WINTRUST FINANCIAL CORP
DEF 14A, 1999-04-14
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 27, 1999


         The  1999  Annual  Meeting  of  Shareholders   of  Wintrust   Financial
Corporation  will be held at The Drake Oak Brook Hotel,  2301 S. York Road,  Oak
Brook,  Illinois 60523, on Thursday,  May 27, 1999, at 2:30 p.m. local time, for
the following purposes:

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

     2.   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 5, 1999.

                                             By order of the Board of Directors,

                                             David A. Dykstra
                                             Secretary

April 14, 1999


WHETHER OR NOT YOU PLAN TO ATTEND THE ANNUAL  MEETING,  IT IS IMPORTANT THAT YOU
COMPLETE,  SIGN,  DATE AND RETURN  THE  ENCLOSED  FORM OF PROXY IN THE  ENVELOPE
PROVIDED FOR THAT PURPOSE.


<PAGE>
                         WINTRUST FINANCIAL CORPORATION
                               727 North Bank Lane
                           Lake Forest, Illinois 60045


                                 PROXY STATEMENT
                         FOR THE 1999 ANNUAL MEETING OF
                 SHAREHOLDERS TO BE HELD THURSDAY, MAY 27, 1999


         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 1999  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 27,  1999,  at 2:30 p.m.  CST,  at the Drake Oak
Brook Hotel, 2301 S. York Road, Oak Brook, Illinois 60523.

PROXIES, OUTSTANDING VOTING SECURITIES, AND SHAREHOLDERS ENTITLED TO VOTE

         The Board of Directors has fixed the close of business on April 5, 1999
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
8,160,795  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 III  Director  as set forth  below  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.  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  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 a
properly executed proxy bearing a later date.  Shareholders  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 return of
your proxy card in the postage-paid envelope provided will be appreciated.

         This Proxy  Statement is being mailed to shareholders on or about April
14, 1999.

                                     - 1 -
<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.


                              ELECTION OF DIRECTORS

         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 III  Directors
will expire at this Annual  Meeting of  Shareholders.  The term of those persons
currently serving as Class I Directors expires at the Annual Shareholder Meeting
to be held in  2000;  the  term of  Class II  Directors  expires  at the  Annual
Shareholder  Meeting to be held in 2001.  Two Class II  directors,  Mr.  Alan W.
Adams and Mr.  Howard D. Adams,  resigned from the Board of Directors in October
1998 and November  1998,  respectively,  and in January 1999, Mr. Thomas J. Neis
was  appointed by the Board of Directors  to fill one of the  vacancies  created
thereby.  Currently,  there are 23  members of the Board of  Directors  with one
Class II vacancy.

         The eight persons named below have been nominated for election as Class
III directors  for a term to end at the Annual  Meeting of  Shareholders  in the
year 2002 or until  their  successors  are  elected  and  qualified.  All of the
nominees currently serve as Class III directors and have indicated a willingness
to continue 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") and Wintrust Asset Management  Company,  N.A.
("WAMC").


            NOMINEES TO SERVE AS CLASS III DIRECTORS UNTIL THE ANNUAL
                    MEETING OF SHAREHOLDERS IN THE YEAR 2002

JOSEPH ALAIMO (68),  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.

                                     - 2 -
<PAGE>
PETER D.  CRIST  (47),  DIRECTOR  SINCE  1996 Mr.  Crist is  President  of Crist
Partners,  Ltd., an executive search firm he founded in 1995.  Immediately prior
thereto he was the Managing  Director of the Chicago office of Russell  Reynolds
Associates, Inc., the largest executive 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 (55),  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. She is a Director of Barrington Bank.

JOHN S.  LILLARD  (68),  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. He is a Director of Lake Forest Bank.

HOLLIS W.  RADEMACHER  (63),  DIRECTOR  SINCE 1996 Mr.  Rademacher  is currently
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.,  Cityscape  Financial  Corp.  and College  Television
Network,  as well as several other private  business  enterprises.  He currently
serves as a Director of each of each of the subsidiary Banks, FIFC and WAMC.

JOHN N. SCHAPER (47),  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 (68), DIRECTOR SINCE 1996 Mr. Schornack is 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 (59),  DIRECTOR SINCE 1996 For the past 34 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.


           CLASS I - CONTINUING DIRECTORS SERVING UNTIL THE YEAR 2000


JAMES E. MAHONEY (61), 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 (47),  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.  

                                     - 3 -
<PAGE>
THOMAS J. NEIS (50), 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.  Mr. Neis is a Director
of Crystal Lake Bank.

J.  CHRISTOPHER  REYES (45),  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 the Boys & Girls Clubs of Chicago and the  Children's  Memorial
Hospital. Mr. Reyes is a Director of Lake Forest Bank.

PETER P. RUSIN (46),  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.

LEMUEL H. TATE, JR. (72),  DIRECTOR SINCE 1996 For the past two years,  Mr. Tate
has 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.

EDWARD J. WEHMER (45), 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 the  Chairman and a Director of FIFC and as
Chairman or Vice Chairman and a Director of each of the subsidiary Banks.  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 a Trustee  of Barat  College,  Lake  Forest,
Illinois,   and  is  involved  in  several   other   charitable   and  fraternal
organizations.


           CLASS II - CONTINUING DIRECTORS SERVING UNTIL THE YEAR 2001

BRUCE K. CROWTHER (47), 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. (72), 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.

                                     - 4 -
<PAGE>
WILLIAM C. GRAFT (37), DIRECTOR SINCE 1997 Mr. Graft is the sole shareholder and
President of his law firm professional corporation, with a practice concentrated
in corporate,  finance and complex  commercial  real estate law.  Until December
1996, 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 and is President of the Board of Directors of the Barrington
Area Arts Council. Mr. Graft is a Director of Barrington Bank.

MARGUERITE  SAVARD MCKENNA (56),  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 and the North  Suburban Bar  Association.  Ms.
McKenna is a Director of North Shore Bank.

ALBIN F. MOSCHNER (46),  DIRECTOR SINCE 1996 Since  September 1997, Mr. Moschner
has been President and Chief Executive  Officer of Millecom,  LLC, a development
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.
Previously  he held the  positions  of Chief  Operating  Officer and Senior Vice
President of Operations of Zenith.  Mr.  Moschner is also a director of Polaroid
Corporation  and Pella  Windows  Corporation.  He serves as a  Director  of Lake
Forest Bank.

INGRID S.  STAFFORD  (45),  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. She is a member of the National Association of
College  and  University  Business  Officers.  Ms.  Stafford  is also the former
President of the Board of  Directors of Childcare  Network of Evanston and chair
of the Board of Directors of the Evanston McGaw YMCA. Ms. Stafford is a Director
of North Shore Bank.

JANE R. STEIN  (54),  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 is also the past  president of the
Chicago  Association  of  Healthcare  Executives.  Ms.  Stein is a  Director  of
Libertyville Bank.

KATHARINE V.  SYLVESTER  (59),  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.


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,  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 

                                     - 5 -
<PAGE>
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
1998, six 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 1998, four Audit Committee meetings were held.

         Risk  Management  Committee.  The Risk Management  Committee  currently
consists of Messrs.  Rademacher (Chairman),  Moschner, Rusin, Schaper, Tate, and
Wehmer  and  Ms.  Horne.  The  Risk  Management  Committee  is  responsible  for
monitoring  and  overseeing  the  Company's  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 1998, two Risk Management
Committee meetings were held.

         Executive  Committee.  The Executive  Committee  currently  consists of
Messrs. Rademacher (Chairman), Crist, Lillard, McCarthy, Reyes, Schornack, Tate,
Wehmer and Wright and Ms.  Stafford.  The  Executive  Committee is authorized to
exercise  certain of the 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 1998.

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 six meetings of the Board
of Directors  during 1998.  Effective May 1998, in addition to regular board and
committee  meeting fees,  the Company  commenced the payment of retainers to the
Chairman of the Board and the  chairman of the Risk  Management  Committee at an
annualized rate of $40,000 and $20,000,  respectively.  Effective  January 1999,
the chairman of the  Compensation  and Nominating  Committee and the chairman of
the Audit Committee also began receiving  retainers in the annualized  amount of
$2,000  each.  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 1998 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 Messrs. Rusin and Mr. Alaimo, and Ms. Stafford who
missed one of the three meetings held after her election in May 1998.

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.

                                     - 6 -
<PAGE>
                        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 (45) --  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 (38) -- Executive Vice President,  Chief Financial  Officer 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  Financial
Institutions  practice. In addition to various civic and charitable  activities,
Mr. Dykstra is a Trustee of the Village of Lake Villa. Mr. Dykstra is a Director
of Libertyville Bank and FIFC.

Lloyd M. Bowden (45) --  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.

Randolph M. Hibben (41) -- Executive  Vice President -- Investments - Mr. Hibben
serves as the Executive Vice President - Investments for the Company and directs
all  securities  investing  and  the  day-to-day  management  of  the  Company's
asset/liability  position. Mr. Hibben joined the Company in 1991 as an Executive
Vice President of Lake Forest Bank. Prior thereto,  Mr. Hibben was employed from
1987 to 1991 in a similar  capacity  by River  Forest  Bancorp,  Inc.,  Chicago,
Illinois, most recently holding the position of Vice President - Investments.

Robert F. Key (44) -- 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 has served
as the Vice  President of Finance  since June 1998.  He is  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.

                                     - 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
                                                     ----------           -------------          --------------      -----------
        DIRECTORS
        ---------
<S>                                                   <C>                     <C>                 <C>                 <C>   
        Joseph Alaimo..........................           7,395                11,473                 18,868              *
        Peter D. Crist.........................          28,884                 2,672                 31,556              *
        Bruce Crowther.........................             645                   255                    900              *
        Maurice F. Dunne, Jr...................          44,302                 9,415                 53,717              *
        William C. Graft.......................           1,000                   340                  1,340              *
        Kathleen R. Horne......................             500                   306                    806              *
        John S. Lillard........................          76,260                 4,507                 80,767              *
        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...................         153,940                 4,005                157,945          1.93%
        Peter P. Rusin.........................           1,000                   187                  1,187              *
        John N. Schaper........................           1,207                 1,208                  2,415              *
        John J. Schornack......................           8,766                 3,804                 12,570              *
        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                 6,070                 21,949              *
        Edward J. Wehmer**.....................         147,000               154,409                301,409          3.62%
        Larry V. Wright(2).....................         429,865                28,492                458,357          5.60%

        OTHER NAMED EXECUTIVE OFFICERS                                                      
        ------------------------------
        Lloyd M. Bowden........................          15,641                14,183                 29,824              *
        David A. Dykstra.......................          18,374                32,518                 50,892              *
        Randolph M. Hibben.....................          19,685                34,220                 53,905              *
        Robert F. Key..........................          22,652                21,554                 44,206              *     

        TOTAL DIRECTORS & EXECUTIVE
        ---------------------------
           OFFICERS (28 PERSONS)  .............       1,098,717               355,557              1,454,274         17.08%
           ---------------------- 

        OTHER SIGNIFICANT SHAREHOLDERS
        ------------------------------
        Howard D. Adams(3) ....................         478,121                 8,735                486,856          5.96%
        Emmett McCarthy(4).....................         390,222                93,302                483,524          5.86%
- ------------------------------------------
<FN>
*    Less than 1%
**   Denotes person serving as Director and as an executive officer.

                                     - 8 -
<PAGE>
(1)  Beneficial ownership 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 the respective 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) 391,884 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  either Mr.  Adams or his wife has voting  power and with
     respect to which Mr. Adams disclaims  beneficial  ownership.  Also includes
     29,626 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  173,661  shares,  28,962 shares  subject to Warrants,  and 17,689
     shares  subject  to  options  held by the Alan W.  Adams  Family  Trust and
     171,320  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 1998, 1997 and 1996.

<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>  
Edward J. Wehmer                     1998       450,000         45,000      9,895              --         1,200
President & Chief                    1997       425,000         40,000     12,420        20,000(7)          881
   Executive Officer                 1996       395,000         40,000      6,431        36,730(4)        1,224

David A. Dykstra                     1998       206,000         30,000      6,517              --            --
Executive Vice President &           1997       176,000         35,000      6,862          18,000           980
    Chief Financial Officer          1996       155,000         32,000      4,790           6,824           582

Robert F. Key                        1998       180,000         18,000      6,482              --           469
Executive Vice President &           1997       165,000         25,000      6,233          10,000           434
   Director of Marketing             1996(5)(6) 121,634         40,000      1,116          29,100            --

Lloyd M. Bowden                      1998       140,500         18,000      2,523              --           332
Executive Vice President &           1997       128,000         15,000      2,533           8,000           296
   Director of Technology            1996(5)(6)  90,000         20,000      2,745          18,670            --

Randolph M. Hibben                   1998       135,000         15,000      4,856              --           228
Executive Vice President -           1997       124,000         12,000      5,368           6,000           228
   Investments                       1996       113,000         10,000      4,749              --           165

Howard D. Adams                      1998       197,917(8)          --         --              --     323,750(8)
Former Chairman and Chief            1997       465,000         55,000      6,504        30,000(7)           --
     Executive Officer               1996(3)    331,250         40,000        373              --            --
- --------------------------------------------
<FN>
(1)      Other annual  compensation  represents the sum of compensation  for the
         use of a Company car and/or the payment of club dues.

(2)      Represents compensation to the executive officer for the aggregate life
         insurance  premium paid on behalf of the named executive officer by the
         Company or other miscellaneous compensation.

(3)      In  addition,   HDA  Capital   Corporation  ("HDA  Capital")  was  paid
         consulting fees and expenses by Crabtree (a predecessor  corporation of
         the Company)  for services of Mr. Adams and other  personnel of $95,548
         for  the  year  ended  December  31,  1996.   Subsequent  to  the  1996
         Reorganization, these consulting fees were discontinued. HDA Capital is
         owned by the Alan W. Adams  Family  Trust and the Sarah K. Adams Family
         Trust.

(4)      Represents  awards under  "Phantom  Stock  Agreements"  entered into in
         1996, by two of the  Company's  predecessor  corporations,  pursuant to
         which  Mr.  Wehmer  became  entitled  to  cash  payments  equal  to any
         appreciation  until  exercised  in the value of an  aggregate of 36,730
         shares of Common  Stock  over fair  market  value as of the date of the
         agreements  (the  weighted  average fair market value as of the date of
         the  agreements was $12.06 per share after  adjustments  resulting from
         the  Reorganization).  Mr. Wehmer  exercised  these stock  appreciation
         rights in 1997.

(5)      Reflects  compensation for partial year service. The 1996 base salaries
         for Messrs. Key and Bowden were $150,000 and $120,000, respectively.

(6)      Includes  signing  bonuses of $15,000 and  $10,000,  respectively,  for
         Messrs. Key and Bowden.

(7)      Represents  grants of options  approved in January 1998 with respect to
         executives'  service in 1997. In the case of Mr.  Adams,  those options
         terminated  unexercised  upon his departure  from  employment  with the
         Company in May 1998.

(8)      Mr.  Adams  served as CEO until May 22,  1998.  The amount of  $197,917
         shown as salary  represents  salary paid to Mr.  Adams from  January 1,
         1998 until May 22,  1998.  Amounts paid to Mr. Adams under the terms of
         his employment agreement subsequent to May 22, 1998 are included in the
         column titled "All Other Compensation".
</FN>
</TABLE>

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

     The  Company  did not grant  options to any Named  Executive  Officer  with
respect to the executives' service in 1998.

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, 1998.

     AGGREGATED OPTION/SAR EXERCISES IN LAST FISCAL YEAR AND FISCAL YEAR-END
                               OPTION/SAR VALUES

<TABLE>
<CAPTION>
                                                                     NUMBER OF
                                                               SECURITIES UNDERLYING       VALUE OF UNEXERCISED
                               SHARES                               UNEXERCISED                IN-THE-MONEY
                           ACQUIRED ON           VALUE            OPTIONS/SARS AT            OPTIONS/SARS AT
           NAME           EXERCISE (#)       REALIZED ($)      DECEMBER 31, 1998 (#)      DECEMBER 31, 1998 ($)
           ----           ------------       ------------      ---------------------      ---------------------
                                                                    EXERCISABLE/               EXERCISABLE/
                                                                  UNEXERCISABLE(1)           UNEXERCISABLE(1)

<S>                            <C>               <C>           <C>        <C>            <C>           <C>     
Edward J. Wehmer..........       --               --           131,271 /  20,000         $1,687,957 /  $ 31,250
David A. Dykstra..........       --               --            27,478 /  28,226            235,343 /   101,072
Robert F. Key.............       --               --            19,554 /  19,546            132,590 /    77,095
Lloyd M. Bowden...........       --               --            12,583 /  14,087             85,835 /    51,908
Randolph M. Hibben........       --               --            33,020 /   6,569            424,261 /    12,893
Howard D. Adams...........      6,794            $79,039           --  /      --               --   /        --
- ----------------------------------------
<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, 1998.
</FN>
</TABLE>


EMPLOYMENT AGREEMENTS

         In 1998,  the Company  entered into a new  employment  agreements  with
Edward J. Wehmer, David A. Dykstra, Robert F. Key, Lloyd M. Bowden, and Randolph
M.  Hibben,   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, Bowden, and Hibben were $469,000, $214,000, $190,000, $149,000 and
$146,000,  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.

                                     - 11 -
<PAGE>
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 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. The current annual base salaries of Messrs. Wehmer, Dykstra, Key, Bowden
and  Hibben  are   $450,000,   $225,000,   $190,000,   $150,500  and   $150,000,
respectively.

         The Company  entered into an  employment  agreement  with Mr. Howard D.
Adams in 1996 pursuant to which Mr. Adams served as the  Company's  Chairman and
Chief Executive Officer until May 22, 1998. The agreement provides for 24 months
of severance payments to Mr. Adams aggregating  $1,110,000,  which is the amount
equal to two times the sum of Mr.  Adams'  1998  annualized  salary and his 1997
bonus,  provided,  however that the severance  amount is subject to reduction by
the amount of income  earned  from any other  employment  during  the  severance
period.  Under  the  agreement,   during  this  two-year  period  following  his
departure,  Mr.  Adams  has  agreed  not to  compete  with the  Company,  not to
participate in opening a bank or other financial  institution  which operates in
the  Company's  market  area,  and not to hire or solicit  employees,  agents or
consultants of the Company for other  employment.  Consistent  with the terms of
the  agreement,  Mr.  Adams is receiving  monthly  severance  payments  from the
Company of $46,250 which are expected to continue until May 2000.

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
and North Shore Bank,  which are responsible for determining the compensation of
the senior officers of those subsidiaries. Joseph Alaimo and Lemuel Tate, senior
officers  of WAMC and North  Shore  Bank,  respectively,  are  Directors  of the
Company.

         Mr.  James  H.  Bishop,   President  and  Chief  Executive  Officer  of
Barrington  Bank,  serves on the  Boards of  Directors  of  Northwest  Community
Healthcare  and  Northwest  Community  Hospital for which Bruce K.  Crowther,  a
director of the Company, serves as President and Chief Executive Officer.

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
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 

                                     - 12 -
<PAGE>
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 component 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.

         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  incentive  opportunities 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 awarded equity  incentives to executives with respect to 1997
employment.  No  additional  stock option  grants were made with respect to 1998
employment.

         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 1998 of $450,000  was  established  by the
Committee  at the  beginning  of the year when he was serving as  President  and
Chief  Operating  Officer.  At the time Mr. Wehmer  assumed the Chief  Executive
Officer role, no additional  base salary  adjustments  were made. The 1998 bonus
amount awarded to Mr. Wehmer was based on the  recognition by the members of the
Committee  of the  additional  responsibilities  Mr.  Wehmer  has  assumed,  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,  

                                     - 13 -
<PAGE>
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  into one of the largest de novo
          banking operations in the seven state Midwest area.

     (2)  The  increase in the  profitability  of the Company to $6.2 million in
          1998 from $4.8  million  in 1997,  and the  exceptional  345% (or $3.7
          million)  increase in pre-tax  earnings  to $4.7  million in 1998 from
          $1.1 million in 1997. 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 1998 of
          $295  million,  $311  million  and  $279  million,  respectively.  The
          increases show growth in these categories in the range of 27% to 39%.

     (4)  The  successful  completion of a public  offering of $31.05 million of
          the Company's Trust Preferred securities and its listing on the Nasdaq
          National Market System.

     (5)  The successful  opening of four 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.

     (6)  Mr. Wehmer's  leadership in the successful  start-up of Wintrust Asset
          Management Company, the Company's new trust and investment subsidiary.

     (7)  The  reduction  in the ratio of  noninterest  expenses as a percent of
          average assets to 3.04% in 1998 from 3.18% in 1996 despite the opening
          of the four  additional  banking  facilities  in 1998,  the opening of
          Crystal  Lake  Bank  in  late  December   1997,   and  other  one-time
          non-recurring charges in 1998.

         Mr. Howard D. Adams served at the  Company's  Chief  Executive  Officer
until May 1998. The factors  discussed above in the "Base Salaries" section were
the  basis  for  determining  the  base  salary  of  Mr.  Adams.  The  Committee
recommended that a 7.5% increase,  or $35,000 increase,  in Mr. Adams' 1998 base
salary to $465,000 from the year-end 1997 level of $465,000 was warranted  based
on the growth of the Company  during 1997,  and other factors  outlined above in
the "Base  Salaries"  section.  The 1998 base salary amount was awarded prior to
the announcement of his departure in May 1998.

         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 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)
                                 JOHN S. LILLARD
                                 JAMES E. MAHONEY
                                 MARGUERITE SAVARD MCKENNA
                                 ALBIN F. MOSCHNER
                                 J. CHRISTOPHER REYES
                                 HOLLIS W. RADEMACHER

                                     - 14 -
<PAGE>
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:

                               1/24/97    6/30/97  12/31/97   6/30/98  12/31/98
                               -------    -------  --------   -------  --------
Wintrust Financial Corporation     100     110.66    111.48    129.51    128.69
Nasdaq - Total US                  100     104.49    114.54    137.90    161.02
Nasdaq - Bank Index                100     118.50    158.61    164.47    157.11


         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, 1998.


                                     - 15 -
<PAGE>
TRANSACTIONS WITH MANAGEMENT AND OTHERS

         Some of the  executive  officers and  Directors of the Company are, and
have been during the preceding  three years,  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,
1998, the Bank had $19.8 million in loans  outstanding to certain  Directors and
executive  officers of the Company and certain executive  officers of the Banks,
which amount represented 26.3% of total shareholders' equity as of that date.

         Mr.  Lemuel  Tate,  a  director  of the  Company,  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 1998, Mr. Tate received an aggregate of $73,500
in fees from the Company and its subsidiaries for such services. The Company has
agreed to pay Mr.  Tate  annual  compensation  of  $72,000  during  1999 for his
continued  consulting  services.  Mr. Tate also serves as the  Chairman of North
Shore Bank and received an annual  retainer of $50,000 in lieu of bank  director
fees for his service in this role in 1998 and will  receive  $56,000 in 1999 for
such services. Mr. Tate is eligible for discretionary bonuses in addition to the
amounts noted above.

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
1998 with the following  exceptions:  (1) former Director Howard D. Adams should
have filed a Form 4 in January 1998 to report the exercise of 7,341 options; the
appropriate  form was filed in February 1998; and (2) Directors  Alaimo and Tate
should  have  filed a Form 5 in  February  1998 to report the grant of 9,000 and
10,000   options  to  acquire  common  stock,   respectively;   the  forms  were
inadvertently not filed until September 1998.


                              INDEPENDENT AUDITORS

         KPMG LLP served as the Company's  independent  auditor for 1998. One or
more  representatives  of KPMG 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.

                                     - 16 -
<PAGE>
                              SHAREHOLDER PROPOSALS

         Shareholders'  proposals intended to be presented at the Company's 2000
Annual Meeting of  Shareholders  must be received in writing by the Secretary of
the Company no later than  December  16,  1999,  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 2000
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. The deadline for such notice is March 26, 2000.


                                 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

                                     - 17 -
<PAGE>
The Directors and Officers of

Wintrust  Financial  Corporation  
cordially invite you to attend our 
1999 Annual Meeting of Shareholders  
Thursday,  May 27, 1999, 2:30 p.m. 
Drake Oak Brook Hotel
2301 S. York Road
Oak Brook, Illinois

IMPORTANT

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



<PAGE>


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.
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.



<PAGE>


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 1999 meeting         ________



<PAGE>


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 as Proxies,
each with the power to appoint  his  substitute  and hereby  authorizes  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 27, 1999 or any  adjournment
thereof.

      PROPOSAL 1 -  ELECTION  OF  DIRECTORS  (To  be  designated  as  Class  III
                   Directors with term ending in 2002.)
                   [   ]    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).

          JOSEPH ALAIMO                      HOLLIS W. RADEMACHER
          PETER D. CRIST                     JOHN N. SCHAPER  
          KATHLEEN R. HORNE                  JOHN J. SCHORNACK
          JOHN S. LILLARD                    LARRY WRIGHT
         



In their discretion, the Proxies are authorized to vote upon such other business
as many properly come before the meeting.

(To be signed on the other side)




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