EXHIBIT 10.23

FIRST AMENDMENT TO
AMENDED AND RESTATED DECLARATION OF TRUST NO. 2

     This FIRST AMENDMENT TO AMENDED AND RESTATED DECLARATION OF TRUST NO. 2
(this “Amendment”) is entered into effective as of January 9, 2009, by and among
Wilmington Trust Company, as Delaware Trustee and Institutional Trustee,
Enterprise Financial Services Corp, as Sponsor, and Frank H. Sanfilippo, Deborah
N. Barstow and Betty L. Lewis, as Administrators (collectively the “Parties”).

     The Parties are party to an Amended and Restated Declaration of Trust No. 2
dated as of December 12, 2008 (the “Declaration”). Each capitalized term that is
used and not otherwise defined in this Amendment has the meaning that the
Declaration assigns to that term.

     The Institutional Trustee has received all opinions, certifications and
consents required as a condition precedent to amending the Declaration and the
Parties have agreed to make certain amendments to the Declaration in accordance
with Section 11.1 of the Declaration.

     Therefore, for good and valuable consideration, the receipt and sufficiency
of which are acknowledged, the Parties hereby agree as follows.

     1. Section 7(b)(II) of Annex A of the Declaration shall be deleted in its
entirety and replaced with the following:

     Except as provided in Section 7(b)(III) below with respect to conversion of
Securities after a Redemption/Distribution Notice has been given, if any
Securities are converted during an Extension Period, the Holder may elect in the
Conversion Request to (x) provided that such election would not cause Sponsor to
be in violation of any shareholder approval requirement of Rule 4350(i) or any
successor rule, as such may be amended, of the NASDAQ Stock Market Rules,
convert all or any part of the accrued and unpaid interest on the converted
Securities (including Additional Interest thereon, if any, to the extent
permitted by applicable laws, rules or regulations) (“Convertible Interest”)
into shares of Common Stock on the Conversion Date in an amount equal to such
Convertible Interest divided by the Conversion Price or (y) receive such accrued
and unpaid interest on the converted Securities up to, but excluding the
Conversion Date, (including Additional Interest thereon, if any, to the extent
permitted by applicable laws, rules or regulations) on the Distribution Payment
Date upon which such Extension Period ends. In the event that the Holder does
not elect either (x) or (y) in the Conversion Request, the Holder shall be
deemed to have elected (y). At any time following the submission of the
Conversion Request and prior to the payment in full of such Convertible
Interest, the Holder may, by delivery of a separate Conversion Request convert
any Convertible Interest into shares of Common Stock in an amount equal to such
Convertible Interest divided by the Conversion Price, such conversion to be
governed by the applicable provisions of this Annex A. If a Holder makes the
election, or is deemed to have made the election, described in clause (y), the
Holder shall receive from the Sponsor a letter agreement in the form of Exhibit
C attached hereto.

     2. Section 7 of Annex A of the Declaration shall be amended to include a
new Section 7(l) which shall read as follows:

     Notwithstanding anything to the contrary contained in this Section 7, a
Holder of Securities may convert Securities or Convertible Interest pursuant to
this Section 7, or receive shares of Common Stock upon such conversion, to the
extent (but only to the extent) that such conversion or receipt would not cause
or result in such Holder and its Affiliates, collectively, being deemed to own,
control or have the power to vote, for purposes of the Bank Holding Company Act
of 1956, as amended (the “BHC Act”), the Change in Bank Control Act of 1978, as
amended (the “CIBC Act”), Section 16 of Securities Exchange Act of 1934, as
amended (“1934 Act”) or Rule 13d-3 of the 1934 Act, and any rules and
regulations promulgated under any of the BHC Act, the CIBC Act or the 1934 Act,
10% or more of any class of outstanding voting securities of the Sponsor
outstanding at such time (it being understood, for the avoidance of doubt, that
no security shall be included in any such percentage calculation to the extent
that it cannot by its terms be converted into or exercisable for outstanding
voting securities of the Sponsor by such Holder or its Affiliates at the time of
such measurement or transfer).

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     3. The Parties agree that the Declaration is hereby deemed amended in such
respects as may be necessary to give effect to the agreements set forth in
Section 1 of this Amendment. Except as amended pursuant to the preceding
sentence, the Declaration remains in full force and effect.

     4. This Amendment may be executed by delivery of a signature by facsimile
or other electronic means reasonably acceptable to both parties and such
signature shall constitute an original for all purposes. This Amendment may be
executed in two or more counterparts, all of which shall be considered one and
the same instrument and shall become effective when one or more counterparts
have been signed by each of the Parties and delivered to the other.

     5. Each of the Parties acknowledges that it has been represented by counsel
in connection with this Amendment and the transactions contemplated by this
Amendment. Accordingly, any rule of law or any legal decision that would require
interpretation of any claimed ambiguities in this Amendment against the drafting
party has no application and is expressly waived.

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     IN WITNESS WHEREOF, the Parties have caused this First Amendment to Amended
and Restated Declaration of Trust No. 2 to be executed effective as of the date
first written above.

 

WILMINGTON TRUST COMPANY,  as Delaware Trustee      By:   /s/ Christopher J.
Slaybaugh            Name: Christopher J. Slaybaugh            Title:     
WILMINGTON TRUST COMPANY,  as Institutional Trustee      By:    
          Name:            Title:      ENTERPRISE FINANCIAL SERVICES CORP, as
Sponsor      By:               Name:            Title:      ADMINISTRATORS OF 
EFSC CAPITAL TRUST VIII      By:   /s/ Frank H. Sanfilippo 
          Name: Frank H. Sanfilippo      By:   /s/ Deborah N. Barstow 
          Name: Deborah N. Barstow      By:   /s/ Betty L. Lewis 
          Name: Betty L. Lewis 

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