Document:

FIRST AMENDMENT TO EMPLOYMENT AGREEMENT
                     ---------------------------------------

         This First Amendment to Employment  Agreement (the "Amendment") is made
by and between WINTRUST FINANCIAL CORPORATION ("Wintrust"),  an Illinois banking
corporation and EDWARD J. WEHMER  ("Executive"),  an individual  resident in the
State of Illinois.

                                WITNESSETH THAT:

         WHEREAS,  Wintrust and Executive have previously  entered an Employment
Agreement (the "Employment  Agreement") executed by such parties on December 22,
1998 (the "Effective Date"); and

         WHEREAS,  the Wintrust and the Executive desire to amend the Employment
Agreement  pursuant  to this  Amendment,  effective  as of the  Effective  Date,
pursuant to Section 11(g) of the Employment Agreement; and

         WHEREAS,  certain  capitalized  terms not defined herein shall have the
meaning ascribed to such terms in the Employment Agreement.

         1.       Subsection  9(e)(B) of the Agreement is hereby amended to read
                  as follows:

                  For the purposes of this Section 9(e),  the Executive will not
                  be deemed to have incurred a  Constructive  Termination  under
                  Section  9(e)(ii)  if there  is a  general  reduction  in base
                  salaries and/or perquisites applicable to the President, Chief
                  Executive Officer and all Vice Presidents of Wintrust.

         2.       Section 9(f) is amended to read as follows:

                           f. Termination  Upon Change In Control.  In the event
                              -----------------------------------
                  that  within  eighteen  (18)  months of a Change in Control of
                  Wintrust  (as defined  below) (i)  Executive's  employment  is
                  terminated  without  Cause (as such term is defined in Section
                  9(h) hereof)  prior to the  expiration  of the initial term or
                  any  succeeding  one (1) year term of this  Agreement  or (ii)
                  Executive suffers a Constructive Termination, Wintrust (or the
                  successor thereto) shall pay Severance Pay to Executive in the
                  amount  described  in Section 9(d) hereof in a lump sum within
                  thirty (30) days following the date of Executive's termination
                  or  Constructive   Termination.   For  the  purposes  of  this
                  Agreement,  a "Change in Control"  shall have the same meaning
                  as  provided  in  Section  12(b) of the  Wintrust  1997  Stock
                  Incentive Plan.  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 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

<PAGE>

                  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.

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

         IN WITNESS  WHEREOF,  the parties  have  executed  and  delivered  this
Amendment to Employment Agreement as of the date and year first above written.

WINTRUST FINANCIAL CORPORATION

         By:__________________________________________
            David A. Dykstra, Chief Financial Officer

         Date: ________________________________________

EXECUTIVE:

         ______________________________________________
                  Edward J. Wehmer

         Date: _________________________________________

<PAGE>TERM NOTE

$1,200,000.00                                              Lake Forest, Illinois
                                                                January 31, 2000

         FOR VALUE RECEIVED, Edward J. Wehmer and Dorothy M. Wehmer (hereinafter
referred  to as  "Borrowers"),  hereby  promise to pay to the order of  Wintrust
Financial Corporation, an Illinois banking company,  (hereinafter referred to as
"Lender") or its  successors  and assigns  ("Holder"),  the principal sum of One
Million Two Hundred Thousand Dollars ($1,200,000.00)  ("Loan"), at the place and
in the manner hereinafter  provided,  together with interest thereon at the rate
described below.

         Unless otherwise  accelerated as provided herein, the principal balance
of the Note shall be due and payable on January 31, 2005 (the "Maturity  Date").
The principal balance of the Note shall bear interest prior to the Maturity Date
at an annual rate of 7%,  compounded  annually.  Interest  not paid on or before
each  anniversary  date of the date of this Note occurring prior to the Maturity
Date  shall be added to the  outstanding  principal  balance  of the  Note.  All
accrued but unpaid  interest  shall be due and payable on the Maturity Date. The
principal  balance  outstanding  and all unpaid but accrued  interest  after the
Maturity Date shall bear  interest at an annual rate of 8% per annum  compounded
annually.

         This  Note is  secured  by a pledge  of 100,000  shares of the stock of
Wintrust Financial  Corporation owned by Dorothy M. Wehmer. During the existence
of any default or delinquency under the terms of this Note or under the terms of
any  instrument  executed or to be executed as security  for the payment  hereof
including  the Stock  Pledge  Agreement  dated  January  31,  2000 (the  "Pledge
Agreement")  between  the  Borrowers  and the Lender,  Lender or any Holder,  is
expressly  authorized  to apply all payments made on this Note to the payment of
such part of any delinquency as it may elect.

         The following shall constitute events of default:

         (a)      Dorothy   M.   Wehmer   breaches   or  is  in  breach  of  any
                  representation,  warranty or covenant  contained in the Pledge
                  Agreement  and such  breach is not cured  within 45 days after
                  written notice from the Holder.

         (b)      Edward J. Wehmer  terminates or is terminated  from the employ
                  of Lender for any reason and has failed to pay all outstanding
                  principal and accrued  interest  within 90 days of the date of
                  such termination.

         (c)      Dorothy M. Wehmer sells or attempts to sell all or any portion
                  of the Pledged Stock,  or such Pledged Stock is subject to any
                  involuntary sale initiated by a creditor of either Borrower.

         Upon the  occurrence  of an event by default,  the Lender or the Holder
may  declare  the  principal   balance  and  all  accrued  but  unpaid  interest
immediately  due and payable,  in which case the  declaration  date shall be the
Maturity Date.

<PAGE>
         The  Borrowers may from time to time prepay the principal sum due under
this Note and any  accrued  and  unpaid  interest  in whole or in part,  without
penalty; provided,  however, that such prepayment shall first be applied against
accrued interest and thereafter against said principal sum.

         Borrowers  represent  and  warrant  that  this  Note is being  incurred
primarily  for a business  purpose and does not consist of or involve any credit
offered or extended to a consumer  primarily for  personal,  family or household
purposes.

         Borrowers and all  endorsers,  guarantors  and all persons liable or to
become liable under this Note hereby waive presentment,  demand, protest, notice
of protest and notice of any other kind in connection with this Note.

         All payments of principal and interest on this Note shall be payable at
the  offices  of Lender in Lake  Forest,  Illinois,  or at such  other  place or
address as Lender or Holder may designate in writing.  If this Note is placed in
the hands of an attorney at law for  collection by reason of default on the part
of Borrowers,  Borrowers  hereby agree to pay to Lender or Holder in addition to
the sums stated above,  the costs of collection,  including  attorney's fees and
expenses.

         The  obligations  of the  Borrowers  on this  Note  shall be joint  and
several.

         This Note may not be changed, amended or modified orally.

         This Note shall be  construed  in  accordance  with and governed by the
internal laws of the State of Illinois (without giving effect to Illinois choice
of law principles).

         The  rights  and  remedies  of the  Lender  and  Holder  hereunder  are
cumulative  and not  exclusive  of any rights or  remedies  which the Lender and
Holder would otherwise have. Any waiver, permit, consent or approval of any kind
or  character  on the part of the  Lender  or Holder  of any  breach or  default
hereunder or any such waiver of any provision or breach or default  hereunder or
any such waiver of any  provision  or  condition of this Note must be in writing
and  shall  be  effective  only to the  extent  specifically  set  forth in such
writing. No notice to or demand to Borrowers in any case shall entitle it to any
other or further notice or demand in other similar circumstances.

                                               /s/ Edward J. Wehmer
                                               ---------------------------------
                                               Edward J. Wehmer

                                               /s/ Dorothy M. Wehmer
                                               ---------------------------------
                                               Dorothy M. Wehmer

                                     - 2 -
<PAGE>
                             STOCK PLEDGE AGREEMENT
                             ----------------------

         This STOCK PLEDGE  AGREEMENT  ("Agreement") is made and entered into as
of the 31st day of January,  2000 by and between  DOROTHY M. WEHMER  ("Pledgor")
and WINTRUST FINANCIAL CORPORATION, an Illinois banking company ("Pledgee").

                              PRELIMINARY STATEMENT
                              ---------------------

         A.  Pledgor owns 100,000 shares of common  stock of Wintrust  Financial
Corporation, (the "Securities").

         B.  Pledgor is  co-borrower  on a loan made to Pledgee and her husband,
EDWARD J. WEHMER, in the amount of  $1,200,000.00,  which amount is evidenced by
that certain Term Note dated January 31, 2000 (the "Note").

         C. The  Pledgor  has  agreed  to  pledge  the  Securities  as  required
hereunder.

         D. To  facilitate  and  perfect  the Pledge,  the  Securities  shall be
deposited  with  Pledgee and Pledgee  shall hold the  Securities  subject to the
terms hereof.

         NOW,  THEREFORE,  in consideration of the premises set forth herein, it
is hereby agreed as follows:

         1. Collateral.  The term "Collateral" shall mean the Securities and all
            ----------
dividends,  distributions  and other amounts or  additional  securities to which
Pledgor (with or without  additional  consideration)  is or becomes  entitled by
virtue  of  its  ownership  of any of the  Securities  or as the  result  of any
corporate reorganization,  merger,  consolidation,  stock split, stock dividend,
conversion, preemptive right or otherwise, and the proceeds thereof.

         2. Deposit of Collateral.  To secure  payment of Pledgor's  obligations
            ---------------------
under the Note,  Pledgor hereby pledges and deposits the Securities with Pledgee
and hereby  grants to Pledgee a valid and  perfected  first lien on and security
interest in the Securities and other items of the Collateral.

         3. Representations, Warranties and Covenants. Pledgor hereby represents
            -----------------------------------------
and warrants to Pledgee that as to the Collateral deposited by such Pledgor with
Pledgee on the date  hereof,  (i) Pledgor is the legal and  beneficial  owner of
such  Collateral;  (ii)  such  Collateral  is  validly  issued,  fully  paid and
non-assessable  and is  registered  in the name of  Pledgor  (iii) the pledge of
Collateral  pursuant  to the  terms  of this  Pledge  Agreement,  together  with
delivery  thereof,  creates a valid and  perfected  first  lien on and  security
interest in such Collateral in favor of Pledgee;  (iv) the assignments  separate
from certificate attached to the certificates  representing such Collateral have
been duly  executed and  delivered by such Pledgor to Pledgee;  (v) none of

such Collateral is subject to any lien;  except for the perfected first security
interest  granted  to

<PAGE>
Pledgee hereby and, so long as any portion of the Note remains  unpaid,  Pledgor
will not create or permit to exist any other lien or security  interest  upon or
with  respect to such  Collateral  without the consent of Pledgee,  (vi) Pledgor
will not sell,  transfer,  convey,  assign, or otherwise divest its interests in
such Collateral, or any part thereof, to any other person.

         4.       Stock Splits, Stock Dividends, Etc.
                  -----------------------------------

                  4.1 Pledgor agrees that if by virtue of Pledgor's ownership of
         the  Collateral,  Pledgor  becomes  entitled  to  other  or  additional
         securities  as the  result  of any  corporate  reorganization,  merger,
         consolidation,  stock split,  stock dividend,  conversion or otherwise,
         such Pledgor shall:

                           4.1.1 Cause the issuer of such additional  securities
                  to deliver to Pledgee the  certificates  evidencing  Pledgor's
                  ownership  thereof and hereby  authorizes and empowers Pledgee
                  to  demand  the same  from  such  issuer,  and  agrees if such
                  certificates  are  delivered  to Pledgor,  to take  possession
                  thereof in trust for Pledgee;

                           4.1.2 Deliver to Pledgee an assignment  separate from
                  certificates  with  respect to such  securities,  executed  in
                  blank by Pledgor;

                           4.1.3  Deliver  to Pledgee  such other  certificates,
                  forms  and  other   instruments  as  Pledgee  may  request  in
                  connection with such pledge.

                  4.2  Pledgor  agrees  that such  additional  securities  shall
         constitute  a portion of the  Collateral  and be subject to this Pledge
         Agreement  in the same manner and to the same extent as the  securities
         pledged hereby to Pledgee on the date hereof.

         5.  Voting  Power.  Unless  and until an event of  default  shall  have
             -------------
occurred  and shall not have been cured  within  ninety (90) days after  notice,
Pledgor shall be entitled to exercise all voting powers in all corporate matters
pertaining  to the  Collateral  for any purpose  not  inconsistent  with,  or in
violation of, the provisions of the Note.

         6.       Default and Remedies.
                  --------------------

                  6.1.1    Declare all  principal  and interest  then due on the
                           Note immediately due and payable, subject to any cure
                           and  notice  provisions   required  by  law,  without
                           notice.

                  6.1.2    Collect  all   Collateral   not  then  in   Pledgee's
                           possession, and at Pledgee's option and to the extent
                           permitted by applicable law, retain possession of the
                           Collateral while suing on the Note.

                                     - 2 -
<PAGE>
                  6.1.3    Sell the Collateral, at Pledgee's direction, in whole
                           or in portions thereof, at any private sale or on the
                           public market upon which such Collateral if regularly
                           traded.  Pledgee  agrees to give Pledgor at least ten
                           days prior  written  notice of any  proposed  private
                           sale or auction of the  Collateral and three business
                           days advance  notice of any sale on the public market
                           unless Pledgee,  in its sole  discretion,  reasonably
                           believes  that  value  of such  Collateral  would  be
                           likely to  decline  if such  notice  was  given.  The
                           notice requirement will be satisfied if Pledgee mails
                           such  notice to  Pledgor  by first  class mail to the
                           last address given by Pledgor to Pledgee.

                  6.1.4    Pledgee  shall be  entitled  to  exercise  all voting
                           powers pertaining to the Collateral.

With  respect to the actions  described in each of  subsections  6.1.3 and 6.1.4
above, Pledgor hereby irrevocably constitutes and appoints Pledgee his proxy and
attorney-in-fact  with full  power of  substitution  and  acknowledges  that the
constitution and appointment of such proxy and attorney-in-fact are coupled with
an interest and are irrevocable.

                  6.2      At any sale  made  pursuant  to  Section  6.1  above,
Pledgee  may bid for and  purchase,  any part or all of the  Collateral  that is
offered for sale.

                  6.3      Pledgee  shall apply the  proceeds of any sale of the
whole or any part of the  Collateral  and any  other  monies at the time held by
Pledgee under the provisions of this Agreement:

         First,  to reimburse  Pledgee for its expenses in  connection  with the
         -----
collection  and sale of the  Collateral  and legal  proceedings  in suing on the
Note,   including   reasonable   attorneys  fees,   court  costs  of  securities
registration, brokers commissions and other costs of sale;

         Second,  to the payment of all  principal and interest due on the Note;
         ------
and

         Third, any excess funds to the Pledgor. The Pledgor remains jointly and
         -----
severally liable with her co-borrower for any deficiency on the Note.

                  6.4  Pledgee  shall not have any duty to  exercise  any of the
rights,  privileges,  options or powers or to sell or otherwise realize upon any
of  the  Collateral,  as  hereinbefore  authorized,  and  Pledgee  shall  not be
responsible for any failure to do so or delay in so doing.

                  6.5 Any sale of all or any portion of the Collateral  pursuant
to Section 6.1 above shall  operate to divest all right,  title and  interest of
the Pledgor to the Collateral which is the subject of any such sale.

                                     - 3 -
<PAGE>
         7. Pledgee's  Obligations,  Custodial  Agreement,  Performance  Rights,
            --------------------------------------------------------------------
Pledge Does Not Make  Pledgee  Shareholder.  Pledgee  shall not have any duty to
------------------------------------------
protect,  preserve or enforce

rights against the Collateral other than a duty of reasonable  custodial care of
any such  Collateral in its possession,  it being  understood that Pledgee shall
have no  responsibility  for (A)  ascertaining  or taking action with respect to
calls, conversions,  exchanges, maturities, tenders or other matters relating to
the  Collateral,  whether or not Pledgee has or is deemed to have  knowledge  of
such matters,  or (B) taking any necessary  steps to preserve rights against any
parties with respect to the Collateral,  or (C) making any capital contributions
or other payments on behalf of Pledgor with respect to the Collateral.

         8.       Termination  of  Pledge   Agreement.   Upon  the  payment  and
                  -----------------------------------
performance in full of all of the  Obligations  and the Pledgee shall deliver to
the Pledgor the Collateral in its possession and this Pledge Agreement thereupon
shall be terminated.

         9.       Miscellaneous.
                  -------------

         9.1 Each and every right, remedy and power granted to Pledgee hereunder
shall  be  cumulative  and in  addition  to any  other  right,  remedy  or power
specifically  granted herein or now or hereafter  existing in equity, at law, by
virtue of statute or otherwise  and may be  exercised  by Pledgee,  from time to
time,  concurrently or  independently  and as often and in such order as Pledgee
may deem  expedient.  Any failure or delay on the part of Pledgee in  exercising
any such right,  remedy or power, or abandonment or  discontinuance  of steps to
enforce  the same,  shall not  operate as a waiver  thereof or affect  Pledgee's
right thereafter to exercise the same, and any single or partial exercise of any
such right, remedy or power shall not preclude any other right, remedy or power,
and no such  failure,  delay,  abandonment  or single  or  partial  exercise  of
Pledgee's  rights  hereunder  shall be deemed to establish a custom or course of
dealing or performance among the parties hereto.

         9.2 Any  modification or waiver of any provision of this Agreement,  or
any consent to any departure by Pledgor therefrom, shall not be effective in any
event  unless  the same is in  writing  and  signed  by  Pledgee,  and then such
modification, waiver or consent shall be effective only in the specific instance
and for the specific  purpose  given.  Any notice to or demand on Pledgor in any
event not specifically  required of Pledgee  hereunder shall not entitle Pledgor
to any  other  or  further  notice  or  demand  in the  same,  similar  or other
circumstances unless specifically required hereunder.

         9.3 Pledgor agrees that at any time,  and from time to time,  after the
execution and delivery of this  Agreement,  Pledgor  shall,  upon the request of
Pledgee and at the expense of Pledgor, promptly execute and deliver such further
documents and do such further acts and things as Pledgee may request in order to
effect  fully the  purposes  of this  Agreement  and to subject to the  security
interest  created hereby any property  intended by the  provisions  hereof to be
covered hereby.

                                     - 4 -
<PAGE>
         9.4 Pledgor agrees that it will warrant, preserve, maintain and defend,
at his own  expense,  the  right,  title and  interest  of Pledgee in and to the
Collateral and all right,  title and interest  represented  thereby  against all
claims, charges and demands of all persons whomsoever.

         9.5 All notices and  communications  under this  Agreement  shall be in
writing  and  shall  be (i)  delivered  in  person,  (ii)  sent by  telecopy  or
telegraph,  or (iii) mailed, postage prepaid,  either by registered or certified
mail, return receipt  requested,  or by overnight express carrier,  addressed in
each case as follows:

                  If to Pledgor:

                                            Dorothy M. Wehmer
                                            454 Buena Road
                                            Lake Forest, Illinois  60045

                  If to Pledgee:

                                            Wintrust Financial Corporation
                                            727 North Bank Lane
                                            Lake Forest, Illinois  60045
                                            Attn: David Dykstra

provided, however, that any party may change its respective address for purposes
of receipt of any such  communication  by giving 10 days prior written notice of
such  change to the other  parties  hereto in the  manner  provided  above.  All
notices sent pursuant to the terms of this Section 9.5 shall be deemed  received
(i) if sent by telecopy or  telegraph,  on the day sent if a business day, or if
such day is not a business  day,  then on the next business day, (ii) if sent by
overnight,  express carrier, on the next business day immediately  following the
day  sent,  or (iii) if sent by  registered  or  certified  mail,  on the  third
business day following the day sent.

         9.6 In the event that any  provision of this  Agreement is deemed to be
invalid  by  reason  of  the   operation  of  any  law,  or  by  reason  of  the
interpretation placed thereon by any court, this Agreement shall be construed as
not containing  such  provision and the  invalidity of such provision  shall not
affect  the  validity  of any  other  provision  hereof,  and any and all  other
provisions  hereof  which  otherwise  are lawful and valid shall  remain in full
force and effect.

         9.7 This  Agreement  shall inure to the benefit of the  successors  and
assigns  of   Pledgee   and  shall  be   binding   upon  the  heirs,   legatees,
administrators, legal representatives, successors and assigns of Pledgor.

                                     - 5 -
<PAGE>
         9.9 This Agreement may be executed in one or more counterparts, each of
which shall be deemed to be an original,  but all of which taken  together shall
be one and the same instrument.

         9.10 This Agreement  shall be governed by the laws and decisions of the
State of Illinois.

        IN WITNESS WHEREOF,  the parties have executed this agreement as of the
date first above written.

                                             Pledgor

                                             /s/ Dorothy M. Wehmer
                                             ---------------------------------
                                             Dorothy M. Wehmer

         Accepted By:                        Pledgee

                                             WINTRUST FINANCIAL CORPORATION

                                             By /s/ David A. Dykstra
                                               ---------------------------------

                                             Its Executive Vice President
                                                --------------------------------

                                     - 6 -

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