EXHIBIT 4.4

                                 TRUST AGREEMENT


         This TRUST AGREEMENT, dated as of September 24, 2004 (this "Trust
Agreement"), among (i) Wintrust Financial Corporation, an Illinois corporation
(the "Depositor"), (ii) Wilmington Trust Company, a Delaware banking
corporation, as trustee, and (iii) David L. Stoehr, an individual, as trustees
(each of such trustees in (ii) and (iii) a "Trustee" and collectively, the
"Trustees"). The Depositor and the Trustees hereby agree as follows:

1.       The trust created hereby (the "Trust") shall be known as "Wintrust
         Capital Trust VI" in which name the Trustees, or the Depositor to the
         extent provided herein, may engage in the transactions contemplated
         hereby, make and execute contracts, and sue and be sued.

2.       The Depositor hereby assigns, transfers, conveys and sets over to the
         Trustees the sum of Twenty-Five Dollars ($25.00). The Trustees hereby
         acknowledge receipt of such amount in trust from the Depositor, which
         amount shall constitute the initial trust estate. The Trustees hereby
         declare that they will hold the trust estate in trust for the
         Depositor. It is the intention of the parties hereto that the Trust
         created hereby constitute a Delaware statutory trust under chapter 38,
         title 12 of the Delaware Code, 12 Del. C. Section 3801, et seq. (the
         "Delaware Trust Act"), and that this document constitute the governing
         instrument of the Trust. The Trustees are hereby authorized and
         directed to execute and file a certificate of trust with the Delaware
         Secretary of State in accordance with the provisions of the Delaware
         Trust Act.

3.       The Depositor and the Trustees will enter into an amended and restated
         Trust Agreement, satisfactory to each such party and substantially in
         the form included as an exhibit to the 1933 Act Registration Statement
         (as defined below), to provide for the contemplated operation of the
         Trust created hereby and the issuance of Preferred Securities and
         Common Securities to be referred to therein. Prior to the execution and
         delivery of such amended and restated Trust Agreement, the Trustees
         shall not have any duty or obligation hereunder or with respect to the
         trust estate, except as otherwise required by applicable law or as may
         be necessary to obtain prior to such execution and delivery any
         licenses, consents or approvals required by applicable law or
         otherwise.

4.       The Depositor and the Trustees hereby authorize and direct the
         Depositor, as the sponsor of the Trust, (i) to file with the Securities
         and Exchange Commission (the "Commission") and execute, in each case on
         behalf of the Trust, (a) the Registration Statement on Form S-3 (the
         "1933 Act Registration Statement") (including any pre-effective or
         post-effective amendments to the 1933 Act Registration Statement)
         relating to the registration under the Securities Act of 1933, as
         amended, of the Preferred Securities of the Trust and possibly certain
         other securities and (b) a Registration Statement on Form 8-A (the
         "1934 Act Registration Statement") (including all pre-effective and
         post-effective amendments thereto) relating to the registration of the
         Preferred Securities of the Trust under the Securities Exchange Act of
         1934, as amended; (ii) to file with the New York Stock Exchange or
         other national stock exchange or automated quotation system (each, an
         "Exchange") and execute on behalf of the Trust one or more listing
         applications and all other applications, statements, certificates,
         agreements and other instruments as shall be necessary or desirable to
         cause the Preferred Securities to be listed on any of the

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         Exchanges; (iii) to file and execute on behalf of the Trust such
         applications, reports, surety bonds, irrevocable consents, appointments
         of attorney for service of process and other papers and documents as
         shall be necessary or desirable to register the Preferred Securities
         under the securities or blue sky laws of such jurisdictions as the
         Depositor, on behalf of the Trust, may deem necessary or desirable; and
         (iv) to execute on behalf of the Trust that certain Underwriting
         Agreement relating to the Preferred Securities, among the Trust, the
         Depositor and the Underwriters named therein, substantially in the form
         included as an exhibit to the 1933 Act Registration Statement. In the
         event that any filing referred to in clauses (i), (ii) and (iii) above
         is required by the rules and regulations of the Commission, an
         Exchange, or state securities or blue sky laws to be executed on behalf
         of the Trust by one or more of the Trustees, each of the Trustees, in
         its or his capacity as a Trustee of the Trust, is hereby authorized
         and, to the extent so required, directed to join in any such filing and
         to execute on behalf of the Trust any and all of the foregoing, it
         being understood that Wilmington Trust Company in its capacity as a
         Trustee of the Trust shall not be required to join in any such filing
         or execute on behalf of the Trust any such document unless required by
         the rules and regulations of the Commission, the Exchange or state
         securities or blue sky laws.

         In connection with the filings referred to above, the Depositor and
         David L. Stoehr, as Trustee and not in his individual capacity, hereby
         constitute and appoint David L. Stoehr, as their true and lawful
         attorneys-in-fact and agents, with full power of substitution and
         resubstitution, for the Depositor or such Trustee or in the Depositor's
         or such Trustee's name, place and stead, in any and all capacities, to
         sign any and all amendments (including post-effective amendments) to
         the 1933 Act Registration Statement and the 1934 Act Registration
         Statement and to file the same, with all exhibits thereto, and other
         documents in connection therewith, with the Commission, the Exchange
         and administrators of the state securities or blue sky laws, granting
         unto said attorneys-in-fact and agents full power and authority to do
         and perform each and every act and thing requisite and necessary to be
         done in connection therewith, as fully to all intents and purposes as
         the Depositor or such Trustee might or could do in person, hereby
         ratifying and confirming all that said attorneys-in-fact and agents or
         any of them, or their respective substitute or substitutes, shall do or
         cause to be done by virtue hereof.

5.       This Trust Agreement may be executed in one or more counterparts.

6.       The number of Trustees initially shall be two (2) and thereafter the
         number of Trustees shall be such number as shall be fixed from time to
         time by a written instrument signed by the Depositor which may increase
         or decrease the number of Trustees; provided, however, that to the
         extent required by the Delaware Trust Act, one Trustee shall either be
         a natural person who is a resident of the State of Delaware or, if not
         a natural person, an entity which has its principal place of business
         in the State of Delaware and otherwise meets the requirements of
         applicable Delaware law. Subject to the foregoing, the Depositor is
         entitled to appoint or remove without cause any Trustee at any time.
         The Trustees may resign upon thirty (30) days' prior notice to the
         Depositor.

7.       This Trust Agreement shall be governed by, and construed in accordance
         with, the laws of the State of Delaware (without regard to conflict of
         laws principles).

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8.       The Trustees (the "Fiduciary Indemnified Persons") shall not be liable,
         responsible or accountable in damages or otherwise to the Trust, the
         Depositor, the Trustees or any holder of the Trust's securities (the
         Trust, the Depositor and any holder of the Trust's securities being a
         "Covered Person") for any loss, damage or claim incurred by reason of
         any act or omission performed or omitted by the Fiduciary Indemnified
         Persons in good faith on behalf of the Trust and in a manner the
         Fiduciary Indemnified Persons reasonably believed to be within the
         scope of authority conferred on the Fiduciary Indemnified Persons by
         this Trust Agreement or by law, except that the Fiduciary Indemnified
         Persons shall be liable for any such loss, damage or claim incurred by
         reason of the Fiduciary Indemnified Person's gross negligence or
         willful misconduct with respect to such acts or omissions.

         The Fiduciary Indemnified Persons shall be fully protected in relying
         in good faith upon the records of the Trust and upon such information,
         opinions, reports or statements presented to the Trust by any person as
         to matters the Fiduciary Indemnified Persons reasonably believe are
         within such other person's professional or expert competence and who
         has been selected with reasonable care by or on behalf of the Trust,
         including information, opinions, reports or statements as to the value
         and amount of the assets, liabilities, profits, losses, or any other
         facts pertinent to the existence and amount of assets from which
         distributions to holders of the Trust's securities might properly be
         paid.

9.       The Depositor agrees, to the fullest extent permitted by applicable
         law,

         (a)      to indemnify and hold harmless each Fiduciary Indemnified
                  Person, or any of its officers, directors, shareholders,
                  employees, representatives or agents, from and against any
                  loss, damage, liability, tax, penalty, expense or claim of any
                  kind or nature whatsoever incurred by the Fiduciary
                  Indemnified Persons by reason of the creation, operation or
                  termination of the Trust in a manner the Fiduciary Indemnified
                  Persons reasonably believed to be within the scope of
                  authority conferred on the Fiduciary Indemnified Persons by
                  this Trust Agreement, except that no Fiduciary Indemnified
                  Persons shall be entitled to be indemnified in respect of any
                  loss, damage or claim incurred by the Fiduciary Indemnified
                  Persons by reason of gross negligence or willful misconduct
                  with respect to such acts or omissions; and

         (b)      to advance expenses (including legal fees) incurred by a
                  Fiduciary Indemnified Person in defending any claim, demand,
                  action, suit or proceeding, from time to time, prior to the
                  final disposition of such claim, demand, action, suit or
                  proceeding, upon receipt by the Trust of an undertaking by or
                  on behalf of such Fiduciary Indemnified Person to repay such
                  amount if it is determined that such Fiduciary Indemnified
                  Person is not entitled to be indemnified as authorized in the
                  preceding subsection.

10.      The provisions of Section 9 shall survive the termination of this Trust
         Agreement or the earlier resignation or removal of the Fiduciary
         Indemnified Persons.


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         IN WITNESS WHEREOF, the parties hereto have caused this Trust Agreement
to be duly executed as of the day and year first above written.


                                  Wintrust Financial Corporation, as Depositor



                                  By: /s/ David L. Stoehr
                                      ------------------------------------------
                                      Name:  David L. Stoehr
                                      Title:  EVP-CFO



                                  Wilmington Trust Company, as Trustee



                                  By: /s/ Kristin Long
                                      ------------------------------------------
                                      Name: Kristin Long
                                      Title: Financial Services Officer


                                  /s/ David L. Stoehr
                                  ----------------------------------, as Trustee
                                  Name:  David L. Stoehr


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