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). 




     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