EMPLOYMENT AGREEMENT

          This Employment Agreement (the “Agreement”) is made by and between
WINTRUST FINANCIAL CORPORATION (“Wintrust”), a bank holding company, and
                                                            , an individual
resident in the State of                          (“Executive”) as of
                           , 200          .

WITNESSETH THAT:

          WHEREAS, Wintrust is a bank holding company;

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

          WHEREAS, by virtue of Executive’s employment with Wintrust, 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 Wintrust or its Affiliates; and

          WHEREAS, Wintrust and Executive desire to 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
Wintrust for Executive’s services, and of Wintrust’s other undertakings in this
Agreement, the parties hereto do hereby agree as follows:

          1. Scope of Employment. Executive will be employed as
                                          of Wintrust and shall perform such
duties as may be assigned to Executive by the Chief Executive Officer and/or the
Chief Operating Officer and/or the Board of Directors of Wintrust in such
position. Executive agrees that during Executive’s employment Executive will be
subject to and abide by the written policies and practices of 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 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

 

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perform services for any Affiliate in addition to serving as
                                         of Wintrust, the provisions of this
Agreement shall also apply to the performance of such services by Executive on
behalf of the Affiliate.

          2. Compensation and Benefits. Executive will be paid such base salary
as may from time to time be agreed upon between Executive and Wintrust.
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 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 Wintrust 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 Wintrust governing transactions with affiliates and ownership
interests in customers); (b) engaging (whether or not during normal business
hours) in any other professional, civic or philanthropic activities provided
that Executive’s engagement does not result in a violation of Executive’s
covenants under this Section or Sections 4 and 5 hereof; or (c) accepting
appointments to the boards of directors of other companies provided that the
Board of Directors of Wintrust 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 or 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 Wintrust and for a period of three years after termination of
Executive’s employment with Wintrust, 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 a principal, owner, senior manager, or in a position
comparable to that held by Executive at any time during Executive’s employment
with Wintrust, for a bank or other financial institution (or any branch or
affiliate thereof) which offers to its customers any of the services provided by
Wintrust or its Affiliates and which operates in the Market Area of Wintrust or
any Affiliate;

               (b) solicit or conduct business which involves any of the
services provided by Wintrust or its Affiliates from or with any person,
corporation or other entity which was (i) a customer of Wintrust or any
Affiliate with whom Executive had direct or indirect contact while employed by
Wintrust or about whom Executive obtained Confidential Information during the
fifteen months prior to the termination of Executive’s

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employment with Wintrust, or (ii) a potential customer with whom Wintrust or any
Affiliate has, at the time of Executive’s termination of employment with
Wintrust, an outstanding oral or written proposal to provide any of the services
provided by Wintrust or its Affiliates and with whom Executive had direct or
indirect contact while employed by Wintrust;

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

               (d) hire, solicit, induce or attempt to solicit or induce any
employee, consultant, or agent of Wintrust or any Affiliate (i) to terminate his
employment or association with Wintrust or any Affiliate or (ii) to become
employed by or to serve in any capacity by a bank or other financial institution
which operates or is planned to operate in the Market Area of Wintrust or of any
Affiliate; or

               (e) in any way participate in planning or opening a bank or other
financial institution which operates or is intended to operate in the Market
Area of Wintrust or of any Affiliate.

          For the purposes of this Agreement, the Market Area of Wintrust or of
an Affiliate shall be the area within a ten (10) mile radius of the principal
office and branches of Wintrust or of any Affiliate.

          Notwithstanding the foregoing, 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 in 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 Wintrust (subject to any and all rules and regulations of
applicable banking regulators or policies of Wintrust 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).

          5. Confidential Information. Executive acknowledges that, during
Executive’s employment with Wintrust, Executive has and will obtain access to
Confidential Information of and for 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 Wintrust or
any Affiliate, including, but not

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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 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
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 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 Wintrust or any Affiliate, including lists
of the same; (f) the identity of suppliers and service providers of 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 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 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 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 Wintrust or any Affiliate; (k) the business and
strategic growth plans of Wintrust or any Affiliate; and (l) confidential
communication materials provided for shareholders of Wintrust or of any
Affiliate. Absent prior authorization by Wintrust or as required in Executive’s
duties for Wintrust, 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 during Executive’s employment with Wintrust 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 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 Wintrust or any Affiliate that may be
conceived, developed, or made by Executive during employment with Wintrust
(hereinafter “Inventions”), either solely or jointly with others, shall
automatically become the sole property of Wintrust or an Affiliate. Executive
shall immediately disclose to Wintrust all such Inventions and shall, without
additional compensation, execute all assignments and other documents deemed
necessary to perfect the property rights of 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 Wintrust. The provisions of

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this Section 6 shall not apply to any Invention for which no equipment,
supplies, facility, or trade secret information of 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 Wintrust or an
Affiliate or (ii) to the actual or demonstrably anticipated research or
development of Wintrust or an Affiliate, or (b) such Invention results from work
performed by Executive for Wintrust.

          7. Remedies. Executive acknowledges that the compliance with the terms
of this Agreement is necessary to protect the Confidential Information and
goodwill of Wintrust and its Affiliates and that any breach by Executive of this
Agreement will cause continuing and irreparable injury to Wintrust and its
Affiliates for which money damages would not be an adequate remedy. Executive
acknowledges that Affiliates are and are intended to be third party
beneficiaries of this Agreement. Executive acknowledges that 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 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 three-year terms, unless either Executive or Wintrust 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 three-year term there is a Change in Control of
Wintrust (as defined in Section 9(f)), then upon the first occurrence of such a
Change in Control, the Initial Term or the successive three-year term of this
Agreement (whichever is in effect as of the date of the Change in Control) shall
automatically extend 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 three-year term is extended due to such a Change in Control,
such extension shall further be extended automatically for successive three-year
terms, unless either Executive or Wintrust 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 Wintrust at any time for any reason, with or without cause, and, except as
otherwise provided in this Section 9, any and all of Wintrust’s obligations
under this Agreement shall terminate, other than Wintrust’s obligation to pay
Executive, within 30 days of

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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
Wintrust 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, Wintrust shall pay Executive an amount equal to three times (3x) 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 Wintrust’s Board of Directors or the Compensation
Committee or any successor committee of Wintrust’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
Wintrust’s Board of Directors or the Compensation Committee or any successor
committee of Wintrust’s Board of Directors. Any bonuses (whether in cash or in
the 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 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
Wintrust in order to enable 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%.

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                    (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 Wintrust for this 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, Wintrust shall have the right to
terminate Executive’s employment. In such event, Wintrust shall pay Executive an
amount equal to three times (3x) 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
36-month period beginning on the first payroll period following such termination
and on each payroll period thereafter during the 36-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 Wintrust or (y) Wintrust 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 Wintrust
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 Wintrust and authorizing such physician or other health
care specialist to discuss Executive’s condition with Wintrust).

                    (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 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 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

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paid under this Section 9(c) shall be not less than an amount to provide
Executive with a gross monthly payment of $20,000.00 during the 36-month
Severance Pay period. Executive agrees to promptly notify Wintrust if Executive
obtains employment of any sort during the applicable Severance Pay period and to
provide Wintrust 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, from the termination date through
the earlier of (A) the date on which Executive becomes eligible for coverage
under another group health insurance plan with no pre-existing condition
limitation or exclusion or (B) the date on which Executive becomes entitled to
benefits under Medicare, Executive (and any qualified dependents) shall be
entitled to group health insurance coverage. Such coverage shall be provided, at
the option of Wintrust, either: (x) under the Wintrust 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 Wintrust’s expense,
subject to any normal employee contributions, if any; or (y) under an individual
health insurance policy having coverage similar to that provided by the Wintrust
group health 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), at
Wintrust’s expense. 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 Wintrust if
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.

               (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
Wintrust during the Term of this Agreement, other than upon the expiration of
the Term of this Agreement, Wintrust shall pay Severance Pay to Executive in the
amount equal to three times (3x) 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 amounts awarded or granted to Executive during
the twelve-month period prior to termination. Severance Pay under this Section
9(d) shall be paid to the Executive ratably over a 36-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 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

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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 be not less
than an amount to provide Executive with a gross monthly payment of $20,000.00
during the 36-month Severance Pay period. Executive agrees to promptly notify
Wintrust if Executive obtains employment of any sort during the applicable
Severance Pay period and to provide Wintrust 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.

                    (iii) Company-Paid Health Insurance. In the event of
Executive’s termination pursuant to this Section 9(d), from the termination date
through the earlier of (A) the date on which Executive becomes eligible for
coverage under another group health insurance plan with no pre-existing
condition limitation or exclusion or (B) the date on which Executive becomes
entitled to benefits under Medicare, Executive (and any qualified dependents)
shall be entitled to group health insurance coverage. Such coverage shall be
provided, at the option of Wintrust, either: (x) under the Wintrust 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
Wintrust’s expense, subject to any normal employee contributions, if any; or
(y) under an individual health insurance policy having coverage similar to that
provided by the Wintrust group health 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), at Wintrust’s expense. 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 Wintrust if 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.

               (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, Wintrust 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, “Constructive Termination” means (A) a material reduction by Wintrust
in the duties and responsibilities of Executive or (B) a reduction by Wintrust
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

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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
Constructive 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 be not less than an amount to provide Executive with a gross
monthly payment of $ 20,000.00 during the 36-month Severance Pay period.
Executive agrees to promptly notify Wintrust if he or she obtains employment of
any sort during the applicable Severance Pay period and to provide Wintrust 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.

                    (iii) Company-Paid Health Insurance. In the event of
Executive’s Constructive Termination pursuant to this Section 9(e), from the
termination date through the earlier of (A) the date on which Executive becomes
eligible for coverage under another group health insurance plan with no
pre-existing condition limitation or exclusion, or (B) the date on which
Executive becomes entitled to benefits under Medicare, Executive (and any
qualified dependents) shall be entitled to group health insurance coverage. Such
coverage shall be provided, at the option of Wintrust, either: (x) under the
Wintrust 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 Wintrust’s expense, subject to any normal employee
contributions, if any; or (y) under an individual health insurance policy having
coverage similar to that provided by the Wintrust group health 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), at Wintrust’s expense. 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 Wintrust if 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.

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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. Wintrust provided car, club dues and
supplemental life insurance) as estimated by Wintrust 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 Wintrust.

                         (B) For the purposes of this Section 9(e), the
Executive will not be deemed to have incurred a reduction by Wintrust 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 Executive and Senior Vice Presidents of Wintrust.

               (f) Termination Upon Change In Control.

                    (i) Payment. In the event that within eighteen months after
a Change in Control of Wintrust (as defined below) (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,
Wintrust (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 thirty (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” shall have the same meaning as provided in Section 12(b)
of the Wintrust 1997 Stock Incentive Plan.

                    (iii) Gross-Up Payment. If it is determined that any amount,
right or benefit paid or payable (or otherwise provided or to be provided) to
the Executive by Wintrust or any of its affiliates under this Agreement or any
other plan, program or arrangement under which Executive participates or is a
party, other than amounts payable under this Section 9(f)(iii) (collectively,
the “Payments”), would constitute an “excess parachute payment” within the
meaning of Section 280G of the Internal Revenue Code, subject to the excise tax
imposed by Section 4999 of the Code, or any interest or penalties with respect
to such excise tax (such excise tax, together with any such interest and
penalties, are collectively referred to as the “Excise Tax”), then Executive
shall be entitled to receive an additional cash payment (a “Gross-Up Payment”)
within 30 days of such determination equal to an amount such that after payment
by Executive of all taxes (including any interest or penalties imposed with
respect to such taxes), including any Excise Tax, imposed upon the Gross-Up
Payment, Executive would retain an amount of the Gross-Up Payment equal to the
Excise Tax imposed upon the total Payments. All

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determinations required to be made under this Section 9(f)(iii), including
whether and when a Gross-Up Payment is required, the amount of such Gross-Up
Payment and the assumptions to be utilized in arriving at such determination,
shall be made by Wintrust’s independent auditor. The auditor shall promptly
provide detailed supporting calculations to both Wintrust and Executive
following any determination that a Gross-Up Payment is necessary. All fees and
expenses of the auditor shall be paid by Wintrust. If no determination by
Wintrust’s auditors is made prior to the time a tax return reflecting the total
Payments is required to be filed by Executive, Executive will be entitled to
receive a Gross-Up Payment calculated on the basis of the total Payments
reported by Executive in such tax return, within 30 days of the filing of such
tax return. All determinations made by such auditor shall be binding upon
Wintrust and Executive. In all events, if any tax authority determines that a
greater Excise Tax should be imposed upon the total Payments than is determined
by Wintrust’s independent auditors or reflected in Executive’s tax return
pursuant to this Section, Executive shall be entitled to receive the full
Gross-Up Payment calculated on the basis of the amount of Excise Tax determined
to be payable by such tax authority from Wintrust within 30 days of such
determination. In the event that any tax authority determines that a lesser
Excise Tax should be imposed on the total Payments than is determined by
Wintrust’s independent auditors or reflected in Executive’s tax return pursuant
to this Section, and Wintrust paid a Gross-Up Payment to the Executive in excess
of the amount of the Gross-Up Payment to which he is actually entitled
hereunder, then such excess shall be reimbursed by the Executive to Wintrust
within 30 days of such determination.

                    (iv) Company-Paid Health Insurance. In the event Executive
becomes entitled to payments under this Section 9(f), from the termination date
through the earlier of (A) the date on which Executive becomes eligible for
coverage under another group health insurance plan with no pre-existing
condition limitation or exclusion, or (B) the date on which Executive becomes
entitled to benefits under Medicare, Executive (and any qualified dependents)
shall be entitled to group health insurance coverage. Such coverage shall be
provided, at the option of Wintrust, either: (x) under the Wintrust 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
Wintrust’s expense, subject to any normal employee contributions, if any; or
(y) under an individual health insurance policy having coverage similar to that
provided by the Wintrust group health 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), at Wintrust’s expense. 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 Wintrust 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.

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               (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, Wintrust (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).

                    (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 Wintrust 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 Wintrust’s obligations under this Agreement shall
terminate immediately except for Wintrust’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 Wintrust’s Board of Directors or the
Compensation Committee or any successor committee of the Wintrust Board of
Directors, all obligations of Wintrust shall terminate immediately except for
Wintrust’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 Wintrust 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;

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               (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 Wintrust or
substantial damage to Wintrust’s reputation;

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

               (vi) A written order requiring the termination of Executive from
Executive’s position with Wintrust or any Affiliate for which Executive is also
providing services 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 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 Wintrust a release in such form as provided by Wintrust 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 Wintrust, 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 Wintrust or relating to or arising out of this Agreement and the
termination thereof.

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

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well as any automobiles, computers or other equipment which were purchased or
leased by Wintrust 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
Wintrust or the termination of such employment (“Claims”), that Executive may
have against Wintrust or against its Affiliates, officers, directors, employees
or agents in their capacity as such or otherwise, or that 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 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 Wintrust 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 Wintrust is found to have violated
any material terms of this Agreement, Wintrust 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.

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          (b) This Agreement may be assigned by Wintrust. This Agreement and the
covenants set forth herein shall inure to the benefit of and shall be binding
upon the successors and assigns of 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) Wintrust 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 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
Wintrust 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 Wintrust desires to terminate the employment of the Executive during
the Term of this Agreement, Wintrust 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 Wintrust 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 Wintrust.

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

WINTRUST FINANCIAL CORPORATION

                  By:

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                Its:

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      Dated:

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                Dated:

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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

 

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EXHIBIT B