consecutive
extensions that are part of such Extension Period) shall exceed 20 consecutive quarterly periods,
or extend beyond the Maturity Date, Redemption Date (to the extent redeemed) or Special Redemption
Date. Upon the termination of any Extension Period and upon the payment of all Deferred Interest,
the Company may commence a new Extension Period, subject to the foregoing requirements. No
interest or Deferred Interest shall be due and payable during an Extension Period, except at the
end thereof, but Deferred Interest shall accrue upon each installment of interest that would
otherwise have been due and payable during such Extension Period until such installment is paid.
The Company must give the Trustee notice of its election to begin any Extension Period or extend an
Extension Period (“Notice”) not later than the related regular record date for the relevant
Interest Payment Date. The Notice shall describe why the Company has elected to begin an Extension
Period. The Notice shall acknowledge and affirm the Company’s understanding that it is prohibited
from issuing dividends and other distributions during the Extension Period. Upon receipt of the
Notice, the Placement Agent shall have the right, at its sole discretion, to disclose the name of
the Company, the fact that the Company has elected to begin an Extension Period and other
information that such Placement Agent, at its sole discretion, deems relevant to the Company’s
election to begin an Extension Period. The Trustee shall give notice of the Company’s election to
begin a new Extension Period to the Securityholders.

     The indebtedness evidenced by this Debt Security is, to the extent provided in the Indenture,
subordinate and junior in right of payment to the prior payment in full of all Senior Indebtedness,
and this Debt Security is issued subject to the provisions of the Indenture with respect thereto.
Each holder of this Debt Security, by accepting the same, (a) agrees to and shall be bound by such
provisions, (b) authorizes and directs the Trustee on such Securityholder’s behalf to take such
action as may be necessary or appropriate to acknowledge or effectuate the subordination so
provided and (c) appoints the Trustee such Securityholder’s attorney-in-fact for any and all such
purposes. Each holder hereof, by such holder’s acceptance hereof, hereby waives all notice of the
acceptance of the subordination provisions contained herein and in the Indenture by each holder of
Senior Indebtedness, whether now outstanding or hereafter incurred, and waives reliance by each
such Securityholder upon said provisions.

     The Company waives diligence, presentment, demand for payment, notice of nonpayment, notice of
protest, and all other demands and notices.

A-6

 

     This Debt Security shall not be entitled to any benefit under the Indenture hereinafter
referred to and shall not be valid or become obligatory for any purpose until the certificate of
authentication hereon shall have been signed by or on behalf of the Trustee.

     The provisions of this Debt Security are continued on the reverse side hereof and such
continued provisions shall for all purposes have the same effect as though fully set forth at this
place.

A-7

 

     IN WITNESS WHEREOF, the Company has duly executed this certificate.

	 	 	 	 	 
	 	 	Wintrust Financial Corporation
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
 
	 

	 	Name:	 	 
	 

	 	 	 	 
 
	 

	 	Title:	 	 
	 

	 	 	 	 
 

Dated:                    , 2006

CERTIFICATE OF AUTHENTICATION

     This represents Debt Securities referred to in the within-mentioned Indenture.

	 	 	 	 	 
	 	 	LaSalle Bank National Association, not in its

individual capacity but solely as Trustee
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Authorized Signatory

     Dated:                    , 2006

A-8

 

[FORM OF REVERSE OF SECURITY]

     This Debt Security is one of a duly authorized series of Debt Securities of the Company, all
issued or to be issued pursuant to an Indenture (the “Indenture”), dated as of September 1, 2006,
duly executed and delivered between the Company and LaSalle Bank National Association, as Trustee
(the “Trustee”), to which Indenture and all indentures supplemental thereto reference is hereby
made for a description of the rights, limitations of rights, obligations, duties and immunities
thereunder of the Trustee, the Company and the holders of the Debt Securities (referred to herein
as the “Debt Securities”) of which this Debt Security is a part. The summary of the terms of this
Debt Security contained herein does not purport to be complete and is qualified by reference to the
Indenture.

     Upon the occurrence and continuation of a Tax Event, an Investment Company Event or a Capital
Treatment Event (each a “Special Event”), this Debt Security may become due and payable, in whole
or in part, at any time, within 90 days following the occurrence of such Tax Event, Investment
Company Event or Capital Treatment Event (the “Special Redemption Date”), as the case may be, at
the Special Redemption Price.

     The Company shall also have the right to redeem this Debt Security at the option of the
Company, in whole or in part, on any March 15, June 15, September 15 or December 15 on or after
September 15, 2011 (a “Redemption Date”), at the Redemption Price.

     Any redemption pursuant to either of the two preceding paragraphs will be made, subject to the
receipt by the Company of prior approval from any regulatory authority with jurisdiction over the
Company if such approval is then required under applicable capital guidelines or policies of such
regulatory authority, upon not less than 30 days’ nor more than 60 days’ notice. If the Debt
Securities are only partially redeemed by the Company, the Debt Securities will be redeemed pro
rata or by lot or by any other method utilized by the Trustee.

     “Redemption Price” means 100% of the principal amount of the Debt Securities being redeemed
plus accrued and unpaid interest on such Debt Securities to the Redemption Date.

     “Special Redemption Price” means 100% of the principal amount of the Debt Securities being
redeemed plus accrued and unpaid interest on such Debt Securities to the Special Redemption Date.

     In the event of redemption of this Debt Security in part only, a new Debt Security or Debt
Securities for the unredeemed portion hereof will be issued in the name of the Securityholder
hereof upon the cancellation hereof.

     In certain cases where an Event of Default pursuant to paragraphs (c), (e), (f) or (g) of
Section 5.01 of the Indenture shall have occurred and be continuing, the principal of all of the
Debt Securities may be declared, and, in certain cases, shall ipso facto become, due and payable,
and upon such declaration of acceleration shall become due and payable, in each case, in the
manner, with the effect and subject to the conditions provided in the Indenture.

     The Indenture contains provisions permitting the Company and the Trustee, with the consent of
the holders of not less than a majority in aggregate principal amount of the Debt

A-9

 

Securities at the time outstanding affected thereby, as specified in the Indenture, to execute
supplemental indentures for the purpose of adding any provisions to or changing in any manner or
eliminating any of the provisions of the Indenture or of any supplemental indenture or of modifying
in any manner the rights of the Securityholders; provided, however, that no such
supplemental indenture shall, among other things, without the consent of the holders of each Debt
Security then outstanding and affected thereby (i) change the Maturity Date of any Debt Security,
or reduce the principal amount thereof or any redemption premium thereon, or reduce the rate (or
manner of calculation of the rate) or extend the time of payment of interest thereon, or reduce
(other than as a result of the maturity or earlier redemption of any such Debt Security in
accordance with the terms of the Indenture and such Debt Security) or increase the aggregate
principal amount of Debt Securities then outstanding, or change any of the redemption provisions,
or make the principal thereof or any interest or premium thereon payable in any coin or currency
other than United States Dollars, or impair or affect the right of any Securityholder to institute
suit for the payment thereof, or (ii) reduce the aforesaid percentage of Debt Securities, the
holders of which are required to consent to any such supplemental indenture. The Indenture also
contains provisions permitting the holders of a majority in aggregate principal amount of the Debt
Securities at the time outstanding, on behalf of all of the Securityholders, to waive any past
default in the performance of any of the covenants contained in the Indenture, or established
pursuant to the Indenture, and its consequences, except (a) a default in payments due in respect of
any of the Debt Securities, (b) in respect of covenants or provisions of the Indenture which cannot
be modified or amended without the consent of the holder of each Debt Security affected, or (c) in
respect of the covenants of the Company relating to its ownership of Common Securities of the
Trust. Any such consent or waiver by the registered holder of this Debt Security (unless revoked as
provided in the Indenture) shall be conclusive and binding upon such Securityholder and upon all
future holders and owners of this Debt Security and of any Debt Security issued in exchange herefor
or in place hereof (whether by registration of transfer or otherwise), irrespective of whether or
not any notation of such consent or waiver is made upon this Debt Security.

     No reference herein to the Indenture and no provision of this Debt Security or of the
Indenture shall alter or impair the obligation of the Company, which is absolute and unconditional,
to pay all payments due on this Debt Security at the time and place and at the rate and in the
money herein prescribed.

     As provided in the Indenture and subject to certain limitations herein and therein set forth,
this Debt Security is transferable by the registered holder hereof on the Debt Security Register of
the Company, upon surrender of this Debt Security for registration of transfer at the office or
agency of the Trustee in Chicago, Illinois accompanied by a written instrument or instruments of
transfer in form satisfactory to the Company or the Trustee duly executed by the registered holder
hereof or such Securityholder’s attorney duly authorized in writing, and thereupon one or more new
Debt Securities of authorized denominations and for the same aggregate principal amount will be
issued to the designated transferee or transferees. No service charge will be made for any such
registration of transfer, but the Company may require payment of a sum sufficient to cover any tax
or other governmental charge payable in relation thereto.

     Prior to due presentment for registration of transfer of this Debt Security, the Company, the
Trustee, any Authenticating Agent, any Paying Agent, any transfer agent and the Debt

A-10

 

Security Registrar may deem and treat the registered holder hereof as the absolute owner
hereof (whether or not this Debt Security shall be overdue and notwithstanding any notice of
ownership or writing hereon) for the purpose of receiving payment of the principal of and premium,
if any, and interest on this Debt Security and for all other purposes, and neither the Company nor
the Trustee nor any Authenticating Agent nor any Paying Agent nor any transfer agent nor any Debt
Security Registrar shall be affected by any notice to the contrary.

     No recourse shall be had for the payment of the principal of or the interest on this Debt
Security, or for any claim based hereon, or otherwise in respect hereof, or based on or in respect
of the Indenture, against any incorporator, stockholder, officer or director, past, present or
future, as such, of the Company or of any predecessor or successor corporation, whether by virtue
of any constitution, statute or rule of law, or by the enforcement of any assessment or penalty or
otherwise, all such liability being, by the acceptance hereof and as part of the consideration for
the issuance hereof, expressly waived and released.

     The Debt Securities are issuable only in registered certificated form without coupons. As
provided in the Indenture and subject to certain limitations herein and therein set forth, Debt
Securities are exchangeable for a like aggregate principal amount of Debt Securities of a different
authorized denomination, as requested by the Securityholder surrendering the same.

     All terms used in this Debt Security that are defined in the Indenture shall have the meanings
assigned to them in the Indenture.

     THE LAW OF THE STATE OF NEW YORK SHALL GOVERN THE INDENTURE AND THE DEBT SECURITIES, WITHOUT
REGARD TO CONFLICT OF LAWS PRINCIPLES THEREOF (OTHER THAN SECTION 5-1401 OF THE GENERAL OBLIGATIONS
LAW).

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