• whether shares of the Preferred Stock will be convertible into or exchangeable for shares of any other class or of any other series of any class of capital stock and the terms and conditions of the conversion or exchange;
   
• the voting powers, full or limited, if any, of shares of the Preferred Stock;
   
• whether the issuance of any additional shares of the Preferred Stock, or of any shares of any other series, will be subject to restrictions as to issuance, or as to the powers, preferences or rights of any of these other series; and
   
• any other preferences, privileges and powers and relative, participating, optional or other special rights and qualifications, limitations or restrictions related to the Preferred Stock.

     The actual effect of the issuance of any shares of the Preferred Stock upon the rights of holders of common stock of the Company cannot be stated until the Board of Directors determines the specific rights of any shares of the Preferred Stock. However, the effects might include, among other things, restricting dividends on the common stock of the Company, diluting the voting power of the common stock of the Company, reducing the market price of the common stock of the Company or impairing the liquidation rights of the common stock of the Company without further action by the common stockholders of the Company. Holders of the Company’s common stock will not have preemptive rights with respect to the Preferred Stock.

     Although the Company may consider issuing shares of the Preferred Stock in the future for purposes of raising additional capital or in connection with acquisition transactions, there are currently no binding agreements or commitments with respect to the issuance of the Preferred Stock.

     The authorization of the preferred stock could also operate to provide anti-takeover protection for the Company. In the event of a proposed merger, tender offer or other attempt to gain control of the Company that the Board of Directors does not believe is in the best interests of the Company or its stockholders, the Board of Directors would have the ability to readily issue available shares of preferred stock as a defensive tactic under a stockholder rights plan, in a private placement or in another transaction that causes substantial dilution to a person or group that attempts to acquire control of the Company. Such issuance could occur whether or not our stockholders favorably view the merger, tender offer or other attempt to gain control of the Company. This proposal is not in response to any attempt to acquire control of the Company. Further, this proposal is not an effort by management of the Company to make it more difficult to replace incumbent members of management and is not part of a plan by the Company to adopt a series of anti-takeover measures. The availability of shares of preferred stock will have no current anti-takeover effect because the Board of Directors currently has no definitive plans to utilize preferred stock to entrench present management and no hostile takeover attempts are, to the Board of Directors’ knowledge, currently threatened.

Why is the amendment to the Certificate of Incorporation of the Company necessary?

     Under the Company’s existing Certificate of Incorporation, the Company does not have the authority to issue shares of preferred stock. The Board of Directors believes that the authorization of preferred stock is advisable and in the best interests of the Company and its stockholders for several reasons. First, the Company has submitted an application to the Treasury to participate in the Capital Purchase Program. The Company’s application is currently under review by the Treasury. The Capital Purchase Program is intended to encourage financial institutions to increase the flow of financing to United States business and consumers and to support the United States economy. If the Company’s application is approved by the Treasury, the Company would be eligible to sell a maximum of $62,000,000 and a minimum $20,900,000 of preferred stock to the Treasury. Although the Company’s capital position remains sound, the Board of Directors desires to consider the opportunity presented by the Treasury and to maximize the Company’s ability to maintain its existing capital, take advantage of current market conditions and support its existing operations and anticipated future growth.

     Second, the authorization of the preferred stock would permit the Board of Directors to issue such stock without further stockholder approvals or delay and, thereby, provide the Company with maximum flexibility in participating in the Capital Purchase Program, in structuring acquisitions, joint ventures, strategic alliances and capital-raising transactions, and for other corporate purposes. The preferred stock would enable the Company to respond promptly to and take advantage of market conditions and other favorable opportunities without incurring the delay and expense associated with calling a special meeting of the stockholders of the Company to approve a contemplated stock issuance. The Board of Directors believes that this will also save costs because it will not have to seek additional stockholder approval to issue the preferred shares unless it is required to obtain stockholder approval for the transaction under the rules of any quotation board or stock exchange to which it is subject. The Company presently contemplates no particular transaction involving the issuance of preferred stock other than consideration of the Capital Purchase Program. However, the Board of Directors believes that even if the Treasury were to deny its application, preferred stock may be a component in future raising of capital for the benefit of the Company.

5

What are the material terms of the Company’s participation in the Capital Purchase Program?

     If the Company’s application is accepted, any shares of preferred stock issued to the Treasury will have the following characteristics, rights, preferences, obligations and duties:

• qualify as Tier 1 capital and rank senior to the common stock of the Company;
• a liquidation preference of $1,000 per share;
• earn cumulative dividends at a rate of 5% per annum for the first 5 years and 9% thereafter, with dividends being paid quarterly;
• be callable at par, in whole or in part, in the sole discretion of the Company after 3 years and prior to the end of such 3 year period, be redeemable only with proceeds from a sale of Tier 1 qualifying preferred stock or common stock for cash that results in aggregate gross proceeds to the Company of not less than 25% of the aggregate gross proceeds from the issuance of the preferred stock;
• generally have no voting rights other than class voting rights on matters that could adversely affect the preferred stock; provided, that if the Company fails to pay dividends on the preferred stock for six quarters, whether or not consecutive, the holders of the preferred stock would have the right, voting as a class, to elect two members of the Company’s Board of Directors; and
• be transferable to a third party at any time.

     The Treasury will also receive warrants to purchase shares of the Company’s common stock having an aggregate market price equal to 15% of the Treasury’s initial investment in the Company. The warrants will be exercisable for a term of ten years. The exercise price of the warrants will be the market price of the Company’s common stock on the date the Company’s application is preliminarily approved by the Treasury calculated on a 20-day trailing average. For example, if the Company issued $62,000,000 of preferred stock to the Treasury, then the Treasury would be entitled to purchase up to $9,300,000 worth of the Company’s common stock. If the Company’s application was accepted on November 18, 2008, then the exercise price of the warrants would be $16.42 per share of common stock and the warrant would be exercisable for 566,382 shares of the Company’s common stock (4.26% of our total issued and outstanding shares of common stock as of the record date assuming the exercise of such warrants). The preceding example is for illustration only, as the exact exercise price for shares which the Treasury is entitled to purchase under the warrants will be determined on the date the preferred stock is preliminarily approved by the Treasury, and the number of shares of the Company’s common stock that the Treasury is entitled to purchase will depend upon the aggregate amount of preferred stock issued to the Treasury.

     In addition, it is possible that in the future, Congress may adopt additional statutes or the Treasury may adopt regulations which impose additional restrictions on participants in the Capital Purchase Program.

     More information about the Capital Purchase Program is available at the Treasury’s web-site: http://www.treas.gov/initiatives/eesa. The foregoing description of the anticipated designations, powers, preferences, rights, qualifications and limitations of the preferred stock is qualified in its entirety by reference to the Treasury’s mandated form of Certificate of Designations for Fixed Rate Cumulative Perpetual Preferred Stock attached to this proxy statement as Appendix B.

How will participation in the Capital Purchase Program affect the Company and its stockholders?

     The preferred stock issued to the Treasury will have economic consequences on the Company and its common stockholders including, without limitation, the following:

• payment of the preferred dividend to the holders of the preferred stock will dilute the economic interests of our common stockholders, but the 5% preferred dividend is competitive with the cost of capital currently being offered to the Company by non-governmental sources;
• current holders of common stock will experience dilution in earnings per share of common stock Company upon the issuance of the warrants at the time of the funding by the Treasury;
• if the holders of the preferred stock exercise the warrant to purchase common stock of the Company, then the other holders of common stock of the Company may experience dilution in the net book value per share, but the exercise price of the warrant and the price per share of the Company’s common stock at the time the warrant is exercised will determine the extent of such dilution to the other holders of common stock of the Company;

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• holders of the common stock of the Company will not have preemptive rights with respect to the preferred stock issued to the Treasury or the common stock issuable upon the exercise of the warrants;
• for so long as the preferred stock is outstanding, unless all accrued and unpaid dividends on the preferred stock have been paid in full, no cash dividend or distribution will be declared or paid on the common stock of the Company or any other shares junior in rank to the preferred Stock;
• until the third anniversary of the investment by the Treasury, unless the preferred stock is earlier entirely redeemed or entirely transferred to third parties, the Company may not increase dividend payable on the Company’s common stock without the prior approval of the Treasury;
• the Company will be obligated, at its cost and expense, to file and maintain as effective one or more shelf registration statements with respect to the shares of preferred stock, the warrants and the shares of common stock issuable upon the exercise of the warrants; and
• the Company will be obligated to use its best efforts to cause the common stock issuable upon exercise of the warrants to be listed on the securities exchange on which the Company’s common stock is listed, presently the NASDAQ Stock Market and, upon request of the Treasury, to cause the preferred stock and the warrants to be so listed.

     The preferred stock generally carries no voting rights other than class voting rights on matters that could adversely affect the preferred stock, but if the Company fails to pay dividends on the preferred stock for six quarters (whether or not consecutive), then holders of the preferred stock would have the right to elect two members of the Company’s Board of Directors, which would give holders of the preferred stock the ability to influence the Company’s management.

     In addition, the Company will be required to meet certain compensation standards for senior executives, including, without limitation:

• ensuring that incentive compensation does not encourage unnecessary and excessive risks that threaten the Company’s value;
• requiring clawbacks of any paid bonus or incentive compensation based on statements of earnings, gains or other criteria that are later proven to be “materially inaccurate”;
• prohibitions on “golden parachute payments” based on the Internal Revenue Code; and
• limitations on the tax deductibility of executive compensation in excess of $500,000 for each senior executive.

     If the Treasury accepts the Company’s application and we elect to participate in the program, the above restrictions will limit our ability to compensate key executives. The Company does not believe that these restrictions will materially affect our ability to retain key executives.

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What are the potential pro forma affects to the Company if capital is raised by selling preferred stock to the Treasury?

     The following unaudited pro forma financial information of the Company for the fiscal year ended December 31, 2007 and the nine months ended September 30, 2008 show the effects of a minimum of $20,900,000 and a maximum of $62,600,000 of Senior Preferred Stock issued to the Treasury pursuant to the Capital Purchase Program. We have included the following unaudited pro forma consolidated financial information solely for the purpose of providing stockholders with information that may be useful for purposes of considering and evaluating the proposal to amend our Certificate of Incorporation.

     The pro forma financial information presented below may change materially under either the “Minimum” or “Maximum” scenario based on the actual proceeds received under the Capital Purchase Program if our application is approved by Treasury, the timing and utilization of the proceeds as well as certain other factors including the strike price of the warrants, any subsequent changes in the Company’s common stock price, and the discount rate used to determine the fair value of the Preferred Stock. The actual amount raised from the Treasury will depend on the Company’s perceived capital needs at the time of the closing of the Treasury’s investment and the Company’s ability to raise capital from private market sources, such as the previously described potential placement of convertible trust preferred securities. Accordingly, the “Minimum” or “Maximum” pro forma scenarios included in the following unaudited pro forma financial information are not likely to be indicative of the actual effects of the Company’s participation in the Capital Purchase Program.

ENTERPRISE FINANCIAL SERVICES CORP
PRO FORMA CONSOLIDATED BALANCE SHEETS

		As Reported				Pro Forma
(In thousands)		September 30, 2008				September 30, 2008
Balance sheet data:						Minimum				Maximum
ASSETS
Cash and due from banks		$	38,641			$	38,641			$	38,641
Securities and other interest earning assets (1)			117,828				138,696				180,428
Loans, net of reserve			1,916,938				1,916,938				1,916,938
Other assets			162,994				162,994				162,994
Total assets		$	2,236,401			$	2,257,269			$	2,299,001
LIABILITIES AND SHAREHOLDERS' EQUITY
Liabilities
Deposits		$	1,688,053			$	1,688,053			$	1,688,053
Borrowings			355,465				355,465				355,465
Other liabilities			7,924				7,924				7,924
Total liabilities			2,051,442				2,051,442				2,051,442
Shareholders' equity
Preferred stock (1)			-				20,868				62,600
Discount on preferred stock (2) (3)			-				(2,408	)			(7,222	)
Common stock			128				128				128
Treasury stock, at cost			(1,743	)			(1,743	)			(1,743	)
Warrants (2)			-				2,408				7,222
Additional paid in capital			109,743				109,743				109,743
Retained earnings			76,549				76,549				76,549
Accumulated other comprehensive income			282				282				282
Total shareholders' equity			184,959				205,827				247,559
Total liabilities and shareholders' equity		$	2,236,401			$	2,257,269			$	2,299,001
CAPITAL RATIOS
Leverage (Tier 1 capital to assets)			8.65	%			9.51	%			11.18	%
Tier 1 capital to risk-weighted assets			8.33	%			9.88	%			12.03	%
Total capital to risk-weighted assets			10.18	%			11.24	%			13.40	%

(1)		This pro forma assumes the issuance of $20,868 (minimum) and $62,600 (maximum) shares of Preferred Stock by the Company on September 30, 2008. This pro forma does not reflect the issuance of any other securities which the Company is currently considering as a means of raising capital, including without limitation, the previously described possible issuance of convertible trust preferred securities.
(2)		The carrying values of the preferred stock and warrants are based on their relative fair values at issue date.
(3)		The discount on the preferred stock will be amortized over a five year period using the effective interest method.

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ENTERPRISE FINANCIAL SERVICES CORP
PRO FORMA CONSOLIDATED STATEMENTS OF INCOME

		As Reported			Pro Forma
		Nine months ended			Nine months ended
(In thousands except per share data)		September 30, 2008			September 30, 2008
Income statement data:					Minimum			Maximum
Total interest income (1)		$	88,818		$	89,131		$	89,757
Total interest expense			39,293			39,293			39,293
Net interest income			49,525			49,838			50,464
Provision for loan losses			8,350			8,350			8,350
Net interest income after provision for loan losses			41,175			41,488			42,114
Total non interest income			17,622			17,622			17,622
Total non interest expense			45,689			45,689			45,689
Income before income tax expense			13,108			13,421			14,047
Income tax expense (2)			4,726			4,832			5,057
Net income		$	8,382		$	8,589		$	8,990
Effective dividend on preferred stock						1,082			3,251
Net income available to common shareholders					$	7,507		$	5,739
Per share amounts:
Basic earnings per share		$	0.67		$	0.60		$	0.46
Basic weighted average common shares outstanding			12,550			12,550			12,550
Diluted earnings per share		$	0.66		$	0.59		$	0.45
Diluted weighted average common shares outstanding (3)			12,749			12,758			12,775

(1)		The pro forma assumes that the funds received from the issuance of preferred stock were invested in Federal funds on January 1, 2008 and earned interest at a rate of 2%. The proceeds from the issuance of preferred stock are actually intended to be used for a combination of supporting loan growth and other purposes, as described in "What plans does the Company have for any capital raised by the sale of preferred stock to the Treasury?"
(2)		An incremental tax rate of 36% was applied.
(3)		The diluted average common shares outstanding includes the estimated effect of the exercise of the warrants and is accounted for under the treasury stock method.

ENTERPRISE FINANCIAL SERVICES CORP
PRO FORMA CONSOLIDATED STATEMENTS OF INCOME

		As Reported			Pro Forma
		Year ended			Year ended
(In thousands except per share data)		December 31, 2007			December 31, 2007
Income statement data:					Minimum			Maximum
Total interest income (1)		$	122,517		$	123,143		$	124,395
Total interest expense			61,465			61,465			61,465
Net interest income			61,052			61,678			62,930
Provision for loan losses			4,615			4,615			4,615
Net interest income after provision for loan losses			56,437			57,063			58,315
Total non interest income			19,673			19,673			19,673
Total non interest expense			49,516			49,516			49,516
Income before income tax expense			26,594			27,220			28,472
Income tax expense (2)			9,016			9,255			9,680
Net income		$	17,578		$	17,965		$	18,792
Effective dividend on preferred stock						1,450			4,357
Net income available to common shareholders					$	16,515		$	14,435
Per share amounts:
Basic earnings per share		$	1.44		$	1.35		$	1.18
Basic weighted average common shares outstanding			12,239			12,239			12,239
Diluted earnings per share		$	1.38		$	1.31		$	1.15
Diluted weighted average common shares outstanding (3)			12,562			12,575			12,602

(1)		The proforma assumes that the funds received from the issuance of preferred stock were invested in Federal funds on January 1, 2007 and earned interest at a rate of 3%.
(2)		An incremental tax rate of 34% was applied.
(3)		The diluted average common shares outstanding includes the estimated effect of the exercise of the warrants and is accounted for under the treasury stock method.

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What plans does the Company have for any capital raised by the sale of preferred stock to the Treasury?

     The Board of Directors has authorized the Company to raise up to $62,000,000 from the sale of up to 62,000 shares of preferred stock, liquidation value $1,000 per share, to the Treasury, the maximum amount available to the Company under the participation formula adopted by the Treasury. The Company is also considering other possibilities to raise regulatory capital, including the issuance of trust preferred securities which would be convertible into shares of the Company’s common stock. To the extent that the Company can secure such other non-governmental sources of capital on terms acceptable to the Company, the Company would decrease its participation in the Capital Purchase Program. The Treasury is not obligated to accept the Company’s application, and there is no guarantee that the Company will receive any funds through the Capital Purchase Program. The Company intends to use any proceeds from the sale of the preferred stock to the Treasury for purposes of funding prudent loan growth at Enterprise Bank & Trust, a wholly-owned subsidiary of the Company (the “Bank”). The Bank historically has focused its lending activities on private businesses and their owner families in the Bank’s markets. Through the first three quarters of 2008, the Bank has increased loans by $301,000,000, or 18%. Almost two thirds of such growth was produced from a wide range of commercial and industrial businesses. In addition, the Company will also consider acquisitions within its St. Louis, Missouri, Kansas City, Missouri, Kansas City, Kansas and Phoenix, Arizona area markets that will increase the Company’s market share and/or add value to the Company.

What will the consequences be if Proposal One is not approved and/or the Company is not approved for participation in the Capital Purchase Program?

     If Proposal One is not approved, or if Proposal One is approved but the Treasury denies the Company’s application to participate in Capital Purchase Program, then the Company will pursue alternative means of raising capital to sustain the Company’s anticipated future growth. While the Company’s capital position is sound, the Board of Directors desires to consider the opportunity presented by the Treasury to support its existing operations and anticipated future growth. However, the Company will also likely consider other sources of capital. The Treasury funding is seen as a desirable source of capital on advantageous terms. If, the Company is unable to participate in the Capital Purchase Program, it may have to rely entirely on alternative private market capital, which could be on terms less favorable than those provided by the Treasury.

THE COMPANY’S BOARD OF DIRECTORS HAS APPROVED AND RECOMMENDS A VOTE “FOR” THE
PROPOSED CERTIFICATE OF AMENDMENT TO THE CERTIFICATE OF INCORPORATION.

 

 

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INFORMATION REGARDING BENEFICIAL OWNERSHIP OF
CERTAIN BENEFICIAL OWNERS AND MANAGEMENT

     The following tables show, as of September 30, 2008 (except where a different date is mentioned), certain information about ownership of the common stock of the Company by: (i) those persons or entities known by management to beneficially own more than 5% of the Company’s common stock, (ii) each director, the named executive officers, and (iii) all directors and executive officers as a group. As of September 30, 2008, there were 12,726,975 shares of common stock of the Company outstanding.

     (a) Security Ownership of Certain Beneficial Owners:

Name & Address of		Number of		Percentage of
Beneficial Owner		Shares		Ownership
Royce & Associates LLC		624,800(1)		5.0%
1414 Avenue of the Americas
New York, NY 10019
(1) Holdings reported on From 13G filed on January 28, 2008

     (b) Security Ownership of Management:

		Number of
		Shares		Percentage of
Beneficial Owner		(1) (2)		Ownership
Kevin C. Eichner (5)		597,646		4.7%
Peter F. Benoist (3) (4) (6)		225,680		1.8%
Robert E. Guest, Jr. (7)		187,035		1.5%
James Murphy		146,089		*
Robert E. Saur (9)		133,931		*
Linda M. Hanson (3) (4) (8)		81,155		*
Henry D. Warshaw (3) (10)		79,549		*
Lewis Levey		72,236		*
Birch M. Mullins		61,948		*
Frank H. Sanfilippo (3) (4)		52,372		*
Stephen P. Marsh (4)		39,834		*
William H. Downey		14,233		*
Sandra VanTrease		11,148		*
Michael A. DeCola (11)		4,275		*
Brenda D. Newberry		267		*
All Directors and Executive Officers
as a Group (15 total)		1,707,398		13.4%
* Less than 1%

(1)		Pursuant to the rules of the Securities and Exchange Commission, certain shares of Common Stock which a person has the right to acquire within 60 days pursuant to the exercise of stock options and warrants reflected in the number of shares shown on this table are deemed to be outstanding for the purpose of computing beneficial ownership and the percentages of ownership of that person, but are not deemed outstanding for the purposes of computing the percentage ownership of any other person. All directors and executive officers as a group hold options to purchase an aggregate of 132,732 shares of Common Stock.
(2)		Unless otherwise indicated, the named person has sole voting and investment power for all shares shown.
(3)		Includes options outstanding and exercisable as of September 30, 2008, or within 60 days thereafter, including those beneficially owned by the named person, as follows: Mr. Benoist, 94,147 shares; Ms. Hanson, 1,886 shares; Mr. Warshaw, 3,637 shares; Mr. Sanfilippo, 33,062 shares, all directors and named executive officers as a group, 132,732 shares.

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(4)		Includes shares indirectly held in the EFSC Incentive Savings Plan beneficially owned by the named person, as follows: Mr. Benoist, 826 shares, Ms. Hanson, 1,667 shares, Mr. Marsh, 399 shares and Mr. Sanfilippo, 1,361 shares.
(5)		Includes 349,650 shares held by Meramec Enterprise Holdings, LLC as to which Mr. Eichner has sole voting and investment power. Includes 80,681 shares held in the name of Mr. Eichner in which he has sole voting and investment power and 167,315 shares held in Mr. Eichner’s trust in which he has sole voting and investment power.
(6)		Includes 111,400 shares held jointly by Mr. Benoist and his spouse as to which Mr. Benoist has shared voting and investment power and 19,307 shares held in the name of Mr. Benoist in which he has sole voting and investment power.
(7)		Includes 137 shares held in the name of Mr. Guest in which he has sole voting and investment power. Includes 39,876 shares held jointly by Mr. Guest and his spouse as to which Mr. Guest has shared voting and investment power; 8,220 shares held in an Individual Retirement Account for the benefit of Mr. Guest’s spouse as to which Mr. Guest has shared voting and investment power; 41,511 shares held in a trust for the benefit of Mr. Guest’s children as to which Mr. Guest is a co-trustee and has shared voting and investment power; includes 73,171 shares held by the spouse of Mr. Guest as to which Mr. Guest has shared voting and investment power, includes 24,120 shares held in an account for the benefit of Mr. Guest’s children of which the spouse of Mr. Guest is the custodian.
(8)		Includes 8,500 shares held in an Individual Retirement Account for the benefit of Ms. Hanson, in which Ms. Hanson has sole voting and investment power, 11,715 shares held in the name of Ms. Hanson, in whish she has sole voting and investment power, 43,472 shares held jointly by Ms. Hanson and her spouse as to which Ms. Hanson has shared voting and investment power, 13,915 shares held for the benefit of Ms. Hanson’s children as to which Ms. Hanson has sole voting and investment power.
(9)		Includes 1,556 shares held in the name of Mr. Saur in which Mr. Saur has sole voting and investment power; 116,940 shares held in a trust for the benefit of Mr. Saur in which Mr. Saur has sole voting and investment power; and 15,435 shares held in a family partnership as to which Mr. Saur has shared voting and investment power.
(10)		Includes 25,740 shares held in an Individual Retirement Account for the benefit of Mr. Warshaw, in which Mr. Warshaw has sole voting and investment power; and 25,980 shares held in an Individual Retirement Account for the benefit of the spouse of Mr. Warshaw, as to which Mr. Warshaw has shared voting and investment power; and 24,192 shares in the name of Mr. Warshaw in which Mr. Warshaw has sole voting and investment power.
(11)		Includes 4,000 shares held jointly by Mr. DeCola and his spouse as to which Mr. DeCola has shared voting and investment power and 275 shares held in the name of Mr. DeCola in which he has sole voting and investment power.

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INCORPORATION OF CERTAIN INFORMATION BY REFERENCE

     The rules of the United States Securities and Exchange Commission (“SEC”) permit the Company to “incorporate by reference” certain information we file with the SEC into this Proxy Statement. This means that we can disclose important information to stockholders by referring the stockholders to another document without restating such information in this Proxy Statement. Any information incorporated by reference into this Proxy Statement is considered to be part of this Proxy Statement from the date we file that information with the SEC. Any reports filed by us with the SEC after the date of this Proxy Statement will automatically update and, where applicable, supercede any information contained in this Proxy Statement or incorporated by reference into this Proxy Statement.

     The following financial statements and other portions of the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2007, as filed with the SEC on March 14, 2008 (the "Form 10-K"), and the Quarterly Report on Form 10-Q for the quarterly period ended September 30, 2008, as filed with the Commission on November 7, 2008 (the "Form 10-Q") are incorporated by reference herein:

• financial statements and supplementary financial information of the Company appearing in Part II, Item 8 to the Form 10-K and in Part I, Item 1 of the Form 10-Q;
   
• management's discussion and analysis of financial condition and results of operations appearing in Part II, Item 7 of the Form 10-K and Part I, Item 2 of the Form 10-Q;
   
• quantitative and qualitative disclosures about market risk appearing in Part II, Item 7A of the Form 10-K and Part 1, Item 3 of the Form 10-Q; and
   
• changes in and disagreements with accountants on accounting and financial disclosure appearing in Part II, Item 9 of the Form 10-K.

     All documents filed by us subsequent to the date hereof pursuant to Section 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and prior to the Special Meeting are also hereby incorporated by reference.

     We are willing to provide, at no charge, to each stockholder of the Company (including beneficial owners) to whom this Proxy Statement is delivered, upon his, her or its written request, by first class mail or other equally prompt means within one business day of receipt of such a request therefor, a copy of any or all documents referred to above that have been or may be incorporated by reference into this Proxy Statement, excluding any exhibit to those documents unless they are specifically incorporated by reference into those documents. Your may submit your request for a copy of the aforementioned documents, without change, by contacting Frank H. Sanfilippo, Chief Financial Officer, at the Company’s offices located at 150 N. Meramec, Clayton, Missouri 63105, or by telephone at (800)396-8141.

     We also maintain an Internet site at enterprisebank.com. Other than as incorporated by reference above, the information found on, or otherwise accessible through, our website is not incorporated by reference into, and is not otherwise a part of, this Proxy Statement or any other document what we file or furnish to the SEC.

PROPOSALS OF STOCKHOLDERS

     Stockholders of the Company are entitled to present proposals for actions at a forthcoming meeting of the stockholders of the Company if they comply with the requirements of the Securities and Exchange Commission proxy rules. Any proposals intended to be presented at the 2009 Annual Meeting of Stockholders of the Company must have been received at the Company’s principal office as 150 N. Meramec, Clayton, Missouri 63105 on or before November 15, 2008 in order to be considered for inclusion in the Company’s proxy statement and form of proxy relating to such meeting.

     For a proper shareholder proposal submitted outside of the process provided by Rule 14a-8 to be eligible for presentation at the Company’s next annual meeting, timely notice must be delivered or mailed to and received by the Secretary of the Company at the principal executive offices of the Corporation not less than ninety days nor more than one hundred twenty days prior to the first anniversary of the preceding year’s annual meeting.

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OTHER MATTERS

     The Board of Directors is not aware of any business to come before the Special Meeting other than those matters described above in this proxy statement. However, if any other matters should properly come before the Special Meeting, including, without limitation, matters relating to the conduct of the Special Meeting, it is the intention of the persons named on the Proxy Card to vote the shares represented thereby in accordance with their judgment as to the best interests of the Company on such matters.

ADDITIONAL INFORMATION

     The Company’s Internet website is enterprisebank.com. We make available free of charge on or through our website, various reports that we file with or furnish to the Securities and Exchange Commission, including, without limitation, our annual reports, quarterly reports, current reports and proxy statements. These reports are made available as soon as reasonably practicable after they are filed with or furnished to the Securities and Exchange Commission.

By order of the Board of Directors,

Noel J. Bortle, Secretary

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APPENDIX A

ENTERPRISE FINANCIAL SERVICES CORP

CERTIFICATE OF AMENDMENT
OF CERTIFICATE OF INCORPORATION

     ENTERPRISE FINANCIAL SERVICES CORP, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware, does hereby certify that the following amendment to the Certificate of Incorporation of said Corporation has been duly adopted in accordance with the provisions of Section 242 of the General Corporation Law of the State of Delaware:

     Article FOUR of the Certificate of Incorporation of the Corporation is amended to read in its entirety as follows:

     The aggregate number of shares of all classes of capital stock which the corporation shall have the authority to issue shall be Thirty-five million (35,000,000) shares divided into two classes as follows:

     (a) Five million (5,000,000) shares of preferred stock having par value of $.01 per share (the “Preferred Stock”); and

     (b) Thirty million (30,000,000) shares of common stock having par value of $.01 per share (the “Common Stock”).

     The Board of Directors of the corporation shall be authorized, subject to any limitations prescribed by the law of the State of Delaware, to provide in a resolution or resolutions for the issuance of shares of the Preferred Stock in one or more series, and, by filing a Certificate of Designation pursuant to the applicable law of the State of Delaware (a “Preferred Stock Designation”), to establish from time to time the number of shares to be included in each such series and to fix the designations, powers, preferences and relative, participating, optional or other rights, if any, and the qualifications, limitations or restrictions thereof, if any. The authority of the Board of Directors of the corporation with respect to each series of the Preferred Stock shall include, but not be limited to, determination of the following:

     (A) the number of shares constituting that class or series and the distinctive designation of that series;

     (B) the dividend rate on the shares of that series, whether dividends shall be cumulative, and, if so, from which date or dates, and the relative rights of priority, if any, of payment of dividends on shares of that series;

     (C) whether that series shall have voting rights, in addition to the voting rights provided by law, and, if so, the terms and conditions of such voting rights, including, without limitation, whether such series shall have the right to vote as a separate class and/or vote on a cumulative or noncumulative basis;

     (D) whether that series shall have conversion privileges, and, if so, the terms and conditions of such conversion including provision for adjustment of the conversion rate upon the occurrence of such events as the Board of Directors of the corporation shall determine;

     (E) whether the shares of that series shall be redeemable, and, if so, the terms and conditions of such redemption, including the date or dates upon or after which they shall be redeemable, and the amount per share payable in case of redemption, which amount may vary under different conditions and at different redemption dates;

     (F) whether that series shall have a sinking fund for the redemption or purchase of shares of the series, and, if so, the terms and amount of such sinking fund;

     (G) the rights and/or preferences of the shares of that series in the event of the voluntary or involuntary liquidation, dissolution or winding up of the corporation, and the relative rights of priority, if any, of payment in respect of shares of that series; and

     (H) any other relative rights, preferences and limitations of that series.

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     The Board of Directors of the corporation is expressly authorized to adopt such resolution or resolutions and issue such Preferred Stock from time to time as it may deem desirable. The Board of Directors of the corporation is further expressly authorized to increase (but not above the total number of authorized shares of the class) or decrease (but not below the number of shares of any such series then outstanding) the number of shares of any series of Preferred Stock, the number of which is fixed by it, subsequent to the issuance of shares then outstanding, subject to the powers, preferences and rights, and the qualifications, limitations and restrictions thereof stated in this Certificate of Incorporation or the resolution or resolutions of the Board of Directors of the corporation originally fixing the number of shares of such series. If the number of shares of any series of Preferred Stock is so decreased, then the shares constituting such decrease shall resume the status which they had prior to the adoption of the resolution or resolutions originally fixing the number of shares of such series of Preferred Stock. The number of authorized shares of Common Stock or Preferred Stock may be increased or decreased (but not below the number of shares of such class then outstanding) by the vote of a majority of the outstanding shares of stock entitled to vote thereon, and no separate class vote of either the Common Stock or the Preferred Stock shall be required to effect any such amendment.

     The shares of the authorized Common Stock shall be identical in all respects and shall have equal rights and privileges, subject only to the senior rights applicable to the Preferred Stock or any series thereof. Except as may be provided in this Certificate of Incorporation or in a Preferred Stock Designation or by applicable law of the State of Delaware, holders of the Preferred Stock shall not be entitled to receive notice of any meeting of stockholders at which they are not entitled to vote, holders of the Common Stock shall have the exclusive right to vote for the election of Directors of the corporation and for all other purposes, and holders of shares of the Common Stock shall be entitled to one vote for each such share upon all questions presented to the stockholders of the corporation; provided, however, that in all elections of Directors of the corporation, each holder of shares of the Common Stock shall have the right to cast as many votes as shall equal (x) the number of shares held by him, her or it, and multiplied by (y) the number of Directors of the corporation to be elected, and he, she or it may cast all such votes for a single Director or may distribute them among the number of Directors to be elected, or any two (2) or more of them, as such shareholder may deem fit. Holders of shares of the Common Stock shall at all times, except as otherwise provided in this Certificate of Incorporation or as required by the law of the State of Delaware, vote as one class, together with the holders of any other class or series of stock of the Corporation accorded such general voting rights.

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APPENDIX B

ENTERPRISE FINANCIAL SERVICES CORP

TREASURY FORM OF CERTIFICATE OF DESIGNATIONS OF
FIXED RATE CUMULATIVE PERPETUAL PREFERRED STOCK

     [Insert name of Corporation], a [corporation] organized and existing under the laws of the [Insert jurisdiction of organization] (the "Corporation"), in accordance with the provisions of Section[s] [·] of the [Insert applicable statute] thereof, does hereby certify:

     The board of directors of the Corporation (the "Board of Directors") or an applicable committee of the Board of Directors, in accordance with the [certificate of incorporation and bylaws] of the Corporation and applicable law, adopted the following resolution on [·] creating a series of [·] shares of Preferred Stock of the Corporation designated as "Fixed Rate Cumulative Perpetual Preferred Stock, Series [·]".

     RESOLVED, that pursuant to the provisions of the [certificate of incorporation and the bylaws] of the Corporation and applicable law, a series of Preferred Stock, par value $[·] per share, of the Corporation be and hereby is created, and that the designation and number of shares of such series, and the voting and other powers, preferences and relative, participating, optional or other rights, and the qualifications, limitations and restrictions thereof, of the shares of such series, are as follows:

     Part 1. Designation and Number of Shares. T here is hereby created out of the authorized and unissued shares of preferred stock of the Corporation a series of preferred stock designated as the "Fixed Rate Cumulative Perpetual Preferred Stock, Series [·]" (the "Designated Preferred Stock"). The authorized number of shares of Designated Preferred Stock shall be [·].

     Part 2. Standard Provisions. The Standard Provisions contained in Annex A attached hereto are incorporated herein by reference in their entirety and shall be deemed to be a part of this Certificate of Designations to the same extent as if such provisions had been set forth in full herein.

     Part. 3. Definitions. The following terms are used in this Certificate of Designations (including the Standard Provisions in Annex A hereto) as defined below:

     (a) "Common Stock" means the common stock, par value $[·] per share, of the Corporation.

     (b) "Dividend Payment Date" means [February 15, May 15, August 15 and November 15] of each year.

     (c) "Junior Stock" means the Common Stock, [Insert titles of any existing Junior Stock] and any other class or series of stock of the Corporation the terms of which expressly provide that it ranks junior to Designated Preferred Stock as to dividend rights and/or as to rights on liquidation, dissolution or winding up of the Corporation.

     (d) "Liquidation Amount" means $[ 1,000)]¹ per share of Designated Preferred Stock.

     (e) "Minimum Amount" means $[Insert $ amount equal to 25% of the aggregate value of the Designated Preferred Stock issued on the Original Issue Date].

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     (f) "Parity Stock" means any class or series of stock of the Corporation (other than Designated Preferred Stock) the terms of which do not expressly provide that such class or series will rank senior or junior to Designated Preferred Stock as to dividend rights and/or as to rights on liquidation, dissolution or winding up of the Corporation (in each case without regard to whether dividends accrue cumulatively or non-cumulatively). Without limiting the foregoing, Parity Stock shall include the Corporation's [Insert title(s) of existing classes or series of Parity Stock].

     (g) "Signing Date" means [Insert date of applicable securities purchase agreement].

     Part. 4. Certain Voting Matters. [To be inserted if the Charter provides for voting in proportion to liquidation preferences: Whether the vote or consent of the holders of a plurality, majority or other portion of the shares of Designated Preferred Stock and any Voting Parity Stock has been cast or given on any matter on which the holders of shares of Designated Preferred Stock are entitled to vote shall be determined by the Corporation by reference to the specified liquidation amount of the shares voted or covered by the consent as if the Corporation were liquidated on the record date for such vote or consent, if any, or, in the absence of a record date, on the date for such vote or consent. For purposes of determining the voting rights of the holders of Designated Preferred Stock under Section 7 of the Standard Provisions forming part of this Certificate of Designations, each holder will be entitled to one vote for each $1,000 of liquidation preference to which such holder's shares are entitled.] [To be inserted if the Charter does not provide for voting in proportion to liquidation preferences: Holders of shares of Designated Preferred Stock will be entitled to one vote for each such share on any matter on which holders of Designated Preferred Stock are entitled to vote, including any action by written consent.]

 

 

 

 

1	If issuer desires to issue shares with a higher dollar amount liquidation preference, liquidation preference references will be modified accordingly. In such case (in accordance with Section 4.7 of the Securities Purchase Agreement), the issuer will be required to enter into a deposit agreement.

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150 N. Meramec       Clayton, MO 63105

VOTE BY INTERNET - www.proxyvote.com Use the Internet to transmit your voting instructions and for electronic delivery of information up until 11:59 P.M. Eastern Time the day before the cut-off date or meeting date. Have your proxy card in hand when you access the web site and follow the instructions to obtain your records and to create an electronic voting instruction form. ELECTRONIC DELIVERY OF FUTURE SHAREHOLDER COMMUNICATIONS If you would like to reduce the costs incurred by Enterprise Financial Services Corp in mailing proxy materials, you can consent to receiving all future proxy statements, proxy cards and annual reports electronically via e-mail or the Internet. To sign up for electronic delivery, please follow the instructions above to vote using the Internet and, when prompted, indicate that you agree to receive or access shareholder communications electronically in future years. VOTE BY PHONE - 1-800-690-6903 Use any touch-tone telephone to transmit your voting instructions up until 11:59 P.M. Eastern Time the day before the cut-off date or meeting date. Have your proxy card in hand when you call and then follow the instructions. VOTE BY MAIL Mark, sign and date your proxy card and return it in the postage-paid envelope we have provided or return it to Enterprise Financial Services Corp., c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717.

 

Vote On Proposals				For	Against	Abstain
1.		To approve a Certificate of Amendment to the Company’s Certificate of Incorporation that will authorize the Company to issue up to 5,000,000 shares of preferred stock of the Company having such designations, powers, preferences, rights, qualifications and limitations as the Board of Directors of the Company may from time to time fix by resolution adopted by the Board of Directors of the Company (The Board of Directors recommend a vote "FOR" this proposal).
2.		To transact such other business as may properly come before the special meeting and at any adjournments or postponements thereof.

Please sign exactly as name appears on the label for this mailing. When stock is registered jointly, all owners must sign. When signing as attorney, executor, administrator, trustee or in another representative capacity, include signature and title. If a corporation, please sign the full corporate name by the President or other authorized officer. If a partnership or limited liability company, please sign in the entity name by an authorized person.
Please indicate if you plan to attend this meeting     yes  ¨     no  ¨
Signature			Date		Signature	Date

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ENTERPRISE FINANCIAL SERVICES CORP

PROXY FOR THE SPECIAL MEETING OF STOCKHOLDERS
FRIDAY, DECEMBER 12, 2008
1281 N. Warson Rd. St. Louis, MO 63132

THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS

The stockholder(s) whose signature(s) appear(s) on the reverse side of this proxy card, having received the Notice of Special Meeting of Stockholders and Proxy Statement for the Special Meeting of Stockholders to be held on Friday, December 12, 2008, and revoking any proxy previously given, hereby appoint(s) Peter F. Benoist, Frank H. Sanfilippo and James J. Murphy, Jr. or any of them, each with full power of substitution, as proxies to vote all shares of the common stock of Enterprise Financial Services Corp (the “Company”) that such stockholder(s) is entitled to vote at the Special Meeting of Stockholders of the Company, to be held at the Company’s Support Center at 1281 N. Warson Rd. St. Louis, MO 63132 on Friday, December 12, 2008, at 10:00 a.m. local time and at any adjournment or postponements thereof and authorize(s) each to vote in such proxy’s discretion upon other business as may properly come before the special meeting or an adjournment or postponement thereof, in each case with the same force and effect as the undersigned might or could do if personally present. The proxies are authorized to vote in accordance with the specifications indicated by the stockholder(s) on the reverse side of this Proxy Card. If this Proxy Card is signed and returned by the stockholder(s) and no specifications are indicated, the proxies are authorized to vote “FOR” Proposal 1 and “FOR” Proposal 2.

(CONTINUED, AND TO BE DATED AND SIGNED ON THE REVERSE SIDE.)

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