EXHIBIT 10.23
EMPLOYMENT AGREEMENT
     This Employment Agreement (the “Agreement”) is made by and between Lake
Forest Bank & Trust Company (“Employer”), a state chartered bank, and Randolph
M. Hibben, an individual resident in the State of Illinois (“Executive”) as of
March 25, 2005.
W I T N E S S E T H   T H A I :
     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 Chairman and Chief
Executive Officer of Employer and shall perform such duties as may be assigned
to Executive by 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

 

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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 Wintrust or any Affiliate in addition to serving as Chairman and
Chief Executive Officer of Employer, 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 1997 Stock Incentive Plan or any successor Plan
thereto.
     3. Extent of Service. Executive shall devote Executive’s entire time,
attention and energies to the business of 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 or any branch office of the Employer;

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          (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 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 or any branch office of
the Employer; 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 the Employer. 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

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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 10 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 or any branch
office of the Employer.
     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
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

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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 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

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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
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
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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.
          (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).

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               (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.
               (iv) 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 Employer’s or 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 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

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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.
               (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 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 the Employer’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 Employer’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 Employer if, prior to the expiration of the maximum period of COBRA
coverage, Executive becomes eligible for coverage under another group health
plan with no preexisting 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,

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“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 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 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 the Employer’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 Employer’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 Employer if, prior to the expiration of the maximum period of COBRA
coverage, Executive becomes eligible for coverage under another group health
plan with no preexisting condition limitation or exclusion or Executive becomes
entitled to benefits under Medicare.

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               (iv) Definitions.
                    (A) For the purposes of this Agreement, “Adjusted Total
Compensation” means the aggregate base salary earned by the Executive plus the
dollar value of all perquisites (i.e. 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. For the purpose of illustration, attached as Exhibit B
to this Agreement is the base salary paid and the dollar value of the
Executive’s perquisites for the last fiscal year of Employer.
                    (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 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 1997 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)(l) 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

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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)(l) 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 the Employer’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 Employer’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 Employer 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, 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).

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               (C) Subsection 9(e)(v)(B) shall not be applicable to a
Constructive Termination following a Change in Control
     (g) Voluntary Termination. Executive may voluntarily terminate employment
during the Term of this Agreement by a delivery to 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;
          (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

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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 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

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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.
          (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

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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.

                 
By:
  /s/ Edward J. Wehmer       /s/ Randolph M. Hibben    
 
               
 
  Edward J. Wehmer       Randolph M. Hibben    
 
  Wintrust Financial Corporation            
 
               
Its:
  President and Chief Executive Officer       Dated: 3/25/05    
 
                Dated: 3/25/05            

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EXHIBIT A
Advantage National Bank
Barrington Bank & Trust Company, N. A.
Beverly Bank & Trust Company, N. A.
Crystal Lake Bank & Trust Company, N. A.
First Insurance Funding Corporation
Focused Investments LLC
Hinsdale Bank & Trust Company
Lake Forest Bank & Trust Company
Libertyville Bank & Trust Company
North Shore Community Bank & Trust Company
Northbrook Bank & Trust Company
Town Bank (Wisconsin)
Tricom, Inc of Milwaukee
Village Bank & Trust-Arlington Heights
Wayne Hummer Asset Management Company
Wayne Hummer Investments, LLC
Wayne Hummer Trust Company, N. A.
Wheaton Bank & Trust Company
Wintrust Information Technology Services Company

 

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EXHIBIT B

         
1) EXECUTIVE NAME:

2) CURRENT TITLE

3) EMPLOYER

4) TITLE AT DATE OF HIRE

5) DATE OF HIRE
  RANDOLPH M HIBBEN   WINTRUST FINANCIAL CORP
TOTAL COMPENSATION HISTORY
SENIOR EXECUTIVE COMPENSATION   CHAIRMAN & CEO               LAKE FOREST BANK &
TRUST   JANUARY 2005

(WINTRUST FINANCIAL CORP LOGO) [c12740n1274046.gif]           SENIOR VP —
CASHIER — LAKE FOREST BANK                 OCTOBER 1991    

                                                                               
              2005     2004     2003     2002     2001     2000     1999    
1998     1997  
5) SIGNING BONUS (IF ANY)
          $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0  
 
                                                                               
6) SALARY HISTORY;
                                                                               
BEGINNING SALARY
          $ 250,000     $ 215,000     $ 208,000     $ 200,000     $ 170,000    
$ 160,000     $ 135,000     $ 124,000     $ 113,000  
INTERIM RAISE
          $ 0     $ 0     $ 0     $ 0     $ 15,000     $ 0     $ 10,000     $ 0
    $ 0  
PRIOR YEAR END RAISE
          $ 10,000     $ 35,000     $ 7,000     $ 8,000     $ 15,000     $
10,000     $ 15,000     $ 11,000     $ 11,000  
OTHER
          $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0  
 
                                                           
ENDING SALARY
          $ 260,000     $ 250,000     $ 215,000     $ 208,000     $ 200,000    
$ 170,000     $ 160,000     $ 135,000     $ 124,000  
PERCENT INCREASE
            4.00 %     16.28 %     3.37 %     4.00 %     17.65 %     6.25 %    
18.52 %     8.87 %     9.73 %
 
                                                                               
7) BONUS HISTORY:
                                                                               
CURRENT YEAR END CASH BONUS
                  $ 0     $ 48,575     $ 47,125     $ 19,602     $ 25,000     $
7,500     $ 15,000     $ 12,000  
STOCK BONUS
                  $ 75,000     $ 18,425     $ 17,875     $ 25,398     $ 0     $
17,200     $ 0     $ 0  
 
                                                               
TOTAL
                  $ 75,000     $ 67,000     $ 65,000     $ 45,000     $ 25,000  
  $ 24,700     $ 15,000     $ 12,000  
 
                                                                               
8) STOCK OPTION HISTORY (WINTRUST EQUIV)
                                                                           
BEGINNING OPTIONS
                    94,380       98,135       90,480       90,480       90,480  
    59,381       59,381       50,381  
CURRENT YEAR GRANTS
                    —       3,500       48,500       —       —       31,100    
  0       9,000  
CURRENT YEAR EXERCISES
                    —       7,255       40,845       —       —       —       0  
    0  
 
                                                               
ENDING OPTIONS
                    94,380       94,380       98,135       90,480       90,480  
    90,480       59,381       59,381  
 
                                                                               
VESTED PORTION OF OPTIONS
                    112,507       47,581       48,536       73,383       66,770
      60,470       51,524       49,316  
 
                                                                               
9) AUTOMOBILE:
                                                                               
2001 Audi A8
                                                                               
COST
                  $ 48,874     $ 33,000     $ 33,000     $ 0     $ 0     $ 0    
$ 30,000     $ 0  
ESTIMATED VALUE PER YEAR
                  $ 7,175     $ 5,658     $ 8,750     $ 7,750     $ 7,750     $
7,750     $ 7,500     $ 6,250  
 
                                                                               
10) CLUBS:
                                                                               
A) CLUB A   DUES* — LAKE FOREST CLUB
            $ 2,760     $ 2,430     $ 2,400     $ 2,280     $ 2,280     $ 2,280
    $ 2,700     $ 2,400  
B) CLUB B   DUES*
                  $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0  
C) CLUB C   DUES*
                  $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0  
 
                                                               
TOTAL
                  $ 2,760     $ 2,430     $ 2,400     $ 2,280     $ 2,280     $
2,280     $ 2,700     $ 2,400  
COUNTRY CLUB ACCOMPANIES PROMOTION TO PRESIDENT AND CEO NSCB&T
                                                       
 
                                                                               
* — SPECIFY CLUB NAME AND INCLUDE ANY INITIATION FEES PAID
                                                       
 
                                                                               
11) SUPPLEMENTAL INSURANCE
  FACE                                                                  
A) BOLI — LIFE INSURANCE:
  AMOUNT                                                                  
i) CLARICA LIFE
>>>   $ 139,050       $ 102     $ 95     $ 163     $ 500     $ 500     $ 500    
$ 500     $ 400  
ii) GREAT WEST
>>>   $ 139,050       $ 254     $ 95     $ 0     $ 0     $ 0     $ 0     $ 0    
$ 0  
iii) MASSMUTUAL
>>>   $ 139,050       $ 81     $ 108     $ 0     $ 0     $ 0     $ 0     $ 0    
$ 0  
 
    $ 417,150                                                                  
B) DISABILITY PREMIUM
    N/A       $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0    
TOTAL
                  $ 437     $ 298     $ 163     $ 500     $ 500     $ 500     $
500     $ 400    
12) EDUCATIONAL EXPENSES PAID
                  $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0  
 
13) OTHER — SPECIFY BELOW
                  $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0     $ 0  
 
14) TOTAL ANNUAL CASH COMPENSATION
                  $ 335,372     $ 290,386     $ 266,438     $ 230,132     $
205,530     $ 178,030     $ 160,700     $ 145,050    
PERCENT INCREASE
                    15.49 %     8.99 %     15.78 %     11.97 %     15,45 %    
10.78 %     10.79 %     9.84 %

     
15) PROMOTED TO:
  4/99-PRESIDENT AND CEO NORTH SHORE COMMUNITY BANK
 
  5/01 — CHAIRMAN AND CEO LAKE FOREST BANK & TRUST
 
  03 — VICE CHAIRMAN NORTH SHORE COMMUNITY BANK
16) CONTRACT (YES OR NO)
  YES  
17) COMMENTS OR NOTES: