Document:

exv10w17

Exhibit 10.17

EMPLOYMENT AGREEMENT

     This Employment Agreement (the “Agreement”) is made by and between WINTRUST FINANCIAL
CORPORATION (“Employer”), a bank holding company, and Leona A. Gleason, an individual resident in
the State of Illinois (“Executive”) as of January 4, 2010.

WITNESSETH THAT:

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

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

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

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

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

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

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

1

 

services for Wintrust or any Affiliate in addition to serving as Executive Vice
President and Chief Administrative Officer, the provisions of this Agreement shall also apply to
the performance of such services by Executive on behalf of Wintrust or any Affiliate.

     2. Compensation and Benefits. Executive will be paid such base salary as may from time
to time be agreed upon between Executive and Employer. Executive will be entitled to coverage under
such compensation plans, insurance plans and other fringe benefit plans and programs as may from
time to time be established for employees of Wintrust and its Affiliates in accordance with the
terms and conditions of such plans and programs. Executive shall also be eligible to participate in
the Wintrust 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 Employer during the Term of this Agreement; but this shall not be
construed as preventing Executive from (a) investing Executive’s personal assets in such form or
manner as will not require any services on the part of Executive in the operation or the affairs of
the corporations, partnerships and other entities in which such investments are made and in which
Executive’s participation is solely that of an investor (subject to any and all rules and
regulations of applicable banking regulators or policies of the Employer governing transactions
with affiliates and ownership interests in customers); (b) engaging (whether or not during normal
business hours) in any other business, professional or civic activities provided that the Board of
Directors of Employer approves of such activities and Executive’s engagement does not result in a
violation of Executive’s covenants under this Section or Sections 4 or 5 hereof; or (c) accepting
appointments to the boards of directors of other companies provided that the Board of Directors of
Employer approves of such appointments and Executive’s performance of Executive’s duties on such
boards does not result in a violation of Executive’s covenants under this Section or Sections 4 and
5 hereof.

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

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

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

2

 

Employer, an outstanding oral or written proposal to provide commercial and community
banking and/or trust and investment services and with whom Executive had direct or indirect contact
while employed by Employer;

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

          (d) hire, solicit, induce or attempt to solicit or induce any employee, consultant, or agent
of Employer, Wintrust or any other Affiliate of Wintrust (i) to terminate his employment or
association with Employer or (ii) to become employed by or serve in any capacity by a bank or other
financial institution which operates or is planned to operate at any facility which is located
within a ten mile radius of the principal office of the Executive; 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 of the Executive.
For the purposes of this Agreement, in the event Executive’s geographic area of responsibility as
specified herein shall change during employment with Employer, or as the result of performing
services for Wintrust or any Affiliate of Wintrust, the Executive’s obligation stated in Sections
4(a), 4(d)(ii) and 4(e) shall apply to a ten mile radius of Executive’s revised geographic area of
responsibility.

     Notwithstanding the foregoing, (a) Executive shall not be prevented from: (i) investing or
owning shares of stock of any corporation engaged in any business provided that such shares are
regularly traded on a national securities exchange or any over-the-counter market; (ii) retaining
any shares of stock in any corporation which Executive owned prior to the date of Executive’s
employment with Employer (subject to any and all rules and regulations of applicable banking
regulators or policies of the Employer governing transactions with affiliates and ownership
interests in customers); or (iii) investing as a limited partner (without decision-making
authority) in any private equity fund, provided that Executive’s involvement in such investment is
solely that of a passive investor (subject to any and all rules and regulations of applicable
banking regulators or policies of the Employer governing transactions with affiliates and ownership
interests in customers), and (b) Executive shall not be in violation of Sections 4(a) or 4(e) of
this Agreement if, during the two-year period following termination of employment Executive accepts
employment or invests in a bank or other financial institution which is within a ten mile radius of
the principal offices or any branch office of Wintrust or any Affiliate of Wintrust (other than
Employer) as long as such facility is not within a ten mile radius of the principal office of the
Executive.

     5. Confidential Information. Executive acknowledges that, during Executive’s
employment with Employer, Executive has and will obtain access to Confidential Information of and
for Employer, Wintrust or its Affiliates. For purposes of this Agreement, “Confidential
Information” shall mean information not generally known or available without restriction to the
trade or industry, including, without limitation, the following categories of information and

3

 

documentation: (a) documentation and information relating to lending customers of Employer,
Wintrust or any Affiliate, including, but not limited to, lists of lending clients with their
addresses and account numbers, credit analysis reports and other credit files, outstanding loan
amounts, repayment dates and instructions, information regarding the use of the loan proceeds, and
loan maturity and renewal dates; (b) documentation and information relating to depositors of
Employer, Wintrust or any Affiliate, including, but not limited to, lists of depositors with their
addresses and account numbers, amounts held on deposit, types of depository products used and the
number of accounts per customer; (c) documentation and information relating to trust customers of
Employer, Wintrust or any Affiliate, including, but not limited to, lists of trust customers with
their addresses and account numbers, trust investment management contracts, identity of investment
managers, trust corpus amounts, and grantor and beneficiary information; (d) documentation and
information relating to investment management clients of Employer, Wintrust or any Affiliate,
including, but not limited to, lists of investors with their addresses, account numbers and
beneficiary information, investment management contracts, amount of
assets held for management, and
the nature of the investment products used; (e) the identity of actual or potential customers of
Employer, Wintrust or any Affiliate, including lists of the same; (f) the identity of suppliers and
service providers of Employer, Wintrust or any Affiliate, including lists of the same and the
material terms of any supply or service contracts; (g) marketing materials and information
regarding the products and services offered by Employer, Wintrust or any Affiliate and the nature
and scope of use of such marketing materials and product information; (h) policy and procedure
manuals and other materials used by Employer, Wintrust or any Affiliate in the training and
development of its employees; (i) identity and contents of all computer systems, programs and
software utilized by Employer, Wintrust or any Affiliate to conduct its operations and manuals or
other instructions for their use; (j) minutes or other summaries of Board of Directors or other
department or committee meetings held by Employer, Wintrust or any Affiliate; (k) the business and
strategic growth plans of Employer, Wintrust or any Affiliate; and (1) confidential communication
materials provided for shareholders of Employer, Wintrust or any Affiliate. Absent prior
authorization by Employer or as required in Executive’s duties for Employer, Executive will not at
any time, directly or indirectly, use, permit the use of, disclose or permit the disclosure to any
third party of any such Confidential Information to which Executive will be provided access. These
obligations apply both during Executive’s employment with
Employer and shall continue beyond the
termination of Executive’s employment and this Agreement.

     6.
Inventions. All discoveries, designs, improvements, ideas, and inventions, whether
patentable or not, relating to (or suggested by or resulting from) products, services, or other
technology of Employer, Wintrust or any Affiliate or relating to (or suggested by or resulting
from) methods or processes used or usable in connection with the business of Employer, Wintrust or
any Affiliate that may be conceived, developed, or made by Executive during employment with
Employer (hereinafter “Inventions”), either solely or jointly with others, shall automatically
become the sole property of Employer, Wintrust or an Affiliate. Executive shall immediately
disclose to Employer all such Inventions and shall, without additional compensation, execute all
assignments and other documents deemed necessary to perfect the property rights of Employer,
Wintrust or any Affiliate therein. These obligations shall continue beyond the termination of
Executive’s employment with respect to Inventions conceived, developed, or made by Executive during
employment with Employer. The provisions of this

4

 

Section 6 shall not apply to any Invention for which no equipment, supplies, facility, or
trade secret information of Employer, Wintrust or any Affiliate is used by Executive and which is
developed entirely on Executive’s own time, unless (a) such Invention relates (i) to the business
of Employer, Wintrust or an Affiliate or (ii) to the actual or demonstrably anticipated research or
development of Employer, Wintrust or an Affiliate, or (b) such Invention results from work
performed by Executive for Employer.

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

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

     9. Termination of Employment.

          (a) General Provisions. Executive’s employment may be terminated by Employer at
any time for any reason, with or without cause, and, except as otherwise provided in this Section
9, any and all of Employer’s obligations under this Agreement shall terminate, other than
Employer’s obligation to pay Executive, within 30 days of Executive’s termination of employment,
the full amount of any earned but unpaid base salary and accrued but unpaid vacation pay earned by
Executive pursuant to this Agreement through and including the date of

5

 

termination and to observe the terms and conditions of any plan or benefit arrangement
which, by its terms, survives such termination of Executive’s employment. The payments to be made
under this Section 9(a) shall be made to Executive, or in the event of Executive’s death, to such
beneficiary as Executive may designate in writing to Employer for that purpose, or if Executive has
not so designated, then to the spouse of Executive, or if none is surviving, then to the estate of
Executive. Notwithstanding the foregoing, termination of employment shall not affect the
obligations of Executive that, pursuant to the express provisions of this Agreement, continue in
effect.

          (b) Termination Due to Death.

               (i) Payment. If Executive should die during the Term of this
Agreement, which event shall result in the termination of Executive’s employment, Employer
shall pay Executive an amount equal to two times (2x) the sum of (A) Executive’s base annual salary
in effect at the time of Executive’s death plus (B) an amount equal to any Cash Bonus amounts paid
to Executive during the twelve-month period prior to Executive’s death and any Stock Bonus amounts
awarded or granted to Executive during the twelve-month period prior to Executive’s death, in a
lump sum within 30 days following the date of Executive’s
death. For the purposes of this
Agreement, “Cash Bonus” shall mean any cash bonus amounts that are included in Executive’s annual
bonus plan, as approved in writing by Employer’s Board of Directors or the Compensation Committee
or any successor committee of Employer’s Board of Directors. For the purposes of this Agreement,
“Stock Bonus” shall mean any restricted shares that are included in Executive’s annual bonus plan,
as approved in writing by the Employer’s Board of Directors or the Compensation Committee or any
successor committee of Employer’s Board of Directors. Any bonuses (whether in cash or in the form
of restricted shares) that are not included in such annual bonus plan shall not be considered to be
Cash Bonus amounts or Stock Bonus awards for purposes of this Agreement. The value of the Stock
Bonus amounts shall be determined as of the date they are awarded or granted to Executive.

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

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

6

 

          (c)
Termination Due to Permanent Disability.

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

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

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

7

 

               (iv) Continued
Participation In Benefit Plans. In the event of
termination due to a permanent disability, from the termination date through the earlier of
(A) the date on which Executive becomes eligible for coverage under another group health insurance
plan with no pre-existing condition limitation or exclusion or (B) the date on which Executive
becomes entitled to benefits under Medicare, Executive (and any qualified dependents and/or spouse)
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 Employer during the Term of this Agreement, other
than upon the expiration of the Term of this Agreement, Employer shall pay Severance Pay to
Executive in the amount equal to two times (2x) the sum of (A) Executive’s base annual salary in
effect at the time of Executive’s termination plus (B) an amount equal to any Cash Bonus amounts
paid to Executive during the twelve-month period prior to termination and any Stock Bonus amounts
awarded or granted to Executive during the twelve-month period prior
to termination. Severance Pay
under this Section 9(d) shall be paid ratably over a 24-month period beginning on the first payroll
period following such termination and on each payroll period thereafter during such Severance Pay
period.

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

8

 

               (iii) Company-Paid Health Insurance. In the event of Executive’s
termination pursuant to this Section 9(d), from the termination date through the earliest of
(A) the 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 and/or spouse)
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.

          (e) Constructive Termination.

               (i) Payment. If Executive suffers a Constructive Termination during the Term of
this Agreement, other than upon the expiration of the Term of this Agreement, Employer shall pay
Severance Pay to Executive in the amounts and at the times described in Section 9(d) hereof. For
the purposes of this Agreement, “Constructive Termination” means (A) a material reduction by
Employer in the duties and responsibilities of Executive or (B) a reduction by Employer of
Executive’s “Adjusted Total Compensation” (as hereinafter defined), to (1) less than seventy-five
percent (75%) of the Adjusted Total Compensation of Executive for the twelve-month period ending as
of the last day of the month immediately preceding the month in which the Constructive Termination
occurs; or (2) less than seventy-five percent (75%) of the Executive’s Adjusted Total Compensation
for the twelve-month period ending as of the last day of the month preceding the Effective Date,
whichever is greater. A Constructive Termination does not include termination for Cause as defined
in Section 9(h), termination without Cause as defined in Section 9(d), or termination due to a
permanent disability as defined in Section 9(c).

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

9

 

payroll or income records and a summary of any contributions received under any deferred
compensation arrangement.

               (iii) Company-Paid Health Insurance. In the event of Executive’s
termination pursuant to this Section 9(e), from the termination date through the earliest of
(A) the 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 and/or spouse)
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.

               (iv) Definitions.

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

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

          (f) Termination
Upon Change In Control.

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

               (ii) Change In Control. For the purposes of this Agreement, a “Change

10

 

in Control” of Employer means (A) the acquisition by any person of 50% or more of
Employer’s then outstanding capital stock; or (B) approval by the stockholders of Employer of a
merger or consolidation effecting a change in ownership of 50% or more of the voting power of the
outstanding capital stock of Employer or a sale for cash of all or substantially all of the assets
of Employer; in each case, the acquiring persons in such merger, consolidation or sale shall be
persons other than the stockholders of Employer, Wintrust or any Affiliate immediately prior to
such transaction. For the purposes of this Agreement, a “Change in Control” of Wintrust shall have
the same meaning as provided in Section 12(b) of the Wintrust 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 Internal Revenue Code of 1986, as amended (the “Code”), is deemed
by Wintrust to be a “parachute payment” under Section 280G(b)(2) of Code, then the amount of
Severance Pay required to be paid under this Section 9(f) shall be automatically reduced to an
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 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 and/or spouse) 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.

               (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)

11

 

with the following modifications:

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

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

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

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

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

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

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

               (iii) Executive’s conviction of a felony;

12

 

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

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

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

               (vii) Executive’s engagement, during the performance of Executive’s duties hereunder, in
acts or omissions constituting fraud, intentional breach of fiduciary obligation, intentional
wrongdoing or malfeasance, or intentional and material violation of applicable banking laws, rules,
or regulations.

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

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

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

     10. Resolution of Disputes. Except as otherwise provided herein, any disputes
arising under or in connection with this Agreement or in any way arising out of, relating to or
associated with the Executive’s employment with Employer or the termination of such employment
(“Claims”), that Executive may have against Employer, Wintrust or any Affiliate of Wintrust, or the
officers, directors, employees or agents of Employer, Wintrust, or any Affiliate of Wintrust in
their capacity as such or otherwise, or that Employer, Wintrust, or any Affiliate of Wintrust may
have against Executive, shall be resolved by binding arbitration, to be held in Chicago, Illinois,
in

13

 

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 Employer or the Executive for
injunctive and/or other equitable relief regarding the covenants set forth in Sections 3, 4, 5 and
6 of this Agreement. Each party shall initially bear their own costs of the arbitration or
litigation, except that, if Employer is found to have violated any material terms of this
Agreement, Employer shall reimburse Executive for the entire amount of reasonable attorneys’ fees
incurred by Executive as a result of the dispute hereunder in addition to the payment of any
damages awarded to Executive.

     11. General Provisions.

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

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

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

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

14

 

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

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

          (g) This instrument constitutes the entire agreement of the parties with respect to its
subject matter. This Agreement may not be changed or amended orally but only by an agreement in
writing, signed by the party against whom enforcement of any waiver, change, modification,
extension, or discharge is sought. Any other understandings and agreements, oral or written,
respecting the subject matter hereof are hereby superseded and canceled.

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

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

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

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

	 	 	 	 	 	 	 	 	 	 	 

	WINTRUST FINANCIAL
CORPORATION	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 
	By:	 	/s/ David A. Dykstra	 	 	 	/s/ Lcona A.  Gleason	 	 
	 	 	 	 	 	 	 	 	 
	 	 	David A. Dykstra	 	 	 	Lcona A. Gleason	 	 
	Its:	 	Sr. EVP and Chief Operating Officer	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 
	Dated:

	 	   1/4/10
 

	 	 
	 	Dated:
	 	  1/4/10
 

	 	 

15

 

EXHIBIT A

Advantage National Bank

Barrington Bank & Trust Company, N.A.

Beverly Bank & Trust Company, N.A.

Crystal Lake Bank & Trust Company, N.A.

First Insurance Funding Corporation

Hinsdale Bank & Trust Company

Lake Forest Bank & Trust Company

Libertyville Bank & Trust Company

North Shore Community Bank & Trust Company

Northbrook Bank & Trust Company

Old Plank Trail Community Bank, N.A.

St. Charles Bank & Trust Company

State Bank of the Lakes

Town Bank (Wisconsin)

Tricom, Inc. of Milwaukee

Village Bank & Trust

Wayne Hummer Asset Management Company

Wayne Hummer Investments, LLC

Wayne Hummer Trust Company, N.A.

Wheaton Bank & Trust Company

Wintrust Information Technology Services Company

Wintrust Mortgage Corporationexv10w42

Exhibit 10.42

THIRD AMENDMENT AGREEMENT

          THIS THIRD AMENDMENT AGREEMENT (this “Amendment”), dated as of December 6, 2010, is among
WINTRUST FINANCIAL CORPORATION (the “Borrower”), the Lenders party to the Credit Agreement
referenced below and BANK OF AMERICA, N.A., as Administrative Agent for the Lenders.

W I T N E S S E T H:

     WHEREAS, the parties hereto are parties to that certain Amended and Restated Credit Agreement
dated as of October 30, 2009 (as previously amended, the “Credit Agreement”); and

     WHEREAS, the parties hereto desire to amend the Credit Agreement in certain respects as set
forth herein.

     NOW, THEREFORE, the parties hereto, in consideration of the premises and the mutual agreements
herein contained, hereby agree as follows:

     Section 1. Credit Agreement Definitions. Capitalized terms used herein that are
defined in the Credit Agreement shall have the same meaning when used herein unless otherwise
defined herein.

     Section 2. Amendments to Credit Agreement. Effective on (and subject to the
occurrence of) the Amendment Effective Date (as defined below), the Credit Agreement is amended as
follows:

(a) Section 7.02 of the Credit Agreement is amended to (i) delete the word “and” appearing
at the end of clause (d) of such section, (ii) delete the “.” appearing at the end of clause
(e) of such section, and to substitute therefor “;” and (iii) add the following new clause
(f) to the end of such section:
 

     “(f) Indebtedness in an aggregate principal amount not to exceed
$60,000,000 in respect of “amortizing notes” of the Borrower issued in
connection with the Borrower’s issuance of “tangible equity units” so long
as (i) the interest rate on such Indebtedness does not exceed 10%, (ii)
there are no financial covenants contained in the documents related to such
Indebtedness, (iii) such Indebtedness is subordinate in right of payment to
the Subordinated Debt, and (iv) such Indebtedness is issued on terms and
conditions that are either:

     (x) substantially similar to the terms and conditions set forth
in the 12/5//10 draft Junior Subordinated Indenture and Supplemental
Indenture each dated December [__], 2010 between the Borrower and
U.S. Bank National Association, as Trustee with respect to the
“amortizing notes” (copies of which were delivered

 

 

to the Administrative Agent and the Lenders on December 6,
2010); or

(y) otherwise reasonably acceptable to the Administrative Agent.”

     (b) Section 7.06 of the Credit Agreement is amended in its entirety to read as follows:

     “7.06 Restricted Payments. Declare or make, directly or
indirectly, any Restricted Payment, or voluntarily purchase, redeem or
defease any Indebtedness permitted under Section 7.02(f), or settle
the forward purchase contracts issued by the Borrower in connection with
such Indebtedness (other than cash payments with respect to fractional
shares) (contingent or otherwise), except that, so long as no Default shall
have occurred and be continuing at the time of any action described below or
would result therefrom, (i) the Borrower may declare and make cash dividend
payments on its Equity Interests or declare and make dividend payments or
other distributions payable solely in the Equity Interests of the Borrower,
(ii) the Borrower may redeem its Series B Preferred Stock and (iii) the
Borrower may make scheduled interest and principal payments on the
Indebtedness permitted under Section 7.02(f).”

     Section 3. Representation and Warranties. In order to induce the Lenders and the
Administrative Agent to execute and deliver this Amendment, the Borrower hereby represents and
warrants to the Lenders and to the Administrative Agent that both before and after giving effect to
the Amendment that:

          (a) no Event of Default or Default has occurred and is continuing or will result from the
execution and delivery or effectiveness of this Amendment; and

          (b) the representations and warranties of the Borrower contained in Article V of the Credit
Agreement are true and correct in all material respect as of the date hereof and the Amendment
Effective Date with the same effect as though made on such date (except to the extent that that any
such representation expressly relates to an earlier date, such representation or warranty shall be
made only as to such earlier date).

     Section 4. Conditions to Effectiveness. The amendments set forth in Section 2 hereof
shall become effective on the date (the “Amendment Effective Date”) when the Administrative Agent
shall have received a counterpart of this Amendment executed by the Borrower, the Administrative
Agent and each Lender.

     Section 5. Reaffirmation of Loan Documents. From and after the date hereof, each
reference to the Credit Agreement that appears in any other Loan Document shall be deemed to be a
reference to the Credit Agreement as amended hereby. As amended hereby, the Credit Agreement is
hereby reaffirmed, approved and confirmed in every respect and shall remain in full force and
effect.

2

 

     Section 6. Counterparts; Effectiveness. This Amendment may be executed by the parties
hereto in any number of counterparts and by the different parties on separate counterparts and each
such counterpart shall be deemed to be an original, but all such counterparts shall together
constitute but one and the same agreement.

     Section 7. Governing Law; Entire Agreement. This Amendment shall be deemed a contract
made under and governed by the laws of the State of Illinois. This Amendment constitutes the
entire understanding among the parties hereto with respect to the subject matter hereof and
supersedes any prior agreements with respect thereto.

     Section 8. Loan Document. This Amendment is a Loan Document.

[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]

3

 

     IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be executed by their
respective officers thereunto duly authorized as of the date and year first above written.

	 	 	 	 	 	 	 

	 	 	WINTRUST FINANCIAL CORPORATION	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ David A. Dykstra
 

	 	 
	 

	 	Title:
	 	EVP and COO	 	 
	 
	 	 	 	 	 	 
	 	 	BANK OF AMERICA, N.A.,	 	 
	 	 	as Administrative Agent, Term Lender and	 	 
	 	 	Revolving Credit Lender	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Mary P. Riggins
 

	 	 
	 

	 	Title:
	 	Senior Vice President	 	 
	 
	 	 	 	 	 	 
	 	 	WELLS FARGO BANK, N.A. , as Revolving	 	 
	 	 	Credit Lender	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ David Schmaltz
 

	 	 
	 

	 	Title:
	 	SVP	 	 

Third
Amendment
 Wintrust

S-1

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00185-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00185-of-00352.parquet"}]]