Document:

EXHIBIT 10.16.1

FOURTH MODIFICATION AGREEMENT

     This
FOURTH MODIFICATION AGREEMENT (this “Agreement”) is made and entered into
as of April 30, 2008, by and between ENTERPRISE FINANCIAL SERVICES CORP., a
Delaware corporation (the “Borrower”), and U.S. BANK NATIONAL ASSOCIATION, a national banking association (the “Lender”).

	
      RECITALS 

	
           A. Pursuant to that certain Amended and Restated Credit Agreement
      dated July 28, 2006, by and between Borrower and Lender (the
      “Credit Agreement”), Lender extended the following credit facilities to
      Borrower: (i) a revolving loan in the principal amount of $11,000,000.00,
      the proceeds of which are to be used solely to finance Borrower’s general
      working capital purposes (the “Revolving Loan”), and (ii) a
      term loan in the principal amount of $4,000,000.00, the proceeds of which
      were to be used to finance Borrower’s acquisition of NorthStar Bancshares,
      Inc (the “Term Loan”). 

     B. The
Revolving Loan is evidenced by an Amended and Restated Revolving Credit Note
dated July 28, 2006, executed by Borrower, as maker, and payable to Lender in a
maximum principal amount equal to the Revolving Credit Commitment (the
“Revolving Note”). 

     C. The
Term Loan is evidenced by a Promissory Note dated July 28, 2006, executed by
Borrower, as maker, and payable to Lender in a maximum principal amount equal to
the Term Credit Commitment (the “Term
Note” and, together with the Revolving Note,
the “Notes”). 

     D. On
December 6, 2006, Borrower and Lender entered into a First Modification
Agreement pursuant to which the parties agreed to add certain financial
covenants to the Credit Agreement (the “First Modification”). 

     E. On
February 23, 2007, Borrower and Lender entered into a Second Modification
Agreement pursuant to which the parties agreed to amend certain covenants
contained in the Credit Agreement (the “Second
Modification”). 

     F. On
April 30, 2007, Borrower and Lender entered into a Third Modification Agreement
pursuant to which the parties agreed to (i) to increase the Revolving Credit
Commitment from $11,000,000.00 to $16,000,000.00, (ii) to extend the Revolving
Credit Termination Date from April 30, 2007 to April 30, 2008, and (iii) to
amend the definition of the term Fixed Charge Coverage Ratio contained in the
Credit Agreement (the “Third
Modification”). 

     G. This Agreement, the Credit Agreement, the Notes, the First Modification,
the Second Modification, the Third Modification and any and all other documents
executed and delivered or relating in any manner to the Loan are collectively
referred to herein as the “Loan
Documents”. 

     H. The
parties enter into this Agreement to extend the Revolving Credit Termination
Date from April 30, 2008 to April 30, 2009. 

     I. Capitalized terms used in this Agreement and not otherwise defined in
this Agreement have the meaning assigned to them in the Credit
Agreement.

     NOW THEREFORE, Lender and Borrower,
for good, sufficient and valuable consideration, the receipt and sufficiency of
which is hereby acknowledged, agree as follows: 

     1. Modification to the Credit Agreement.
The Credit Agreement is modified by deleting the reference to “April 30, 2008”
contained in the definition of the term “Revolving Credit Termination Date”
appearing in Section 1.1 and inserting a reference to “April 30, 2009” in lieu
thereof.

     2. Modification to the Other Loan Documents. Each of the other Loan Documents is hereby modified such that
references to the Credit Agreement shall refer to the Credit Agreement as
modified by this Agreement. 

     3. No Other Modifications. Except as
expressly set forth herein, all other terms and conditions of the Loan Documents
shall remain unmodified and in full force and effect, and Borrower hereby
confirms and ratifies such terms and conditions and agrees to perform and comply
with the same.

     4. Accuracy of Representations and Warranties. Borrower represents and warrants to Lender that Borrower is duly
authorized and has all requisite power to execute and deliver this Agreement.
Borrower further represents and warrants that each of the representations and
warranties contained in the Loan Documents is true and correct in all material
respects as of the date of this Agreement (except to the extent such
representations and warranties are expressly made as of a particular date, in
which event such representations and warranties were true and correct as of such
date). 

     5. No Impairment. Nothing in this
Agreement shall be deemed to, or shall in any manner, prejudice or impair
Lender’s rights under the Loan Documents. This Agreement shall not be deemed to
be nor shall it constitute any alteration, waiver, annulment or variation of the
Loan Documents or the terms and conditions of or any rights, powers or remedies
under the Loan Documents, except as expressly set forth in this Agreement.

     6. Waiver of Claims and Defenses.
Borrower hereby waives and releases any and all claims, defenses or rights of
set-off, known or unknown, existing as of the date of this Agreement, which in
any manner arise out of or relate to the Loan or any of the Loan Documents.

     7. Further Acts and Assurances. Borrower
agrees to comply with any and all requirements of Lender hereafter made by
Lender from time to time so long as the Loan is outstanding, and Borrower agrees
to make, execute and deliver to Lender any and all further instruments,
documents and agreements required by Lender. 

     8. Entire Agreement. This Agreement and
the other Loan Documents embody the entire agreement and understanding between
the parties hereto and supersede all prior agreements and understandings
relating to the subject matter hereof. 

     9. Binding Agreement. This Agreement
shall be binding upon and inure to the benefit of the parties hereto and their
respective successors and assigns. 

     10. Applicable Law. This Agreement shall
be governed by and construed in accordance with the laws of the State of
Missouri, except to the extent superseded by Federal law. 

     11. Counterparts. This Agreement may be
executed in any number of counterparts, all of which taken together shall
constitute one agreement, and any party hereto may execute this Agreement by
signing any such counterpart. In making proof of this Agreement, it shall not be
necessary to produce or account for more than one such counterpart. 

     12. NO ORAL AGREEMENTS. ORAL AGREEMENTS OR COMMITMENTS TO LOAN MONEY, EXTEND CREDIT OR TO FORBEAR
FROM ENFORCING REPAYMENT OF A DEBT INCLUDING PROMISES TO EXTEND OR RENEW SUCH
DEBT ARE NOT ENFORCEABLE, REGARDLESS OF THE LEGAL THEORY UPON WHICH IT IS BASED,
THAT IS IN ANY WAY RELATED TO THE CREDIT AGREEMENT. TO PROTECT YOU (BORROWER)
AND US (LENDER) FROM MISUNDERSTANDING OR DISAPPOINTMENT, ANY AGREEMENTS WE REACH
COVERING SUCH MATTERS ARE CONTAINED IN THIS WRITING, WHICH IS THE COMPLETE AND
EXCLUSIVE STATEMENT OF THE AGREEMENT BETWEEN US, EXCEPT AS WE MAY LATER AGREE IN
WRITING TO MODIFY IT. 

[Signature Page Follows] 

     IN WITNESS WHEREOF, the parties hereto
have caused their duly authorized officers to execute and deliver this Agreement
as of the date set forth above.

 

	BORROWER: 
  
	  
	ENTERPRISE FINANCIAL SERVICES
      CORP.,  
	a Delaware
      corporation  
	  
	  
	By:  	/s/ Frank H.
      Sanfilippo 
	                Frank H. Sanfilippo  
	                Chief
      Financial Officer  
	  
	  
	LENDER: 

	  
	U.S. BANK NATIONAL
      ASSOCIATION,  
	a national banking
      association  
	  
	  
	By:  	/s/ Jaycee D.
      Greene 
	                Jaycee
      D. Greene  
	                Vice
      President  

FIFTH MODIFICATION AGREEMENT

     This
FIFTH MODIFICATION AGREEMENT (this “Agreement”) is made and entered into
as of June 30, 2008, by and between ENTERPRISE
FINANCIAL SERVICES CORP., a Delaware
corporation (the “Borrower”), and U.S. BANK NATIONAL
ASSOCIATION, a national banking association
(the “Lender”).

	
      RECITALS 

	
           J. Pursuant to that certain Amended and Restated Credit Agreement
      dated July 28, 2006, by and between Borrower and Lender (the
      “Credit Agreement”), Lender extended the following credit facilities to
      Borrower: (i) a revolving loan in the original principal amount of
      $11,000,000.00, the proceeds of which are to be used by Borrower for
      general working capital purposes (the “Revolving Loan”), and (ii) a
      term loan in the principal amount of $4,000,000.00, the proceeds of which
      were to be used to finance Borrower’s acquisition of NorthStar Bancshares,
      Inc (the “Term Loan” and together with the Revolving Loan, the
      “Loans”). 

     K. The
Revolving Loan is evidenced by an Amended and Restated Revolving Credit Note
dated July 28, 2006, executed by Borrower, as maker, and payable to Lender in a
maximum principal amount equal to the Revolving Credit Commitment (the
“Revolving Note”). 

     L. The
Term Loan is evidenced by a Promissory Note dated July 28, 2006, executed by
Borrower, as maker, and payable to Lender in a maximum principal amount equal to
the Term Credit Commitment (the “Term
Note” and, together with the Revolving Note,
the “Notes”). 

     M. On
December 6, 2006, Borrower and Lender entered into a First Modification
Agreement pursuant to which the parties agreed to add certain financial
covenants to the Credit Agreement (the “First Modification”). 

     N. On
February 23, 2007, Borrower and Lender entered into a Second Modification
Agreement pursuant to which the parties agreed to amend certain covenants
contained in the Credit Agreement (the “Second
Modification”). 

     O. On
April 30, 2007, Borrower and Lender entered into a Third Modification Agreement
pursuant to which the parties agreed to (i) increase the Revolving Credit
Commitment from $11,000,000.00 to $16,000,000.00, (ii) extend the Revolving
Credit Termination Date from April 30, 2007 to April 30, 2008, and (iii) amend
the definition of the term Fixed Charge Coverage Ratio contained in the Credit
Agreement (the “Third
Modification”). 

     P. On
April 30, 2008, Borrower and Lender entered into a Fourth Modification Agreement
pursuant to which the parties agreed to extend the Revolving Credit Termination
Date from April 30, 2008 to April 30, 2009 and to modify a financial covenant
(the “Fourth Modification”). 

     Q. This Agreement, the Credit Agreement, the Notes, the First Modification,
the Second Modification, the Third Modification, the Fourth Modification and any
and all other documents executed and delivered or relating in any manner to the
Loans are collectively referred to herein as the “Loan Documents”. 

     R. The
parties enter into this Agreement to provide for a temporary increase in the
Revolving Credit Commitment from $16,000,000.00 to $18,000,000.00. 

     S. Capitalized terms used in this Agreement and not otherwise defined in
this Agreement have the meaning assigned to them in the Credit
Agreement.

     NOW THEREFORE, Lender and Borrower,
for good, sufficient and valuable consideration, the receipt and sufficiency of
which is hereby acknowledged, agree as follows: 

     1. Modifications to the Revolving
Note. The Revolving Note is modified as
follows: 

     (a) The reference to
“$16,000,000.00” contained in the upper left-hand corner of the Revolving Note
is deleted and replaced with a reference to “$18,000,000.00”.

     (b) The reference to “SIXTEEN
MILLION AND NO/100 DOLLARS ($16,000,000.00)” appearing in the first paragraph is
deleted and replaced with a reference to “EIGHTEEN MILLION AND NO/100 DOLLARS
($18,000,000.00)”.

     (c) The following is inserted after the first
sentence appearing on the first page of the Note: 

“On or
before August 31, 2008 (the “Principal
Reduction Date”), Borrower shall make a
payment of principal under this Note in an amount sufficient to reduce the then
outstanding principal balance of this Note to an amount not greater than
$16,000,000.00 and from and after the Principal Reduction Date, the principal
amount available to be borrowed under this Note is limited to $16,000,000.00.”

     2. Modifications to the Credit
Agreement. The Credit Agreement is modified
as follows: 

     (a) The reference to “SIXTEEN MILLION AND NO/100 DOLLARS
($16,000,000.00)” contained in the recitals is deleted and replaced with a
reference to EIGHTEEN MILLION AND NO/100 DOLLARS ($18,000,000.00)”.

     (b) The definition of the term “Revolving Credit Commitment”
appearing in Section 1.1 is deleted and replaced with the following: 

“Revolving Credit
Commitment” shall mean (i) from June 30, 2008
until August 31, 2008, an amount equal to $18,000,000.00, and (ii) from and
after September 1, 2008, an amount equal to $16,000,000.00.”

     3. Modification to the Other Loan Documents. Each of the other Loan Documents is hereby modified such that
references to the Credit Agreement and the Revolving Note shall refer to the
Credit Agreement and the Revolving Note, respectively, as modified by this
Agreement. 

     4. No Other Modifications. Except as
expressly set forth herein, all other terms and conditions of the Loan Documents
shall remain unmodified and in full force and effect, and Borrower hereby
confirms and ratifies such terms and conditions and agrees to perform and comply
with the same.

     5. Accuracy of Representations and Warranties. Borrower represents and warrants to Lender that Borrower is duly
authorized and has all requisite power to execute and deliver this Agreement.
Borrower further represents and warrants that each of the representations and
warranties contained in the Loan Documents is true and correct in all material
respects as of the date of this Agreement (except to the extent such
representations and warranties are expressly made as of a particular date, in
which event such representations and warranties were true and correct as of such
date). 

     6. No
Impairment. Nothing in this Agreement shall be deemed to, or shall in any
manner, prejudice or impair Lender’s rights under the Loan Documents. This
Agreement shall not be deemed to be nor shall it constitute any alteration,
waiver, annulment or variation of the Loan Documents or the terms and conditions
of or any rights, powers or remedies under the Loan Documents, except as
expressly set forth in this Agreement. 

     7. Waiver of Claims and Defenses.
Borrower hereby waives and releases any and all claims, defenses or rights of
set-off, known or unknown, existing as of the date of this Agreement, which in
any manner arise out of or relate to the Loans or any of the Loan Documents.

     8. Further Acts and Assurances. Borrower
agrees to comply with any and all requirements of Lender hereafter made by
Lender from time to time so long as either of the Loans are outstanding, and
Borrower agrees to make, execute and deliver to Lender any and all further
instruments, documents and agreements required by Lender. 

     9. Entire Agreement. This Agreement and
the other Loan Documents embody the entire agreement and understanding between
the parties hereto and supersede all prior agreements and understandings
relating to the subject matter hereof. 

     10. Binding Agreement. This Agreement
shall be binding upon and inure to the benefit of the parties hereto and their
respective successors and assigns. 

     11. Applicable Law. This Agreement shall
be governed by and construed in accordance with the laws of the State of
Missouri, except to the extent superseded by Federal law. 

     12. Counterparts. This Agreement may be
executed in any number of counterparts, all of which taken together shall
constitute one agreement, and any party hereto may execute this Agreement by
signing any such counterpart. In making proof of this Agreement, it shall not be
necessary to produce or account for more than one such counterpart. 

     13. NO ORAL AGREEMENTS. ORAL AGREEMENTS OR COMMITMENTS TO LOAN MONEY, EXTEND CREDIT OR TO FORBEAR
FROM ENFORCING REPAYMENT OF A DEBT INCLUDING PROMISES TO EXTEND OR RENEW SUCH
DEBT ARE NOT ENFORCEABLE, REGARDLESS OF THE LEGAL THEORY UPON WHICH IT IS BASED,
THAT IS IN ANY WAY RELATED TO THE CREDIT AGREEMENT. TO PROTECT YOU (BORROWER)
AND US (LENDER) FROM MISUNDERSTANDING OR DISAPPOINTMENT, ANY AGREEMENTS WE REACH
COVERING SUCH MATTERS ARE CONTAINED IN THIS WRITING, WHICH IS THE COMPLETE AND
EXCLUSIVE STATEMENT OF THE AGREEMENT BETWEEN US, EXCEPT AS WE MAY LATER AGREE IN
WRITING TO MODIFY IT. 

[Signature Page Follows] 

     IN
WITNESS WHEREOF, the parties hereto have caused their duly authorized officers
to execute and deliver this Agreement as of the date set forth above.

 

	BORROWER:  
	  
	ENTERPRISE FINANCIAL SERVICES CORP.,  
	a
      Delaware corporation  
	  
	  
	By:  	/s/ Frank H. Sanfilippo 
	                Frank H. Sanfilippo  
	                Chief
      Financial Officer  
	  
	  
	LENDER:  
	  
	U.S.
      BANK NATIONAL ASSOCIATION,  
	a
      national banking association  
	  
	  
	By:  	/s/ Jaycee D. Greene 
	                Jaycee D. Greene  
	                Vice
      President  

SIXTH MODIFICATION AGREEMENT

     This
SIXTH MODIFICATION AGREEMENT (this “Agreement”) is made and entered into
as of December 11, 2008, by and between ENTERPRISE FINANCIAL SERVICES CORP., a
Delaware corporation (the “Borrower”), and U.S. BANK NATIONAL ASSOCIATION, a national banking association (the “Lender”).

	
      RECITALS 

	
           T. Pursuant to that certain Amended and Restated Credit Agreement
      dated July 28, 2006, by and between Borrower and Lender (the
      “Credit Agreement”), Lender extended the following credit facilities to
      Borrower: (i) a revolving loan in the original principal amount of
      $11,000,000.00, the proceeds of which are to be used by Borrower for
      general working capital purposes (the “Revolving Loan”), and (ii) a
      term loan in the principal amount of $4,000,000.00, the proceeds of which
      were to be used to finance Borrower’s acquisition of NorthStar Bancshares,
      Inc (the “Term Loan” and together with the Revolving Loan, the
      “Loans”). 

     U. The
Revolving Loan is evidenced by an Amended and Restated Revolving Credit Note
dated July 28, 2006, executed by Borrower, as maker, and payable to Lender in a
maximum principal amount equal to the Revolving Credit Commitment (the
“Revolving Note”). 

     V. The
Term Loan is evidenced by a Promissory Note dated July 28, 2006, executed by
Borrower, as maker, and payable to Lender in a maximum principal amount equal to
the Term Credit Commitment (the “Term
Note” and, together with the Revolving Note,
the “Notes”). 

     W. On
December 6, 2006, Borrower and Lender entered into a First Modification
Agreement pursuant to which the parties agreed to add certain financial
covenants to the Credit Agreement (the “First Modification”). 

     X. On
February 23, 2007, Borrower and Lender entered into a Second Modification
Agreement pursuant to which the parties agreed to amend certain covenants
contained in the Credit Agreement (the “Second
Modification”). 

     Y. On
April 30, 2007, Borrower and Lender entered into a Third Modification Agreement
pursuant to which the parties agreed to (i) increase the Revolving Credit
Commitment from $11,000,000.00 to $16,000,000.00, (ii) extend the Revolving
Credit Termination Date from April 30, 2007 to April 30, 2008, and (iii) amend
the definition of the term Fixed Charge Coverage Ratio contained in the Credit
Agreement (the “Third
Modification”). 

     Z. On
April 30, 2008, Borrower and Lender entered into a Fourth Modification Agreement
pursuant to which the parties agreed to extend the Revolving Credit Termination
Date from April 30, 2008 to April 30, 2009 and to modify a financial covenant
(the “Fourth Modification”). 

     AA. On
June 30, 2008, Borrower and Lender entered into a Fifth Modification Agreement
pursuant to which the parties agreed to provide for a temporary increase in the
Revolving Credit Commitment from $16,000,000.00 to $18,000,000.00 (the
“Fifth Modification”). 

     BB. This Agreement, the Credit Agreement, the Notes, the First Modification,
the Second Modification, the Third Modification, the Fourth Modification, the
Fifth Modification and any and all other documents executed and delivered or
relating in any manner to the Loans are collectively referred to herein as the
“Loan Documents”. 

     CC. The parties enter into this Agreement to amend the restriction on
indebtedness of Borrower appearing in the Credit Agreement as more specifically
described therein. 

     DD. Capitalized terms used in this Agreement and not otherwise defined in
this Agreement have the meaning assigned to them in the Credit
Agreement.

AGREEMENT 

     Lender and Borrower, for good,
sufficient and valuable consideration, the receipt and sufficiency of which is
hereby acknowledged, agree as follows: 

     1. Modification to the Credit Agreement.
The Credit Agreement is modified by deleting Section 8.1 and inserting the
following in place thereof: 

“8.1Restriction on
Indebtedness. Create, incur, assume or have
outstanding any indebtedness for borrowed money (including capitalized leases)
except (i) indebtedness under the Revolving Note or the Term Note issued under
this Agreement, (ii) other indebtedness to the Lender, (iii) fed funds
transactions in the ordinary course of business, (iv) indebtedness owing to any
Federal Home Loan Bank (or any successor thereto), (v) indebtedness on account
of the Subsidiary Bank maintaining deposit accounts in the ordinary course of
business, (vi) any other indebtedness outstanding on the date hereof, and shown
on the Borrower’s financial statements delivered to the Lender prior to the date
hereof, together with restatements, substitutions and refinancings of such
indebtedness, (vii) trust preferred securities issued by Borrower on February
26, 2007 in the amount of $14,000,000.00 with a maturity of March 30, 2037,
(viii) trust preferred securities issued by Borrower on September 30, 2007 in
the amount of $4,000,000.00 with a maturity of December 15, 2037, and (ix) trust
preferred securities to be issued by Borrower (in one or more issuances) on or
about December 11, 2008 in the amount of $25,000,000.00 with a maturity on or
about December ___, 2038.”

     2. Modification to the Other Loan Documents. Each of the other Loan Documents is hereby modified such that
references to the Credit Agreement and the Revolving Note shall refer to the
Credit Agreement and the Revolving Note, respectively, as modified by this
Agreement. 

     3. No Other Modifications. Except as
expressly set forth herein, all other terms and conditions of the Loan Documents
shall remain unmodified and in full force and effect, and Borrower hereby
confirms and ratifies such terms and conditions and agrees to perform and comply
with the same.

     4. Accuracy of Representations and Warranties. Borrower represents and warrants to Lender that Borrower is duly
authorized and has all requisite power to execute and deliver this Agreement.
Borrower further represents and warrants that each of the representations and
warranties contained in the Loan Documents is true and correct in all material
respects as of the date of this Agreement (except to the extent such
representations and warranties are expressly made as of a particular date, in
which event such representations and warranties were true and correct as of such
date). 

     5. No Impairment. Nothing in this
Agreement shall be deemed to, or shall in any manner, prejudice or impair
Lender’s rights under the Loan Documents. This Agreement shall not be deemed to
be nor shall it constitute any alteration, waiver, annulment or variation of the
Loan Documents or the terms and conditions of or any rights, powers or remedies
under the Loan Documents, except as expressly set forth in this
Agreement.

     6. Waiver of Claims and Defenses.
Borrower hereby waives and releases any and all claims, defenses or rights of
set-off, known or unknown, existing as of the date of this Agreement, which in
any manner arise out of or relate to the Loans or any of the Loan Documents.

     7. Further Acts and Assurances. Borrower
agrees to comply with any and all requirements of Lender hereafter made by
Lender from time to time so long as either of the Loans are outstanding, and
Borrower agrees to make, execute and deliver to Lender any and all further
instruments, documents and agreements required by Lender. 

     8. Entire Agreement. This Agreement and
the other Loan Documents embody the entire agreement and understanding between
the parties hereto and supersede all prior agreements and understandings
relating to the subject matter hereof. 

     9. Binding Agreement. This Agreement
shall be binding upon and inure to the benefit of the parties hereto and their
respective successors and assigns. 

     10. Applicable Law. This Agreement shall
be governed by and construed in accordance with the laws of the State of
Missouri, except to the extent superseded by Federal law. 

     11. Counterparts. This Agreement may be
executed in any number of counterparts, all of which taken together shall
constitute one agreement, and any party hereto may execute this Agreement by
signing any such counterpart. In making proof of this Agreement, it shall not be
necessary to produce or account for more than one such counterpart. 

     12. NO ORAL AGREEMENTS. ORAL AGREEMENTS OR COMMITMENTS TO LOAN MONEY, EXTEND CREDIT OR TO FORBEAR
FROM ENFORCING REPAYMENT OF A DEBT INCLUDING PROMISES TO EXTEND OR RENEW SUCH
DEBT ARE NOT ENFORCEABLE, REGARDLESS OF THE LEGAL THEORY UPON WHICH IT IS BASED,
THAT IS IN ANY WAY RELATED TO THE CREDIT AGREEMENT. TO PROTECT YOU (BORROWER)
AND US (LENDER) FROM MISUNDERSTANDING OR DISAPPOINTMENT, ANY AGREEMENTS WE REACH
COVERING SUCH MATTERS ARE CONTAINED IN THIS WRITING, WHICH IS THE COMPLETE AND
EXCLUSIVE STATEMENT OF THE AGREEMENT BETWEEN US, EXCEPT AS WE MAY LATER AGREE IN
WRITING TO MODIFY IT. 

[Signature Page Follows] 

     IN
WITNESS WHEREOF, the parties hereto have caused their duly authorized officers
to execute and deliver this Agreement as of the date set forth above.

 

	BORROWER:  
	  
	ENTERPRISE FINANCIAL SERVICES CORP.,  
	a
      Delaware corporation  
	  
	  
	By:  	/s/ Frank H. Sanfilippo 
	                Frank H. Sanfilippo  
	                Chief
      Financial Officer  
	  
	  
	LENDER:  
	  
	U.S.
      BANK NATIONAL ASSOCIATION,  
	a
      national banking association  
	  
	  
	By:  	/s/ Jaycee D. Greene 
	                Jaycee
      D. Greene  
	                Vice
      PresidentEXHIBIT 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.

[The remainder of this page is intentionally left
blank.]

     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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