Document:

exv10w23

 

EXHIBIT 10.23

EMPLOYMENT AGREEMENT

     This Employment Agreement (the “Agreement”) is made by and between Lake Forest Bank & Trust
Company (“Employer”), a state chartered bank, and Randolph M. Hibben, an individual resident in
the State of Illinois (“Executive”) as of March 25,
2005.

W I T N
E S S E T H
  T H A I :

     WHEREAS, Employer is engaged in the business of general
banking;

     WHEREAS, Employer is an affiliate of Wintrust Financial Corporation (“Wintrust”),
an Illinois bank holding company;

     WHEREAS, Executive has particular expertise and knowledge concerning the business of
Employer and its operations and is a valued member of Employer’s senior management;

     WHEREAS, by virtue of Executive’s employment with Employer, Executive will become acquainted
with certain confidential information regarding the services, customers, methods of doing business,
strategic plans, marketing, and other aspects of the business of Employer, Wintrust or its
Affiliates;

     WHEREAS, Employer and Executive desire to state and set forth in this Agreement the terms,
conditions and obligations of the parties with respect to such employment effective as of the date
first written above (the “Effective Date”) and this Agreement is intended by the parties to
supersede all previous agreements and understanding, whether written or oral, concerning such
employment.

     NOW THEREFORE, in consideration of the covenants and agreements contained herein, of
Executive’s employment, of the compensation to be paid by Employer for Executive’s services, and of
Employer’s other undertakings in this Agreement, the parties hereto do hereby agree as follows:

     1. Scope of Employment. Executive will be employed as Chairman and Chief
Executive Officer of Employer and shall perform such duties as may be assigned to Executive by the
Board of Directors of Employer in such position. Executive agrees that during Executive’s
employment Executive will be subject to and abide by the written policies and practices of Employer
and Wintrust, Executive also agrees to assume such new or additional positions and responsibilities
as Executive may from time to time be assigned for or on behalf of Employer, Wintrust, or any
Affiliate of Wintrust Notwithstanding the foregoing, during the Term (as defined in Section 8
herein) of this Agreement, Executive will not be required without Executive’s consent to move
Executive’s principal business location to another location more than a .35 mile radius from
Executive’s principal business location. For purposes of this Agreement, the term “Affiliate” shall
include but not be limited to the entities listed in Exhibit A to this

 

 

Agreement and any subsidiary of any of such entities and shall further include any present or
future affiliate of any of them as defined by the rules and regulations of the Federal Reserve
Board. In the event Executive shall perform services for Wintrust or any Affiliate in addition to
serving as Chairman and Chief Executive Officer of Employer, the provisions of this Agreement shall
also apply to the performance of such services by Executive on behalf of Wintrust or any Affiliate.

     2. Compensation and Benefits. Executive will be paid such base salary as may
from time to time be agreed upon between Executive and Employer. Executive will be entitled to
coverage under such compensation plans, insurance plans and other fringe benefit plans and programs
as may from time to time be established for employees of Wintrust and its Affiliates in accordance
with the terms and conditions of such plans and programs. Executive shall also be eligible to
participate in the Wintrust 1997 Stock Incentive Plan or any successor Plan thereto.

     3. Extent of Service. Executive shall devote Executive’s entire time,
attention and energies to the business of Employer during the Term of this Agreement; but this
shall not be construed as preventing Executive from (a) investing Executive’s personal assets in
such form or manner as will not require any services on the part of Executive in the operation or
the affairs of the corporations, partnerships and other entities in which such investments are made
and in which Executive’s participation is solely that of an investor (subject to any and all rules
and regulations of applicable banking regulators or policies of the Employer governing transactions
with affiliates and ownership interests in customers); (b) engaging (whether or not during normal
business hours) in any other business, professional or civic activities provided that the Board of
Directors of Employer approves of such activities and Executive’s engagement does not result in a
violation of Executive’s covenants under this Section or Sections 4 or 5 hereof; or (c) accepting
appointments to the boards of directors of other companies provided that the Board of Directors of
Employer approves of such appointments and Executive’s performance of Executive’s duties on such
boards does not result in a violation of Executive’s covenants under this Section or Sections 4 and
5 hereof.

     4 Competition. Other than in connection with Executive’s performance of
Executive’s duties hereunder, during the period in which Executive performs services for Employer
and for a period of  two years after termination of Executive’s employment with Employer, regardless
of the reason, Executive shall not directly or indirectly, either alone or in conjunction with any
other person, firm, association, company or corporation:

          (a) serve as an owner, principal, senior manager, or in a position comparable to that
held by Executive at any time during Executive’s employment with Employer, for a bank or other
financial institution (or any branch or affiliate thereof) which offers to its customers commercial
and community banking and/or trust and investment services, and which is located within ten miles
of the principal office or any branch office of the Employer;

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          (b) solicit or conduct business which involves commercial and
community banking and/or trust and investment services with any person, corporation or
other entity which was (i) a customer of the Employer, Wintrust or any other Affiliate of
Wintrust with whom Executive had direct or indirect contact while employed by
Employer or about whom Executive obtained Confidential Information during the fifteen
months prior to the termination of Executive’s employment with Employer, or (ii) a
potential customer with whom Employer, Wintrust, or any Affiliate has, at the time of
Executive’s termination of employment with Employer, an outstanding oral or written
proposal to provide commercial and community banking and/or trust and investment
services and with whom Executive had direct or indirect contact while employed by
Employer;

          (c) request, advise or directly or indirectly invite any of the existing
customers, suppliers or service providers of Employer, Wintrust or any other Affiliate of
Wintrust to withdraw, curtail or cancel its business with Employer, Wintrust or any other
Affiliate of Wintrust, other than through mass mailings or general advertisements not
specifically directed at customers of Employer, Wintrust or any Affiliate;

          (d) hire, solicit, induce or attempt to solicit or induce any employee,
consultant, or agent of Employer, Wintrust or any other Affiliate of Wintrust (i) to
terminate his employment or association with Employer or (ii) to become employed by or
serve in any capacity by a bank or other financial institution which operates or is planned
to operate at any facility which is located within a ten mile radius of the principal office
or any branch office of the Employer; or

          (e) in any way participate in planning or opening a bank or other
financial institution which is located or will be located within a ten mile radius of the
principal office or any branch office of the Employer. For the purposes of this
Agreement, in the event Executive’s geographic area of responsibility as specified herein
shall change during employment with Employer, or as the result of performing services
for Wintrust or any Affiliate of Wintrust, the Executive’s obligation stated in Sections
4(a), 4(d)(ii) and 4(e) shall apply to a ten mile radius of Executive’s revised geographic
area of responsibility.

     Notwithstanding the foregoing, (a) Executive shall not be prevented from: (i) investing or
owning shares of stock of any corporation engaged in any business provided that such shares are
regularly traded on a national securities exchange or any over-the-counter market; (ii) retaining
any shares of stock in any corporation which Executive owned prior to the date of Executive’s
employment with Employer (subject to any and all rules and regulations of applicable banking
regulators or policies of the Employer governing transactions with affiliates and ownership
interests in customers); or (iii) investing as a limited partner (without decision-making
authority) in any private equity fund, provided that Executive’s involvement in such investment is
solely that of a passive investor (subject to any and all rules and regulations of applicable
banking regulators or policies of the Employer governing transactions with affiliates and ownership
interests in customers), and (b) Executive shall not be in violation of Sections 4(a) or 4(e) of
this

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Agreement if, during the two-year period following termination of employment Executive accepts
employment or invests in a bank or other financial institution which is within a 10 mile radius of
the principal offices or any branch office of Wintrust or any
Affiliate of Wintrust (other than
Employer) as long as such facility is not within a ten mile radius of the principal office or any
branch office of the Employer.

     5. Confidential Information. Executive acknowledges that, during Executive’s
employment with Employer, Executive has and will obtain access to Confidential Information of and
for Employer, Wintrust or its Affiliates. For purposes of this Agreement, “Confidential
Information” shall mean information not generally known or available without restriction to the
trade or industry, including, without limitation, the following categories of information and
documentation: (a) documentation and information relating to lending customers of Employer,
Wintrust or any Affiliate, including, but not limited to, lists of lending clients with their
addresses and account numbers, credit analysis reports and other credit files, outstanding loan
amounts, repayment dates and instructions, information regarding the use of the loan proceeds, and
loan maturity and renewal dates; (b) documentation and information relating to depositors of
Employer, Wintrust or any Affiliate, including, but not limited to, lists of depositors with their
addresses and account numbers, amounts held on deposit, types of depository products used and the
number of accounts per customer; (c) documentation and information relating to trust customers of
Employer, Wintrust or any Affiliate, including, but not limited to, lists of trust customers with
their addresses and account numbers, trust investment management contracts, identity of investment
managers, trust corpus amounts, and grantor and beneficiary information; (d) documentation and
information relating to investment management clients of Employer, Wintrust or any Affiliate,
including, but not limited to, lists of investors with their addresses, account numbers and
beneficiary information, investment management contracts, amount of assets held for management, and
the nature of the investment products used; (e) the identity of actual or potential customers of
Employer, Wintrust or any Affiliate, including lists of the same; (f) the identity of suppliers and
service providers of Employer, Wintrust or any Affiliate, including lists of the same and the
material terms of any supply or service contracts; (g) marketing materials and information
regarding the products and services offered by Employer, Wintrust or any Affiliate and the nature
and scope of use of such marketing materials and product information; (h) policy and procedure
manuals and other materials used by Employer, Wintrust or any Affiliate in the training and
development of its employees; (i) identity and contents of all computer systems, programs and
software utilized by Employer, Wintrust or any Affiliate to conduct its operations and manuals or
other instructions for their use; (j) minutes or other summaries of Board of Directors or other
department or committee meetings held by Employer, Wintrust or any Affiliate; (k) the business and
strategic growth plans of Employer, Wintrust or any Affiliate; and (1) confidential communication
materials provided for shareholders of Employer, Wintrust or any Affiliate Absent prior
authorization by Employer or as required in Executive’s duties for Employer, Executive will not at
any time, directly or indirectly, use, permit the use of, disclose or permit the disclosure to any
third party of any such Confidential Information to which Executive will be provided access. These
obligations apply both

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during Executive’s employment with Employer and shall continue beyond the termination
of Executive’s employment and this Agreement.

     6. Inventions. All discoveries, designs, improvements, ideas, and inventions,
whether patentable or not, relating to (or suggested by or resulting from) products, services, or
other technology of Employer, Wintrust or any Affiliate or relating to (or suggested by or
resulting from) methods or processes used or usable in connection with the business of Employer,
Wintrust or any Affiliate that may be conceived, developed, or made by Executive during employment
with Employer (hereinafter “Inventions”), either solely or jointly with others, shall automatically
become the sole property of Employer, Wintrust or an Affiliate. Executive shall immediately
disclose to Employer all such Inventions and shall, without additional compensation, execute all
assignments and other documents deemed necessary to perfect the property rights of Employer,
Wintrust or any Affiliate therein. These obligations shall continue beyond the termination of
Executive’s employment with respect to Inventions conceived, developed, or made by Executive during
employment with Employer. The provisions of this Section 6 shall not apply to any Invention for
which no equipment, supplies, facility, or trade secret information of Employer, Wintrust or any
Affiliate is used by Executive and which is developed entirely on Executive’s own time, unless (a)
such Invention relates (i) to the business of Employer, Wintrust or an Affiliate or (ii) to the
actual or demonstrably anticipated research or development of Employer, Wintrust or an Affiliate,
or (b) such Invention results from work performed by Executive for Employer.

     7. Remedies. Executive acknowledges that compliance with the terms of this
Agreement is necessary to protect the Confidential Information and goodwill of Employer, Wintrust
and its Affiliates and that any breach by Executive of this Agreement will cause continuing and
irreparable injury to Employer, Wintrust and its Affiliates for which money damages would not be an
adequate remedy. Executive acknowledges that Wintrust and all other Affiliates are and are intended
to be third party beneficiaries of this Agreement. Executive acknowledges that Employer, Wintrust
and any Affiliate shall, in addition to any other rights or remedies they may have, be entitled to
injunctive relief for any breach by Executive of any part of this Agreement. This Agreement shall
not in any way limit the remedies in law or equity otherwise available to Employer, Wintrust and
its Affiliates.

     8. Term of Agreement. Unless terminated sooner as provided in Section 9,
the initial term of Executive’s employment pursuant to this Agreement (“Initial Term”) shall be
three years, commencing on the date of this Agreement. After such Initial Term, this Agreement
shall be extended automatically for successive one-year terms, unless either Executive or Employer
gives contrary written notice not less than 60 days in advance of the expiration of the Initial
Term or any succeeding term of this Agreement or unless terminated sooner as provided in Section 9.
Notwithstanding the foregoing, if at any time during the Initial Term or any successive one-year
term there is a Change in Control of Employer (as defined in Section 9(f)), then upon the first
occurrence of such a Change in Control, the Initial Term or the successive one-year term of this
Agreement (whichever is in effect as of the date of the Change in Control) shall automatically
extend

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for the greater of: (a) the amount of time remaining on Executive’s Initial Term of employment if
such first occurrence of a Change in Control occurs during the Initial Term, or (b) two years from
the date of such first occurrence of a Change in Control. In the event that Executive’s Initial
Term or successive one-year term is extended due to such a Change in Control, such extension shall
further be extended automatically for successive one-year terms unless either Executive or Employer
gives contrary written notice not less than 60 days in advance of the expiration of the extension
of this Agreement or unless terminated sooner as provided in Section 9. The Initial Term, together
with any extension thereof in accordance with this Section 8, shall be referred to herein as the
“Term.”

     9. Termination of Employment.

          (a) General Provisions. Executive’s employment may be terminated
by Employer at any time for any reason, with or without cause, and, except as otherwise
provided in this Section 9, any and all of Employer’s obligations under this Agreement
shall terminate, other than Employer’s obligation to pay Executive, within 30 days of
Executive’s termination of employment, the full amount of any earned but unpaid base
salary and accrued but unpaid vacation pay earned by Executive pursuant to this
Agreement through and including the date of termination and to observe the terms and
conditions of any plan or benefit arrangement which, by its terms, survives such
termination of Executive’s employment. The payments to be made under this Section
9(a) shall be made to Executive, or in the event of Executive’s death, to such beneficiary
as Executive may designate in writing to Employer for that purpose, or if Executive has
not so designated, then to the spouse of Executive, or if none is surviving, then to the
estate of Executive. Notwithstanding the foregoing, termination of employment shall not
affect the obligations of Executive that, pursuant to the express provisions of this
Agreement, continue in effect.

          (b) Termination Due to Death.

               (i) Payment.
If Executive should die during the Term of this Agreement, which
event shall result in the termination of Executive’s employment, Employer shall pay Executive an
amount equal to two times (2x) the sum of (A) Executive’s base annual salary in effect at the time
of Executive’s death plus (B) an amount equal to any Cash Bonus amounts paid to Executive during
the twelve-month period prior to Executive’s death and any Stock Bonus amounts awarded or granted
to Executive during the twelve-month period prior to Executive’s death, in a lump sum within 30
days following the date of Executive’s death. For the purposes of this Agreement, “Cash Bonus”
shall mean any cash bonus amounts that are included in Executive’s annual bonus plan, as approved
in writing by Employer’s Board of Directors or the Compensation Committee or any successor
committee of Employer’s Board of Directors. For the purposes of this Agreement, “Stock Bonus”
shall mean any restricted shares that are included in Executive’s annual bonus plan, as approved in
writing by the Employer’s Board of Directors or the Compensation Committee or any successor
committee of Employer’s Board of Directors. Any bonuses (whether in cash or in the

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form of restricted shares) that are not included in such annual bonus plan shall not be considered
to be Cash Bonus amounts or Stock Bonus awards for purposes of this Agreement. The value of the
Stock Bonus amounts shall be determined as of the date they are awarded or granted to Executive.

               (ii) Reduction of Payment Due To Life Insurance Benefits.
The amount to be paid to Executive pursuant to this Section 9(b) shall be reduced by the amount of
any life insurance benefit payments paid or payable to Executive from policies of insurance
maintained and/or paid for by Employer or Wintrust; provided that in the event the life insurance
benefits exceed the amount to be paid to Executive pursuant to this Section 9(b), Executive shall
remain entitled to receive the excess life insurance payments. The Executive will cooperate with
the Employer or Wintrust in order to enable the Employer or Wintrust to pay for a policy or
policies of life insurance on the life of the Executive. To the extent that the Executive is not
insurable or a life insurance policy is not reasonably obtainable, then the payments due under this
Section 9(b) shall be reduced by 50%.

               (iii) Beneficiary. The payments to be made under this Section
9(b) shall be made to such beneficiary as Executive may designate in writing to Employer for that
purpose, or if Executive has not so designated, then to the spouse of Executive, or if none is
surviving, then to the estate of Executive.

          (c) Termination Due to Permanent Disability.

               (i) Payment. If Executive should suffer a permanent disability during the Term
of this Agreement, Employer shall have the right to terminate Executive’s employment. In such
event, Employer shall pay Executive an amount equal to two times (2x) the sum of (A) Executive’s
base annual salary in effect at the time of Executive’s permanent disability plus (B) an amount
equal to any Cash Bonus amounts paid to Executive during the twelve-month period prior to
Executive’s permanent disability and any Stock Bonus amounts awarded or granted to Executive during
the twelve-month period prior to Executive’s permanent disability. Such amount shall be paid to
Executive ratably over a 24-month period beginning on the first payroll period following such
termination and on each payroll period thereafter during the 24-month period. For the purposes of
this Agreement, “permanent disability” means any mental or physical illness, disability or
incapacity that renders Executive unable to perform Executive’s duties hereunder where (x) such
permanent disability has been determined to exist by a physician selected by Employer or (y)
Employer has reasonably determined, based on such physician’s advice, that such disability will
continue for 180 days or more within any 365-day period, of which at least 90 days are consecutive.
Executive shall cooperate in all respects with Employer if a question arises as to whether he has
become disabled (including, without limitation, submitting to an examination by a physician or
other health care specialist selected by Employer and authorizing such physician or other health
care specialist to discuss Executive’s condition with Employer).

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               (ii) Reduction of Payment Due To Long Term Disability
Insurance Benefits. The amount to be paid to Executive pursuant to this Section 9(c) shall
be reduced by the amount of any long-term disability benefit payments paid or payable to Executive
during such payment period from policies of insurance maintained and/or paid for by Employer or
Wintrust; provided that in the event the long-term disability benefits exceed the amount to be paid
to Executive pursuant to this Section 9(c), Executive shall remain entitled to receive the excess
long-term disability insurance payments.

               (iii) Reduction of Payment Due To Earned Income. The amount to be paid to
Executive under this Section 9(c) shall also be reduced by any income earned by Executive, whether
paid to Executive immediately or deferred until a later date, during the applicable Severance Pay
period from employment of any sort, including without limitation full, part time or temporary
employment or work as an independent contractor or as a consultant; provided that, if Executive was
a member of the board of directors of another company at the time of Executive’s termination, the
amount of Severance Pay under this Section 9(c) shall not be reduced by any income earned by
Executive during the applicable Severance Pay period due to Executive’s continued service in such
capacity. Notwithstanding the foregoing, Executive’s Severance Pay to be paid under this Section
9(c) shall be not less than an amount to provide Executive with a gross monthly payment of
$8,333.34 during the 24-month Severance Pay period. Executive agrees to promptly notify Employer if
Executive obtains employment of any sort during the applicable Severance Pay period and to provide
Employer with a copy of any W-2 or 1099 forms or other payroll or income records and a summary of
contributions received under any deferred compensation arrangement.

               (iv) Continued Participation In Benefit Plans. In the event of termination due to
a permanent disability, Executive’s or Executive’s dependents’ participation in any medical,
health, accident, disability, death, life insurance or similar plan in which Executive was
participating immediately prior to termination shall continue (to the extent Executive and
Executive’s dependents are eligible to participate in such plans pursuant to the terms of such
plans) for the period in which payments are being made under this Section 9(c) at Employer’s or
Wintrust’s expense (subject to any normal employee contributions, if any), although any
continuation of health coverage shall count toward the “COBRA” continuation of coverage period.

          (d) Termination Without Cause.

               (i) Payment. In the event Executive’s employment is
terminated without Cause (as such term is defined in Section 9(h) hereof) by Employer during the
Term of this Agreement, other than upon the expiration of the Term of this Agreement, Employer
shall pay Severance Pay to Executive in the amount equal to two
times (2x) the sum of (A)
Executive’s base annual salary in effect at the time of Executive’s termination plus (B) an amount
equal to any Cash Bonus amounts paid to Executive during the twelve-month period prior to
termination and any Stock Bonus

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amounts awarded or granted to Executive during the twelve-month period prior to termination
Severance Pay under this Section 9(d) shall be paid ratably over a 24-month period beginning on the
first payroll period following such termination and on each payroll period thereafter during such
Severance Pay period.

               (ii) Reduction of Payment Due To Earned Income. The
amount of Severance Pay under this Section 9(d) shall also be reduced by any income earned by
Executive, whether paid to Executive immediately or deferred until a later date, during the
applicable Severance Pay period from employment of any sort, including without limitation full,
part time or temporary employment or work as an independent contractor or as a consultant; provided
that, if Executive was a member of the board of directors of another company at the time of
Executive’s termination, the amount of Severance Pay under this Section 9(d) shall not be reduced
by any income earned by Executive during the applicable Severance Pay period due to Executive’s
continued service in such capacity. Notwithstanding the foregoing, Executive’s Severance Pay to be
paid under this Section 9(d) shall not be less than an amount to provide Executive with a gross
monthly payment of $8,333 34 during the 24-month Severance Pay period Executive agrees to promptly
notify Employer if Executive obtains employment of any sort during the applicable Severance Pay
period and to provide Employer with a copy of any W-2 or 1099 forms or other payroll or income
records and a summary of any contributions received under any deferred compensation arrangement.

               (iii) Company-Paid Health Insurance. In the event of
Executive’s termination pursuant to this Section 9(d), from the termination date through the
earliest of (A) the expiration of the maximum period of COBRA coverage, (B) the date on which
Executive becomes eligible for coverage under another group health insurance plan with no
pre-existing condition limitation or exclusion, or (C) the date on which Executive becomes
entitled to benefits under Medicare, Executive (and any qualified dependents) shall be entitled to
group health insurance coverage under the Employer’s group health insurance plan for employees (as
such plan is then in effect and as it may be amended at any time and from time to time during the
period of coverage) in which Executive was participating immediately prior to termination, at
Employer’s expense, subject to any normal employee contributions, if any. The period during which
Executive is being provided with health insurance under this Agreement shall be credited against
Executive’s period of COBRA coverage, if any. Executive shall promptly notify Employer if, prior to
the expiration of the maximum period of COBRA coverage, Executive becomes eligible for coverage
under another group health plan with no preexisting condition limitation or exclusion or Executive
becomes entitled to benefits under Medicare.

          (e) Constructive Termination.

               (i) Payment. If Executive suffers a Constructive Termination during the Term of
this Agreement, other than upon the expiration of the Term of this Agreement, Employer shall pay
Severance Pay to Executive in the amounts and at the times described in Section 9(d) hereof. For
the purposes of this Agreement,

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“Constructive Termination” means (A) a material reduction by Employer in the duties and
responsibilities of Executive or (B) a reduction by Employer of Executive’s “Adjusted Total
Compensation” (as hereinafter defined), to (1) less than seventy-five percent (75%) of the Adjusted
Total Compensation of Executive for the twelve-month period ending as of the last day of the month
immediately preceding the month in which the Constructive Termination occurs; or (2) less than
seventy-five percent (75%) of the Executive’s Adjusted Total Compensation for the twelve-month
period ending as of the last day of the month preceding the Effective Date, whichever is greater.
A Constructive Termination does not include termination for’ Cause as defined in Section 9(h),
termination without Cause as defined in Section 9(d), or termination due to a permanent disability
as defined in Section 9(c)

               (ii) Reduction of Payment Due To Earned Income. The
amount of Severance Pay under this Section 9(e) shall be reduced by any income earned by Executive,
whether paid to Executive immediately or deferred until a later date, during such Severance Pay
period from employment of any sort, including without limitation full, part time or temporary
employment or work as an independent contractor or as a consultant; provided that, if Executive was
a member of the board of directors of another company at the time of Executive’s termination, the
amount of Severance Pay under this Section 9(e) shall not be reduced by any income earned by
Executive during the applicable Severance Pay period due to Executive’s continued service in such
capacity, Notwithstanding the foregoing, Executive’s Severance Pay to be paid under this Section
9(e) shall not be less than an amount to provide Executive with a gross monthly payment of $
8,333,34 during the 24-month Severance Pay period. Executive agrees to promptly notify Employer if
Executive obtains employment of any sort during the applicable Severance Pay period and to provide
Employer with a copy of any W-2 or 1099 forms or other payroll or income records and a summary of
any contributions received under any deferred compensation arrangement.

               (iii) Company-Paid Health Insurance. In the event of
Executive’s termination pursuant to this Section 9(e), from the termination date through the
earliest of (A) the expiration of the maximum period of COBRA coverage, (B) the date on which
Executive becomes eligible for coverage under another group health insurance plan with no
pre-existing condition limitation or exclusion, or (C) the date on which Executive becomes entitled
to benefits under Medicare, Executive (and any qualified dependents) shall be entitled to group
health insurance coverage under the Employer’s group health insurance plan for employees (as such
plan is then in effect and as it may be amended at any time and from time to time during the period
of coverage) in which Executive was participating immediately prior to termination, at Employer’s
expense, subject to any normal employee contributions, if any. The period during which Executive is
being provided with health insurance under this Agreement shall be credited against Executive’s
period of COBRA coverage, if any Executive shall promptly notify Employer if, prior to the
expiration of the maximum period of COBRA coverage, Executive becomes eligible for coverage under
another group health plan with no preexisting condition limitation or exclusion or Executive
becomes entitled to benefits under Medicare.

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               (iv) Definitions.

                    (A) For the purposes of this Agreement, “Adjusted
Total Compensation” means the aggregate base salary earned by the Executive plus the dollar value
of all perquisites (i.e. Employer provided car, club dues and supplemental life insurance) as
estimated by Employer in respect of the Executive for the relevant twelve-month period. Adjusted
Total Compensation shall exclude any Cash Bonus, Stock Bonus, or other bonus payments paid or
earned by the Executive. For the purpose of illustration, attached as Exhibit B to this Agreement
is the base salary paid and the dollar value of the Executive’s perquisites for the last fiscal
year of Employer.

                    (B) For the purposes of this Section 9(e), the Executive
will not be deemed to have incurred a reduction by Employer of Executive’s Adjusted Total
Compensation if there is a general reduction in base salaries and/or perquisites applicable to the
President, Chief Executive Officer and all Vice Presidents of Employer.

          (f) Termination Upon Change In Control.

               (i) Payment. In the event that within eighteen months after a Change in Control
(as defined below) of Employer or Wintrust (A) Executive’s employment is terminated without Cause
(as such term is defined in Section 9(h) hereof) prior to the expiration of the Term of this
Agreement or (B) Executive suffers a Constructive Termination prior to the expiration of the Term
of this Agreement, Employer (or the successor thereto) shall pay Severance Pay to Executive in the
amount that is equivalent to the amount described in Section 9(d) hereof in a lump sum within 30
days following the date of Executive’s termination or Constructive Termination.

               (ii) Change In Control. For the purposes of this Agreement, a “Change in
Control” of Employer means (A) the acquisition by any person of 50% or more of Employer’s then
outstanding capital stock; or (B) approval by the stockholders of Employer of a merger or
consolidation effecting a change in ownership of 50% or more of the voting power of the outstanding
capital stock of Employer or a sale for cash of all or substantially all of the assets of Employer;
in each case, the acquiring persons in such merger, consolidation or sale shall be persons other
than the stockholders of Employer, Wintrust or any Affiliate immediately prior to such transaction.
For the purposes of this Agreement, a “Change in Control” of Wintrust shall have the same meaning
as provided in Section 12(b) of the Wintrust 1997 Stock Incentive Plan.

               (iii) Section 280G. Notwithstanding the foregoing, if the
payment required to be paid under this Section 9(f), when considered either alone or with other
payments paid or imputed to the Executive from Wintrust or an Affiliate that would be deemed
“excess parachute payments” under Section 280G(b)(l) of the Internal Revenue Code of 1986, as
amended (the “Code”), is deemed by Wintrust to be a “parachute payment” under Section 280G(b)(2) of
Code, then the amount of Severance Pay required to be paid under this Section 9(f) shall be
automatically reduced to an

 - 11 - 

 

amount equal to $1,00 less than three times (3x) the “base amount” (as defined in Section
280G(3) of the Code) (the “Reduced Amount”). Provided, however, the preceding
sentence shall not apply if the sum of (A) the amount of Severance Pay described in this Section
9(f) less (B) the amount of excise tax payable by the Executive under Section 4999 of the Code with
respect to the amount of such Severance Pay and any other payments paid or imputed to the Executive
from Wintrust or an Affiliate that would be deemed to be “excess parachute payments” under Section
280G(b)(l) of the Code, is greater than the Reduced Amount, The decision of Wintrust (based upon
the recommendations of ‘its tax counsel and accountants) as to the characterization of payments as
parachute payments, the value of parachute payments, the amount of excess parachute payments, and
the payment of the Reduced Amount shall be final.

          (iv) Company-Paid Health Insurance. In the event Executive becomes entitled to
payments under this Section 9(f), from the termination date through the earliest of (A) the
expiration of the maximum period of COBRA coverage, (B) the date on which Executive becomes
eligible for coverage under another group health insurance plan with no pre-existing condition
limitation or exclusion, or (C) the date on which Executive becomes entitled to benefits under
Medicare, Executive (and any qualified dependents) shall be entitled to group health insurance
coverage under the Employer’s group health insurance plan for employees (as such plan is then in
effect and as it may be amended at any time and from time to time during the period of coverage) in
which Executive was participating immediately prior to termination, at Employer’s expense, subject
to any normal employee contributions, if any. The period during which Executive is being provided
with health insurance under this Agreement shall be credited against Executive’s period of COBRA
coverage, if any. Executive shall promptly notify Employer if, prior to the expiration of the
maximum period of COBRA coverage, Executive becomes eligible for coverage under another group
health plan with no pre-existing condition limitation or exclusion or Executive becomes entitled to
benefits under Medicare,

          (v) Definitions, For the purposes of this Section 9(f), the term “Constructive
Termination” shall have the same meaning as such term is defined in Section 9(e) with the following
modifications:

               (A) A Constructive Termination shall be deemed to
have occurred if after a Change in Control, the Executive’s Adjusted Total Compensation is reduced
to less than (1) 100% of the Adjusted Total Compensation of Executive for the twelve-month period
ending as of the last day of the month immediately preceding the month in which the Constructive
Termination occurs or (2) 100% percent of the Executive’s Adjusted Total Compensation for the
twelve-month period ending as of the last day of the month preceding the Effective Date, whichever
is greater.

               (B) A Constructive Termination shall also be deemed to
have occurred if after a Change in Control, Employer (or the successor thereto) delivers written
notice to Executive that it will continue to employ Executive but will reject this Agreement (other
than due to the expiration of the Term of this Agreement).

- 12 -

 

               (C) Subsection 9(e)(v)(B) shall not be applicable to a Constructive Termination following a
Change in Control

     (g) Voluntary
Termination. Executive may voluntarily terminate employment during the
Term of this Agreement by a delivery to Employer of a written notice at least 60 days in advance of
the termination date, If Executive voluntarily terminates employment prior to the expiration of the
Term of this Agreement, any and all of the Employer’s obligations under this Agreement shall
terminate immediately except for the Employer’s obligations contained in Section 9(a) hereof
Notwithstanding the foregoing, termination of employment shall not affect the obligations of
Executive that, pursuant to the express provisions of this Agreement, continue in effect,

     (h) Termination
For Cause. If Executive is terminated for Cause as determined by the
written resolution of Employer’s Board of Directors or the Compensation Committee or any successor
committee of Employer’s Board of Directors, all obligations of the Employer shall terminate
immediately except for Employer’s obligations described in Section 9(a) hereof Notwithstanding the
foregoing, termination of employment shall not affect the obligations of Executive that, pursuant
to the express provisions of this Agreement, continue in effect For purposes of this Agreement,
termination for “Cause” means:

          (i) Executive’s failure or refusal, after written notice thereof and after reasonable
opportunity to cure, to perform specific directives approved by a majority of the Employer’s or
Wintrust’s Board of Directors which are consistent with the scope and nature of Executive’s duties
and responsibilities as provided in Section 1 of this Agreement;

          (ii) Habitual drunkenness or illegal use of drugs which interferes with the performance
of Executive’s duties and obligations under this Agreement;

          (iii) Executive’s conviction of a felony;

          (iv) Any defalcation or acts of gross or willful misconduct of Executive resulting in or
potentially resulting in economic loss to Employer or Wintrust or substantial damage to Employer’s
or Wintrust’s reputation;

          (v) Any breach of Executive’s covenants contained in Sections 4 through 6 hereof;

          (vi) A written order requiring termination of Executive from Executive’s position with
Employer by any regulatory agency or body; or

          (vii) Executive’s engagement, during the performance of Executive’s duties hereunder, in acts
or omissions constituting fraud, intentional breach

- 13 -

 

of fiduciary obligation, intentional wrongdoing or malfeasance, or intentional and material
violation of applicable banking laws, rules, or regulations.

          (i) Executive’s right to receive Severance Pay per Sections 9(c) through 9(f) hereof is
contingent upon (i) Executive having executed and delivered to Employer a release in such form as
provided by Employer and (ii) Executive not violating any of Executive’s on-going obligations under
this Agreement.

          (j) The payment of Severance Pay to Executive pursuant to Sections 9(c) through 9(f) hereof
shall be liquidated damages for and in full satisfaction of any and all claims Executive may have
relating to or arising out of Executive’s employment and termination of employment by Employer, any
and all claims Executive may have relating to or arising out of this Agreement and the termination
thereof and any and all claims Executive may have arising under any statute, ordinance or
regulation or under common law Executive expressly acknowledges and agrees that, except for
whatever claim Executive may have to Severance Pay, Executive shall not have any claim for damages
or other relief of any sort relating to or arising out of Executive’s employment or termination of
employment by Employer or relating to or arising out of this
Agreement and the termination thereof.

          (k) Upon termination of employment with Employer for any reason, Executive shall promptly
deliver to Employer all writings, records, data, memoranda, contracts, orders, sales literature,
price lists, client lists, data processing materials, and other documents, whether or not obtained
from Employer, Wintrust or any Affiliate, which pertain to or were used by Executive in connection
with Executive’s employment by Employer or which pertain to Wintrust or any other Affiliate,
including, but not limited to, Confidential Information, as well as any automobiles, computers or
other equipment which were purchased or leased by Employer for
Executive.

     10.
Resolution of Disputes. Except as otherwise provided herein, any disputes arising
under or in connection with this Agreement or in any way arising out of, relating to or associated
with the Executive’s employment with Employer or the termination of such employment (“Claims”),
that Executive may have against Employer, Wintrust or any Affiliate of Wintrust, or the officers,
directors, employees or agents of Employer, Wintrust, or any Affiliate of Wintrust in their
capacity as such or otherwise, or that Employer, Wintrust, or any Affiliate of Wintrust may have
against Executive, shall be resolved by binding arbitration, to be held in Chicago, Illinois, in
accordance with the rules and procedures of the National Rules for the Resolution of Employment
Disputes of the American Arbitration Association (the “AAA”) and the parties hereby agree to
expedite such arbitration proceedings to the extent permitted by the AAA Judgment upon the award
rendered by the arbitrator(s) may be entered in any court having jurisdiction thereof The Claims
covered by this Agreement include, but are not limited to: claims for wages or other compensation
due; claims for breach of any contract or covenant, express or implied; tort claims; claims for
discrimination, including but not limited to discrimination based on race, sex, sexual orientation,
religion, national origin, age, marital status, handicap, disability or medical condition or
harassment on any of the foregoing bases; claims for benefits, except as excluded in the following
paragraph; and

- 14 -

 

claims for violation of any federal, state or other governmental constitution, statute, ordinance,
regulation, or public policy. The Claims covered by this Agreement do not include claims for
workers’ compensation benefits or compensation; claims for unemployment compensation benefits;
claims based upon an employee pension or benefit plan, the terms of which contain an arbitration or
other non-judicial resolution procedure, in which case the provisions of such plan shall apply; and
claims made by either Employer or the Executive for injunctive and/or other equitable relief
regarding the covenants set forth in Sections 3, 4, 5 and 6 of this Agreement. Each party shall
initially bear their own costs of the arbitration or litigation, except that, if Employer is found
to have violated any material terms of this Agreement, Employer shall reimburse Executive for the
entire amount of reasonable attorneys’ fees incurred by Executive as a result of the dispute
hereunder in addition to the payment of any damages awarded to Executive.

     11. General Provisions

          (a) All provisions of this Agreement are intended to be interpreted and construed in a manner
to make such provisions valid, legal, and enforceable. To the extent that any Section of this
Agreement or any word, phrase, clause, or sentence hereof shall be deemed by any court to be
illegal or unenforceable, such word, clause, phrase, sentence, or Section shall be deemed modified,
restricted, or omitted to the extent necessary to make this Agreement
enforceable. Without limiting
the generality of the foregoing, if the scope of any covenant in this Agreement is too broad to
permit enforcement to its full extent, such covenant shall be enforced to the maximum extent
provided by law; and Executive agrees that such scope may be judicially modified accordingly.

          (b) This
Agreement may be assigned by Employer. This Agreement and the covenants set forth
herein shall inure to the benefit of and shall be binding upon the successors and assigns of
Employer and Wintrust.

          (c) This Agreement may not be assigned by Executive, but shall be binding upon Executive’s
executors, administrators, heirs, and legal representatives.

          (d) No waiver by either party of any breach by the other party of any of the obligations,
covenants, or representations under this Agreement shall constitute a waiver of any prior or
subsequent breach.

          (e) Where in this Agreement the masculine gender is used, it shall include the feminine
if the sense so requires.

          (f) Employer may withhold from any payment that it is required to make under this Agreement
amounts sufficient to satisfy applicable withholding requirements under any federal, state, or
local law.

          (g) This instrument constitutes the entire agreement of the parties with respect to its
subject matter. This Agreement may not be changed or amended orally but

- 15 -

 

only by an agreement in writing, signed by the party against whom enforcement of any waiver,
change, modification, extension, or discharge is sought. Any other understandings and agreements,
oral or written, respecting the subject matter hereof are hereby superseded and canceled,

          (h) The provisions of Sections 4, 5, 6, 7, 9(i), 9(j), 10, 11, and 12 of this Agreement shall
survive the termination of Executive’s employment with Employer and the expiration or termination
of this Agreement.

     12.
Governing Law. The parties agree that this Agreement shall be construed and
governed by the laws of the State of Illinois, excepting its conflict
of laws principles. Further,
the parties acknowledge and specifically agree to the jurisdiction of
the courts of the State of
Illinois in the event of any dispute regarding Sections 3, 4, 5,
or 6 of this Agreement.

     13.
Notice of Termination. Subject to the provisions of
Section 8, in the event that
Employer desires to terminate the employment of the Executive during the Term of this Agreement,
Employer shall deliver to Executive a written notice of termination, stating whether the
termination constitutes a termination in accordance with
Section 9(c), 9(d), 9(e), 9(f), or 9(h). In
the event that Executive determines in good faith that Executive has experienced a Constructive
Termination, Executive shall deliver to Employer a written notice stating the circumstances that
constitute such Constructive Termination. In the event that the Executive desires to effect a
voluntary termination of Executive’s employment in accordance with Section 9(g), Executive shall
deliver a written notice of such voluntary termination to Employer.

     IN WITNESS WHEREOF, the parties have executed and delivered this Agreement as of the
date written opposite their signatures.

	 	 	 	 	 	 	 	 	 
	By:

	 	/s/ Edward J. Wehmer
	 	 	 	/s/ Randolph M. Hibben
	 	 
	 

	 	 
	 	 	 	 	 	 
	 

	 	Edward J. Wehmer
	 	 	 	Randolph M. Hibben	 	 
	 

	 	Wintrust Financial Corporation	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	Its:

	 	President and Chief Executive Officer
	 	 	 	Dated: 3/25/05	 	 
	 
	 	 	 	 	 	 	 	 
	Dated: 3/25/05	 	 	 	 	 	 

- 16 -

 

EXHIBIT A

Advantage National Bank

Barrington Bank & Trust Company, N. A.

Beverly Bank & Trust Company, N. A.

Crystal Lake Bank & Trust Company, N. A.

First Insurance Funding Corporation

Focused Investments LLC

Hinsdale Bank & Trust Company

Lake Forest Bank & Trust Company

Libertyville Bank & Trust Company

North Shore Community Bank & Trust Company

Northbrook Bank & Trust Company

Town Bank (Wisconsin)

Tricom, Inc of Milwaukee

Village Bank & Trust-Arlington Heights

Wayne Hummer Asset Management Company

Wayne Hummer Investments, LLC

Wayne Hummer Trust Company, N. A.

Wheaton Bank & Trust Company

Wintrust Information Technology Services Company

 

 

EXHIBIT B

	 	 	 	 	 
	1) EXECUTIVE NAME:

2) CURRENT TITLE

3) EMPLOYER

4) TITLE AT DATE OF HIRE

5) DATE OF HIRE

	 	RANDOLPH M HIBBEN
	 	WINTRUST FINANCIAL CORP

TOTAL COMPENSATION HISTORY

SENIOR EXECUTIVE COMPENSATION
	 	CHAIRMAN & CEO	 	 
	 	 	 	 
	 	LAKE FOREST BANK & TRUST
	 	JANUARY 2005

	 	 	 	 
	 	SENIOR VP — CASHIER — LAKE FOREST BANK	 	 
	 	 	 	 
	 	 	OCTOBER 1991	 	 

	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	2005	 	 	2004	 	 	2003	 	 	2002	 	 	2001	 	 	2000	 	 	1999	 	 	1998	 	 	1997	 
	5) SIGNING BONUS (IF ANY)

	 	 	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	6) SALARY HISTORY;
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	BEGINNING SALARY
	 	 	 	 	 	$	250,000	 	 	$	215,000	 	 	$	208,000	 	 	$	200,000	 	 	$	170,000	 	 	$	160,000	 	 	$	135,000	 	 	$	124,000	 	 	$	113,000	 
	INTERIM RAISE

	 	 	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	15,000	 	 	$	0	 	 	$	10,000	 	 	$	0	 	 	$	0	 
	PRIOR YEAR END RAISE
	 	 	 	 	 	$	10,000	 	 	$	35,000	 	 	$	7,000	 	 	$	8,000	 	 	$	15,000	 	 	$	10,000	 	 	$	15,000	 	 	$	11,000	 	 	$	11,000	 
	OTHER

	 	 	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	ENDING SALARY
	 	 	 	 	 	$	260,000	 	 	$	250,000	 	 	$	215,000	 	 	$	208,000	 	 	$	200,000	 	 	$	170,000	 	 	$	160,000	 	 	$	135,000	 	 	$	124,000	 
	PERCENT INCREASE

	 	 	 	 	 	 	4.00	%	 	 	16.28	%	 	 	3.37	%	 	 	4.00	%	 	 	17.65	%	 	 	6.25	%	 	 	18.52	%	 	 	8.87	%	 	 	9.73	%
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	7) BONUS HISTORY:
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	CURRENT YEAR END CASH BONUS
	 	 	 	 	 	 	 	 	 	$	0	 	 	$	48,575	 	 	$	47,125	 	 	$	19,602	 	 	$	25,000	 	 	$	7,500	 	 	$	15,000	 	 	$	12,000	 
	STOCK BONUS
	 	 	 	 	 	 	 	 	 	$	75,000	 	 	$	18,425	 	 	$	17,875	 	 	$	25,398	 	 	$	0	 	 	$	17,200	 	 	$	0	 	 	$	0	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	TOTAL
	 	 	 	 	 	 	 	 	 	$	75,000	 	 	$	67,000	 	 	$	65,000	 	 	$	45,000	 	 	$	25,000	 	 	$	24,700	 	 	$	15,000	 	 	$	12,000	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	8) STOCK OPTION HISTORY (WINTRUST EQUIV)
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	BEGINNING OPTIONS
	 	 	 	 	 	 	 	 	 	 	94,380	 	 	 	98,135	 	 	 	90,480	 	 	 	90,480	 	 	 	90,480	 	 	 	59,381	 	 	 	59,381	 	 	 	50,381	 
	CURRENT YEAR GRANTS
	 	 	 	 	 	 	 	 	 	 	—	 	 	 	3,500	 	 	 	48,500	 	 	 	—	 	 	 	—	 	 	 	31,100	 	 	 	0	 	 	 	9,000	 
	CURRENT YEAR EXERCISES
	 	 	 	 	 	 	 	 	 	 	—	 	 	 	7,255	 	 	 	40,845	 	 	 	—	 	 	 	—	 	 	 	—	 	 	 	0	 	 	 	0	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	ENDING OPTIONS
	 	 	 	 	 	 	 	 	 	 	94,380	 	 	 	94,380	 	 	 	98,135	 	 	 	90,480	 	 	 	90,480	 	 	 	90,480	 	 	 	59,381	 	 	 	59,381	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	VESTED PORTION OF OPTIONS
	 	 	 	 	 	 	 	 	 	 	112,507	 	 	 	47,581	 	 	 	48,536	 	 	 	73,383	 	 	 	66,770	 	 	 	60,470	 	 	 	51,524	 	 	 	49,316	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	9) AUTOMOBILE:
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	2001 Audi A8
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	COST
	 	 	 	 	 	 	 	 	 	$	48,874	 	 	$	33,000	 	 	$	33,000	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	30,000	 	 	$	0	 
	ESTIMATED VALUE PER YEAR
	 	 	 	 	 	 	 	 	 	$	7,175	 	 	$	5,658	 	 	$	8,750	 	 	$	7,750	 	 	$	7,750	 	 	$	7,750	 	 	$	7,500	 	 	$	6,250	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	10) CLUBS:
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	A) CLUB A   DUES* — LAKE FOREST CLUB
	 	 	 	 	 	 	$	2,760	 	 	$	2,430	 	 	$	2,400	 	 	$	2,280	 	 	$	2,280	 	 	$	2,280	 	 	$	2,700	 	 	$	2,400	 
	B) CLUB B   DUES*
	 	 	 	 	 	 	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	C) CLUB C   DUES*
	 	 	 	 	 	 	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	TOTAL
	 	 	 	 	 	 	 	 	 	$	2,760	 	 	$	2,430	 	 	$	2,400	 	 	$	2,280	 	 	$	2,280	 	 	$	2,280	 	 	$	2,700	 	 	$	2,400	 
	COUNTRY CLUB ACCOMPANIES PROMOTION TO PRESIDENT AND CEO NSCB&T
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	* — SPECIFY CLUB NAME AND INCLUDE ANY INITIATION FEES PAID
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	11) SUPPLEMENTAL INSURANCE
	 	FACE	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	A) BOLI — LIFE INSURANCE:
	 	AMOUNT	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	i) CLARICA LIFE 
	>>>	 	$	139,050	 	 	 	$	102	 	 	$	95	 	 	$	163	 	 	$	500	 	 	$	500	 	 	$	500	 	 	$	500	 	 	$	400	 
	ii) GREAT WEST 
	>>>	 	$	139,050	 	 	 	$	254	 	 	$	95	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	iii) MASSMUTUAL 
	>>>	 	$	139,050	 	 	 	$	81	 	 	$	108	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	 
	 	 	$	417,150	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	B) DISABILITY PREMIUM
	 	 	N/A	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	 
	TOTAL
	 	 	 	 	 	 	 	 	 	$	437	 	 	$	298	 	 	$	163	 	 	$	500	 	 	$	500	 	 	$	500	 	 	$	500	 	 	$	400	 
	 
	12) EDUCATIONAL EXPENSES PAID
	 	 	 	 	 	 	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	 
	13) OTHER — SPECIFY BELOW
	 	 	 	 	 	 	 	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 	 	$	0	 
	 
	14) TOTAL ANNUAL CASH COMPENSATION
	 	 	 	 	 	 	 	 	 	$	335,372	 	 	$	290,386	 	 	$	266,438	 	 	$	230,132	 	 	$	205,530	 	 	$	178,030	 	 	$	160,700	 	 	$	145,050	 
	 
	PERCENT INCREASE
	 	 	 	 	 	 	 	 	 	 	15.49	%	 	 	8.99	%	 	 	15.78	%	 	 	11.97	%	 	 	15,45	%	 	 	10.78	%	 	 	10.79	%	 	 	9.84	%

	 	 	 
	15)
PROMOTED TO:

	 	4/99-PRESIDENT AND CEO NORTH
SHORE COMMUNITY BANK
	 

	 	5/01 — CHAIRMAN AND CEO LAKE FOREST BANK & TRUST
	 

	 	03 — VICE CHAIRMAN NORTH SHORE COMMUNITY BANK
	16) CONTRACT (YES OR NO)

	 	YES
	 
	17) COMMENTS OR NOTES:exv10w31

 

Exhibit 10.31

WINTRUST FINANCIAL CORPORATION

NONQUALIFIED STOCK OPTION AGREEMENT

     This Nonqualified Stock Option Agreement (“Agreement”) is entered into as of «Date_of_Award»,
between Wintrust Financial Corporation (hereinafter called the “Company”) and «Name» (hereinafter
called “Key Employee”).

     WHEREAS, the Wintrust Financial Corporation 2007 Stock Incentive Plan (the “Plan”) was adopted
by the Board of Directors of Wintrust Financial Corporation and approved by the shareholders of the
Company, and the Company desires to provide the Key Employee with an opportunity to acquire an
equity interest in the business of the Company, and through stock ownership an increased personal
interest in its continued success and progress.

     NOW, THEREFORE, in consideration of the premises, the mutual covenants hereinafter set forth
and other good and valuable consideration, the Company and Key Employee agree as follows:

     1. The Company hereby grants to Key Employee the option (“Option”) to purchase an aggregate
of «Shares» of the Company’s Common Shares, no par value, on the terms and conditions hereinafter
set forth at the purchase price of «Strike_Price» per share. The number of shares and the price
per share are subject to adjustment as provided in the Plan.

     2. It is understood that this Agreement is subject to the terms of the Plan, to which
reference is hereby made for more detailed description of the terms to which the option is subject
and by which reference the Plan is incorporated herein. The Plan shall control in the event there
is any conflict between the Plan and this Agreement and on such matters as are not contained in
this Agreement.

     3. (a) The Key Employee’s Option will vest and become exercisable as follows:

	 	 	 
	«Date_Year_1»

«Date_Year_2»

«Date_Year_3»

«Date_Year_4»

«Date_Year_5»
	 	«Vest_Year_1»

«Vest_Year_2»

«Vest_Year_3»

«Vest_Year_4»

«Vest_Year_5»

To the extent not exercised, installments shall be cumulative and may be exercised in whole or in
part.

 

 

«Name»

Nonqualified Stock Option Agreement

Dated «Date_of_Award»

     (b) The Option may not be exercised at any one time for less than 500 shares or the number of
shares then purchasable under the Option, whichever is less.

     (c) Unless otherwise permitted by the Committee under the terms of the Plan, during the
lifetime of Key Employee the Option may be exercised only by him.

     (d) In the event of a Change in Control of the Company, as defined in the Plan, all awards
still then outstanding shall vest 100%, whereupon all Options shall become exercisable in full.

     (e) Unless earlier terminated hereunder or under the Plan, the Option shall expire on
«Term_Date».

     4. The Option shall not be subject to execution, collateral assignment, attachment or similar
process, unless otherwise permitted by the Committee under the terms of the Plan. Any such
attempted action or other disposition of the Option contrary to the provisions of the Plan shall be
null and void, and in such event the Company shall have the right to terminate the Option. Such
termination shall not prejudice any rights or remedies which the Company or a subsidiary
corporation may have under this Agreement or otherwise.

     5. Subject to the terms and conditions of this Agreement, the Option shall be exercisable by
delivery of written notice of exercise accompanied by payment of the exercise price and any
applicable tax withholding in cash, shares of common stock, cash by a broker-dealer acceptable to
the Company to whom the Key Employee has submitted an irrevocable notice of exercise, or a
combination thereof as provided in the Plan.

     6. Key Employee shall not be deemed for any purpose to be a shareholder of the Company with
respect to any of the optioned shares except to the extent that this Option shall have been
exercised with respect thereto and a stock certificate issued therefore. No adjustment shall be
made for dividends or other rights for which the record date is prior to the date such stock
certificate is issued.

     7. Termination of Employment.

     (a) Termination of Employment by Reason of Death. In the event the employment of a
Key Employee is terminated by reason of death, any Option that has not been exercised, including
any unvested portions, shall become immediately exercisable at any time prior to the expiration
date of the Options or within one year after such date of termination of employment, whichever
period is shorter, by such person or persons as shall have acquired the Key Employee’s rights under
the Option by will or by the laws of descent and distribution.

 

 

«Name»

Nonqualified Stock Option Agreement

Dated «Date_of_Award»

     (b) Termination of Employment by Reason of Disability. In the event the employment of
Key Employee is terminated by reason of Disability, any Option that has not been exercised,
including any unvested portions, shall become immediately exercisable at any time prior to the
expiration date of the Options or within one year after such date of termination of employment,
whichever period is shorter. For purposes of this Agreement, Disability means a permanent and
total disability as determined by the Committee in good faith, upon receipt of sufficient competent
medical advice.

     (c) Termination of Employment by Reason of Retirement. In the event the employment of
a Key Employee is terminated by reason of retirement (as determined by the Committee), the Option
to the extent then vested shall remain exercisable until the expiration date of the Options or
within one year after such date of termination, whichever period is shorter, whereupon such vested
portion shall expire and the unvested portion, unless extended by the Committee, shall expire upon
termination of employment.

     (d) Termination of Employment for Other Reasons. If the employment of the Key
Employee shall terminate for any reason other than death, Disability, retirement, or for Cause, the
Option to the extent then vested shall remain exercisable until the expiration date of the Options
or three months after such date of termination, whichever period is shorter, whereupon such vested
portion shall expire and the unvested portion shall expire upon termination of employment.

     (e) Termination of Employment for Cause. If the employment of the Key Employee shall
be terminated for Cause, this Option shall expire, and the Key Employee’s rights hereunder shall be
immediately terminated, upon termination of employment. For purposes of this Agreement, “Cause”
shall mean the following:

	 	(i)	 	misappropriation of any funds or property of the Company or its
subsidiaries; or
	 
	 	(ii)	 	attempting to obtain any personal profit from any transaction
in which the Key Employee has a personal financial interest, unless the Key
Employee shall have first obtained the consent of the Board of Directors; or
	 
	 	(iii)	 	material neglect or refusal to perform the duties reasonably
assigned to the Key Employee given the Key Employee’s current job description;
or
	 
	 	(iv)	 	participating in a course of conduct which is injurious to the
Company or its subsidiaries, as interpreted by the Board of Directors; or
	 
	 	(v)	 	being convicted of a felony; or
	 
	 	(vi)	 	being adjudicated a bankrupt; or
	 
	 	(vii)	 	suspension due to the direction of any authorized bank
regulatory agency.

To the extent that there is a dispute arising over the application of the definition of Cause, the
Committee or the Board of Directors of the Company shall have the authority to interpret and apply
such definitions in a reasonable manner.

 

 

«Name»

Nonqualified Stock Option Agreement

Dated «Date_of_Award»

     8. Each notice relating to this Agreement shall be in writing and delivered in person or by
registered mail to the Company at its office, 727 North Bank Lane, Lake Forest, Illinois 60045,
attention of the President, or at such other address designated by the Company. All notices to Key
Employee or other person or persons then entitled to exercise the Option shall be delivered to Key
Employee or such other person or persons at Key Employee’s address as it then appears on the
Company’s records.

     9. Any dispute or disagreement which shall arise under, as a result of, or in any way shall
relate to the interpretation or construction or this Agreement shall be determined by the Committee
or by the Board of Directors of the Company (or any successor corporation), and any such
determination shall be final, binding and conclusive for all purposes.

     10. This agreement shall be governed by laws of the State of Illinois and shall inure to the
benefit of and be binding upon the Company and its successors and assigns and Key Employee and Key
Employee’s heirs, executors, administrators and successors.

Wintrust Financial Corporation by:

	 	 	 
	  
              
             
             
              
              
          

Edward J. Wehmer, President

	 	      
              

Date
	 
	 	 
	Key Employee:
	 	 
	 
	 	 
	  
              
             
             
              
              
          

«Name»

	 	        
            

Date
	 
	 	 
	Attest
	 	 
	 
	 	 
	  
              
             
             
              
              
          

David A. Dykstra

	 	                    

Date

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