EX-10.8






Exhibit 10.8




AMENDED AND RESTATED EMPLOYMENT AGREEMENT




     This Amended and Restated Employment Agreement (the “Agreement”) is made by and between
Wintrust Financial Corporation (“Wintrust”), a bank holding
company, and John S. Fleshood, an
individual resident in the State of Illinois (“Executive”) as of December 19, 2008.



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;



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



     NOW THEREFORE, in consideration of the covenants and agreements contained herein, of
Executive’s employment, of the compensation to be paid by 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 Executive Vice President of
Risk Management of Wintrust and shall perform such duties as may be assigned to Executive by the
Chief Executive Officer and 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 of Wintrust in addition to serving as Executive
Vice President of Risk Management of Wintrust, the provisions of this



1









 







Agreement shall also apply to
the performance of such services by Executive on behalf of such any Affiliate.



     2. Compensation and Benefits. Executive will be paid such base salary as may from
time to time be agreed upon between Executive and 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 and its Affiliates in accordance with
the terms and conditions of such plans and programs. Executive shall also be eligible to
participate in the Wintrust 2007 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 business, professional or civic activities provided that the Board of
Directors of Wintrust approves of such activities and Executive’s engagement does not result in a
violation of Executive’s covenants under this Section or Sections 4 or 5 hereof; or (c) accepting
appointments to the boards of directors of other companies provided that the Board of Directors of
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 and
5 hereof.



     4. Competition. Other than in connection with Executive’s performance of Executive’s
duties hereunder, during the period in which Executive performs services for 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 an owner, principal, 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 commercial and
community banking and/or trust and investment services, and which is located within ten miles of
the principal office or any branch office of Wintrust;



          (b) solicit or conduct business which involves commercial and community banking and/or trust
and investment services with any person, corporation or other entity which was: (i) a customer of
Wintrust or any other Affiliate of Wintrust 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 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 commercial and
community banking and/or trust and investment services and with whom Executive had direct or
indirect contact while employed by Wintrust;



2









 





          (c) request, advise or directly or indirectly invite any of the existing customers, suppliers
or service providers of Wintrust or any Affiliate of Wintrust to withdraw, curtail or cancel its
business with Wintrust or any Affiliate of Wintrust, 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 of Wintrust (i) to terminate his employment or association with
Wintrust or (ii) to become employed by or serve in any capacity by a bank or other financial
institution which operates or is planned to operate at any facility which is located within a ten
mile radius of the principal office or any branch office of Wintrust; or



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



     Notwithstanding the foregoing, Executive shall not be prevented from: (i) investing or owning
shares of stock of any corporation engaged in any business provided that such shares are regularly
traded on a national securities exchange or any over-the-counter market; (ii) retaining any shares
of stock in any corporation which Executive owned prior to the date of Executive’s employment with
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
Wintrust 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 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



3









 







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 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 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 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 Wintrust and all other 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



4









 







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 until August
15, 2010. After such Initial Term, this Agreement shall be extended automatically for successive
one-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 one-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 one-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) one-year from the date of such first occurrence of a
Change in Control. In the event that Executive’s Initial Term or successive one-year term is
extended due to such a Change in Control, such extension shall further be extended automatically
for successive one-year terms unless either Executive or 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 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 Executive’s Target



5









 







Cash Bonus for the year in which
Executive’s death occurs and Executive’s Target Stock Bonus for the year in which Executive’s death
occurs, in a lump sum within 30 days following the date of Executive’s death. For the purposes of
this Agreement, “Target Cash Bonus” shall mean the target cash bonus for the applicable year, 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, “Target Stock
Bonus” shall mean the target amount of restricted shares for such year 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.



               (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%.



               (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 that purpose, or if
Executive has not so designated, then to the spouse of Executive, or if none is surviving, then to
the estate of Executive.



          (c) Termination Due to Permanent Disability.



               (i) Payment. If Executive should suffer a permanent disability during the Term of
this Agreement, 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
Executive’s Target Cash Bonus for the year in which Executive’s permanent disability occurs and
Executive’s Target Stock Bonus for the year in which Executive’s permanent disability occurs. 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).



6









 





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



          (d) Termination Without Cause.



               (i) Payment. In the event Executive’s employment is terminated without Cause (as such
term is defined in Section 9(h) hereof) by 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 Executive’s Target Cash Bonus for the
year in which such termination occurs and Executive’s Target Stock Bonus for the year in which such
termination occurs. Severance Pay under this Section 9(d) shall be paid 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) Company-Paid Health Insurance. In the event of Executive’s termination pursuant
to this Section 9(d), from the termination date through the earliest of (A) the expiration of the
maximum period of COBRA coverage, (B) the date on which Executive becomes eligible for coverage
under another group health insurance plan with no pre-existing condition limitation or exclusion,
or (C) the date on which Executive becomes entitled to benefits under Medicare, Executive (and any
qualified dependents) shall be entitled to group health insurance coverage under Wintrust’s group
health insurance plan for employees (as such plan is then in effect and as it may be amended at any
time and from time to time during the period of coverage) in which Executive was participating
immediately prior to termination, at Wintrust’s expense, subject to any normal employee
contributions, if any. The period during which Executive is being provided with health insurance
under this Agreement shall be credited against Executive’s period of COBRA coverage, if any.
Executive shall promptly notify 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.



          (e) Constructive Termination.



7









 





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



               (iii) 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.



                    (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 Vice
Presidents of Wintrust.



          (f) Termination Upon Change In Control.



8









 





               (i) Payment. In the event that within eighteen months after a Change in Control (as
defined below) of Wintrust (A) Executive’s employment is terminated without Cause (as such term is
defined in Section 9(h) hereof) prior to the expiration of the Term of this Agreement or (B)
Executive suffers a Constructive Termination prior to the expiration of the Term of this Agreement,
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 30 days following
the date of Executive’s termination or Constructive Termination; provided, however, that if such
Change in Control is not a “change in control event,” within the meaning of Section 409A of the
Internal Revenue Code of 1986, as amended (the “Code”), then such Severance Pay shall be paid
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) 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 2007 Stock Incentive Plan.



               (iii) Section 280G. Notwithstanding the foregoing, if the payment required to be paid
under this Section 9(f), when considered either alone or with other payments paid or imputed to the
Executive from Wintrust or an Affiliate that would be deemed “excess parachute payments” under
Section 280G(b)(1) of the Code, is deemed by Wintrust to be a “parachute payment” under Section
280G(b)(2) of Code, then the amount of Severance Pay required to be paid under this Section 9(f)
shall be automatically reduced to an amount equal to $1.00 less than three times (3x) the “base
amount” (as defined in Section 280G(3) of the Code) (the “Reduced Amount”). Provided,
however, the preceding sentence shall not apply if the sum of (A) the amount of Severance
Pay described in this Section 9(f) less (B) the amount of excise tax payable by the Executive
under Section 4999 of the Code with respect to the amount of such Severance Pay and any other
payments paid or imputed to the Executive from Wintrust or an Affiliate that would be deemed to be
“excess parachute payments” under Section 280G(b)(1) of the Code, is greater than the Reduced
Amount. The decision of Wintrust (based upon the recommendations of its tax counsel and
accountants) as to the characterization of payments as parachute payments, the value of parachute
payments, the amount of excess parachute payments, and the payment of the Reduced Amount shall be
final.



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



9









 







becomes eligible for coverage under another group
health plan with no pre-existing condition limitation or exclusion or Executive becomes entitled to
benefits under Medicare.



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



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



                    (B) A Constructive Termination shall also be deemed to have occurred if after a Change in
Control, 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)(iii)(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 Wintrust’s 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 Wintrust’s Board of
Directors which are consistent with the scope and nature of Executive’s duties and responsibilities
as provided in Section 1 of this Agreement;



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



10









 





               (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 termination of Executive from Executive’s position with
Wintrust 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 Wintrust or any other Affiliate, including,
but not limited to, Confidential Information, as well as any automobiles, computers or other
equipment which were purchased or leased by 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 any Affiliate of Wintrust, or the officers, directors,
employees or agents of Wintrust, or any Affiliate of Wintrust in their capacity as such or
otherwise, or that Wintrust, or any Affiliate of Wintrust may have against Executive,



11









 







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.



          (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.



12









 





          (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. Section 409A. This Agreement shall be interpreted and construed in a manner that
avoids the imposition of additional taxes and penalties under Section 409A of the Code (“409A
Penalties”). In the event the terms of this Agreement would subject Executive to 409A Penalties,
Wintrust and Executive shall cooperate diligently to amend the terms of the Agreement to avoid such
409A Penalties, to the extent possible. The payments to Executive pursuant to Section 9 of this
Agreement are intended to be exempt from Section 409A of the Code to the maximum extent possible,
under either the separation pay exemption pursuant to Treasury regulation §1.409A-1(b)(9)(iii) or
as a short-term deferral pursuant to Treasury regulation §1.409A-1(b)(4), and for purposes of the
separation pay exemption, each installment paid to Executive under Section 9 shall be considered a
separate payment. Notwithstanding any other provision in this Agreement, if on the date of
Executive’s separation from service, within the meaning of Section 409A of the Code (the
“Separation Date”), (i) Wintrust is a publicly traded corporation and (ii) Executive is a
“specified employee,” as defined in Section 409A of the Code, then to the extent any amount payable
under this Agreement constitutes the payment of nonqualified deferred compensation, within the
meaning of Section 409A of the Code, that under the terms of this Agreement would be payable prior
to the six- month anniversary of the Separation Date, such payment shall be delayed until the
earlier to occur of (A) the six-month anniversary of the Separation Date or (B) the date of
Executive’s death. For purposes of determining the timing of payments to Executive pursuant to
Section 9, all references to Executive’s termination of employment shall mean the Separation Date.



     14. 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).



13









 







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.



14









 





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



	 	 	 	 	 	 	 	 	 
	WINTRUST FINANCIAL CORPORATION	 	 	 	JOHN S. FLESHOOD	 	 
	 
	 	 	 	 	 	 	 	 
	By:

	 	/s/ David A. Dykstra
	 	 	 	/s/ John S. Fleshood
	 	 
	 

	 	 
	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	Its:

	 	Senior EVP and Chief Operating Officer
	 	 	 	Dated: December 19, 2008	 	 
	 
	 	 	 	 	 	 	 	 
	Dated:

	 	December 19, 2008	 	 	 	 	 	 






15









 






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

Hinsdale Bank & Trust Company

Lake Forest Bank & Trust Company

Libertyville Bank & Trust Company

North Shore Community Bank & Trust Company

Northbrook Bank & Trust Company

Old Plank Trail Community Bank, N.A.

St. Charles Bank & Trust Company

State Bank of the Lakes

Town Bank (Wisconsin)

Tricom, Inc. of Milwaukee

Village Bank & Trust

Wayne Hummer Asset Management Company

Wayne Hummer Investments, LLC

Wayne Hummer Trust Company, N.A.

Wheaton Bank & Trust Company

Wintrust Information Technology Services Company

Wintrust Mortgage Corporation