Document:

EXHIBIT 4.10.4 

GUARANTEE AGREEMENT

by and between

ENTERPRISE FINANCIAL SERVICES CORP.

and

WILMINGTON TRUST COMPANY

Dated as of October 11, 2005

GUARANTEE AGREEMENT

          This GUARANTEE AGREEMENT (this “Guarantee”), dated as of October 11, 2005, is executed and delivered by Enterprise Financial Services Corp., a Delaware corporation (the “Guarantor”), and Wilmington Trust Company, a Delaware banking corporation, as trustee (the “Guarantee Trustee”), for the benefit of the Holders (as defined herein) from time to time of the Capital Securities (as defined herein) of EFSC Statutory Trust IV, a Delaware statutory trust (the “Issuer”). 

          WHEREAS, pursuant to an Amended and Restated Declaration of Trust (the “Declaration”), dated as of the date hereof among Wilmington Trust Company, not in its individual capacity but solely as institutional trustee, the administrators of the Issuer named therein, the Guarantor, as sponsor, and the holders from time to time of undivided beneficial interests in the assets of the Issuer, the Issuer is issuing on the date hereof those undivided beneficial interests, having an aggregate liquidation amount of $10,000,000.00 (the “Capital Securities”); and 

          WHEREAS, as incentive for the Holders to purchase the Capital Securities, the Guarantor desires irrevocably and unconditionally to agree, to the extent set forth in this Guarantee, to pay to the Holders of Capital Securities the Guarantee Payments (as defined herein) and to make certain other payments on the terms and conditions set forth herein;  

          NOW, THEREFORE, in consideration of the purchase by each Holder of the Capital Securities, which purchase the Guarantor hereby agrees shall benefit the Guarantor, the Guarantor executes and delivers this Guarantee for the benefit of the Holders. 

ARTICLE I

DEFINITIONS AND INTERPRETATION

          Section 1.1     Definitions and Interpretation. In this Guarantee, unless the context otherwise requires: 

          (a)          capitalized terms used in this Guarantee but not defined in the preamble above have the respective meanings assigned to them in this Section 1.1; 

          (b)          a term defined anywhere in this Guarantee has the same meaning throughout; 

          (c)          all references to “the Guarantee” or “this Guarantee” are to this Guarantee as modified, supplemented or amended from time to time; 

          (d)          all references in this Guarantee to “Articles” or “Sections” are to Articles or Sections of this Guarantee, unless otherwise specified; 

          (e)          terms defined in the Declaration as at the date of execution of this Guarantee have the same meanings when used in this Guarantee, unless otherwise defined in this Guarantee or unless the context otherwise requires; and 

          (f)          a reference to the singular includes the plural and vice versa. 

          “Affiliate” has the same meaning as given to that term in Rule 405 of the Securities Act of 1933, as amended, or any successor rule thereunder. 

          “Beneficiaries” means any Person to whom the Issuer is or hereafter becomes indebted or liable. 

          “Capital Securities” has the meaning set forth in the recitals to this Guarantee. 

          “Common Securities” means the common securities issued by the Issuer to the Guarantor pursuant to the Declaration. 

          “Corporate Trust Office” means the office of the Guarantee Trustee at which the corporate trust business of the Guarantee Trustee shall, at any particular time, be principally administered, which office at the date of execution of this Guarantee is located at Rodney Square North, 1100 North Market Street, Wilmington, Delaware  19890-1600, Attention:  Corporate Trust Administration. 

          “Covered Person” means any Holder of Capital Securities. 

          “Debentures” means the debt securities of the Guarantor designated the Fixed/Floating Rate Junior Subordinated Deferrable Interest Debentures due 2035 held by the Institutional Trustee (as defined in the Declaration) of the Issuer. 

          “Declaration Event of Default” means an “Event of Default” as defined in the Declaration. 

          “Event of Default” has the meaning set forth in Section 2.4(a). 

          “Guarantee Payments” means the following payments or distributions, without duplication, with respect to the Capital Securities, to the extent not paid or made by the Issuer:  (i) any accrued and unpaid Distributions (as defined in the Declaration) which are required to be paid on such Capital Securities to the extent the Issuer shall have funds available therefor, (ii) the Redemption Price to the extent the Issuer has funds available therefor, with respect to any Capital Securities called for redemption by the Issuer, (iii) the Special Redemption Price to the extent the Issuer has funds available therefor, with respect to Capital Securities redeemed upon the occurrence of a Special Event, and (iv) upon a voluntary or involuntary liquidation, dissolution, winding-up or termination of the Issuer (other than in connection with the distribution of Debentures to the Holders of the
Capital Securities in exchange therefor as provided in the Declaration), the lesser of (a) the aggregate of the liquidation amount and all accrued and unpaid Distributions on the Capital Securities to the date of payment, to the extent the Issuer shall have funds available therefor, and (b) the amount of assets of the Issuer remaining available for distribution to Holders in liquidation of the Issuer (in either case, the “Liquidation Distribution”). 

          “Guarantee Trustee” means Wilmington Trust Company, until a Successor Guarantee Trustee has been appointed and has accepted such appointment pursuant to the terms of this Guarantee and thereafter means each such Successor Guarantee Trustee. 

          “Guarantor” means Enterprise Financial Services Corp. and each of its successors and assigns. 

          “Holder” means any holder, as registered on the books and records of the Issuer, of any Capital Securities; provided, however, that, in determining whether the Holders of the requisite percentage of Capital Securities have given any request, notice, consent or waiver hereunder, “Holder” shall not include the Guarantor or any Affiliate of the Guarantor. 

          “Indemnified Person” means the Guarantee Trustee, any Affiliate of the Guarantee Trustee, or any officers, directors, shareholders, members, partners, employees, representatives, nominees, custodians or agents of the Guarantee Trustee. 

          “Indenture” means the Indenture dated as of the date hereof between the Guarantor and Wilmington Trust Company, not in its individual capacity but solely as trustee, and any indenture supplemental thereto pursuant to which the Debentures are to be issued to the institutional trustee of the Issuer.

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          “Issuer” has the meaning set forth in the opening paragraph to this Guarantee. 

          “Liquidation Distribution” has the meaning set forth in the definition of “Guarantee Payments” herein. 

          “Majority in liquidation amount of the Capital Securities” means Holder(s) of outstanding Capital Securities, voting together as a class, but separately from the holders of Common Securities, of more than 50% of the aggregate liquidation amount (including the stated amount that would be paid on redemption, liquidation or otherwise, plus accrued and unpaid Distributions to the date upon which the voting percentages are determined) of all Capital Securities then outstanding. 

          “Obligations” means any costs, expenses or liabilities (but not including liabilities related to taxes) of the Issuer other than obligations of the Issuer to pay to holders of any Trust Securities the amounts due such holders pursuant to the terms of the Trust Securities. 

          “Officer’s Certificate” means, with respect to any Person, a certificate signed by one Authorized Officer of such Person. Any Officer’s Certificate delivered with respect to compliance with a condition or covenant provided for in this Guarantee shall include: 

	
   
 	
  
          (a)          a   statement that the officer signing the Officer’s Certificate has read the   covenant or condition and the definitions relating thereto;
  
	
   
 	
   
 
	
   
 	
  
          (b)          a   brief statement of the nature and scope of the examination or investigation   undertaken by the officer in rendering the Officer’s Certificate;
  
	
   
 	
   
 
	
   
 	
  
          (c)          a   statement that the officer has made such examination or investigation as, in   such officer’s opinion, is necessary to enable such officer to express an   informed opinion as to whether or not such covenant or condition has been   complied with; and
  
	
   
 	
   
 
	
   
 	
            (d)          a   statement as to whether, in the opinion of the officer, such condition or   covenant has been complied with.
  

          “Person” means a legal person, including any individual, corporation, estate, partnership, joint venture, association, joint stock company, limited liability company, trust, unincorporated association, or government or any agency or political subdivision thereof, or any other entity of whatever nature. 

          “Redemption Price” has the meaning set forth in the Indenture. 

          “Responsible Officer” means, with respect to the Guarantee Trustee, any officer within the Corporate Trust Office of the Guarantee Trustee including any Vice President, Assistant Vice President, Secretary, Assistant Secretary or any other officer of the Guarantee Trustee customarily performing functions similar to those performed by any of the above designated officers and also, with respect to a particular corporate trust matter, any other officer to whom such matter is referred because of that officer’s knowledge of and familiarity with the particular subject. 

          “Special Event” has the meaning set forth in the Indenture. 

          “Special Redemption Price” has the meaning set forth in the Indenture. 

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          “Successor Guarantee Trustee” means a successor Guarantee Trustee possessing the qualifications to act as Guarantee Trustee under Section 3.1. 

          “Trust Securities” means the Common Securities and the Capital Securities. 

ARTICLE II

POWERS, DUTIES AND RIGHTS OF 
 GUARANTEE TRUSTEE

          Section 2.1.     Powers and Duties of the Guarantee Trustee.

          (a)          This Guarantee shall be held by the Guarantee Trustee for the benefit of the Holders of the Capital Securities, and the Guarantee Trustee shall not transfer this Guarantee to any Person except a Holder of Capital Securities exercising his or her rights pursuant to Section 4.4(b) or to a Successor Guarantee Trustee on acceptance by such Successor Guarantee Trustee of its appointment to act as Successor Guarantee Trustee.  The right, title and interest of the Guarantee Trustee shall automatically vest in any Successor Guarantee Trustee, and such vesting and cessation of title shall be effective whether or not conveyancing documents have been executed and delivered pursuant to the appointment of such Successor Guarantee Trustee. 

          (b)          If an Event of Default actually known to a Responsible Officer of the Guarantee Trustee has occurred and is continuing, the Guarantee Trustee shall enforce this Guarantee for the benefit of the Holders of the Capital Securities. 

          (c)          The Guarantee Trustee, before the occurrence of any Event of Default and after curing all Events of Default that may have occurred, shall undertake to perform only such duties as are specifically set forth in this Guarantee, and no implied covenants shall be read into this Guarantee against the Guarantee Trustee.  In case an Event of Default has occurred (that has not been waived pursuant to Section 2.4) and is actually known to a Responsible Officer of the Guarantee Trustee, the Guarantee Trustee shall exercise such of the rights and powers vested in it by this Guarantee, and use the same degree of care and skill in its exercise thereof, as a prudent person would exercise or use under the circumstances in the conduct of his or her own affairs. 

          (d)          No provision of this Guarantee shall be construed to relieve the Guarantee Trustee from liability for its own negligent action, its own negligent failure to act, or its own willful misconduct, except that: 

	
   
 	
  
          (i)          prior   to the occurrence of any Event of Default and after the curing or waiving of   all such Events of Default that may have occurred:
  
	
   
 	
   
 	
   
 
	
   
 	
   
 	
  
          (A)          the   duties and obligations of the Guarantee Trustee shall be determined solely by   the express provisions of this Guarantee, and the Guarantee Trustee shall not   be liable except for the performance of such duties and obligations as are   specifically set forth in this Guarantee, and no implied covenants or   obligations shall be read into this Guarantee against the Guarantee Trustee;   and
  
	
   
 	
   
 	
   
 
	
   
 	
   
 	
  
          (B)          in   the absence of bad faith on the part of the Guarantee Trustee, the Guarantee   Trustee may conclusively rely, as to the truth of the statements and the   correctness of the opinions expressed therein, upon any certificates or   opinions furnished to the Guarantee Trustee and conforming to the   requirements of this Guarantee; but in the
  

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case of any such certificates or opinions that by any provision   hereof are specifically required to be furnished to the Guarantee Trustee,   the Guarantee Trustee shall be under a duty to examine the same to determine   whether or not they conform to the requirements of this Guarantee;
  
	
   
 	
   
 	
   
 
	
   
 	
  
          (ii)         the   Guarantee Trustee shall not be liable for any error of judgment made in good   faith by a Responsible Officer of the Guarantee Trustee, unless it shall be   proved that such Responsible Officer of the Guarantee Trustee or the   Guarantee Trustee was negligent in ascertaining the pertinent facts upon   which such judgment was made;
  
	
   
 	
   
 
	
   
 	
  
          (iii)        the   Guarantee Trustee shall not be liable with respect to any action taken or   omitted to be taken by it in good faith in accordance with the written   direction of the Holders of not less than a Majority in liquidation amount of   the Capital Securities relating to the time, method and place of conducting   any proceeding for any remedy available to the Guarantee Trustee, or relating   to the exercise of any trust or power conferred upon the Guarantee Trustee   under this Guarantee; and
  
	
   
 	
   
 
	
   
 	
            (iv)        no   provision of this Guarantee shall require the Guarantee Trustee to expend or   risk its own funds or otherwise incur personal financial liability in the   performance of any of its duties or in the exercise of any of its rights or   powers, if the Guarantee Trustee shall have reasonable grounds for believing   that the repayment of such funds is not reasonably assured to it under the   terms of this Guarantee or security and indemnity, reasonably satisfactory to   the Guarantee Trustee, against such risk or liability is not reasonably   assured to it.
  
	
   
 	
   
 
	
   
 	
  
Section 2.2.     Certain Rights of Guarantee Trustee.
  
	
   
 	
   
 
	
   
 	
  
(a)      Subject to the provisions of   Section 2.1:
  
	
   
 	
   
 
	
   
 	
  
          (i)          The   Guarantee Trustee may conclusively rely, and shall be fully protected in   acting or refraining from acting upon, any resolution, certificate,   statement, instrument, opinion, report, notice, request, direction, consent,   order, bond, debenture, note, other evidence of indebtedness or other paper or   document believed by it to be genuine and to have been signed, sent or   presented by the proper party or parties.
  
	
   
 	
   
 
	
   
 	
            (ii)         Any   direction or act of the Guarantor contemplated by this Guarantee shall be   sufficiently evidenced by an Officer’s Certificate.
  
	
   
 	
   
 
	
   
 	
  
          (iii)        Whenever,   in the administration of this Guarantee, the Guarantee Trustee shall deem it   desirable that a matter be proved or established before taking, suffering or   omitting any action hereunder, the Guarantee Trustee (unless other evidence   is herein specifically prescribed) may, in the absence of bad faith on its   part, request and conclusively rely upon an Officer’s Certificate of the   Guarantor which, upon receipt of such request, shall be promptly delivered by   the Guarantor.
  
	
   
 	
   
 
	
   
 	
  
          (iv)        The   Guarantee Trustee shall have no duty to see to any recording, filing or   registration of any instrument (or any re-recording, refiling or re-registration   thereof).
  
	
   
 	
   
 
	
   
 	
  
          (v)         The   Guarantee Trustee may consult with counsel of its selection, and the advice   or opinion of such counsel with respect to legal matters shall be full and   complete authorization and protection in respect of any action taken,   suffered or omitted by it hereunder in good faith and in accordance with such   advice or opinion. Such counsel may be counsel to the Guarantor or any
  

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of its Affiliates and may include any of its employees.  The Guarantee Trustee shall have the right   at any time to seek instructions concerning the administration of this   Guarantee from any court of competent jurisdiction.
  
	
   
 	
   
 
	
   
 	
  
          (vi)        The   Guarantee Trustee shall be under no obligation to exercise any of the rights   or powers vested in it by this Guarantee at the request or direction of any   Holder, unless such Holder shall have provided to the Guarantee Trustee such   security and indemnity, reasonably satisfactory to the Guarantee Trustee,   against the costs, expenses (including attorneys’ fees and expenses and the   expenses of the Guarantee Trustee’s agents, nominees or custodians) and   liabilities that might be incurred by it in complying with such request or   direction, including such reasonable advances as may be requested by the   Guarantee Trustee; provided, however, that nothing contained in   this Section 2.2(a)(vi) shall relieve the Guarantee Trustee, upon the   occurrence of an Event of Default, of its obligation to exercise the rights   and
powers vested in it by this Guarantee.
  
	
   
 	
   
 
	
   
 	
  
          (vii)      The   Guarantee Trustee shall not be bound to make any investigation into the facts   or matters stated in any resolution, certificate, statement, instrument,   opinion, report, notice, request, direction, consent, order, bond, debenture,   note, other evidence of indebtedness or other paper or document, but the   Guarantee Trustee, in its discretion, may make such further inquiry or   investigation into such facts or matters as it may see fit.
  
	
   
 	
   
 
	
   
 	
            (viii)     The   Guarantee Trustee may execute any of the trusts or powers hereunder or perform   any duties hereunder either directly or by or through agents, nominees,   custodians or attorneys, and the Guarantee Trustee shall not be responsible   for any misconduct or negligence on the part of any agent or attorney   appointed with due care by it hereunder.
  
	
   
 	
   
 
	
   
 	
  
          (ix)       Any   action taken by the Guarantee Trustee or its agents hereunder shall bind the   Holders of the Capital Securities, and the signature of the Guarantee Trustee   or its agents alone shall be sufficient and effective to perform any such   action.  No third party shall be   required to inquire as to the authority of the Guarantee Trustee to so act or   as to its compliance with any of the terms and provisions of this Guarantee,   both of which shall be conclusively evidenced by the Guarantee Trustee’s or   its agent’s taking such action.
  
	
   
 	
   
 
	
   
 	
  
          (x)       Whenever   in the administration of this Guarantee the Guarantee Trustee shall deem it   desirable to receive instructions with respect to enforcing any remedy or   right or taking any other action hereunder, the Guarantee Trustee (i) may   request instructions from the Holders of a Majority in liquidation amount of   the Capital Securities, (ii) may refrain from enforcing such remedy or right   or taking such other action until such instructions are received, and (iii)   shall be protected in conclusively relying on or acting in accordance with   such instructions.
  
	
   
 	
   
 
	
   
 	
            (xi)       The   Guarantee Trustee shall not be liable for any action taken, suffered, or   omitted to be taken by it in good faith, without negligence, and reasonably   believed by it to be authorized or within the discretion or rights or powers   conferred upon it by this Guarantee.
  

          (b)          No provision of this Guarantee shall be deemed to impose any duty or obligation on the Guarantee Trustee to perform any act or acts or exercise any right, power, duty or obligation conferred or imposed on it, in any jurisdiction in which it shall be illegal or in which the Guarantee Trustee shall be unqualified or incompetent in accordance with applicable law to perform any such act or acts or to exercise any such right, power, duty or obligation. No permissive power or authority available to the Guarantee Trustee shall be construed to be a duty. 

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          Section 2.3.     Not Responsible for Recitals or Issuance of Guarantee. The recitals contained in this Guarantee shall be taken as the statements of the Guarantor, and the Guarantee Trustee does not assume any responsibility for their correctness.  The Guarantee Trustee makes no representation as to the validity or sufficiency of this Guarantee. 

          Section 2.4.     Events of Default; Waiver. 

          (a)          An Event of Default under this Guarantee will occur upon the failure of the Guarantor to perform any of its payment or other obligations hereunder. 

          (b)          The Holders of a Majority in liquidation amount of the Capital Securities may, voting or consenting as a class, on behalf of the Holders of all of the Capital Securities, waive any past Event of Default and its consequences. Upon such waiver, any such Event of Default shall cease to exist, and shall be deemed to have been cured, for every purpose of this Guarantee, but no such waiver shall extend to any subsequent or other default or Event of Default or impair any right consequent thereon. 

          Section 2.5.     Events of Default; Notice. 

          (a)          The Guarantee Trustee shall, within 90 days after the occurrence of an Event of Default, transmit by mail, first class postage prepaid, to the Holders of the Capital Securities and the Guarantor, notices of all Events of Default actually known to a Responsible Officer of the Guarantee Trustee, unless such defaults have been cured before the giving of such notice, provided, however, that the Guarantee Trustee shall be protected in withholding such notice if and so long as a Responsible Officer of the Guarantee Trustee in good faith determines that the withholding of such notice is in the interests of the Holders of the Capital Securities. 

          (b)          The Guarantee Trustee shall not be deemed to have knowledge of any Event of Default unless the Guarantee Trustee shall have received written notice from the Guarantor or a Holder of the Capital Securities (except in the case of a payment default), or a Responsible Officer of the Guarantee Trustee charged with the administration of this Guarantee shall have obtained actual knowledge thereof. 

ARTICLE III

GUARANTEE TRUSTEE

          Section 3.1.     Guarantee Trustee; Eligibility. 

          (a)          There shall at all times be a Guarantee Trustee which shall: 

	
   
 	
  
          (i)          not   be an Affiliate of the Guarantor, and
  
	
   
 	
   
 
	
   
 	
  
          (ii)         be   a corporation organized and doing business under the laws of the United   States of America or any State or Territory thereof or of the District of   Columbia, or Person authorized under such laws to exercise corporate trust   powers, having a combined capital and surplus of at least 50 million U.S.   dollars ($50,000,000), and subject to supervision or examination by Federal,   State, Territorial or District of Columbia authority. If such corporation   publishes reports of condition at least annually, pursuant to law or to the   requirements of the supervising or examining authority referred to above,   then, for the purposes of this Section 3.1(a)(ii), the combined capital and   surplus of such corporation shall be deemed to be its combined capital and   surplus as set forth in its most recent report of condition so published.

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          (b)          If at any time the Guarantee Trustee shall cease to be eligible to so act under Section 3.1(a), the Guarantee Trustee shall immediately resign in the manner and with the effect set out in Section 3.2(c). 

          (c)          If the Guarantee Trustee has or shall acquire any “conflicting interest” within the meaning of Section 310(b) of the Trust Indenture Act, the Guarantee Trustee shall either eliminate such interest or resign to the extent and in the manner provided by, and subject to this Guarantee. 

          Section 3.2.     Appointment, Removal and Resignation of Guarantee Trustee. 

          (a)          Subject to Section 3.2(b), the Guarantee Trustee may be appointed or removed without cause at any time by the Guarantor except during an Event of Default. 

          (b)          The Guarantee Trustee shall not be removed in accordance with Section 3.2(a) until a Successor Guarantee Trustee has been appointed and has accepted such appointment by written instrument executed by such Successor Guarantee Trustee and delivered to the Guarantor. 

          (c)          The Guarantee Trustee appointed to office shall hold office until a Successor Guarantee Trustee shall have been appointed or until its removal or resignation.  The Guarantee Trustee may resign from office (without need for prior or subsequent accounting) by an instrument in writing executed by the Guarantee Trustee and delivered to the Guarantor, which resignation shall not take effect until a Successor Guarantee Trustee has been appointed and has accepted such appointment by an instrument in writing executed by such Successor Guarantee Trustee and delivered to the Guarantor and the resigning Guarantee Trustee. 

          (d)          If no Successor Guarantee Trustee shall have been appointed and accepted appointment as provided in this Section 3.2 within 60 days after delivery of an instrument of removal or resignation, the Guarantee Trustee resigning or being removed may petition any court of competent jurisdiction for appointment of a Successor Guarantee Trustee.  Such court may thereupon, after prescribing such notice, if any, as it may deem proper, appoint a Successor Guarantee Trustee. 

          (e)          No Guarantee Trustee shall be liable for the acts or omissions to act of any Successor Guarantee Trustee. 

          (f)          Upon termination of this Guarantee or removal or resignation of the Guarantee Trustee pursuant to this Section 3.2, the Guarantor shall pay to the Guarantee Trustee all amounts owing to the Guarantee Trustee under Sections 7.2 and 7.3 accrued to the date of such termination, removal or resignation. 

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ARTICLE IV

GUARANTEE

          Section 4.1.     Guarantee.

          (a)          The Guarantor irrevocably and unconditionally agrees to pay in full to the Holders the Guarantee Payments (without duplication of amounts theretofore paid by the Issuer), as and when due, regardless of any defense (except the defense of payment by the Issuer), right of set-off or counterclaim that the Issuer may have or assert.  The Guarantor’s obligation to make a Guarantee Payment may be satisfied by direct payment of the required amounts by the Guarantor to the Holders or by causing the Issuer to pay such amounts to the Holders. 

          (b)          The Guarantor hereby also agrees to assume any and all Obligations of the Issuer and in the event any such Obligation is not so assumed, subject to the terms and conditions hereof, the Guarantor hereby irrevocably and unconditionally guarantees to each Beneficiary the full payment, when and as due, of any and all Obligations to such Beneficiaries.  This Guarantee is intended to be for the benefit of, and to be enforceable by, all such Beneficiaries, whether or not such Beneficiaries have received notice hereof. 

          Section 4.2.     Waiver of Notice and Demand. The Guarantor hereby waives notice of acceptance of this Guarantee and of any liability to which it applies or may apply, presentment, demand for payment, any right to require a proceeding first against the Issuer or any other Person before proceeding against the Guarantor, protest, notice of nonpayment, notice of dishonor, notice of redemption and all other notices and demands. 

          Section 4.3.     Obligations Not Affected. The obligations, covenants, agreements and duties of the Guarantor under this Guarantee shall in no way be affected or impaired by reason of the happening from time to time of any of the following: 

          (a)          the release or waiver, by operation of law or otherwise, of the performance or observance by the Issuer of any express or implied agreement, covenant, term or condition relating to the Capital Securities to be performed or observed by the Issuer; 

          (b)          the extension of time for the payment by the Issuer of all or any portion of the Distributions, Redemption Price, Special Redemption Price, Liquidation Distribution or any other sums payable under the terms of the Capital Securities or the extension of time for the performance of any other obligation under, arising out of or in connection with, the Capital Securities (other than an extension of time for payment of Distributions, Redemption Price, Special Redemption Price, Liquidation Distribution or other sum payable that results from the extension of any interest payment period on the Debentures or any extension of the maturity date of the Debentures permitted by the Indenture); 

          (c)          any failure, omission, delay or lack of diligence on the part of the Holders to enforce, assert or exercise any right, privilege, power or remedy conferred on the Holders pursuant to the terms of the Capital Securities, or any action on the part of the Issuer granting indulgence or extension of any kind; 

          (d)          the voluntary or involuntary liquidation, dissolution, sale of any collateral, receivership, insolvency, bankruptcy, assignment for the benefit of creditors, reorganization, arrangement, composition or readjustment of debt of, or other similar proceedings affecting, the Issuer or any of the assets of the Issuer; 

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(e)
  	
  
any invalidity of, or defect or deficiency in, the Capital   Securities; 
  
	
   
 	
   
 	
   
 
	
   
 	
  
(f)
  	
  
the settlement or compromise of any obligation guaranteed hereby or   hereby incurred; or 
  
	
   
 	
   
 	
   
 
	
  
          (g)       any
other circumstance whatsoever that might otherwise constitute a legal or
equitable discharge or defense of a guarantor, it being the intent of this
Section 4.3 that the obligations of the Guarantor hereunder shall be absolute
and unconditional under any and all circumstances. 
 

          There shall
be no obligation of the Holders to give notice to, or obtain consent of, the
Guarantor with respect to the happening of any of the foregoing. 

          Section
4.4.    Rights of Holders. 

          (a)          The Holders of a Majority in liquidation amount of the Capital Securities have the right to direct the time, method and place of conducting any proceeding for any remedy available to the Guarantee Trustee in respect of this Guarantee or to direct the exercise of any trust or power conferred upon the Guarantee Trustee under this Guarantee; provided, however, that (subject to Section 2.1) the Guarantee Trustee shall have the right to decline to follow any such direction if the Guarantee Trustee being advised by counsel determines that the action or proceeding so directed may not lawfully be taken or if the Guarantee Trustee in good faith by its board of directors or trustees, executive committees or a trust committee of directors or trustees and/or Responsible Officers shall determine that the action or proceedings so directed
would involve the Guarantee Trustee in personal liability. 

          (b)          Any Holder of Capital Securities may institute a legal proceeding directly against the Guarantor to enforce the Guarantee Trustee’s rights under this Guarantee, without first instituting a legal proceeding against the Issuer, the Guarantee Trustee or any other Person.  The Guarantor waives any right or remedy to require that any such action be brought first against the Issuer, the Guarantee Trustee or any other Person before so proceeding directly against the Guarantor. 

          Section 4.5.    Guarantee of Payment. This Guarantee creates a guarantee of payment and not of collection. 

          Section 4.6.    Subrogation. The Guarantor shall be subrogated to all (if any) rights of the Holders of Capital Securities against the Issuer in respect of any amounts paid to such Holders by the Guarantor under this Guarantee; provided, however, that the Guarantor shall not (except to the extent required by mandatory provisions of law) be entitled to enforce or exercise any right that it may acquire by way of subrogation or any indemnity, reimbursement or other agreement, in all cases as a result of payment under this Guarantee, if, after giving effect to any such payment, any amounts are due and unpaid under this Guarantee.  If any amount shall be paid to the Guarantor in violation of the preceding sentence, the Guarantor agrees to hold such amount in trust for the Holders and to pay over such amount to the Holders. 

          Section 4.7.     Independent Obligations. The Guarantor acknowledges that its obligations hereunder are independent of the obligations of the Issuer with respect to the Capital Securities and that the Guarantor shall be liable as principal and as debtor hereunder to make Guarantee Payments pursuant to the terms of this Guarantee notwithstanding the occurrence of any event referred to in subsections (a) through (g), inclusive, of Section 4.3 hereof. 

          Section 4.8.     Enforcement by a Beneficiary. A Beneficiary may enforce the obligations of the Guarantor contained in Section 4.1(b) directly against the Guarantor and the Guarantor waives any right or remedy to require that any action be brought against the Issuer or any other person or entity 

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before proceeding against the Guarantor.  The Guarantor shall be subrogated to all rights (if any) of any Beneficiary against the Issuer in respect of any amounts paid to the Beneficiaries by the Guarantor under this Guarantee; provided, however, that the Guarantor shall not (except to the extent required by mandatory provisions of law) be entitled to enforce or exercise any rights that it may acquire by way of subrogation or any indemnity, reimbursement or other agreement, in all cases as a result of payment under this Guarantee, if at the time of any such payment, and after giving effect to such payment, any amounts are due and unpaid under this Guarantee. 

ARTICLE V

LIMITATION OF TRANSACTIONS; SUBORDINATION

          Section 5.1.     Limitation of Transactions. So long as any Capital Securities remain outstanding, if (a) there shall have occurred and be continuing an Event of Default or a Declaration Event of Default or (b) the Guarantor shall have selected an Extension Period as provided in the Declaration and such period, or any extension thereof, shall have commenced and be continuing, then the Guarantor shall not and shall not permit any Affiliate to (x) declare or pay any dividends or distributions on, or redeem, purchase, acquire, or make a liquidation payment with respect to, any of the Guarantor’s or such Affiliate’s capital stock (other than payments of dividends or distributions to the Guarantor) or make any guarantee payments with respect to the foregoing or (y) make any payment of principal of or interest or premium, if any, on or repay, repurchase or
redeem any debt securities of the Guarantor or any Affiliate that rank pari passu in all respects with or junior in interest to the Debentures (other than, with respect to clauses (x) and (y) above, (i) repurchases, redemptions or other acquisitions of shares of capital stock of the Guarantor in connection with any employment contract, benefit plan or other similar arrangement with or for the benefit of one or more employees, officers, directors or consultants, in connection with a dividend reinvestment or stockholder stock purchase plan or in connection with the issuance of capital stock of the Guarantor (or securities convertible into or exercisable for such capital stock) as consideration in an acquisition transaction entered into prior to the occurrence of the Event of Default, Declaration Event of Default or Extension Period, as applicable, (ii) as a result of any exchange or conversion of any class or series of the Guarantor’s capital stock (or any capital stock of a subsidiary of
the Guarantor) for any class or series of the Guarantor’s capital stock or of any class or series of the Guarantor’s indebtedness for any class or series of the Guarantor’s capital stock, (iii) the purchase of fractional interests in shares of the Guarantor’s capital stock pursuant to the conversion or exchange provisions of such capital stock or the security being converted or exchanged, (iv) any declaration of a dividend in connection with any stockholders’ rights plan, or the issuance of rights, stock or other property under any stockholders’ rights plan, or the redemption or repurchase of rights pursuant thereto, (v) any dividend in the form of stock, warrants, options or other rights where the dividend stock or the stock issuable upon exercise of such warrants, options or other rights is the same stock as that on which the dividend is being paid or ranks pari passu with or junior to such stock and any cash payments in lieu of fractional shares issued in
connection therewith, or (vi) payments under this Guarantee). 

          Section 5.2.     Ranking. This Guarantee will constitute an unsecured obligation of the Guarantor and will rank subordinate and junior in right of payment to all present and future Senior Indebtedness (as defined in the Indenture) of the Guarantor.  By their acceptance thereof, each Holder of Capital Securities agrees to the foregoing provisions of this Guarantee and the other terms set forth herein. 

          The right of the Guarantor to participate in any distribution of assets of any of its subsidiaries upon any such subsidiary’s liquidation or reorganization or otherwise is subject to the prior claims of creditors of that subsidiary, except to the extent the Guarantor may itself be recognized as a creditor of that subsidiary.  Accordingly, the Guarantor’s obligations under this Guarantee will be effectively 

11

subordinated to all existing and future liabilities of the Guarantor’s subsidiaries, and claimants should look only to the assets of the Guarantor for payments hereunder.  This Guarantee does not limit the incurrence or issuance of other secured or unsecured debt of the Guarantor, including Senior Indebtedness of the Guarantor, under any indenture that the Guarantor may enter into in the future or otherwise. 

ARTICLE VI

TERMINATION

          Section 6.1.     Termination.  This Guarantee shall terminate as to the Capital Securities (i) upon full payment of the Redemption Price or Special Redemption Price of all Capital Securities then outstanding, (ii) upon the distribution of all of the Debentures to the Holders of all of the Capital Securities or (iii) upon full payment of the amounts payable in accordance with the Declaration upon dissolution of the Issuer. This Guarantee will continue to be effective or will be reinstated, as the case may be, if at any time any Holder of Capital Securities must restore payment of any sums paid under the Capital Securities or under this Guarantee. 

ARTICLE VII

INDEMNIFICATION

          Section 7.1.     Exculpation. 

          (a)          No Indemnified Person shall be liable, responsible or accountable in damages or otherwise to the Guarantor or any Covered Person for any loss, damage or claim incurred by reason of any act or omission performed or omitted by such Indemnified Person in good faith in accordance with this Guarantee and in a manner that such Indemnified Person reasonably believed to be within the scope of the authority conferred on such Indemnified Person by this Guarantee or by law, except that an Indemnified Person shall be liable for any such loss, damage or claim incurred by reason of such Indemnified Person’s negligence or willful misconduct with respect to such acts or omissions. 

          (b)          An Indemnified Person shall be fully protected in relying in good faith upon the records of the Issuer or the Guarantor and upon such information, opinions, reports or statements presented to the Issuer or the Guarantor by any Person as to matters the Indemnified Person reasonably believes are within such other Person’s professional or expert competence and who, if selected by such Indemnified Person, has been selected with reasonable care by such Indemnified Person, including information, opinions, reports or statements as to the value and amount of the assets, liabilities, profits, losses, or any other facts pertinent to the existence and amount of assets from which Distributions to Holders of Capital Securities might properly be paid. 

          Section 7.2.     Indemnification. 

          (a)          The Guarantor agrees to indemnify each Indemnified Person for, and to hold each Indemnified Person harmless against, any and all loss, liability, damage, claim or expense incurred without negligence or willful misconduct on the part of the Indemnified Person, arising out of or in connection with the acceptance or administration of the trust or trusts hereunder, including, but not limited to, the costs and expenses (including reasonable legal fees and expenses) of the Indemnified Person defending itself against, or investigating, any claim or liability in connection with the exercise or performance of any of the Indemnified Person’s powers or duties hereunder.  The obligation to indemnify as set forth in this Section 7.2 shall survive the resignation or removal of the Guarantee Trustee and the termination of this Guarantee.

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          (b)          Promptly after receipt by an Indemnified Person under this Section 7.2 of notice of the commencement of any action, such Indemnified Person will, if a claim in respect thereof is to be made against the Guarantor under this Section 7.2, notify the Guarantor in writing of the commencement thereof; but the failure so to notify the Guarantor (i) will not relieve the Guarantor from liability under paragraph (a) above unless and to the extent that the Guarantor did not otherwise learn of such action and such failure results in the forfeiture by the Guarantor of substantial rights and defenses and (ii) will not, in any event, relieve the Guarantor from any obligations to any Indemnified Person other than the indemnification obligation provided in paragraph (a) above.  The Guarantor shall be entitled to appoint counsel of the Guarantor’s
choice at the Guarantor’s expense to represent the Indemnified Person in any action for which indemnification is sought (in which case the Guarantor shall not thereafter be responsible for the fees and expenses of any separate counsel retained by the Indemnified Person or Persons except as set forth below); provided, however, that such counsel shall be reasonably satisfactory to the Indemnified Person. Notwithstanding the Guarantor’s election to appoint counsel to represent the Guarantor in an action, the Indemnified Person shall have the right to employ separate counsel (including local counsel), and the Guarantor shall bear the reasonable fees, costs and expenses of such separate counsel if (i) the use of counsel chosen by the Guarantor to represent the Indemnified Person would present such counsel with a conflict of interest, (ii) the actual or potential defendants in, or targets of, any such action include both the Indemnified Person and the Guarantor and the Indemnified
Person shall have reasonably concluded that there may be legal defenses available to it and/or other Indemnified Person(s) which are different from or additional to those available to the Guarantor, (iii) the Guarantor shall not have employed counsel satisfactory to the Indemnified Person to represent the Indemnified Person within a reasonable time after notice of the institution of such action or (iv) the Guarantor shall authorize the Indemnified Person to employ separate counsel at the expense of the Guarantor.  The Guarantor will not, without the prior written consent of the Indemnified Persons, settle or compromise or consent to the entry of any judgment with respect to any pending or threatened claim, action, suit or proceeding in respect of which indemnification or contribution may be sought hereunder (whether or not the Indemnified Persons are actual or potential parties to such claim or action) unless such settlement, compromise or consent includes an unconditional release of each
Indemnified Person from all liability arising out of such claim, action, suit or proceeding. 

          Section 7.3.     Compensation; Reimbursement of Expenses.   The Guarantor agrees: 

          (a)          to pay to the Guarantee Trustee from time to time such compensation for all services rendered by it hereunder as the parties shall agree to from time to time (which compensation shall not be limited by any provision of law in regard to the compensation of a trustee of an express trust); and 

          (b)          except as otherwise expressly provided herein, to reimburse the Guarantee Trustee upon request for all reasonable expenses, disbursements and advances incurred or made by it in accordance with any provision of this Guarantee (including the reasonable compensation and the expenses and disbursements of its agents and counsel), except any such expense, disbursement or advance as may be attributable to its negligence or willful misconduct. 

          For purposes of clarification, this Section 7.3 does not contemplate the payment by the Guarantor of acceptance or annual administration fees owing to the Guarantee Trustee for services to be provided by the Guarantee Trustee under this Guarantee or the fees and expenses of the Guarantee Trustee’s counsel in connection with the closing of the transactions contemplated by this Guarantee.  The provisions of this Section 7.3 shall survive the resignation or removal of the Guarantee Trustee and the termination of this Guarantee. 

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ARTICLE VIII 

MISCELLANEOUS 

          Section 8.1.     Successors and Assigns. All guarantees and agreements contained in this Guarantee shall bind the successors, assigns, receivers, trustees and representatives of the Guarantor and shall inure to the benefit of the Holders of the Capital Securities then outstanding.  Except in connection with any merger or consolidation of the Guarantor with or into another entity or any sale, transfer or lease of the Guarantor’s assets to another entity, in each case, to the extent permitted under the Indenture, the Guarantor may not assign its rights or delegate its obligations under this Guarantee without the prior approval of the Holders of at least a Majority in liquidation amount of the Capital Securities. 

          Section 8.2.     Amendments. Except with respect to any changes that do not adversely affect the rights of Holders of the Capital Securities in any material respect (in which case no consent of Holders will be required), this Guarantee may be amended only with the prior approval of the Holders of not less than a Majority in liquidation amount of the Capital Securities.  The provisions of the Declaration with respect to amendments thereof apply to the giving of such approval. 

          Section 8.3.     Notices. All notices provided for in this Guarantee shall be in writing, duly signed by the party giving such notice, and shall be delivered, telecopied or mailed by first class mail, as follows: 

          (a)          If given to the Guarantee Trustee, at the Guarantee Trustee’s mailing address set forth below (or such other address as the Guarantee Trustee may give notice of to the Holders of the Capital Securities and the Guarantor): 

	
   
 	
  
Wilmington Trust Company
  
	
   
 	
  
Rodney Square North 
  
	
   
 	
  
1100 North Market Street 
  
	
   
 	
  
Wilmington, Delaware    19890-1600 
  
	
   
 	
  Attention: Corporate Trust Administration 
  
	
   
 	
  
Telecopy:  302-636-4140
  

          (b)          If given to the Guarantor, at the Guarantor’s mailing address set forth below (or such other address as the Guarantor may give notice of to the Holders of the Capital Securities and to the Guarantee Trustee): 

	
   
 	
  
Enterprise Financial Services Corp. 
  
	
   
 	
  
150 North Meramec Avenue, Suite 300
  
	
   
 	
  
St. Louis, Missouri  63105
  
	
   
 	
  
Attention: Frank Sanfilippo 
  
	
   
 	
  
Telecopy:  314-812-1576
  

          (c)          If given to any Holder of the Capital Securities, at the address set forth on the books and records of the Issuer. 

          All such notices shall be deemed to have been given when received in person, telecopied with receipt confirmed, or mailed by first class mail, postage prepaid, except that if a notice or other document is refused delivery or cannot be delivered because of a changed address of which no notice was given, such notice or other document shall be deemed to have been delivered on the date of such refusal or inability to deliver. 

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          Section 8.4.     Benefit. This Guarantee is solely for the benefit of the Beneficiaries and, subject to Section 2.1(a), is not separately transferable from the Capital Securities. 

          Section 8.5.     Governing Law. THIS GUARANTEE SHALL BE GOVERNED BY, AND CONSTRUED AND INTERPRETED IN ACCORDANCE WITH, THE LAW OF THE STATE OF NEW YORK, WITHOUT REGARD TO CONFLICT OF LAWS PRINCIPLES THEREOF (OTHER THAN SECTION 5-1401 OF THE NEW YORK GENERAL OBLIGATIONS LAW). 

          Section 8.6.     Counterparts. This Guarantee may be executed in one or more counterparts, each of which shall be an original, but all of which taken together shall constitute one and the same instrument. 

          Section 8.7.     Separability. In case one or more of the provisions contained in this Guarantee shall for any reason be held to be invalid, illegal or unenforceable in any respect, such invalidity, illegality or unenforceability shall not affect any other provisions of this Guarantee, but this Guarantee shall be construed as if such invalid or illegal or unenforceable provision had never been contained herein. 

Signatures appear on the following page

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THIS GUARANTEE is executed as of the day and year first above written.

	
   
 	
  ENTERPRISE FINANCIAL SERVICES CORP., as 
Guarantor
  
	
   
 	
   
 	
   
 
	
   
 	
  
By: 
  	
   
 
	
   
 	
   
 	
  

  
	
   
 	
  
Name:
  
	
   
 	
  
Title:
  	
   
 
	
   
 	
   
 	
   
 
	
   
 	
   
 	
   
 
	
   
 	
  
WILMINGTON TRUST COMPANY,
 as Guarantee Trustee
  
	
   
 	
   
 	
   
 
	
   
 	
  
By:
  	
   
 
	
   
 	
   
 	
  

  
	
   
 	
  Name:
  	
   
 
	
   
 	
  Title:
  	
   
 

16Exhibit 10.1

                            STOCK PURCHASE AGREEMENT
                            ------------------------

     THIS  STOCK  PURCHASE AGREEMENT ("Agreement") is made as of the 23rd day of
February,  2006, by and between Island Residences Club, Inc ("IRCI"), a Delaware
Corporation,  Richard Woods, individual and/or their assignees ("Purchaser")  on
the  one hand and RotateBlack, LLC, ("RBL") a Michigan limited liability company
("Seller"),  on  the  other  hand.
     For  and  in  consideration  of  the  mutual  premises and covenants herein
contained,  the  parties  hereto  agree  as  follows:
1.     Purchase  and  Sale  of  Securities.
       -----------------------------------
1.1     Sale  and Issuance of Securities. Subject to the terms and conditions of
        --------------------------------
this  Agreement, Purchaser agrees to purchase at the Closing (defined in Section
1.3),  and the Company agrees to cause RBL to, and RBL agrees to, sell, transfer
and  assign  to  Purchaser  at  the  Closing, Nine Million Four Hundred Thousand
(9,400,000)  shares (the "Shares") of the common stock, $.01 par value per share
("Common  Stock"),  of  DTLL,  Inc.,  a  Minnesota  corporation  ("DTLL").
1.2     Purchase  Price.  The  purchase  price  for the Shares to be paid at the
        ---------------
Closing  (the  "Purchase  Price")  shall  be  One  Million Five Hundred Thousand
($1,500,000)  Dollars. The purchase price shall be paid at a closing in the form
of  Five  Hundred  Fifty  Thousand  ($500,000) and a Secured Note payable in the
amount  of  One Million ($1,000,000) Dollars due on or before the closing of the
Reno Hilton but no later than April 10th, 2006. The Note shall be secured by the
shares  on  terms  to  be  agreed  between  the  parties.
1.3     Closing.
        -------
(a)     The  purchase  and  sale  of  the  Shares  shall take place on or before
February  28th,  2006,  at  such time and place as shall be mutually agreed upon
between  Purchaser  and  the  Company  (the  "  Closing").
(b)     At  the Closing, Purchaser shall deliver to RBL, the cash requirement of
the  Purchase  Price  of  then immediately available funds by certified check or
wire  transfer  to  an  account  designated  by  the  RBL.
(c)     At the Closing, RBL shall deliver to Purchaser an endorsed  certificate,
signature  guaranteed,  for  the  Shares  along with instruments satisfactory to
Purchaser  to  ensure  the  effective  and  efficient  transfer of the Shares to
Purchaser,  such  as  a  legal  opinion  of the Company's or RBL's counsel and a
letter  of  instruction  to  the  transfer  agent  of  DTLL.
(d)     Purchaser,  the  Company  and  RBL  shall deliver to the other party any
other  documents  and instruments that the other party or its counsel reasonably
requests.
(e)     Notwithstanding  anything  to  the contrary contained in this Agreement,
Purchaser's  obligations  under  this Agreement are conditioned upon Purchaser's
satisfaction  of  its  legal  due  diligence  investigation  of  DTLL.  Seller's
obligations  under  this agreement are conditioned upon Seller's satisfaction of
its legal due diligence investigation of the transaction on or before closing on
February  28,  2006.
2.     Representations  and  Warranties  of  the Company. Except as noted in the
       -------------------------------------------------
financial  statements  identified  in  Section  2.6,  DTLL's  filings  with  the
Securities  and  Exchange  Commission,  or  the  Schedule of Exceptions attached
hereto,  each  of  the Company and RBL, jointly and severally, hereby represents
and  warrants  to  Purchaser  that:
2.1     Organization;  Good  Standing;  Qualification  and  Corporate  Power.
        --------------------------------------------------------------------
(a)     The  Company,  RBL  and  DTLL  are  corporations duly organized, validly
existing  and in good standing under the laws of the State of Minnesota and each
has  all requisite corporate power and authority to carry on its business as now
conducted  and  as  proposed to be conducted. The Company, RBL and DTLL are each
duly  qualified  to  transact  business  and  each  is  in good standing in each
jurisdiction  in  which  the failure so to qualify would have a material adverse
effect  on  its  business  or  properties.
(b)     Each  of the Company and RBL has all requisite legal and corporate power
and  authority  to execute and deliver this Agreement, to sell the Shares and to
carry  out  and perform its obligations under the terms of this Agreement and to
consummate  the transactions contemplated hereby. All necessary corporate action
has  been  taken  by the Company and RBL with respect to the execution, delivery
and performance by the Company and RBL of this Agreement and the consummation of
     the  transactions  contemplated  hereby.
2.2     Capitalization  and  Voting  Rights.
        -----------------------------------
(a)     Common  Stock.  The authorized capital of DTLL, immediately prior to the
        -------------
Closing,  consists of One Hundred Million (100,000,000) shares of capital stock,
of which Fifty Million (50,000,000) shares are designated as Common Stock, $0.01
     par value per share. Thirteen Million Five Hundred Twenty Five Thousand Six
Hundred  Ninety  Three  (13,525,693)  shares  of Common Stock will be issued and
outstanding  immediately  prior  to the Closing. Other than the Common Stock, no
other  shares  of  capital  stock  are  issued  or outstanding. The Shares sold,
transferred  and  assigned  to Purchaser hereunder shall represent approximately
70%  of  DTLL's  issued  and  outstanding  Common  Stock.
(b)     Derivative  Securities;  Voting  Agreements.  Except  as  set  forth  in
        -------------------------------------------
Schedule  2.2(b), immediately prior to the Closing, there will be no outstanding
       ---------
options,  warrants,  rights  (including  conversion  or  preemptive  rights)  or
agreements  for  the  purchase  or  acquisition  from  DTLL of any shares of its
capital stock. DTLL is not a party nor subject to any agreement or understanding
     of  any  kind,  and,  to  the  Company's  and  RBL's knowledge, there is no
agreement  or  understanding  of  any  kind between any individual, corporation,
partnership,  limited  liability  company, association, trust or other entity or
organization,  including  a  government or political subdivision or an agency or
instrumentality  thereof  (a  "Person"),  which  affects  or  relates  to  the
acquisition, disposition or voting or giving of written consents with respect to
any  security  of  DTLL.
2.3     Subsidiaries;  Interests  of  the  Company. DTLL has no subsidiaries and
        ------------------------------------------
does  not  currently own or control, directly or indirectly, any interest in any
other  Person.  DTLL,  on  or  before  closing,  shall  form  a new wholly owned
subsidiary,  the  be  named  "RotateBlack  Real  Estate  Ventures".
2.4     Authorization.  This  Agreement  has  been duly authorized, executed and
        -------------
delivered  by  the  Company and RBL and constitutes the legal, valid and binding
obligations  of  the  Company and RBL, enforceable in accordance with its terms,
subject  to (i) applicable bankruptcy, insolvency, reorganization and moratorium
laws,  (ii)  other  laws  of  general  application  affecting the enforcement of
creditors'  rights  generally  and  general  principles  of  equity,  (iii)  the
discretion  of the court before which any proceeding therefor may be brought and
(iv)  the  limitation by federal or state securities laws or by public policy of
rights  to  indemnification.
2.5     Valid  Issuance  of  Common  Stock.  The  Shares,  when issued, sold and
        ----------------------------------
delivered  in  accordance with the terms of this Agreement for the consideration
expressed  herein,  will  be  duly  and  validly  issued,  fully  paid,  and
nonassessable, will not have been issued in violation of any preemptive right of
stockholders  or  rights of first refusal, and Purchaser will have good title to
the  Shares,  free and clear of all liens, security interests, pledges, charges,
encumbrances  and  stockholder  agreements.
2.6     Financial  Statements;  Contracts.  Each of the Company and RBL has made
        ---------------------------------
available  to  Purchaser  the  audited  balance sheet of DTLL as of December 31,
2004, and the related statements of operations and cash flows for the year ended
December  31, 2004, its unaudited balance sheet dated September 30, 2005 and the
related  unaudited  Statements  of  Operation and Cash Flows for the nine months
ended  September 30, 2005 (the "Financial Statements"). The Financial Statements
are  complete  and  correct  and  (i) fairly present the financial condition and
results  of  operations of DTLL as of the dates and during the periods indicated
therein,  subject to adjustments necessary in accordance with generally accepted
accounting principles ("GAAP") and, in the case of interim financial statements,
year-end  adjustments,  (ii)  except  as  noted  therein,  have been prepared in
accordance  with  GAAP  applied  on  a  consistent  basis throughout the periods
involved  and  (iii)  are  in  accordance  with  the  books and records of DTLL.
2.7     Governmental Consents. No consent, approval, order, or authorization of,
        ---------------------
or  registration,  qualification,  designation,  declaration or filing with, any
federal,  state, local or provincial governmental authority on the part of DTLL,
the  Company  or  RBL  is  required  in  connection with the consummation of the
transactions  contemplated by this Agreement. DTLL has complied (and in carrying
out  its  business  DTLL  will  be  in compliance) with all laws, ordinances and
regulations  applicable to it and its business, which the failure to comply with
would,  either  individually or in the aggregate, have a material adverse effect
upon  DTLL.  DTLL  has  obtained  all material federal, state, local and foreign
governmental  licenses  and  permits material to and necessary in the conduct of
its  business,  such  licenses  and  permits  are  in  full force and effect, no
material violations are or have been recorded in respect of any such licenses or
permits,  and no proceeding is pending or, to the best of the Company's or RBL's
knowledge,  threatened  to revoke or limit any thereof. There are no consents or
waivers from such governmental authorities necessary for the consummation of the
transactions  contemplated  by  this  Agreement.
2.8     Litigation. Except as set forth in Schedule 2.8, (i) there is no action,
        ----------                         -------------
suit,  proceeding  or  investigation  pending  or,  to  the  Company's  or RBL's
knowledge,  threatened  against  DTLL or, to the knowledge of the Company or RBL
after  due  inquiry,  its officers (nor, to the Company's or RBL's knowledge, is
there  any  reasonable  basis  therefor); (ii) DTLL (or, to the knowledge of the
Company or RBL, any of its officers after due inquiry) is not a party or subject
to  the  provisions  of  any order, writ, injunction, judgment, or decree of any
court  or  government  agency  or  instrumentality  (other than those of general
applicability);  and (iii) there is no action, suit, proceeding or investigation
involving DTLL or, to the knowledge of the Company or RBL after due inquiry, its
officers  which  such  parties  intend  to  initiate.
2.9     Compliance  with Other Instruments. Neither DTLL, the Company nor RBL is
        ----------------------------------
in violation or default of any provisions of its Certificate of Incorporation or
Bylaws,  as  amended,  or  of  any instrument, judgment, order, writ, decree, or
contract  to  which it is a party or by which it is bound or of any provision of
Federal  or  state statute, rule or regulation, license, or permit applicable to
it,  the  violation  or default of which would have a material adverse effect on
DTLL,  the  Company  or  RBL.  The  execution, delivery, and performance of this
Agreement  and the consummation of the transactions contemplated hereby will not
result  in  any  such  violation  or  be in conflict with or constitute, with or
without  the  passage  of  time and giving of notice, either a default under any
such  provision, instrument, judgment, order, writ, decree, or material contract
or  an  event  which results in the creation of any lien, charge, or encumbrance
upon any assets of DTL, the Company or RBL. Neither the Company nor RBL has  any
knowledge  of  any  termination or material breach or anticipated termination or
material  breach  by the other parties to any material contract or commitment to
which DTLL is a party or to which any of its assets is subject. To the Company's
and  RBL's  knowledge,  there  are  no warranty claims or other uninsured claims
against  DTLL  under completed contracts which might involve a material monetary
liability  which  is  not  reserved  against  in  the  Financial  Statements.
2.10     Title to Property and Assets. DTLL has good and marketable title to its
         ----------------------------
property  and  assets  free  and  clear  of  all  mortgages,  liens,  loans  and
encumbrances, except (i) such encumbrances and liens which arise in the ordinary
course  of  business and do not materially impair DTLL's use of such property or
assets,  (ii)  liens for taxes, assessments and governmental charges not yet due
and  payable, (iii) liens in connection with workers' compensation, unemployment
insurance  or  other  similar obligations and (iv) statutory mechanics, material
liens or other like liens arising in the ordinary course of business not yet due
and  payable.  With  respect  to  the  property and assets it leases, DTLL is in
compliance  in  all material respects with such leases and, to the Company's and
RBL's  knowledge, holds a valid leasehold interest free of any liens, claims, or
encumbrances.  All  DTLL 's properties and assets are, in all material respects,
in  good  operating  and  usable  condition,  subject  to  normal wear and tear.
2.11     Intellectual  Property.
         ----------------------
(a)     As  used  herein,  the  term  "Intellectual  Property  Right"  means any
trademark, service mark, trade name, invention, patent, trade secret, copyright,
     know-how  (including  any registrations or applications for registration of
any  of  the  foregoing)  or  any other similar type of proprietary intellectual
property  right,  in  each  case  which  is  used  or  held for use or otherwise
necessary  in  connection  with  the conduct of the business of DTLL. DTLL owns,
free  and  clear of all liens and encumbrances, all Intellectual Property Rights
necessary  in  connection  with the conduct of its business and has the right to
use  the  foregoing  without  the  payment  of  any  royalty.
(b)     DTLL  has  not been sued nor charged in writing with or been a defendant
in  any  claim, suit, action or proceeding relating to its business that has not
been  finally  terminated  prior to the date hereof and that involves a claim of
infringement  by DTLL of any Intellectual Property Right of any other Person. No
Intellectual  Property  Right  is  subject  to  any outstanding order, judgment,
decree,  stipulation  or  agreement  restricting  the  use  thereof  by  DTLL or
restricting  the  licensing  thereof by DTLL to any Person. DTLL has not entered
into  any  agreement  to  indemnify  any  other  Person  against  any  charge of
infringement  of  any  Intellectual  Property  Right.
(c)     DTLL  has  taken  all reasonable precautions to protect and maintain the
confidentiality  of  all proprietary processes, research and development results
and  other  know-how  of  DTLL,  the  value  of which to DTLL is contingent upon
maintenance  of  the  confidentiality  thereof. All employees and consultants of
DTLL  have  executed  DTLL's  standard  form  of  confidentiality  agreement.
2.12     Compliance  with  Laws;  No  Defaults.
         -------------------------------------
(a)     DTLL  is  not in violation of any provisions of any law or regulation or
in  violation  of  any  judgment,  injunction,  order  or decree binding upon or
applicable  to  DTLL,  except  for  violations  that  have not had and would not
reasonably  be  expected  to  have, individually or in the aggregate, a material
adverse  effect  on  DTLL.
(b)     Neither  DTLL nor any officer, director or employee of DTLL has made any
payment  of  funds  of  DTLL, or purchased any property with funds of DTLL, in a
manner  prohibited  by  law  and no funds of DTLL or property purchased with the
funds  of DTLL have been set aside to be used for any payment prohibited by law.
DTLL  has  not  made,  offered  or  agreed  to  offer  anything  of value to any
government  official,  political party or candidate for political office (or any
person that DTLL knows or has reason to know will offer anything of value to any
such  person)  in  violation  of  the  Foreign Corrupt Practices Act of 1977, as
amended.
(c)     DTLL is not in default, nor has it been notified by any other party that
it  is  in  default,  under any material contract, and, to the best knowledge of
DTLL, no other party to any such contract is in default thereunder. DTLL has not
received  notice  that  any  party to any material contract intends to cancel or
terminate  any  such  agreement.
2.13     Commissions/Finders'  Fees.  There  is  no  investment  banker, broker,
         --------------------------
finder  or other intermediary which has been retained by or is authorized to act
on  behalf  of the Company or RBL who might be entitled to any fee or commission
from  Purchaser, DTLL or any of their respective affiliates upon consummation of
the  transactions  contemplated  by  this  Agreement.
2.14     Tax  and Other Liabilities. All taxes required by law which are due and
         --------------------------
payable  by  DTLL  have  been paid; all taxes DTLL is obligated to withhold from
amounts  owing  to  any  employee or third party have been withheld; and all tax
returns  and  reports  required by law to have been filed by DTLL have been duly
filed  and  reflect  the amounts due and paid. There are in effect no waivers of
applicable  statutes  of  limitations  with  respect  to any taxes, governmental
charges, duties, imports, levies or fees for any year and DTLL has not agreed to
any  extension of time with respect to any tax assessment or deficiency. The tax
returns  of DTLL have not been and are not being audited by the Internal Revenue
Service  for  any of DTLL's tax periods. No tax liens have been asserted against
any  of  DTLL's assets, and any potential assessment or any additional taxes for
periods for which returns have been filed is not expected to exceed the recorded
liability  therefor.
2.15     Securities  Act.  Neither  the  registration  of any security under the
         ---------------
Securities  Act  or  the  securities laws of any state is required in connection
with  the  issuance,  execution  and  delivery  of  the  Shares  in  the  manner
contemplated  hereunder.
2.16     Government  Consents.  The  execution,  delivery and performance by the
         --------------------
Company  and  RBL  of  this  Agreement  and the transactions contemplated hereby
require  no  action  by  or  in  respect  of,  or  filing with, any governmental
authority  other  than  (a)  compliance  with the applicable requirements of the
Securities  Act;  and  (b) compliance with any state securities or Blue Sky Laws
that, individually or in the aggregate, could not reasonably be expected to have
a  material  adverse  effect  on  the  Company.
3.     Representations  and  Warranties  of  Purchaser. Purchaser represents and
       -----------------------------------------------
warrants  to  the  Company  that:
3.1     Organization;  Good  Standing;  Qualification  and  Corporate  Power.
        --------------------------------------------------------------------
(a)     Purchaser  is  a  limited  liability  company  duly  organized,  validly
existing  and  in  good standing under the laws of the State of Michigan and has
all  requisite power and authority to carry on its business as now conducted and
as  proposed  to  be conducted. Purchaser is duly qualified to transact business
and  is in good standing in each jurisdiction in which the failure so to qualify
would  have  a  material  adverse  effect  on  its  business  or  properties.
(b)     Purchaser  has  all requisite legal and corporate power and authority to
execute  and deliver this Agreement, to purchase the Shares and to carry out and
perform  its obligations under the terms of this Agreement and to consummate the
transactions contemplated hereby. All necessary limited liability company action
     has  been  taken  by  Purchaser with respect to the execution, delivery and
performance  by  Purchaser  of  this  Agreement  and  the  consummation  of  the
transactions  contemplated  hereby.
3.2     Authorization.  This  Agreement  has  been duly authorized, executed and
        -------------
delivered  by Purchaser and constitutes the legal, valid and binding obligations
of  Purchaser,  enforceable  in  accordance  with  its  terms,  subject  to  (i)
applicable  bankruptcy,  insolvency,  reorganization  and  moratorium laws, (ii)
other laws of general application affecting the enforcement of creditors' rights
     generally  and  general  principles  of equity, (iii) the discretion of the
court  before  which  any  proceeding  therefor  may  be  brought  and  (iv) the
limitation  by federal or state securities laws or by public policy of rights to
indemnification.
3.3     Commissions/Finders' Fees. There is no investment banker, broker, finder
        -------------------------
or  other  intermediary  which  has  been retained by or is authorized to act on
behalf  of  Purchaser  who  might  be entitled to any fee or commission from the
Company  or its affiliates upon consummation of the transactions contemplated by
this  Agreement.
3.4     Purchase  Entirely  for  Own  Account;  No  Public  Solicitation.  This
        ----------------------------------------------------------------
Agreement  is made with Purchaser in reliance upon Purchaser's representation to
the  Company  that,  and  Purchaser  hereby  represents that, the Shares will be
acquired  for investment for Purchaser's own account, not as a nominee or agent,
and not with a view to the resale or distribution of any part thereof. Purchaser
has no present intention of selling, granting any participation in, or otherwise
distributing  the  Shares  acquired  by  Purchaser.  Purchaser  has no contract,
undertaking,  agreement  or  arrangement with any Person to sell or transfer, or
grant  any  participation to such Person or to any third Person, with respect to
the  Shares  to be acquired by Purchaser. Purchaser is not participating in this
transaction  as  a  result  of  or subsequent to (i) any advertisement, article,
notice  or  other  communication published in any newspaper, magazine or similar
media or broadcast over television, radio or the Internet or (ii) any seminar or
meeting whose attendees have been invited by any general solicitation or general
advertising.
3.5     Disclosure  of  Information.  Purchaser  has  received and has carefully
        ---------------------------
reviewed  a  copy  of  DTLL's  Form  10-K  for  the year ended December 31, 2004
(including  all  of  the  exhibits thereto), DTLL's Financial Statements, DTLL's
Form  10-Q  for the quarter ended  September 30, 2005 and DTLL's current reports
on  Form  8-K.  Purchaser  has  had  an  opportunity to discuss DTLL's business,
management  and  financial  affairs  with  qualified  representatives  of DTLL's
management  and  to ask questions about DTLL's business and prospects. Purchaser
understands  that such discussions, as well as the written information issued by
the  Company,  were intended to describe the aspects of DTLL's business which it
believes to be material and all such questions have been answered to Purchaser's
satisfaction.
3.6     Restricted  Securities.  Purchaser  understands that the Shares have not
        ----------------------
been  registered  under  the Securities Act. The purchase and sale of the Shares
pursuant to this Agreement is being made pursuant to appropriate exemptions from
the  registration and prospectus requirements of the securities rules. Purchaser
understands that the Shares are a "restricted security" under applicable federal
and  state  securities  laws.
3.7     Accredited  Investor. Purchaser is an "accredited investor" as that term
        --------------------
is  defined  in Rule 501(a) of Regulation D promulgated under the Securities Act
and  is an investor familiar with the types of risks inherent in the acquisition
of  the  Shares.  By reason of Purchasers' knowledge and experience in financial
and  business  matters  in  general, and investments of this type in particular,
Purchaser  is capable of evaluating the merits and risks of an investment in the
Shares,  and  can  afford  to bear such risks, including the risks of losing the
entire  investment.
4.     Miscellaneous.
       -------------
4.1     Survival of Warranties. The representations, warranties and covenants of
        ----------------------
     the  Company,  RBL  and  Purchaser  contained  in  or made pursuant to this
Agreement  shall  survive  the  Closing;  provided  that the representations and
warranties  of  the  Company  and  RBL contained in Sections 2.6, 2.7, 2.8, 2.9,
2.11,  2.12,  2.13,  2.14  and  2.16 shall survive for a period of two years (it
being understood that all other representations and warranties shall survive for
the  applicable  statute  of  limitations).
4.2     Successors  and  Assigns.  The  provisions  of  this  Agreement shall be
        ------------------------
binding upon and inure to the benefit of the parties hereto and their respective
successors  and  assigns;  provided that neither the Company nor RBL may assign,
delegate  or  otherwise  transfer  any  of  its rights or obligations under this
Agreement  without  the  consent  of  Purchaser.  Except  as provided under this
Section 5, neither this Agreement nor any provision hereof is intended to confer
upon  any Person other than the parties hereto any rights or remedies hereunder.
4.3     Governing  Law.  This Agreement shall be governed by and construed under
        --------------
the  laws of the State of Illinois, without regard to principles of conflicts of
laws  and  rules  of  such  state.
4.4     Counterparts.  This  Agreement  may  be  executed  in  two  or  more
        ------------
counterparts,  each  of  which  shall  be  deemed  an original, but all of which
        ----
together  shall  constitute  one  and  the  same  instrument.
4.5     Titles  and  Subtitles.  The titles and subtitles used in this Agreement
        ----------------------
are  used  for  convenience  only  and are not to be considered in construing or
interpreting  this  Agreement.
4.6     Notices.  Unless  otherwise  provided,  any notice required or permitted
        -------
under  this  Agreement shall be given in writing and shall be deemed effectively
given (i) upon personal delivery to the party to be notified, (ii) four (4) days
after  deposit  with  the  United States Post Office, by registered or certified
mail, postage prepaid, or (iii) one day after deposit with a reputable overnight
courier  service  and  addressed  to  the  party  to  be notified at the address
indicated  for such party on the signature page hereof, or at such other address
as  such  party  may  designate  by ten (10) days' advance written notice to the
other  parties,  with a copy for Purchaser to April Frisby, Weed & Co and Seller
RBL  to  Connelly  etal.
4.7     Entire  Agreement;  Amendments  and Waivers. This Agreement  constitutes
        -------------------------------------------
the full and entire understanding and agreement among the parties with regard to
the  subjects  hereof.  Any  term  of  this  Agreement  may  be  amended and the
observance of any term of this Agreement may be waived (either generally or in a
particular  instance  and  either retroactively or prospectively), only with the
written  consent  of  the  Company,  RBL  and Purchaser. Any amendment or waiver
effected  in  accordance with this Section 5.7 shall be binding upon each holder
of  any  securities purchased under this Agreement at the time outstanding, each
future  holder  of  all  such  securities,  and  the  Company  and  RBL.
4.8     Severability. If one or more provisions of this Agreement are held to be
        ------------
unenforceable  under  applicable law, such provision shall be excluded from this
Agreement  and  the  balance  of  the  Agreement shall be interpreted as if such
provision  were  so  excluded  and  shall  be enforceable in accordance with its
terms.
4.9     Expenses.  Each party to this Agreement shall pay all costs and expenses
        --------
incurred  by such party with respect to the negotiation, execution, delivery and
performance  of  this  Agreement  and  the  ancillary  documents.
     IN WITNESS WHEREOF, the parties have executed this Agreement as of the date
first  above  written.

PURCHASER:

ISLAND  RESIDENCES  CLUB,  INC

By:  /s/Graham  Bristow
     ------------------
Its:  Director/CEO
      ------------

RICHARD  WOODS

By:  /s/Richard  Woods
     -----------------
Name:  individual
Richard  Woods

SELLER:

ROTATE  BLACK  LLC

By:  /s/John  W.  Paulsen
     --------------------
Name:  John  W.  Paulsen
Its:  Managing  Director

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