Item 1.01 Entry into a Material Definitive Agreement.

     On December 19, 2008, as part of the Capital Purchase Program (the “CPP”) offered under the Emergency Economic Stabilization Act of 2008, we (“EFSC”), entered into an agreement (the “Agreement”), with the United States Department of the Treasury (the “Treasury”) to sell to the Treasury 350,000 shares of our Fixed Rate Cumulative Perpetual Preferred Stock, Series A, (the “Preferred Stock”). We also issued to the Treasury a ten-year Warrant (the “Warrant”) to purchase 324,074 shares (the “Warrant Shares”) of our common stock (“Common Stock”). In consideration for the Preferred Stock and the Warrant, EFSC received proceeds of $35,000,000. We intend to use the proceeds from the sale of the Preferred Stock for purposes of funding prudent loan growth at Enterprise Bank & Trust, our wholly-owned bank subsidiary (the “Bank”). Through the first three quarters of 2008, the Bank 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, we will also consider acquisitions within the Bank’s St. Louis, Missouri, Kansas City, Missouri, Kansas City, Kansas and Phoenix, Arizona area markets that will increase the our market share and/or add value to EFSC.

     The Preferred Stock qualifies as Tier 1 capital of EFSC and will pay cumulative dividends at a rate of 5% per annum for the first five years, and at a rate of 9% per annum thereafter. The Preferred Stock carries with it a liquidation preference of $1,000 per share over our Common Stock. The Preferred Stock has no mandatory redemption or maturity date and is generally non-voting. We have the right to redeem the Preferred Stock at our option at any time for a price per share equal to the liquidation preference plus accrued and unpaid dividends at any time, but until December 19, 2011, we may only exercise that right if and to the extent that we have raised aggregate gross proceeds of not less than $8,750,000 from the sale of our Common Stock or perpetual preferred stock qualifying as Tier 1 capital.

     Prior to December 19, 2011, unless EFSC redeems the Preferred Stock or the Treasury transfers the preferred Stock to a non-affiliated third party, the consent of the Treasury will be required for us to (i) make distributions or pay dividends on our Common Stock (other than regular quarterly dividends of not more than $.0525 per share, which is the amount of our most recently declared regular dividend) or (ii) redeem, purchase or acquire shares of Common Stock or other equity or capital securities of EFSC, other than in connection with the administration of its benefit plans consistent with past practice and certain other circumstances specified in the Agreement. In addition, pursuant to the Certificate of Designations approved by EFSC’s Board of Directors and filed with the Secretary of State of Delaware on December 17, 2008, creating the Preferred Stock, our ability to declare or pay dividends or distributions on, or repurchase Common Stock or other equity or capital securities of EFSC (including trust preferred securities) will be subject to restrictions in the event we fail to declare and pay full dividends on the Preferred Stock (or set aside a sum sufficient for payment thereof).

     The Warrant is immediately exercisable upon its issuance and has an initial exercise price of $16.20 per share of Common Stock. The Warrant includes customary anti-dilution provisions which provide for the adjustment of the exercise price and the number of Warrant Shares upon the occurrence of certain events set forth in the Warrant. Pursuant to the Agreement, the Treasury has also agreed not to exercise voting power with respect to any Warrant Shares issued upon exercise of the Warrant.