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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



 









 




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:


	 	 	 	

	 
	 	 	 	 	 	 	 	 
	Its:


	 	 	 	Dated:



	 
	 	 	 	 	 	 	 	 
	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