WINTRUST FINANCIAL CORP
DEF 14A, 2000-04-20
STATE COMMERCIAL BANKS
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                            SCHEDULE 14A INFORMATION
           PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES
                              EXCHANGE ACT OF 1934


Filed by the Registrant {x} Filed by a Party other than the Registrant { } Check
the appropriate box: { } Preliminary  Proxy Statement { } Confidential,  for use
of the Commission Only (as permitted by Rule
     14a-6(e)(2))
{X} Definitive Proxy Statement
{ } Definitive  Additional Materials
{ } Soliciting Material Pursuant to 240.14a-11(c) or 240.14a-12

                         WINTRUST FINANCIAL CORPORATION

- --------------------------------------------------------------------------------
                (Name of Registrant as Specified in its Charter)


- --------------------------------------------------------------------------------
    (Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):
{X} No fee required.
{ } Fee  computed on table below per Exchange  Act Rules  14a-6(i)(1)  and 0-11

        (1) Title of each class of securities to which transaction applies:

        (2) Aggregate number of securities to which transaction applies:

        (3) Per unit price or other  underlying  value of  transaction  computed
            pursuant  to  Exchange  Act Rule 0-11 (set forth the amount on which
            the filing fee is calculated and state how it was determined):

        (4) Proposed maximum aggregate value of transaction:

        (5) Total fee paid:

{ } Fee paid previously with preliminary materials:
{   } Check box if any part of the fee is offset as  provided  by  Exchange  Act
    Rule  0-11(a)(2)  and identify the filing for which the  offsetting  fee was
    paid  previously.  Identify the previous  filing by  registration  statement
    number, or Form or Schedule and the date of its filing.

        (1) Amount Previously Paid:

        (2) Form, Schedule or Registration Statement No.:

        (3) Filing Party:

        (4) Date Filed:

<PAGE>
                         WINTRUST FINANCIAL CORPORATION
                    NOTICE OF ANNUAL MEETING OF SHAREHOLDERS
                                  MAY 25, 2000


         The  2000  Annual  Meeting  of  Shareholders   of  Wintrust   Financial
Corporation  will be held at the  Michigan  Shores Club,  911  Michigan  Avenue,
Wilmette,  Illinois 60091, on Thursday,  May 25, 2000, at 10:00 a.m. local time,
for the following purposes:

        1.      To elect eight Class I directors to hold office for a three-year
                term;

        2.      To  consider  a  proposal  to  amend  the   Wintrust   Financial
                Corporation  1997 Stock Incentive Plan to increase the number of
                shares authorized under the Plan;

        3.      To transact such other  business as may properly come before the
                Meeting and any adjournment thereof.

The record date for determining  shareholders entitled to notice of, and to vote
at, the Meeting is the close of business on April 3, 2000. To make it easier for
you to vote, we are introducing  internet and telephone voting. The instructions
printed on your proxy card  describe how to use these  convenient  services.  Of
course,  if you prefer,  you can vote by mail by completing  your proxy card and
returning it in the enclosed postage-paid envelope.

                                           By order of the Board of Directors,

                                           David A. Dykstra
                                           Secretary

April 20, 2000


WHETHER OR NOT YOU PLAN TO ATTEND THE ANNUAL  MEETING,  IT IS IMPORTANT THAT YOU
VOTE BY ONE OF THE METHODS NOTED ABOVE.
<PAGE>
                         WINTRUST FINANCIAL CORPORATION
                               727 North Bank Lane
                           Lake Forest, Illinois 60045

                                 PROXY STATEMENT
                         FOR THE 2000 ANNUAL MEETING OF
                 SHAREHOLDERS TO BE HELD THURSDAY, MAY 25, 2000


         These proxy materials are furnished in connection with the solicitation
by the Board of Directors of Wintrust Financial Corporation (the "Company"),  an
Illinois  corporation,  of  proxies  to be used at the 2000  Annual  Meeting  of
Shareholders of the Company and at any adjournment of such meeting.

         You are  cordially  invited to attend the Company's  Annual  Meeting of
Shareholders  to be held on May 25, 2000, at 10:00 a.m., at the Michigan  Shores
Club, 911 Michigan Avenue, Wilmette, Illinois 60091.

PROXIES, OUTSTANDING VOTING SECURITIES, AND SHAREHOLDERS ENTITLED TO VOTE

         The Board of Directors has fixed the close of business on April 3, 2000
as the record date for  determining  shareholders  entitled to notice of, and to
vote at, the Annual  Meeting.  On the record date,  the Company had  outstanding
8,752,643  shares  without  par  value  Common  Stock  ("Common  Stock").   Each
outstanding   share  of  Common   Stock   entitles   the  holder  to  one  vote.
Representation at the meeting of a majority of shares will constitute a quorum.

         Proxies received from  shareholders in proper form will be voted at the
meeting  and, if  specified,  as directed by the  shareholder.  Unless  contrary
instructions  are given, the proxy will be voted at the meeting FOR the election
of each of the nominees for Class I Director as set forth below, FOR approval of
the amendment to the 1997 Stock  Incentive Plan and, in accordance with the best
judgment of the persons  voting the proxies,  with respect to any other business
which may  properly  come before the meeting and is  submitted  to a vote of the
shareholders.  Under  Illinois  law and the  Company's  By-laws,  directors  are
elected by a plurality  of votes cast.  Approval of Proposal  No. 2 requires the
affirmative vote of a majority of the shares present in person or represented by
proxy at the meeting and entitled to vote.  Therefore  abstentions will have the
effect of  voting  against  Proposal  No. 2. With  respect  to  brokers  who are
prohibited from  exercising  discretionary  authority for beneficial  owners who
have not returned  proxies to the brokers,  those shares WILL NOT be included in
                                                         --------
the vote totals,  although both  abstentions and broker non-votes are counted as
shares present for the purpose of determining  whether the shares represented at
the meeting constitute a quorum. A proxy may be revoked at any time prior to its
exercise by means of a written  revocation or submission of a properly  executed
proxy bearing a later date.  Shareholders of record having executed and returned
a proxy who attend the meeting and desire to vote in person are  requested to so
notify the  Secretary of the Company  prior to or at the time of a vote taken at
the meeting.

         YOUR VOTE IS IMPORTANT.  Because many  shareholders  cannot  personally
         ----------------------
attend the Annual Meeting, it is necessary that a large number be represented by
proxy.  Whether or not you plan to attend the meeting in person,  prompt  voting
will be appreciated.  This year,  registered  shareholders can vote their shares
via the  Internet or by using a toll-free  telephone  number.  Instructions  for
using these  convenient  new services are provided on the proxy card. Of course,
you may still  vote your  shares  on the proxy  card.  To do so, we ask that you
complete,  sign,  date and  return  the  enclosed  proxy  card  promptly  in the
postage-paid envelope.

         This Proxy  Statement is being mailed to shareholders on or about April
20, 2000.


<PAGE>
COST OF PROXY SOLICITATION

         The  cost of  soliciting  proxies  has  been or  will be  borne  by the
Company.  Directors,  officers,  employees and agents of the Company may solicit
proxies in person or by mail, telephone, facsimile transmission and other means.
Directors,  officers and employees will receive no additional  compensation  for
solicitation  services.  Brokerage  houses,  nominees,   fiduciaries  and  other
custodians have been requested to forward soliciting materials to the beneficial
owners  of  shares  of  record  held by them and will be  reimbursed  for  their
expenses.


                                 PROPOSAL NO. 1
                  ELECTION OF DIRECTORS AND OWNERSHIP OF SHARES

         The By-laws of the Company  provide that the number of directors of the
Company  shall be 24,  divided  into three  classes of eight  Directors  who are
elected  to  hold  office  for  staggered   three-year   terms.  Each  year  the
shareholders  elect members of one class of Directors for a term of three years.
The term of office of those persons  currently serving as Class I Directors will
expire  at this  Annual  Meeting  of  Shareholders.  The term of  those  persons
currently  serving  as Class II  Directors  expires  at the  Annual  Shareholder
Meeting to be held in 2001;  and the term of Class III Directors  expires at the
Annual Shareholder Meeting to be held in 2002. In January 2000, Mr. John Leopold
was  appointed by the Board of  Directors to fill a Class I vacancy.  Currently,
there are 24 members of the Board of Directors.

         The eight persons named below have been nominated for election as Class
I directors for a term to end at the Annual Meeting of  Shareholders in the year
2003 or until their  successors are elected and  qualified.  All of the nominees
currently serve as Class I directors except nominee Ms. Dorothy Mueller who is a
director of the Company's  subsidiary,  Crystal Lake Bank & Trust Company.  Each
nominee has indicated a willingness to serve,  and the Board of Directors has no
reason to believe that any of the nominees  will not be available  for election.
However,  if any of the nominees is not available  for election,  proxies may be
voted for the  election of other  persons  selected  by the Board of  Directors.
Proxies  cannot,  however,  be voted for a greater  number of  persons  than the
number of nominees named.  Shareholders of the Company have no cumulative voting
rights with respect to the election of directors.

         The  following  sections  set forth the names of  nominees,  continuing
directors  of each  class,  their  ages,  a brief  description  of their  recent
business  experience,  including  present  occupation  and  employment,  certain
directorships  held by each, and the year in which they became  directors of the
Company.  Director  positions in the Company's  subsidiaries are included in the
biographical  information set forth below. Such subsidiaries include Lake Forest
Bank & Trust  Company  ("Lake  Forest  Bank"),  Hinsdale  Bank &  Trust  Company
("Hinsdale  Bank"),  North Shore  Community  Bank & Trust Company  ("North Shore
Bank"), Libertyville Bank & Trust Company ("Libertyville Bank"), Barrington Bank
& Trust Company,  N.A.  ("Barrington Bank"),  Crystal Lake Bank & Trust Company,
N.A. ("Crystal Lake Bank"),  Crabtree Capital  Corporation  ("Crabtree"),  First
Insurance  Funding Corp.  ("FIFC"),  Wintrust  Asset  Management  Company,  N.A.
("WAMC"), and Tricom, Inc. of Milwaukee ("Tricom").


             NOMINEES TO SERVE AS CLASS I DIRECTORS UNTIL THE ANNUAL
                    MEETING OF SHAREHOLDERS IN THE YEAR 2003

JAMES E. MAHONEY (62), DIRECTOR SINCE 1996 From 1978 to present, Mr. Mahoney has
been the owner and  President  of  Heidi's  Cheese  Products,  Inc.,  Mundelein,
Illinois. Mr. Mahoney is a Director of Libertyville Bank.

JAMES B. MCCARTHY (48),  DIRECTOR SINCE 1996 From 1991 to present,  Mr. McCarthy
has been Chairman and Chief Executive Officer of Gemini Consulting Group,  Inc.,
Oak Brook, Illinois, an international management consulting firm focusing on the
health care industry. Mr. McCarthy is a Director of Hinsdale Bank.

                                     - 2 -
<PAGE>
John W. Leopold (56), DIRECTOR SINCE 2000 From 1989 to present,  Mr. Leopold has
been  President  of Tricom,  Inc. of  Milwaukee,  the newly  acquired  financial
services  subsidiary  of the Company.  Mr.  Leopold  serves as a Director of the
National Technical Services Association. Mr. Leopold is a Director of Tricom.

DOROTHY M. MUELLER (45), DIRECTOR NOMINEE For the past 23 years, Ms. Mueller has
been Vice President of Mark I  Construction,  Crystal Lake,  Illinois,  a custom
home building company. Ms. Mueller is a Director of Crystal Lake Bank.

THOMAS J. NEIS (51), DIRECTOR SINCE 1999 Mr. Neis is the owner of Neis Insurance
Agency, Inc., Longaker Insurance Agency and Neis Insurance Consultants, Inc. and
is an independent insurance agent with these companies.  He serves as a director
of the McHenry County Fondation,  the McHenry County Economic  Development Corp.
and several other charitable and fraternal organizations. Mr. Neis is a Director
of Crystal Lake Bank.

J.  CHRISTOPHER  REYES (46),  DIRECTOR SINCE 1996 Mr. Reyes is Chairman of Reyes
Holdings which owns businesses in beverage  distribution,  food distribution and
processing with  headquarters in Lake Forest,  IL. Mr. Reyes serves on the board
of  directors  of Dean Foods  Co.,  the Boys & Girls  Clubs of  Chicago  and the
Children's Memorial Hospital. Mr. Reyes is a Director of Lake Forest Bank.

PETER P. RUSIN (47),  DIRECTOR  SINCE 1997 Since 1994,  Mr.  Rusin has served as
Executive  Director  of JFK Health  World,  a not for profit  children's  health
education  center and museum,  located in Barrington,  Illinois.  Mr. Rusin is a
Director of Barrington Bank.

EDWARD J. WEHMER (46), DIRECTOR SINCE 1996 Since May 1998, Mr. Wehmer has served
as President  and Chief  Executive  Officer of Wintrust  Financial  Corporation.
Prior to May 1998,  he served as President  and Chief  Operating  Officer of the
Company  since its  formation in 1996. He served as the President of Lake Forest
Bank from 1991 to 1998.  He was one of the  principal  organizers of each of the
banking  subsidiaries  and serves as Chairman or Vice Chairman and a Director of
each of the  subsidiary  Banks,  FIFC,  WAMC and  Tricom.  Prior to joining  the
Company,  Mr.  Wehmer  was,  from 1985 to 1991,  Senior  Vice  President,  Chief
Financial Officer,  and a director of River Forest Bancorp,  Chicago,  Illinois.
Mr. Wehmer is also a certified public accountant and earlier in his career spent
seven years with the accounting  firm of Ernst & Young LLP  specializing  in the
banking field and particularly in the area of bank mergers and acquisitions. Mr.
Wehmer is involved in several other charitable and fraternal organizations.

           CLASS II - CONTINUING DIRECTORS SERVING UNTIL THE YEAR 2001

BRUCE K. CROWTHER (48), DIRECTOR SINCE 1998 Mr. Crowther has served as President
and  Chief  Executive  Officer  of  Northwest  Community  Healthcare,  Northwest
Community  Hospital and certain of its affiliates  since January 1992.  Prior to
that time he served as Executive Vice President and Chief Operating Officer from
1989 to 1991. He is a Fellow of the American  College of Healthcare  Executives.
Mr.  Crowther is the past  Chairman of the Board of  Directors  of the  Illinois
Hospital  and Health  Systems  Association  as well as a member of the boards of
directors of the Chicago Hospital Risk Pooling Program and Dianon Systems,  Inc.
Mr. Crowther is a Director of Barrington Bank.

MAURICE F. DUNNE, JR. (73), DIRECTOR SINCE 1996 Mr. Dunne has been the President
of Maurice F. Dunne Ltd., an educational  consulting firm, since September 1991.
Prior  thereto,  he served as  President of the Lake Forest  Graduate  School of
Management,  Lake Forest, Illinois for more than 25 years. Mr. Dunne also served
as the chief operating  officer of the Northern  Illinois  Business  Association
from  September  1991 to June 1993.  Mr. Dunne is a Director of Lake Forest Bank
and North Shore Bank.

WILLIAM C. GRAFT (38), DIRECTOR SINCE 1997 Since December 1999, Mr. Graft is the
founding managing partner of Graft,  Sciaccotta & Associates,  a law firm with a
practice  concentrated  in general  corporate  matters,  commercial  litigation,
finance and complex commercial real estate law. From April 1996 to December 1999
he was the sole

                                     - 3 -
<PAGE>
shareholder and President of his law firm.  Until December 1995, Mr. Graft was a
partner  in the  national  law firm of Keck  Mahin & Cate.  Mr.  Graft is also a
principal and general partner of several real estate investment partnerships and
corporations  actively owning and developing  commercial and medical real estate
facilities.  He serves on the Good Shepherd  Hospital  Development  Council,  is
President  of the Board of  Directors  of the  Barrington  Area Arts Council and
serves as a director of several other private business enterprises. Mr. Graft is
a Director of Barrington Bank.

MARGUERITE  SAVARD MCKENNA (57),  DIRECTOR SINCE 1996 Ms. McKenna,  an attorney,
has  practiced law in Wilmette  since 1983.  She is a member of the Rotary Club,
the Wilmette Chamber of Commerce, the North Suburban Bar Assoc. and President of
New Trier High School  Parents  Association.  Ms. McKenna is a Director of North
Shore Bank.

ALBIN F. MOSCHNER (47),  DIRECTOR  SINCE 1996 Since December 1999, Mr.  Moschner
has been President and Chief  Executive  Officer of One Point  Services,  LLC, a
telecommunications  company.  From September 1997 to November 1999, he served as
President and Chief Executive  Officer of Millecom,  LLC, a developmental  stage
internet  communications  company. From August 1996 to August 1997, he served as
Vice  Chairman and director and an officer of Diba,  Inc., a  development  stage
internet  technology  company.  Mr.  Moschner  served as President and CEO and a
director of Zenith Electronics,  Glenview, Illinois, from 1991 to July 1996. Mr.
Moschner  is  also  a  director  of  Polaroid   Corporation  and  Pella  Windows
Corporation. Mr. Moschner serves as a Director of Lake Forest Bank.

INGRID S.  STAFFORD  (46),  DIRECTOR  SINCE 1998 Ms.  Stafford  has held various
positions  since  1977 with  Northwestern  University,  where  she is  currently
Associate Vice President for Finance and Controller.  She has been a Director of
Wittenberg  University  since 1993 and serves as its Vice Chair. She is a member
of the National  Association of College and University  Business  Officers.  Ms.
Stafford is the Chair of Leadership  Evanston and a board member of the Evanston
Community Foundation. She is also the former President of the Board of Directors
of  Childcare  Network of Evanston and former chair of the Board of Directors of
the Evanston McGaw YMCA. Ms. Stafford is a Director of North Shore Bank.

JANE R. STEIN  (55),  DIRECTOR  SINCE 1996 Since  1983,  Ms.  Stein has been the
Executive Director of the Lake County Medical Society, Vernon Hills, Illinois, a
not-for-profit  professional  association  for physicians in Lake County.  Since
February,  1999, she has been the Executive  Director of the Illinois Society of
Oral and  Maxillofacial  Surgeons.  Ms. Stein also serves as President of Marble
House,  Ltd., a management  education and consulting  firm. She is also the past
president of the Chicago  Association of Healthcare  Executives.  Ms. Stein is a
Director of Libertyville Bank.

KATHARINE V.  SYLVESTER  (60),  DIRECTOR  SINCE 1996 Since  November  1997,  Ms.
Sylvester has been the Office Manager for Fibrex Sales,  Ltd. Ms.  Sylvester has
been active in civic affairs in the Hinsdale area for many years.  She is on the
Board of Trustees of the Hinsdale  Community House and is an Associate Member of
the Women's  Auxiliary  of the Robert  Crown  Center for Health  Education.  Ms.
Sylvester is a Director of Hinsdale Bank and Tricom.

          CLASS III - CONTINUING DIRECTORS SERVING UNTIL THE YEAR 2002

JOSEPH ALAIMO (69),  DIRECTOR  SINCE 1997 Since  September  1998, Mr. Alaimo has
been the  President of WAMC.  Immediately  prior  thereto,  Mr. Alaimo served as
Director of Trust  Investments at Lake Forest Bank since December 1994. Prior to
joining Lake Forest Bank, he was employed for more than 30 years by  Continental
Bank,  where he served most  recently as  Director  of Investor  Relations.  Mr.
Alaimo held various senior positions in the trust department at Continental Bank
before he became their Director of Investor Relations. Mr. Alaimo also currently
serves as a trustee of Loomis Sayles Funds. Mr. Alaimo is a Director of WAMC.

PETER D. CRIST (48),  DIRECTOR  SINCE 1996 Since  December  1999,  Mr. Crist has
served as Vice  Chairman of  Korn/Ferry,  International,  the largest  executive
search firm in the world.  Previously he was President of Crist Partners,  Ltd.,
an  executive   search  firm  he  founded  in  1995  and  sold  to   Korn/Ferry,
International in 1999. Immediately prior thereto he was the Managing Director of
the Chicago office of Russell Reynolds  Associates,  Inc., the largest executive

                                     - 4 -
<PAGE>
search firm in the Midwest,  where he was  employed for more than 18 years.  Mr.
Crist also serves as a director of Northwestern  Memorial  Corporation.  He is a
Director of Hinsdale Bank.

KATHLEEN R. HORNE (56),  DIRECTOR SINCE 1997 Mrs.  Horne is a former  elementary
school  teacher.  For 14  years  she was  Vice  President  of the  International
Creative Group - London/Chicago  Ltd., a  creative-marketing  consultancy.  From
1995 to 1997,  she  served as  President  of the  Woman's  Board of the  Chicago
Horticultural  Society  and as a  member  of the  Board  of  Directors  of  that
organization.  Currently, Mrs. Horne is National Advisor to the Flower Arranging
Study  Group  of The  Garden  Club of  America.  Mrs.  Horne  is a  Director  of
Barrington Bank.

JOHN S.  LILLARD  (69),  DIRECTOR  SINCE  1996 Mr.  Lillard  has  served  as the
Company's  Chairman  since May 1998. He spent more than 15 years as an executive
with JMB Institutional Realty Corporation,  a real estate investment firm, where
he served as President  from 1979 to 1991 and as Chairman from 1992 to 1994. Mr.
Lillard was a general  partner of Scudder  Stevens & Clark until  joining JMB in
1979.  Mr.  Lillard  currently  serves as a director of Cintas  Corporation  and
Stryker Corporation. Mr. Lillard is a Director of Lake Forest Bank and WAMC.

HOLLIS W. RADEMACHER (64),  DIRECTOR SINCE 1996 Mr.  Rademacher is self-employed
as a business  consultant  and  private  investor.  He has  participated  in the
organization  of five of the six Banks.  From 1957 to 1993, Mr.  Rademacher held
various  positions,  including  Officer in Charge,  U.S. Banking  Department and
Chief Credit Officer,  of Continental Bank, N.A.,  Chicago,  Illinois,  and from
1988 to 1993 held the position of Chief Financial  Officer.  Mr. Rademacher is a
director of Schawk,  Inc.  and College  Television  Network,  as well as several
other  private  business  enterprises.  Mr.  Rademacher  currently  serves  as a
Director of each of the subsidiary Banks, FIFC, WAMC and Tricom.

JOHN N. SCHAPER (48),  DIRECTOR  SINCE 1996 Since 1991,  Mr.  Schaper has been a
general  agent for American  United Life  Insurance  Company.  Mr.  Schaper is a
Director of Libertyville Bank.

JOHN J. SCHORNACK (69),  DIRECTOR SINCE 1996 Since 1999 Mr. Schornack has served
as  Chairman  of Strong Arm  Products,  LLC.  Mr.  Schornack  is also the former
Chairman and CEO of KraftSeal Corporation,  Lake Forest, Illinois, a position he
held  from  1991 to 1997,  and  retired  Chairman  of Binks  Sames  Corporation,
Chicago,  Illinois.,  where he served from 1996 to 1998.  From 1955 to 1991, Mr.
Schornack was with Ernst & Young LLP, serving most recently as Vice Chairman and
Managing  Partner of the  Midwest  Region.  He is a Life  Trustee of the Chicago
Symphony  Orchestra,  a  trustee  of the Kohl  Children's  Museum  and The Night
Ministry.  He also is the  retired  Chairman  of the Board of  Trustees of Barat
College, Lake Forest,  Illinois. Mr. Schornack is a Director of North Shore Bank
and several other private business enterprises.

LARRY V. WRIGHT (60),  DIRECTOR SINCE 1996 For the past 35 years, Mr. Wright has
been Vice President of Milbank  Corporation,  Chicago,  Illinois,  an investment
advisory firm. Mr. Wright also serves as a director of Milbank Corporation.

                     RETIRING DIRECTOR AND DIRECTOR EMERITUS

LEMUEL H. TATE, JR. (73), DIRECTOR SINCE 1996 For the past three years, Mr. Tate
has,  from  time  to  time  served  as a  consultant  to  the  Company  and  its
subsidiaries regarding real estate leasing and acquisition matters in connection
with  expansion  activities.  From 1982 to 1988,  Mr. Tate was an executive with
Northwestern  Telecommunication Services (now known as Northwestern Technologies
Group) which is a venture partnership  jointly owned by Northwestern  University
and  Northwestern  Memorial  Hospital  Group.  He retired as President and Chief
Operating  Officer of the  company in 1988.  Since  1988,  he has been active in
volunteer work in the local Chicago area. He is a member of the Evanston  Rotary
Club and is active  in the  International  Executive  Service  Corps.  Since its
inception  in 1994,  Mr.  Tate has been  Chairman  and a Director of North Shore
Bank.  Effective at the Annual Meeting, Mr. Tate will become a Director Emeritus
for a one year term that is  renewable  at the  Board's  discretion  and will be
available to consult with the Board.

                                     - 5 -
<PAGE>
BOARD OF DIRECTORS' COMMITTEES AND COMPENSATION

BOARD OF DIRECTORS' COMMITTEES

         Members of the  Company's  Board of  Directors  have been  appointed to
serve on various  committees of the Board of  Directors.  The Board of Directors
has established four committees:  (i) the Compensation and Nominating Committee;
(ii) the Audit  Committee;  (iii) the Risk  Management  Committee;  and (iv) the
Executive Committee.

         Compensation and Nominating Committee.  The Compensation and Nominating
Committee is composed  entirely of outside  directors  who are not now, and have
never been, officers of the Company.  Currently, the members of the Compensation
and  Nominating  Committee  are  Messrs.  Crist  (Chairman),  Lillard,  Mahoney,
Moschner,  Neis,  Rademacher and Reyes and Ms.  McKenna.  The  Compensation  and
Nominating  Committee is  responsible  for reviewing the Company's  compensation
policies and  administering  the Company's  employee benefit and stock incentive
programs,   and   reports  to  the  Board   regarding   executive   compensation
recommendations.  This  Committee  also  functions as a nominating  committee to
propose to the full Board a slate of nominees for election as directors.  During
1999, five Compensation Committee meetings were held.

         Audit  Committee.  The Audit Committee is composed  entirely of outside
directors  who are not now,  and  have  never  been,  officers  of the  Company.
Currently,  the members of the Audit Committee are Messrs. Schornack (Chairman),
Crowther,  Dunne, and Graft and Ms. Stein and Ms. Sylvester. The Audit Committee
is  responsible  for  oversight  of  the  Company's  accounting,  reporting  and
financial  controls  practices,  reports to the Board regarding audit activities
and  examinations,  and  annually  reviews  the  qualifications  of  independent
auditors. During 1999, six Audit Committee meetings were held.

         Risk  Management  Committee.  The Risk Management  Committee  currently
consists of Messrs.  Rademacher (Chairman),  Moschner,  Rusin, Schaper, and Tate
and Ms. Horne.  The Risk Management  Committee is responsible for monitoring and
overseeing the Company's  insurance program,  interest rate risk and credit risk
exposure on a consolidated basis and at the subsidiaries. This Committee is also
responsible  for  development  and   implementation  of  the  Company's  overall
asset/liability   management  and  credit  policies.   During  1999,  four  Risk
Management Committee meetings were held.

         Executive  Committee.  The Executive  Committee  currently  consists of
Messrs. Rademacher (Chairman), Crist, Lillard, Reyes, Schornack, and Wehmer, and
Ms. Stafford.  The Executive  Committee is authorized to exercise certain powers
of the  Board,  and  meets as  needed,  usually  in  situations  where it is not
feasible to take action by the full Board. No Executive  Committee meetings were
held during 1999.

BOARD OF DIRECTORS' COMPENSATION

         Non-employee  members of the Board of Directors are  compensated by the
Company at the rate of $500 for each Board of  Directors  meeting  attended  and
$200 for each committee meeting attended.  There were five meetings of the Board
of Directors  during 1999. In addition to regular  board and  committee  meeting
fees, the Company pays  retainers to the Chairman of the Board,  the chairman of
the Risk Management  Committee,  the chairman of the Compensation and Nominating
Committee and the chairman of the Audit  Committee.  During 1999, such retainers
were  $40,000,  $20,000,  $2,000  and  $2,000,  respectively,  and are set to be
$50,000, $30,000, $3,000 and $3,000, resprectively, in 2000. Employee members of
the  Board  of  Directors  receive  no  Board  of  Director  compensation.   All
non-employee  directors who serve on the subsidiary boards of directors are also
entitled to compensation  for such service.  For the period during 1999 in which
they served,  all of the directors  attended at least 75% of the total number of
meetings held of the Board and those Committees on which they served, except for
Directors Crowther, Horne, McCarthy, Moschner, Rusin, and Wright.

                                     - 6 -
<PAGE>
DEFERRED COMPENSATION FOR NON-EMPLOYEE DIRECTORS

         The Wintrust  Financial  Corporation  Deferred Director Fee Plan allows
non-employee  Directors to elect to defer receipt of director fees and retainers
due such Directors.  The deferred director fees and retainers are payable at the
Director's  option as a lump sum or in installments  over a period not to exceed
ten years. Cumulative deferred amounts bear interest at the 91-day Treasury Bill
discount rate, adjusted monthly,  until paid. Payments under the plan, which are
unfunded obligations of the Company, begin at the date specified by the Director
or upon cessation of service as a Director.

                        EXECUTIVE OFFICERS OF THE COMPANY

         The Company's  Executive Officers are elected annually by the Company's
Board of  Directors  at the first  meeting  of the Board  following  the  Annual
Meeting of Shareholders.  Certain information regarding those persons serving as
the Company's Executive Officers is set forth below.

Edward J. Wehmer (46) --  President  and Chief  Executive  Officer - Mr.  Wehmer
serves as the  Company's  President  and  performs  the  functions  of the Chief
Executive Officer.  Accordingly,  he is responsible for overseeing the execution
of the  Company's  day-to-day  operations  and  strategic  initiatives.  See the
description  above under  "Election of Directors"  for  additional  biographical
information.

David A. Dykstra (39) -- Executive  Vice  President,  Chief  Financial  Officer,
Secretary and Treasurer - Mr.  Dykstra serves as the Company's  Chief  Financial
Officer and oversees all financial  affairs of the Company,  including  internal
and external financial  reporting.  Prior thereto, Mr. Dykstra was employed from
1990 to 1995 by River Forest Bancorp,  Inc.,  Chicago,  Illinois,  most recently
holding the position of Senior Vice President and Chief Financial Officer. Prior
to his association with River Forest Bancorp, Mr. Dykstra spent seven years with
KPMG LLP,  most  recently  holding the position of Audit  Manager in the banking
practice. Mr. Dykstra is a Director of Libertyville Bank, FIFC and Tricom.

Lloyd M. Bowden (46) --  Executive  Vice  President --  Technology - Mr.  Bowden
serves  as  Executive  Vice  President  -  Technology  for  the  Company  and is
responsible  for  planning,  implementing  and  maintaining  all  aspects of the
subsidiary  banks' internal data processing  systems and technology  designed to
service the  subsidiary  banks'  customer base. Mr. Bowden joined the Company in
April  1996 to serve as the  Director  of  Technology  with  responsibility  for
implementing technological improvements to enhance customer service capabilities
and operational efficiencies.  Prior thereto, he was employed by Electronic Data
Systems,  Inc. in various  capacities  since 1982, most recently in an executive
management  position with the Banking  Services  Division and  previously in the
Banking Group of the Management Consulting Division.

Robert F. Key (45) -- Executive  Vice President -- Marketing - Mr. Key serves as
the  Executive  Vice  President  -  Marketing  for the  Company  and directs all
advertising  and marketing  programs for each of the subsidiary  banks and WAMC.
Mr. Key joined the Company in March 1996 to serve as Executive Vice President of
Marketing.  From 1978 through March 1996,  Mr. Key was a Vice  President/Account
Director at Leo Burnett Company.

Todd A. Gustafson (36) -- Vice  President -- Finance - Mr.  Gustafson  served as
the Vice  President of Finance from June 1998 until April 2000 when he relocated
his employment to Rockford,  Illinois.  He was responsible for the management of
all  accounting,  audit,  financial  and tax  activities  of the Company and its
subsidiaries.  Previously,  Mr. Gustafson was employed from 1990 to 1996 as Vice
President  and  Corporate  Controller  for  Amcore  Financial,  Inc.,  Rockford,
Illinois  and from 1997 to 1998 as Manager of Financial  Reporting  and Analysis
for Woodward Governor Company, Rockford,  Illinois. Mr. Gustafson is a certified
public  accountant  and  previously  specialized  in the financial  institutions
industry as a Senior Audit Manager for BDO Seidman,  LLP and as an Audit Manager
for KPMG LLP.

David J. Galvan (39) -- Vice President -- Investments - Mr. Galvan has served as
the Vice  President of  Investments  since June 1999. He directs all  securities
investment activity, wholesale funding and interest rate risk management for the
Company.  Previously,  Mr. Galvan was employed for 16 years at Amcore Financial,
Inc., Rockford, Illinois, where he served as Vice President and Funds Manager.

                                     - 7 -
<PAGE>
    SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS, DIRECTORS AND MANAGEMENT

         The following  table sets forth the beneficial  ownership of the Common
Stock as of the Annual  Meeting  Record Date,  with respect to (i) each Director
and  each  Named  Executive  Officer  of the  Company;  (ii) all  Directors  and
executive officers of the Company as a group; and (iii) any shareholder known to
hold in excess of 5% of any class of the Company's voting securities.

<TABLE>
<CAPTION>
                                                     AMOUNT OF              CURRENTLY                 TOTAL
                                                   COMMON SHARES           EXERCISABLE             AMOUNT OF           TOTAL
                                                    BENEFICIALLY            OPTIONS &              BENEFICIAL       PERCENTAGE
                                                      OWNED(1)             WARRANTS (1)           OWNERSHIP(1)       OWNERSHIP
                                                  ----------------       ---------------         --------------    -------------
<S>                                                     <C>                    <C>                   <C>              <C>
        DIRECTORS
        ---------
        Joseph Alaimo..........................           7,395                22,873                 30,268              *
        Peter D. Crist.........................          28,884                 2,672                 31,556              *
        Bruce Crowther.........................             645                   255                    900              *
        Maurice F. Dunne, Jr...................          44,902                 9,415                 54,317              *
        William C. Graft.......................          10,000                   340                10,340               *
        Kathleen R. Horne......................             500                   306                   806               *
        John W. Leopold........................         188,442                    --                188,442          2.15%
        John S. Lillard........................         109,760                 4,507                114,267          1.30%
        James E. Mahoney.......................          10,720                 1,208                 11,928              *
        James B. McCarthy......................          13,840                 2,551                 16,391              *
        Marguerite Savard McKenna..............          15,074                 4,156                 19,230              *
        Albin F. Moschner......................           8,869                    --                  8,869              *
        Thomas J. Neis.........................             100                    --                    100              *
        Hollis W. Rademacher...................          51,007                10,136                 61,143              *
        J. Christopher Reyes...................         163,940                 4,005                167,945          1.92%
        Peter P. Rusin.........................           1,000                   187                 1,187               *
        John N. Schaper........................           1,207                 1,208                  2,415              *
        John J. Schornack......................           9,500                 3,804                 13,304              *
        Ingrid Stafford........................           2,992                 3,887                  6,879              *
        Jane R. Stein..........................              --                 1,208                  1,208              *
        Katharine V. Sylvester.................           3,120                 2,793                  5,913              *
        Lemuel H. Tate.........................          15,879                10,070                 25,949              *
        Edward J. Wehmer**.....................         147,000               173,076                320,076          3.59%
        Larry V. Wright(2).....................         389,865                28,492                418,357          4.76%

        OTHER NAMED EXECUTIVE OFFICERS
        ------------------------------
        Lloyd M. Bowden........................          15,641                23,819                 39,460              *
        David A. Dykstra.......................          18,574                52,706                 71,280              *
        Todd A. Gustafson .....................              --                 1,500                  1,500              *
        Robert F. Key..........................          22,652                36,186                 58,838              *

        TOTAL DIRECTORS & EXECUTIVE
        ---------------------------
           OFFICERS (29 PERSONS)  .............       1,282,108               401,360             1,683,468           18.39%
           ---------------------

        DIRECTOR NOMINEE NOT CURRENTLY SERVING
        --------------------------------------
        Dorothy M. Mueller.....................             150                    --                   150              *

        OTHER SIGNIFICANT SHAREHOLDERS
        ------------------------------
        Howard D. Adams(3) ....................         463,340                 8,735                472,075          5.39%
        Emmett McCarthy(4).....................         367,952                93,302                461,254          5.21%
<FN>
*    Less than 1%
**   Denotes person serving as Director and as an executive officer.

                                     - 8 -
<PAGE>
(1)  Beneficial  ownership and percentages are calculated in accordance with SEC
     Rule  13d-3  promulgated  under  the  Securities   Exchange  Act  of  1934.
     Information  for  Other  Significant  Shareholders  is based on their  most
     recent Schedule 13G filings with the SEC.

(2)  Includes  (i) 21,433  shares and 4,667  shares  subject  to  Warrants  held
     directly by Larry  Wright;  (ii) 3,000  shares held by Milbank  Corporation
     ("Milbank")  of  which  Mr.  Wright  is  an  officer,   director  and  sole
     shareholder and with respect to which shares he exercises shared voting and
     investment  power;  (iii) 8,721 shares and 1,092 shares subject to Warrants
     held by an  employee  retirement  plan of Milbank of which Mr.  Wright is a
     trustee with shared voting and  investment  power;  (iv) 351,884 shares and
     22,733  shares  subject to  Warrants  held in Deerpath  Investments  LLP, a
     limited  partnership  ("Deerpath"),  to which Milbank  serves as investment
     advisor and with respect to which Mr.  Wright  exercises  shared voting and
     investment  power;  and (v) 4,827 shares held in certain  family  trusts of
     another  officer  of  Milbank  with  respect  to which Mr.  Wright  acts as
     co-trustee and exercises  shared voting power. The address of Mr. Wright is
     135 South LaSalle Street, Chicago, Illinois 60603.

(3)  Includes  30,137  shares held in certain  family  trusts for the benefit of
     Howard D. Adams' son and 3,957 shares held in a charitable  foundation with
     respect to which  shares Mr. Adams  disclaims  beneficial  ownership.  Also
     includes 29,463 shares held by Mr. Adams' wife. Does not include additional
     shares held directly by, or indirectly  through certain other family trusts
     (for  which  neither  Mr.  Adams nor his wife acts as  co-trustee)  for the
     benefit of Mr. Adams' two adult  children.  The address of Mr. Adams is 570
     Crabtree Lane, Lake Forest, Illinois 60045.

(4)  Includes  16,367  shares owned by Emmett D.  McCarthy and his family.  Also
     reflects  169,930  shares,  28,962 shares  subject to Warrants,  and 17,689
     shares  subject  to  options  held by the Alan W.  Adams  Family  Trust and
     152,781  shares,  28,962  shares  subject to  Warrants,  and 17,689  shares
     subject to options  held by the Sarah K. Adams  Family  Trust,  irrevocable
     trusts for which  Emmett D.  McCarthy  and either Alan W. Adams or Sarah K.
     Adams,  respectively,  serve  as  co-trustees.  The  beneficiaries  of  the
     respective trusts are Alan W. Adams and Sarah K. Adams,  respectively,  the
     two adult children of Howard D. Adams.  Mr. McCarthy  disclaims  beneficial
     ownership of all such shares. Also reflects 28,874 shares held by the Sarah
     Katherine  Adams Trust,  an irrevocable  trust for which Emmett D. McCarthy
     serves as trustee,  the  beneficiary of which trust is Sarah K. Adams.  The
     address of Mr. McCarthy, as Trustee, is c/o 570 Crabtree Lane, Lake Forest,
     Illinois 60045.
</FN>
</TABLE>

                                     - 9 -
<PAGE>
                             EXECUTIVE COMPENSATION

SUMMARY COMPENSATION TABLE

         The following table summarizes the compensation paid by the Company and
its  subsidiaries to those persons  serving as Chief  Executive  Officer and the
four other most highly  compensated  executive  officers  (the "Named  Executive
Officers")  during 1999,  1998 and 1997. In determining  the level of bonuses in
1999,  the  Company's  Compensation  Committee  evaluated  the  bonus  amount in
conjunction with stock incentive awards. See further discussion of the Company's
overall  compensation  philosophy  in  the  "Compensation  Committee  Report  on
Executive Compensation" contained later in this Proxy Statement.

<TABLE>
<CAPTION>
                                                            Summary Compensation Table
                               -------------------------------------------------------------------------------------
                                                                                         Long-Term
                                                                                       Compensation
                                                        Annual Compensation               Awards
                                                -----------------------------------------------------

                                                                       Other Annual    Securities      All Other
                                                                          Compen-      Underlying       Compen-
           Name and                              Salary         Bonus     sation(1)      Options/       sation(2)
      Principal Position             Year          ($)            ($)        ($)         SARs (#)           ($)
      ------------------             ----         ----           ----       ----        ---------          ----

<S>                                  <C>        <C>             <C>         <C>            <C>              <C>
Edward J. Wehmer                     1999       450,000         11,000      9,446          14,667           900
President & Chief                    1998       450,000         45,000      9,895              --         1,200
   Executive Officer                 1997       425,000         40,000     12,420        20,000(3)          881

David A. Dykstra                     1999       225,000          8,000      6,911          10,667            --
Executive Vice President &           1998       206,000         30,000      6,517              --            --
    Chief Financial Officer          1997       176,000         35,000      6,862          18,000           980

Robert F. Key                        1999       190,000          4,500      6,003           5,600           720
Executive Vice President &           1998       180,000         18,000      6,482              --           469
   Director of Marketing             1997       165,000         25,000      6,233          10,000           434

Lloyd M. Bowden                      1999       150,500          4,000      2,222           5,333           450
Executive Vice President &           1998       140,500         18,000      2,523              --           332
   Director of Technology            1997       128,000         15,000      2,533           8,000           296

Todd A. Gustafson                    1999       123,000         14,000        --            5,000            --
Vice President - Finance             1998(4)     60,596         15,000        --            7,500            --

- --------------------------------------------
<FN>
(1)      Other annual compensation  represents the value of certain perquisites,
         including the use of a Company car and/or the payment of club dues.

(2)      Represents the aggregate  life insurance  premium paid on behalf of the
         named  executive  officer by the  Company  and/or  other  miscellaneous
         benefits.

(3)      Represents  grants of options  approved in January 1998 with respect to
         executive's service in 1997.

(4)      Reflects  compensation  for partial  year  service  during  executive's
         initial year of employment  with the Company.  The 1998 base salary for
         Mr.  Gustafson was $115,000.  The 1998 bonus amount  includes a signing
         bonus of $5,000.
</FN>
</TABLE>



OPTION/SAR GRANTS IN LAST FISCAL YEAR

         The table on the following  page  summarizes  for each Named  Executive
Officer  certain  information  about  options  which were granted by the Company
under the 1997 Stock Incentive Plan with respect to the  executives'  service in
1999.  All options were granted at per share  exercise  prices equal to the fair
market value per share on the date of grant.

                                     - 10 -
<PAGE>
<TABLE>
<CAPTION>
                                               OPTION/SAR GRANTS IN LAST FISCAL YEAR

                                               % OF TOTAL                               POTENTIAL REALIZABLE
                                 NUMBER OF        OPTIONS/                                 VALUE AT ASSUMED
                                  SHARES           SARS                                    ANNUAL RATES OF
                                UNDERLYING       GRANTED TO  EXERCISE                        STOCK PRICE
                                OPTIONS/         EMPLOYEES    OR BASE                       APPRECIATION
                                  SARS           IN FISCAL     PRICE   EXPIRATION        FOR OPTION/SAR TERM
                                                                                         ---------------------
           NAME                  GRANTED           YEAR        ($/SH)     DATE                5%           10%
           ----                 --------          -----       -------     -----          -------      --------
<S>                               <C>             <C>        <C>        <C>   <C>         <C>          <C>
Edward J. Wehmer (1).......       14,667          5.62%      $ 17.00    10/28/09          $156,808     $397,382
David A. Dykstra (1).......       10,667          4.08%        17.00    10/28/09           114,043      289,008
Robert F. Key (1)..........        5,600          2.14%        17.00    10/28/09            59,871      151,724
Lloyd M. Bowden (1)........        5,333          2.04%        17.00    10/28/09            57,016      144,490
Todd A. Gustafson (2)......        5,000          1.91%        18.44     4/29/09            57,976      146,923
- -------------------------------------------------
<FN>
(1)      Pursuant to the terms of the option  awards,  all such  Options  vested
         100% as of December 31, 1999.
(2)      Options  were to vest in 20% annual  increments  beginning on April 29,
         2000. Such options were forfeited upon Mr.  Gustafson's  departure from
         the Company in April, 2000.
</FN>
</TABLE>


AGGREGATED OPTION/SAR EXERCISES AND YEAR-END VALUES

     The following table summarizes for each Named Executive  Officer the number
of shares of Common Stock subject to outstanding  Options/SARs  and the value of
such Options/SARs that were unexercised at December 31, 1999.

<TABLE>
<CAPTION>
             AGGREGATED OPTION/SAR EXERCISES IN LAST FISCAL YEAR AND FISCAL YEAR-END OPTION/SAR VALUES

                                                                     NUMBER OF
                                                               SECURITIES UNDERLYING       VALUE OF UNEXERCISED
                               SHARES                               UNEXERCISED                IN-THE-MONEY
                           ACQUIRED ON           VALUE            OPTIONS/SARS AT            OPTIONS/SARS AT
           NAME           EXERCISE (#)       REALIZED ($)      DECEMBER 31, 1999 (#)      DECEMBER 31, 1999 ($)
           ----           ------------       ------------      ---------------------      ---------------------
                                                                    EXERCISABLE/               EXERCISABLE/
                                                                  UNEXERCISABLE(1)           UNEXERCISABLE(1)
                                                               ---------------------      ---------------------
<S>                              <C>              <C>         <C>           <C>         <C>           <C>
Edward J. Wehmer..........       --               --           149,938 /     16,000      $1,121,851 /  $      0
David A. Dykstra..........       --               --            47,666 /     18,705         134,048 /    11,643
Robert F. Key.............       --               --            34,186 /     10,514          64,719 /     3,848
Lloyd M. Bowden...........       --               --            22,219 /      9,784          35,289 /     9,440
Todd A. Gustafson.........       --               --             1,500 /     11,000               0 /         0
- ----------------------------------------
<FN>
(1)  The  numbers  and  amounts  represent  shares of Common  Stock  subject  to
     outstanding  Options/SARs  granted by the Company or its predecessors  that
     were unexercised as of December 31, 1999.
</FN>
</TABLE>

                                     - 11 -
<PAGE>
EMPLOYMENT AGREEMENTS

         In 1998,  the Company  entered into a new  employment  agreements  with
Edward J. Wehmer, David A. Dykstra,  Robert F. Key, and Lloyd M. Bowden, as well
as certain other  officers of the Company and its  subsidiaries.  The employment
agreements   contain   confidentiality   agreements  and  two-year   non-compete
provisions in the event of termination of employment for any reason, and provide
for up to 24 months of severance pay at an annual rate equal to the  executive's
current base salary and prior year bonus amount in the event of (i)  termination
without cause, (ii) a material reduction in duties and  responsibilities,  (iii)
permanent  disability (as defined in the  agreement),  or (iv) reduction in base
annual  compensation  to  less  than  75% of  the  executive's  "Adjusted  Total
Compensation",  as defined in the  agreement to be the aggregate of current base
salary plus the dollar value of all perquisites  for the preceding  twelve month
period. "Adjusted Total Compensation" excludes any bonus payments paid or earned
by the executives. The severance amounts payable under the agreement are subject
to reduction  for any income  earned from other  employment  during the two-year
period  or,  in the  case of  disability,  any  long-term  disability  insurance
benefits from policies  maintained or paid for by the Company.  In addition,  in
the event of the executive's  death resulting in termination of employment,  the
executive's  beneficiaries  are  entitled  to a lump  sum  payment  equal to the
aggregate  severance pay amount,  reduced by any life  insurance  benefits under
policies paid for by the Company.  The "Adjusted Total  Compensation"  as of the
respective dates of such agreements for Messrs. Wehmer, Dykstra, Key, and Bowden
were $469,000, $214,000, $190,000 and $149,000, respectively. In addition to any
increases  in base  salaries  that  may be  agreed  to from  time to  time,  the
executives  are entitled to  participate  in any employee  insurance  and fringe
benefit  programs that may be established by the Company for its employees.  The
current  annual base  salaries of Messrs.  Wehmer,  Dykstra,  Key and Bowden are
$470,000, $250,000, $200,000 and $160,000, respectively.

         The  employment  agreements  also provide for a lump sum payment in the
event the executive's  employment is terminated without cause (or constructively
terminated  due to a  material  reduction  in duties and  responsibilities  or a
reduction in Adjusted Total  Compensation  as described  above) within 12 months
following a change in control (as defined in the agreement) of the Company. Such
change in control payment shall be equal to two times the sum of the executive's
base annual  salary plus prior  year's  bonus,  subject to  reduction in certain
circumstances if the amount payable under the agreement  together with any other
amounts  payable by the Company to the  executive is deemed to result in "excess
parachute  payments"  under  Section  280G of the  Internal  Revenue  Code.  The
agreement  does not  require the amount to be scaled back to satisfy the Section
280G limit,  however,  if the  contractual  change in control  payment minus the
excise  taxes that would be payable by the  executive  would be greater than the
reduced amount.

         Pursuant to an amendment made to Mr. Wehmer's  employment  agreement in
January  2000,  he is also  entitled to certain  special  bonus  payments to pay
interest on a loan made to him by the Company. See "Certain Transactions."

COMPENSATION AND NOMINATING COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION

         The Committee that determines executive  compensation consists entirely
of  non-employee  Directors,  although  Edward J.  Wehmer,  President  and Chief
Executive  Officer  of the  Company,  makes  recommendations  to  the  Committee
regarding  compensation of officers other than himself. Mr. Wehmer serves on the
compensation committees of each of the Company's  subsidiaries,  including WAMC,
North  Shore  Bank  and  Tricom  which  are   responsible  for  determining  the
compensation of the senior officers of those subsidiaries. Joseph Alaimo, Lemuel
Tate, and John Leopold,  senior officers of WAMC,  North Shore Bank, and Tricom,
respectively, are Directors of the Company.

COMPENSATION COMMITTEE REPORT ON EXECUTIVE COMPENSATION

         OVERALL  COMPENSATION  PHILOSOPHY:   The  Compensation  and  Nominating
Committee of the Board of Directors (the "Committee") has the  responsibility to
monitor and implement the overall executive compensation program of the Company.
The objectives of the Company's compensation policies are to enhance shareholder
value;  to create  and  sustain  high  performance;  to  attract  and  retain as
executives  individuals who can contribute  substantially to the Company's short
and long term goals;  and to align the interests of executives with those of the

                                     - 12 -
<PAGE>
shareholders  of the Company.  The  philosophy  is to provide  competitive  base
salaries which reflect  individual  levels of  responsibility  and  performance,
annual  bonuses  based upon personal  achievement  and  contributions  to annual
corporate performance,  and stock-based incentive awards. The combined result is
a  strengthening  of  the  mutuality  of  interest  in the  Company's  long-term
performance between its executive officers and the Company's shareholders.

         BASE SALARIES:  Base salaries for executive officers were determined at
the time of hire by comparing  responsibilities  of the  position  with those of
other  similar   executive   officer   positions  in  the  marketplace  and  the
individual's  experience.  Annual salary adjustments have been determined giving
consideration to the Company's performance and the individual's  contribution to
that   performance.   While  there  are  no  specific   performance   weightings
established,  the salary  recommendations are based on performance criteria such
as:

         o        financial  performance  of the Company with a balance  between
                  long and short  term  growth in  earnings,  revenue  and asset
                  growth;
         o        role in development and  implementation of long term strategic
                  plans;
         o        responsiveness   to  changes  in  the  financial   institution
                  marketplace; and
         o        growth and diversification of the Company.

         In the  absence  of  similar  de novo  bank  holding  companies,  it is
difficult to identify  appropriate peer group  comparisons for the base salaries
of the  Company's  executives.  In addition,  the  Company's  strategy is to pay
executives very  competitive  salaries in an effort to attract and retain highly
qualified,  well-experienced  individuals  which,  given  the  relatively  young
history of the Company,  currently  may be higher than those paid by  comparably
sized financial  institutions.  However,  as the Company matures,  the Committee
believes that increases to total cash compensation  should  increasingly be more
heavily  weighted toward the bonus and stock incentive  components than the base
salary  component.  This  philosophy is intended to ensure a pay for performance
compensation framework which is aligned with shareholder value.

         BONUSES:   Executives  may  earn  annual  cash  bonuses  based  upon  a
pay-for-performance philosophy which are determined at year-end. In recommending
bonuses,  the Committee considers the achievements of each executive officer for
that  year,  as well  as the  Company's  performance.  The  achievements  may be
quantitative or qualitative.  Qualitative factors include but are not limited to
commitment, dedication,  demonstration of the entrepreneurial spirit, creativity
and  initiative,  and  attention  to personnel  relations.  The  Committee  also
evaluates the bonus amount in conjunction with stock incentive awards, if any.

         Given the size of the Company and its  relatively  early growth  stage,
the  Committee  believes it is feasible to  evaluate  the  different  individual
contributions of each of the Company's executive  officers,  and, as a matter of
policy,  there has not been a  defined  bonus  plan  established.  However,  the
Committee did evaluate the attainment of certain specific Company and individual
objectives in determining the bonus amounts  awarded to executives.  The primary
objectives  were based upon net income,  deposit  growth,  loan growth,  certain
financial  performance  measures  such as net  interest  margin and net overhead
ratios, and tailored personal objectives for each executive.  The Committee used
these measurable  objectives as a guideline to establish executive bonuses,  but
the end  determination of such bonuses was ultimately a discretionary  decision.
Accordingly,  the policy  used by the Board to set cash  bonuses  is  considered
subjective.  The  bonuses  for each of the  executive  officers  other  than the
President and CEO were set at the levels recommended by management.

         STOCK  OPTIONS:  To ensure a direct  connection  between the  executive
officer  interests and the shareholders of the Company,  the Company has awarded
and intends to award stock-based incentives which are longer term in nature than
the base  salary and  annual  bonus  components  of  overall  compensation.  The
incentives  have been primarily in the form of stock options granted at exercise
prices at or above fair market value on the date of grant.  The  intention is to
incentivize  employees to create  shareholder value over the long term since the
full  benefit  of  the  compensation   package  cannot  be  realized  unless  an
appreciation  in the share price  occurs over a specified  number of years.  The
Company did not award equity  incentives for 1998. In 1999, the Company  granted
non-qualified  stock

                                     - 13 -
<PAGE>
options to senior management as part of their overall  compensation  package and
in lieu of larger cash bonuses.  The equity  incentives  were  determined in the
fourth quarter of 1999. Such stock options were granted at exercise prices equal
to fair market value on the date of grant, were fully exercisable as of December
31, 1999 and have a term of ten years.

         CHIEF  EXECUTIVE  OFFICER  COMPENSATION:   Mr.  Edward  J.  Wehmer  was
appointed Chief Executive Officer, in addition to his role as President,  in May
1998. Mr.  Wehmer's base salary for 1999 was established by the Committee at the
beginning of the year and the salary level of $450,000  was held  constant  with
the base salary level of 1998.  The  Committee  determined  that the base salary
level  was  appropriate  and that Mr.  Wehmer's  compensation  level  should  be
influenced  more  heavily by  incentive-based  compensation  than by base salary
increases.

         The 1999 bonus  amount and stock  options  awarded to Mr.  Wehmer  were
based on the  recognition  by the members of the Committee of his  dedication to
the   success  of  the   Company  as   exhibited   through   long-term   vision,
entrepreneurial  spirit,  hard work ethic,  knowledge of the financial  services
industry,  strong operational and financial control knowledge and his ability to
recruit a  management  team  with  similar  characteristics.  In  addition,  the
Committee considered the following corporate achievements:

         (1)      The  continued  growth of the Company as one of the largest de
                  novo banking operations in the Midwest area.

         (2)      The  increase  in the  profitability  of the  Company  to $9.4
                  million in 1999 from $6.2 million in 1998, and the exceptional
                  201% (or $9.4 million)  increase in pre-tax  earnings to $14.2
                  million  in 1999  from $4.7  million  in 1998.  The  Committee
                  considers  the  increase  in  pre-tax  profits  to be a better
                  barometer of growth in core earnings.

         (3)      The growth of the Company's assets,  deposits and loans during
                  1999  of  $331   million,   $234  million  and  $286  million,
                  respectively. The increases show growth in these categories in
                  the range of 19% to 29%.

         (4)      The  successful  acquisition of Tricom,  Inc. of Milwaukee,  a
                  financial services firm to the temporary staffing industry.

         (5)      The successful completion of a private placement of additional
                  common  stock  during  the year that  provided  for  continued
                  growth of the Company while  maintaining an efficient  capital
                  structure.

         (6)      The successful  opening of three additional banking facilities
                  during the year that  expanded the  geographical  reach of the
                  organization and enlarged the platform utilized by the Company
                  to effectuate continued growth.

         (7)      The  reduction  in the  ratio  of  noninterest  expenses  as a
                  percent of average  assets to 2.65% in 1999 from 3.04% in 1998
                  despite the opening of the three additional banking facilities
                  in 1999.

         (8)      The  improvement in the Company's net interest margin to 3.54%
                  in 1999 from 3.43% in 1998 and his commitment to improving the
                  margin  through  the  strategy of having the Company be "asset
                  driven" through a diverse set of earning asset portfolios.

         (9)      The   continuing   stability  in  the   manageable   level  of
                  non-performing assets.


         SECTION  162(M):  The  Compensation  and Nominating  Committee does not
believe that the  provisions of Section  162(m) of the Internal  Revenue Code of
1986, as amended (the "Code"),  relating to the  deductibility  of  compensation
paid to the  Named  Executive  Officers,  will  limit the  deductibility  of the
executive  compensation  currently  expected  to be  paid  by the  Company.  The
Compensation  and  Nominating  Committee will continue to


                                     - 14 -
<PAGE>
evaluate the impact of such provisions and to consider compensation policies and
programs appropriate for an organization of the Company's size and history in an
effort to address the potential impact, if any, in the future.

         CONCLUSION: The Compensation Committee believes the executive officers'
individual  compensation  packages are designed in a manner which is  consistent
with the Company's overall compensation philosophy.

     PETER D. CRIST (Chairman of the Committee)           ALBIN F. MOSCHNER
     JOHN S. LILLARD                                      THOMAS J. NEIS
     JAMES E. MAHONEY                                     J. CHRISTOPHER REYES
     MARGUERITE SAVARD MCKENNA                            HOLLIS W. RADEMACHER


PERFORMANCE GRAPH

         The following  performance  graph compares the percentage change in the
Company's  cumulative  shareholder  return on  common  stock  compared  with the
cumulative  total return on composites of (1) all Nasdaq  National Market stocks
for United States  companies  (broad  market index) and (2) all Nasdaq  National
Market bank stocks (peer group  index).  Cumulative  total return is computed by
dividing  the sum of the  cumulative  amount of  dividends  for the  measurement
period and the difference  between the Company's  share price at the end and the
beginning of the  measurement  period by the share price at the beginning of the
measurement period. The Nasdaq National Market for United States companies index
comprises all domestic  common shares traded on the Nasdaq  National  Market and
the Nasdaq  Small-Cap  Market.  The Nasdaq  National  Market bank  stocks  index
comprises  all  banks  traded  on the  Nasdaq  National  Market  and the  Nasdaq
Small-Cap Market.


The Total Return Performance Graph omitted represented a graph of date points as
follows:


<TABLE>
<CAPTION>

                                          1/24/97      6/30/97     12/31/97     6/30/1998   12/31/1998    6/30/1999    12/31/1999
<S>                                          <C>       <C>          <C>           <C>          <C>          <C>           <C>
Wintrust Financial Corporation               100       110.66       111.48        129.51       128.69       115.57        100.00
Nasdaq - Total US                            100       104.49       114.41        137.58       161.22       197.32        291.27
Nasdaq - Bank Index                          100       118.50       158.61        164.23       157.51       162.27        151.40
</TABLE>


         The Company  became  subject to reporting  its  cumulative  shareholder
returns as of January 24, 1997 when the Company  became a  registrant  under the
Securities Exchange Act of 1934. Accordingly,  the graph presents the cumulative
shareholder returns from January 24, 1997 through December 31, 1999.

                                     - 15 -
<PAGE>
TRANSACTIONS WITH MANAGEMENT AND OTHERS

         Some of the  executive  officers and  Directors of the Company are, and
have been during the preceding   year,  customers of the Bank, and some of
the officers and  Directors of the Company are direct or indirect  owners of 10%
or more of the  stock of  corporations  which  are,  or have  been in the  past,
customers of the Bank.  As such  customers,  they have had  transactions  in the
ordinary  course of business  of the Bank,  including  borrowings,  all of which
transactions  are or were on substantially  the same terms  (including  interest
rates and  collateral on loans) as those  prevailing at the time for  comparable
transactions  with  nonaffiliated  persons.  In the opinion of management of the
Company,  none  of the  transactions  involved  more  than  the  normal  risk of
collectibility  or presented  any other  unfavorable  features.  At December 31,
1999, the Bank had $22.1 million in loans  outstanding to certain  Directors and
executive  officers of the Company and certain executive  officers of the Banks,
which amount represented 23.8% of total shareholders' equity as of that date.

         Mr.  Lemuel Tate,  a director of the Company  whose term expires at the
meeting,  provides  consulting  services to the  Company  related to real estate
leasing  and  property  acquisitions  for new banking  locations.  Mr. Tate also
oversees certain  construction  projects at various bank premises.  During 1999,
Mr. Tate  received an  aggregate  of  $67,179 in fees from the Company and its
subsidiaries  for such  services.  Mr. Tate also serves as the Chairman of North
Shore Bank and received an annual  retainer of $56,000 in lieu of bank  director
fees for his service in this role in 1999 and is expected to receive  $56,000 in
2000  for  continued  service  in  this  capacity.  Mr.  Tate  is  eligible  for
discretionary bonuses in addition to the amounts noted above.

         In  October  1999,  the  Company  acquired  100%  of  Tricom,  Inc.  of
Milwaukee.  Mr.  Leopold was the  majority  shareholder  of Tricom  prior to the
acquisition by the Company.  Subsequent to the acquisition, in January 2000, Mr.
Leopold became a director of the Company. Mr. Leopold received 188,442 shares of
the  Company's  common  stock and cash of  approximately  $2.8 million  from the
Company as consideration for his ownership  interest in Tricom. Mr. Leopold also
entered into an employment agreement with the Company for an initial term of one
year. The employment agreement is renewable at the mutual consent of Mr. Leopold
and the Company.

         During the organization of the Company's predecessor companies,  Edward
J. Wehmer,  President and Chief Executive  Officer,  purchased various shares of
Company stock using  borrowed  funds.  Mr. Wehmer  maintained  the loan for such
purchases at an  unaffiliated  bank. In January 2000, the Company entered into a
term note agreement with Mr. Wehmer and his spouse and loaned them $1,200,000 in
order for Mr. Wehmer to retire the debt at the unaffiliated bank. The note has a
maturity  date of January 31,  2005 and bears  interest at an annual rate of 7%,
compounded annually.  Interest is payable annually. The note is full recourse to
the  borrowers  and is also is  secured  by a pledge  of  100,000  shares of the
Company's common stock. If Mr. Wehmer's  employment with the Company  terminates
for any reason, the Company has the right to immediately accelerate the maturity
of the Note if the  principal  and  accrued  interest on the Note is not paid in
full within 90 days of the date of termination. The Company also agreed to amend
Mr.  Wehmer's  employment  agreement to provide for a special annual bonus to be
paid to Mr.  Wehmer in the amount  equal to the  accrued  interest  on the note,
payable one business day prior to each  anniversary  of the date of the Note. If
Mr. Wehmer is terminated  without cause,  or if he resigns for any reason within
18 months  following  a change of  control,  he is entitled to receive a special
severance payment equal to accumulated interest through his termination date.

SECTION 16(A) BENEFICIAL OWNERSHIP REPORTING COMPLIANCE

         Section  16(a) of the  Securities  Exchange  Act of 1934  requires  the
Company's  Directors  and  executive  officers to file  reports of holdings  and
transactions in the Company's  Common Stock with the the Securities and Exchange
Commission.  Based upon its review of copies of such  reports  and of trading in
the Company's  common stock, the Company is not aware of any late filings during
1999 with the following  exception:  Director Neis should have filed a Form 3 in
February,  1999 to report his  holdings  at the time he became a director of the
Company in January,  1999;  however,  the  appropriate  form was not filed until
December, 1999 due to an oversight on the part of the Company to properly inform
the new director of the reporting requirements.

                                     - 16 -
<PAGE>
                                 PROPOSAL NO. 2
                      SHAREHOLDER APPROVAL OF AMENDMENT TO
                            1997 STOCK INCENTIVE PLAN

         Introduction. At the Annual Meeting, there will be submitted a proposal
to approve an amendment to the Wintrust  Financial  Corporation  1997  Incentive
Plan (the "Stock Incentive Plan" or the "Plan").  The Board of Directors adopted
the amendment on January 27, 2000, subject to shareholder  approval, to increase
the number of shares of Common  Stock  authorized  to be issued  under the Stock
Incentive Plan by 450,000 shares.

         The  Stock  Incentive  Plan was  originally  adopted  in 1997 to amend,
restate and  continue the prior  stock-based  incentive  plans of the  Company's
predecessor  corporations into a single plan and was approved by shareholders at
the 1997 Annual Meeting of Shareholders.

         Approval of the amendment to the Plan requires the affirmative  vote of
a majority of the shares  represented in person or by proxy and entitled to vote
at the 2000 Annual Meeting of Shareholders.

         The following  description of the Plan sets forth the material terms of
the Plan,  as  amended;  however,  it is a summary,  and does not  purport to be
complete and is qualified in its entirety by reference to the  provisions of the
Plan.  A copy of the Plan can be obtained  upon  written  request  from David A.
Dykstra,   Executive  Vice  President  and  Chief  Financial  Officer,  Wintrust
Financial Corporation, 727 North Bank Lane, Lake Forest, Illinois 60045.

         Purpose.  The Stock  Incentive  Plan is intended to provide the Company
with the ability to provide market-responsive,  stock-based incentives and other
rewards for  employees  and  directors of the Company and its  subsidiaries  and
consultants to the Company and its  subsidiaries  (i) to provide such employees,
directors  and  consultants  a stake in the growth of the  Company,  and (ii) to
encourage  them to continue in the service of the Company and its  subsidiaries.
Because  there are only 63,621  shares  remaining to be awarded  under the Stock
Incentive  Plan,  the Board of  Directors  believes  that it is  appropriate  to
increase  the shares  reserved for  issuance  under the Plan by 450,000  shares.
Additionally, some of the Company's existing options will be exercised or expire
during the next two years,  reducing the total option shares outstanding.

         These shares will enable the Company to be  competitive  in  attracting
key  employees  to manage  planned  additional  bank and  branch  location.  For
example,  management  estimates that it typically requires  approximately 70,000
option shares to attract  management  to staff a new de novo banking  operation.
The  additional  shares will also be important  to promote the  retention of key
employees while at the same time aligning their interests  closely with those of
the  shareholders.  Accordingly,  additional  option  shares  are  an  important
component in continuing the Company's growth.


         Participants.  All of the  approximately  412  employees and all of the
non-employee   directors  of  the  Company  and  its   subsidiaries,   currently
approximately  86, will be eligible to  participate  in the Plan.  In  addition,
certain  persons  who  have  consulting  arrangements  with the  Company  or its
subsidiaries  may be selected to participate  if it is determined  that any such
individual  has a significant  responsibility  for the success and future growth
and profitability of the Company.

         Authorization.  The Stock  Incentive Plan  currently  provides that the
total number of shares of Common Stock as to which awards may be granted may not
exceed 1,937,359 shares.  Approval by shareholders of the proposed  amendment to
the Stock Incentive Plan will increase this maximum to 2,387,359 shares. Of this
amount,  the number of shares that would be  available  for new awards  would be
513,621  shares.  A total of 229,024 shares have already been issued pursuant to
the exercise of prior awards under the Plan.

         The shares of Common Stock subject to awards under the Stock  Incentive
Plan and  available  for future  awards will be reserved for issuance out of the
Company's  total  authorized  shares.  A participant in the Plan is

                                     - 17 -
<PAGE>
permitted  to  receive  multiple  grants of  stock-based  awards.  The terms and
provisions of a type of award with respect to any recipient need not be the same
with respect to any other recipient of such award. The Plan provides that during
any calendar year the maximum number of shares of Common Stock which may be made
subject to award to any single participant may not exceed 100,000.

         Administration. The Board of Directors of the Company has delegated the
administration  of the Stock Incentive Plan to its  Compensation  Committee (the
"Committee").  The  Committee  will  make  determinations  with  respect  to the
participation of employees, directors and consultants in the Plan and, except as
otherwise  required  by law or the  Plan,  the grant  terms of awards  including
vesting schedules, price, length of relevant performance,  restriction or option
period,  dividend rights,  rights to dividend  equivalents,  post-retirement and
termination rights, payment alternatives, and such other terms and conditions as
the Committee  deems  appropriate.  The Committee may designate other persons to
carry out its  responsibilities  under such conditions and limitations as it may
set, other than its authority with regard to awards granted to employees who are
executive officers or directors of the Company.

         The disposition of an award in the event of the retirement, disability,
death or other termination of a participant's  employment shall be as determined
by the Committee as set forth in the award Agreement.

                  Awards. The following types of awards may be granted under the
         Stock Incentive Plan:

                  Stock  Options.  Stock  Options  may be granted in the form of
         incentive  stock  options  within the  meaning  of  Section  422 of the
         Internal  Revenue Code (the  "Code") or stock  options not meeting such
         Code definition ("nonqualified stock options"). The Plan permits all of
         the  shares  available  under  the  Plan to be  awarded  in the form of
         incentive  stock options if the Committee so  determines.  The exercise
         period for any stock option will be  determined by the Committee at the
         time of grant which may provide  that  options  may be  exercisable  in
         installments.  The  exercise  price per  share of  Common  Stock of any
         option may not be less than the fair market  value of a share of Common
         Stock on the date of grant.  Each  stock  option  may be  exercised  in
         whole,  at any time,  or in part,  from  time to time,  after the grant
         becomes  exercisable.  The exercise price is payable in cash, in shares
         of already owned Common Stock or in any combination of cash and shares,
         or by such methods as the Committee may deem appropriate, including but
         not limited to loans by the Company on such terms and conditions as the
         Committee may determine.  No award other than stock options may be made
         to any  director  (other than a director who is an employee at the time
         of the award).

                  Stock Appreciation  Rights. Stock appreciation rights ("SARs")
         may be granted  independently of any stock option or in tandem with all
         or any part of a stock option  granted under the Plan,  upon such terms
         and  conditions as the Committee may determine.  Upon exercise,  an SAR
         entitles a  participant  to receive the excess of the fair market value
         of a share of Common  Stock on the date the SAR is  exercised  over the
         fair  market  value of a share of  Common  Stock on the date the SAR is
         granted. The Committee will determine whether an SAR will be settled in
         cash,  Common Stock or a  combination  of cash and Common  Stock.  Upon
         exercise  of an SAR granted in  conjunction  with a stock  option,  the
         option  or the  portion  thereof  to  which  the  SAR  relates  will be
         surrendered.

                  Restricted  Shares.  Restricted  shares  are  shares of Common
         Stock that may not be sold or otherwise disposed of during a restricted
         period after grant,  the  duration of which will be  determined  by the
         Committee. The Committee may provide for the lapse of such restrictions
         in  installments.  Restricted  shares  may be voted  by the  recipient.
         Dividends on the  restricted  shares may be payable to the recipient in
         cash or in  additional  restricted  shares.  A recipient  of a grant of
         restricted  shares will generally earn  unrestricted  ownership thereof
         only if the  individual  is  continuously  employed by the Company or a
         subsidiary during the entire restricted period.

                                     - 18 -
<PAGE>
                  Performance Shares. Performance shares are grants of shares of
         Common  Stock  which are earned by  achievement  of  performance  goals
         established  for the  award by the  Committee.  During  the  applicable
         performance period determined by the Committee for an award, the shares
         may be voted by the  recipient  and the  recipient is also  entitled to
         receive dividends thereon unless the Committee determines otherwise. If
         the  applicable  performance  criteria  are  met,  at  the  end  of the
         applicable  performance  period,  the  shares  are  earned  and  become
         unrestricted.  The  Committee  may  provide  that a certain  percentage
         (which  may be greater  than  100%) of the number of shares  originally
         awarded  may be earned  based upon the  attainment  of the  performance
         goals.

                  Stock Units. Stock units are fixed or variable share or dollar
         denominated units valued, at the Committee's discretion, in whole or in
         part by reference  to, or otherwise  based on, the fair market value of
         the Company's  Common Stock. The Committee will determine the terms and
         conditions   applicable  to  stock  units,   including  any  applicable
         restrictions,  conditions  or  contingencies,  which may be  related to
         individual,  corporate or other categories of performance. A stock unit
         may be payable  in Common  Stock,  cash or a  combination  of both.  An
         employee  who  receives  a stock unit may be given  rights to  dividend
         equivalents on such stock units,  payable in cash, stock, or additional
         stock units, subject to any conditions the Committee may impose.

                  Other Incentive Awards. The Committee may grant other types of
         awards of Common Stock or awards based in whole or in part by reference
         to Common Stock ("Other Incentive Awards"). Such Other Incentive Awards
         include, without limitation,  restricted share units, performance share
         units,  unrestricted  stock grants (to other than executive  officers),
         dividend  or  dividend  equivalent  rights  or  awards  related  to the
         establishment  or acquisition by the Company or any subsidiary of a new
         or start-up business or facility. The Committee will determine the time
         at which grants of such Other Incentive Awards are to be made, the size
         of such awards and all other  conditions of such awards,  including any
         restrictions,   deferral  period  or  performance   requirements.   The
         recipient  will have the right to  receive  currently  or on a deferred
         basis  as  determined  by the  Committee,  interest  or  dividends,  or
         interest or dividend equivalents.  Common Stock issued on a bonus basis
         pursuant  to  Other  Incentive   Awards  may  be  issued  for  no  cash
         consideration to nonexecutive officers of the Company.

         Except to the extent  permitted by specific  terms of any  nonqualified
stock options,  no award will be assignable or transferable  except by will, the
laws of descent and distribution or, in the Committee's  discretion,  in certain
other manners.

         Adjustments. In the event there is a change in the capital structure of
the  Company  as a result of any  stock  dividend  or  split,  recapitalization,
merger,  consolidation  or  spin-off  or other  similar  corporate  change,  the
Committee  may make an  adjustment  in the  number of  shares  of  Common  Stock
available for issuance,  the number of shares covered by any  outstanding  award
and the price per share  thereof.  In the event there is a change of control (as
defined  in the  Stock  Incentive  Plan) of the  Company  all  options  and SARs
outstanding  shall become  immediately  exercisable  and remain  exercisable for
their entire term, all restrictions on restricted  shares will lapse and, unless
otherwise  specified in a participant's  award agreement,  all performance goals
applicable to any awards shall be deemed attained at the maximum payment level.

         Amendments  and  Termination.  The Board of  Directors  may at any time
amend, suspend or terminate the Stock Incentive Plan, to the extent permitted by
law; provided, however, no such action may affect in any material way any awards
previously granted thereunder.  Any such action by the Board of Directors may be
taken without the approval of the shareholders of the Company to the extent that
such approvals are not required by applicable law or regulation. There is no set
termination date for the Plan, although no incentive options may be granted more
than 10 years after the effective date of the Plan.

                                     - 19 -
<PAGE>
         Federal Income Tax Considerations.  The following discussion summarizes
the federal income tax  consequences to  participants  who may receive grants of
awards  under  the  Stock   Incentive   Plan.   The  discussion  is  based  upon
interpretations of the Code in effect as of January 1, 2000, and the regulations
promulgated thereunder as of such date.

                  Nonqualified  Stock Options.  For federal income tax purposes,
         no  income  is  recognized  by  a  participant  upon  the  grant  of  a
         nonqualified  stock option  under the Stock  Incentive  Plan.  Upon the
         exercise of a  nonqualified  option,  compensation  taxable as ordinary
         income will be realized by the  participant  in an amount  equal to the
         excess of the fair market  value of a share of Common Stock on the date
         of such exercise over the exercise price. A subsequent sale or exchange
         of such shares will result in gain or loss  measured by the  difference
         between (a) the exercise price,  increased by any compensation reported
         upon  the  participant's  exercise  of the  option  and (b) the  amount
         realized on such sale or exchange. Such gain or loss will be capital in
         nature if the shares were held as a capital asset and will be long-term
         if such shares were held for more than one year.

                  The Company is entitled to a deduction for  compensation  paid
         to a  participant  at the  same  time  and in the  same  amount  as the
         participant  is considered to have realized  compensation  by reason of
         the exercise of an option.

                  Incentive Stock Options.  No taxable income is realized by the
         participant  pursuant to the  exercise  of an  incentive  stock  option
         granted  under  the  Stock  Incentive  Plan,  and  if no  disqualifying
         disposition of such shares is made by such participant within two years
         after the date of grant or within one year after the  transfer  of such
         shares  to such  participant,  then (a) upon sale of such  shares,  any
         amount  realized  in excess of the  option  price will be taxed to such
         participant as a long-term  capital gain and any loss sustained will be
         a long-term  capital loss,  and (b) no deduction will be allowed to the
         Company for Federal income tax purposes.  Upon exercise of an incentive
         stock option, the participant may be subject to alternative minimum tax
         on certain items of tax preference.

                  If the shares of Common Stock acquired upon the exercise of an
         incentive  stock option are disposed of prior to the  expiration of the
         two-years-from-grant/one-year-from-transfer  holding period,  generally
         (a)  the  participant  will  realize  ordinary  income  in the  year of
         disposition  in an  amount  equal  to the  excess  (if any) of the fair
         market  value of the  shares  at  exercise  (or,  if less,  the  amount
         realized  on the  disposition  of the  shares)  over the  option  price
         thereof,  and (b) the Company  will be entitled to deduct such  amount.
         Any  further  gain or loss  realized  will be  taxed as  short-term  or
         long-term capital gain or loss, as the case may be, and will not result
         in any deduction by the Company.

                  If an incentive stock option is exercised at a time when it no
         longer qualifies as an incentive stock option, the option is treated as
         a nonqualified stock option.

                  Stock Appreciation  Rights. No taxable income is recognized by
         a participant  upon the grant of an SAR under the Stock Incentive Plan.
         Upon the exercise of an SAR, however,  compensation taxable as ordinary
         income will be realized by the  participant  in an amount  equal to the
         cash received upon exercise,  plus the fair market value on the date of
         exercise of any shares of Common Stock received upon  exercise.  Shares
         of Common Stock received on the exercise of an SAR will be eligible for
         capital gain treatment, with the capital gain holding period commencing
         on the date of exercise of the SAR.

                  The Company is entitled to a deduction for  compensation  paid
         to a  participant  at the  same  time  and in the  same  amount  as the
         participant  is considered to have realized  compensation  by reason of
         the exercise of the SAR.

                                     - 20 -
<PAGE>
                  Restricted and Performance  Shares.  A recipient of restricted
         shares  or  performance  shares  generally  will be  subject  to tax at
         ordinary  income  rates on the fair market value of the Common Stock at
         the time the  restricted  shares or  performance  shares  are no longer
         subject to forfeiture. However, a recipient who so elects under Section
         83(b) of the Code  within  30 days of the date of the  grant  will have
         ordinary  taxable  income  on the date of the  grant  equal to the fair
         market value of the restricted  shares or performance  shares as if the
         restricted  share were  unrestricted  or the  performance  shares  were
         earned and could be sold  immediately.  If the  shares  subject to such
         election  are  forfeited,  the  recipient  will not be  entitled to any
         deduction,  refund  or  loss  for  tax  purposes  with  respect  to the
         forfeited  shares.  Upon sale of the  restricted  shares or performance
         shares after the forfeiture  period has expired,  the holding period to
         determine  whether the recipient  has  long-term or short-term  capital
         gain or loss begins when the restriction  period expires.  However,  if
         the  recipient  timely  elects to be taxed as of the date of the grant,
         the holding period commences on the date of the grant and the tax basis
         will be equal to the fair market value of the shares on the date of the
         grant  as if the  shares  were  then  unrestricted  and  could  be sold
         immediately.

                  Stock  Units.  A recipient  of stock units will  generally  be
         subject to tax at ordinary income rates on the fair market value of any
         Common  Stock  issued  pursuant to such an award,  and the Company will
         generally  be  entitled  to a  deduction  equal  to the  amount  of the
         ordinary income realized by the recipient. The fair market value of any
         Common  Stock  received  will  generally  be  included in income (and a
         corresponding  deduction will generally be available to the Company) at
         the time of receipt.  The capital gain or loss  holding  period for any
         Common Stock  distributed  under an award will begin when the recipient
         recognizes ordinary income in respect of that distribution.

                  Other Incentive Awards. The federal income tax consequences of
         Other  Incentive  Awards will depend on how such awards are structured.
         Generally,  the Company will be entitled to a deduction with respect to
         such awards only to the extent that the recipient realizes compensation
         income in connection  with such awards.  It is  anticipated  that Other
         Incentive  Awards will  usually  result in  compensation  income to the
         recipient in some amount. However, some forms of Other Incentive Awards
         may not  result  in any  compensation  income to the  recipient  or any
         income tax deduction for the Company.

         Performance Goals and Maximum Awards.  Section 162(m) disallows federal
income tax deductions for certain  compensation in excess of $1,000,000 per year
paid to each of the Company's  Chief  Executive  Officer and its other four most
highly compensated executive officers  (collectively,  the "Covered Employees").
Under Section 162(m),  compensation  that qualifies as "other  performance-based
compensation"  is not subject to the  $1,000,000  limit.  One of the  conditions
necessary  to  qualify  certain  incentive  awards as  "other  performance-based
compensation"  is that the material terms of the  performance  goals under which
the award is made must be disclosed to, and approved by, the shareholders of the
Company before the incentive compensation is paid.

         For those types of awards under the Stock  Incentive Plan which require
performance  criteria  to  meet  the  definition  of  "other   performance-based
compensation"  the  Committee  will,  from time to time,  establish  performance
criteria with respect to an award. These performance criteria may be measured in
absolute  terms or measured  against,  or in  relationship  to, other  companies
comparably,  similarly  or  otherwise  situated and may be based on, or adjusted
for, other objective goals, events, or occurrences  established by the Committee
for  a  performance  period,  including  earnings,  earnings  growth,  revenues,
expenses, stock price, market share, charge-offs, loan loss reserves, reductions
in  non-performing  assets,  return  on  assets,  return  on  equity,  return on
investment,  regulatory  compliance,  satisfactory  internal or external audits,
improvements  in  financial  ratings,  achievement  of  balance  sheet or income
statement   objectives,   extraordinary   charges,   losses  from   discontinued
operations,  restatements  and accounting  changes and other  unplanned  special
charges such as restructuring expenses, acquisition expenses including goodwill,
unplanned  stock offerings and strategic loan loss  provisions.  The performance
criteria  related to an award

                                     - 21 -
<PAGE>
must be  established  by the  Committee  prior to the  completion  of 25% of the
performance  period or such earlier date as may be required by Section 162(m) of
the Code.

         At the end of each performance  period for an award, the Committee will
determine  the  extent to which the  performance  criteria  established  for the
performance  period  have  been  achieved  and  determine  the  pay  out  of the
performance  award.  The  committee  may,  in its  sole  discretion,  reduce  or
eliminate  the  payout  of any  award to the  extent  permitted  under the Stock
Incentive Plan and applicable law.
         Plan Benefits.  The following table provides  certain  information with
respect to all awards which have been made under the 1997 Stock  Incentive  Plan
(and  certain   predecessor  plans)  to  specific   individuals  and  groups  of
individuals,   specifying  the  amounts  granted  to  Named  Executive  Officers
individually,  all current directors who are not executive  officers as a group,
all director nominees  individually,  all current executive  officers as a group
and all employees, including current officers who are not executive officers, as
a group.

<TABLE>
<CAPTION>
                                                                           NUMBER OF UNITS 1
                                                                           -----------------
                                                             PERFORMANCE              STOCK     RESTRICTED
NAME AND POSITION                                               SHARES               OPTIONS      SHARES
- -----------------                                               ------               -------      ------
<S>                                                                                  <C>
Edward J. Wehmer,                                                 --                 165,938         --
President  and Chief Executive Officer

David A. Dykstra,                                                 --                  66,371         --
Executive Vice President / Chief Financial Officer

Robert F. Key,                                                    --                  44,700         --
Executive Vice President / Director of Marketing

Lloyd M. Bowden,                                                  --                  32,003         --
Executive Vice President / Director of Technology

Todd A. Gustafson                                                 --                   1,500         --
Vice President / Finance

Director Nominees, named individually
   James E. Mahoney                                               --                   1,208         --
   James B. McCarthy                                              --                   2,051         --
   John W. Leopold                                                   --                      --         --
   Dorothy M. Mueller                                                --                      --         --
   Thomas J. Neis                                                 --                      --         --
   J. Christopher Reyes                                           --                   4,005         --
   Peter P. Rusin                                                 --                     187         --
   Edward J. Wehmer                                               --                 165,938         --

Executive Officer Group                                           --                 328,012         --

Non-Executive Officer Director Group                              --                  92,688         --

Non-Executive Officer Employee Group                              --               1,116,546         --

<FN>
         (1)      Includes all awards to each  specified  individual or group of
                  individuals made prior to April 15, 2000.
</FN>
</TABLE>

         THE BOARD OF DIRECTORS RECOMMENDS SHAREHOLDERS VOTE FOR APPROVAL OF THE
AMENDMENT TO THE 1997 STOCK INCENTIVE PLAN.
                                     - 22 -
<PAGE>
                              INDEPENDENT AUDITORS

         Ernst and Young LLP served as the  Company's  independent  auditor  for
1999. One or more  representatives of Ernst and Young LLP will be present at the
meeting and will have the  opportunity  to make a statement if they desire to do
so and will be available at the meeting to respond to appropriate questions.


                              SHAREHOLDER PROPOSALS

         Shareholders'  proposals intended to be presented at the Company's 2001
Annual Meeting of  Shareholders  must be received in writing by the Secretary of
the Company no later than  December  22,  2000,  in order to be  considered  for
inclusion in the proxy material for that meeting.  Any such  proposals  shall be
subject to the  requirements  of the proxy rules  adopted  under the  Securities
Exchange  Act of 1934  (the  "Exchange  Act").  Furthermore,  in  order  for any
shareholder  to properly  propose any  business  for  consideration  at the 2001
Annual  Meeting,  including  the  nomination  of any  person for  election  as a
director,  or any other matter  raised other than  pursuant to Rule 14a-8 of the
proxy rules adopted under the Exchange Act, written notice of the  shareholder's
intention to make such  proposal  must be furnished to the Company in accordance
with the By-laws.  Under the  provisions  of the By-laws,  the deadline for such
notice is March 25, 2001.


                                 OTHER BUSINESS

         The  Company  is  unaware  of any other  matter to be acted upon at the
annual  meeting for  shareholder  vote.  In case of any matter  properly  coming
before the meeting for shareholder vote, unless discretionary authority has been
denied the proxy holders named in the proxy  accompanying  this statement  shall
vote them in accordance with their best judgment.


                                            BY ORDER OF THE BOARD OF DIRECTORS




                                            David A. Dykstra
                                            Secretary

                                     - 23 -
<PAGE>
The Directors and Officers of

Wintrust  Financial  Corporation
cordially invite you to attend our
2000 Annual Meeting of Shareholders
Thursday,  May 25, 2000, 10:00 a.m.
Michigan Shores Club
911 Michigan Avenue
Wilmette, Illinois


   YOU CAN VOTE IN ONE OF THREE WAYS: 1) BY MAIL, 2) BY PHONE, 3) BY INTERNET.
              See the reverse side of this sheet for instructions.


IF YOU ARE NOT VOTING BY TELEPHONE OR BY  INTERNET,  COMPLETE  BOTH SIDES OF THE
           ---
        PROXY CARD, DETACH HERE AND RETURN IN THE ENCLOSED ENVELOPE TO:

                           Illinios Stock Transfer Co.
                      209 West Jackson Boulevard, Suite 903
                             Chicago, Illinois 60606


                                   IMPORTANT
                                   ---------
           Please complete both sides of the PROXY CARD, sign, date,
                  detach and return in the enclosed envelope.

- --------------------------------------------------------------------------------
THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF  DIRECTORS.  IF NOT  OTHERWISE
SPECIFIED ON THE REVERSE SIDE,  THIS PROXY WILL BE VOTED FOR ALL NOMINEES LISTED
AND FOR PROPOSAL 2. THE UNDERSIGNED REVOKES ALL PROXIES HERETOFORE GIVEN TO VOTE
AT SUCH MEETING AND ALL ADJOURNMENTS OR POSTPONEMENTS.






Dated _____________________

___________________________

___________________________
(Please sign here)


Please sign your name as it appears above. If executed by a corporation,  a duly
authorized officer should sign. Executors, administrators,  attorneys, guardians
and trustees  should so indicate  when signing.  If shares are held jointly,  at
least one holder must sign.

- --------------------------------------------------------------------------------

Wintrust Financial Corporation

If you  personally  plan to attend the Annual  Meeting of  Shareholders,  please
check the box below and list the names of attendees on reverse side.

Return this stub in the enclosed envelope with your completed proxy card.


I/We do plan to attend
the 2000 meeting         ________



<PAGE>
                                 TO VOTE BY MAIL

To vote by mail, complete both sides, sign and date the proxy card below. Detach
the card below and return it in the envelope provided.

                              TO VOTE BY TELEPHONE

Your telephone vote is quick, confidential and immediate. Just follow these easy
steps:

1. Read the accompanying Proxy Statement.
2. Using a Touch-Tone  telephone,  call Toll Free  1-800-555-8140 and follow the
instructions.
3. When asked for your Voter Control Number, enter the number printed just above
your name on the front of the proxy card below.  Please note that all votes cast
by telephone  must be submitted  prior to midnight  Central Time,  May 23, 2000.
Your telephone vote authorizes the named proxies to vote your shares to the same
extent as if you marked, signed, dated and returned the proxy card.

      If You Vote By TELEPHONE Please Do Not Return Your Proxy Card By Mail

                               TO VOTE BY INTERNET

Your  internet  vote  is  quick,  confidential  and  your  vote  is  immediately
submitted. Just follow the se easy steps:

1. Read the accompanying Proxy Statement.

2. Visit our Internet  voting Site at  HTTP://WWW.EPROXYVOTE.COM/IST-WFCCM/  and
follow the instructions on the screen.

3. When prompted for your Voter Control  Number,  enter the number  printed just
above your name on the front of the proxy card.  Please note that all votes cast
by internet must be submitted prior to midnight Central Time, May 23, 2000. Your
Internet  vote  authorizes  the named  proxies  to vote your  shares to the same
extent as if you marked, signed, dated and returned the proxy card.

THIS IS A "SECURED" WEB PAGE SITE. YOUR SOFTWARE  AND/OR INTERNET  PROVIDER MUST
BE ENABLED TO ACCESS THIS SITE.  PLEASE CALL YOUR SOFTWARE OR INTERNET  PROVIDER
FOR FURTHER INFORMATION.

      If You Vote By Internet, Please Do Not Return Your Proxy Card By Mail

- --------------------------------------------------------------------------------


Wintrust Financial Corporation
REVOCABLE PROXY

THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS

The undersigned  hereby appoints John S. Lillard and Edward J. Wehmer and either
of themas  Proxies,  each with the power to appoint his  substitute,  and hereby
authorizes  each them to represent  and to vote, as  designated  below,  all the
shares of Common Stock of Wintrust  Financial  Corporation which the undersigned
is entitled to vote at the Annual Meeting of  Shareholders to be held on May 25,
2000 or any  adjournment  thereof.  If any other  business is  presented  at the
Annual Metting, including whether or not to adjourn the metting, this proxy will
be voted,  to the extent  legally  permissable,  by those named in this proxy in
their best judgement.

      PROPOSAL 1 -  ELECTION  OF  DIRECTORS  (To  be  designated  as  Class  I
                   Directors with term ending in 2003.)
                   [   ]    FOR ALL NOMINEES LISTED BELOW
                            (Except as marked to the contrary below).

                   [   ]    WITHHOLD AUTHORITY to vote for all nominees below.
                            (INSTRUCTIONS: TO WITHHOLD AUTHORITY TO VOTE FOR
                            ANY INDIVIDUAL NOMINEE, STRIKE A LINE THROUGH THE
                            NOMINEE'S NAME).

          01 JAMES E. MAHONEY                05 THOMAS J. NEIS
          02 JAMES B. MCCARTHY               06 J. CHRISTOPHER REYES
          03 JOHN W. LEOPOLD                 07 PETER P. RUSIN
          04 DOROTHY M. MUELLER              08 EDWARD J. WEHMER


     PROPOSAL 2 - APPROVAL OF AN AMENDMENT TO THE 1997 STOCK INCENTIVE PLAN,
                  AS DESCRIBED IN THE PROCY STATEMENT

                  [   ] FOR   [   ] AGAINST   [   ] ABSTAIN


                        (To be signed on the other side)

<PAGE>


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