Document:

EX-10.5

Exhibit 10.5

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 David A. Dykstra, 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; 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 Senior Executive Vice
President and Chief Operating Officer of Wintrust and shall perform such duties as may be assigned
to Executive by the Chief Executive 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. Subject to Sections 9(e) and 9(f)
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 Senior Executive Vice President and Chief Operating Officer 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 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

 

 

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 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 limited to, lists of lending clients with their addresses and account numbers,
credit analysis reports

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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 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 until
January 24, 2011. 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

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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 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 Cash Bonus for the year in
which Executive’s death occurs and Executive’s Target Stock Bonus or 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 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 Executive’s Target Cash Bonus for the year in which Executive’s

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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).

               (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, 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. 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
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 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) 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. Executive shall promptly notify Wintrust if Executive

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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) the assignment to
Executive of any duties substantively inconsistent with Executive’s position (including status,
offices, titles and reporting requirements), authority, duties or responsibilities as contemplated
by Section 1, or any other diminution in such position, authority, duties or responsibilities
(including, without limitation, any diminution occurring solely as a result of Wintrust ceasing to
be a publicly traded entity or becoming a wholly owned subsidiary of another entity) or 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; provided, however, that the
occurrence of any such condition shall not constitute Constructive Termination unless Executive
provides notice to Wintrust of the existence of such condition not later than 90 days after the
initial existence of such condition, and Wintrust shall have failed to remedy such condition within
30 days after receipt of such notice. 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
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. 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.

               (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 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

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thirty (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) 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 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. 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.

               (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:

7

 

                    (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 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;

               (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

8

 

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 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.

          (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.

9

 

          (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).
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.

10

 

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

	 	 	 	 	 	 	 
	WINTRUST FINANCIAL CORPORATION	 	DAVID A. DYKSTRA	 	 
	 
	 	 	 	 	 	 
	By:

	 	/s/ Edward Wehmer
 

	 	/s/ David A. Dykstra
 

	 	 
	 
	 	 	 	 	 	 
	Its: Chief Executive Officer	 	Dated: December 19, 2008	 	 
	 
	 	 	 	 	 	 
	Dated: December 19, 2008	 	 	 	 

11

 

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

12EX-10.6

Exhibit 10.6

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 David L. Stoehr, an
individual resident in the State of Illinois (“Executive”) as of December 19, 2008.

WITNESSETH THAT:

     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 and Chief Financial Officer of Wintrust and shall perform such duties as may be assigned
to Executive by the Chief Executive Officer of 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 and Chief Financial Officer of Wintrust, the provisions of this
Agreement shall also apply to the performance of such services by Executive on behalf of such
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;

          (c) request, advise or directly or indirectly invite any of the existing
customers, suppliers or service providers of Wintrust or any other Affiliate of Wintrust to
withdraw, curtail or cancel its business with Wintrust or any other 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 other 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).

2

 

     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 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 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.

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     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
January 26, 2009. 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) two years from the date of such first occurrence of
a Change in Control. In the event that Executive’s Initial Term or successive one-year term is
extended due to such a Change in Control, such extension shall further be extended automatically
for successive one-year terms unless either Executive or 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 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%.

4

 

               (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).

               (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

5

 

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.

               (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. 

               (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

6

 

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 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)(iv)(B) shall not be applicable to a Constructive
Termination following a Change in Control.

7

 

          (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;

               (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 any other

8

 

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, 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.

          (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

9

 

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).
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.

10

 

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

	 	 	 	 	 	 	 
	WINTRUST FINANCIAL CORPORATION	 	DAVID L. STOEHR	 	 
	 
	 	 	 	 	 	 
	By:

	 	/s/ David A. Dykstra
 

	 	/s/ David L. Stoehr
 

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

11

 

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

12

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