INVESTMENT AGREEMENT

Exhibit 10.1 Execution Copy   INVESTMENT AGREEMENT dated as of August 26, 2008 between Wintrust Financial Corporation and CIVC-WTFC LLC  

TABLE OF CONTENTS

INDEX OF DEFINED TERMS

LIST OF SCHEDULES AND EXHIBITS

      INVESTMENT AGREEMENT, dated as of August 26, 2008 (this " Agreement "), between Wintrust Financial Corporation, an Illinois corporation (the " Company ") and CIVC-WTFC LLC , a Delaware limited liability company (the " Investor "). RECITALS:      A.  The Investment . The Company intends to sell to the Investor, and the Investor intends to purchase from the Company, as an investment in the Company, shares of a series of non-cumulative perpetual convertible preferred stock, no par value, of the Company, having the terms set forth on Exhibit A (the " Convertible Preferred Stock ").      B.  The Securities . The term " Securities " refers collectively to (1) the shares of Convertible Preferred Stock purchased under this Agreement and (2) the shares of Common Stock into which the Convertible Preferred Stock is convertible. When purchased, the Convertible Preferred Stock will be evidenced by a share certificate incorporating the terms set forth in a certificate of designations for the Convertible Preferred Stock in the form attached as Exhibit A (the " Preferred Stock Certificate of Designations ") made a part of the Company’s Amended and Restated Articles of Incorporation, as amended (the " Articles of Incorporation ") by the filing of the Preferred Stock Certificate of Designations with the Secretary of State of the State of Illinois (the " Illinois Secretary ").       NOW, THEREFORE, in consideration of the premises, and of the representations, warranties, covenants and agreements set forth herein, the parties agree as follows: ARTICLE I PURCHASE; CLOSING      1.1 Purchase . On the terms and subject to the conditions set forth herein, the Investor will purchase from the Company, and the Company will sell to the Investor, 50,000 shares of Convertible Preferred Stock.      1.2 Closing .      (a) The closing of the purchase of the Securities referred to in Section 1.1 by the Investor pursuant hereto (the " Closing ") shall occur at 8:30 a.m., Chicago time, on the date hereof, at the offices of Sidley Austin LLP located at One South Dearborn Street, Chicago, Illinois 60603 or such other time or location as agreed by the parties. The date of the Closing is referred to as the " Closing Date ."      (b) At the Closing,      (1) the Company will deliver to the Investor:      (A) a certificate representing the number of shares of Convertible Preferred Stock sold to the Investor as provided in Section 1.1 ;

     (B) the opinion of Sidley Austin LLP, counsel to the Company, addressed to the Investor and dated the Closing Date, to the effect set forth in Exhibit B ;      (2) the Investor will deliver to the Company, by wire transfer of immediately available funds, an amount equal to $50,000,000 (the " Purchase Price "). ARTICLE II REPRESENTATIONS AND WARRANTIES      2.1 Disclosure . (a) On or prior to the date hereof, the Company delivered to the Investor and the Investor delivered to the Company a schedule (a " Disclosure Schedule ") setting forth, among other things, items the disclosure of which is necessary or appropriate either in response to an express disclosure requirement contained in a provision hereof or as an exception to one or more representations or warranties contained in Section 2.2 with respect to the Company, or in Section 2.3 with respect to the Investor, or to one or more covenants contained in Article III.      (b) As used in this Agreement, any reference to any fact, change, circumstance or effect being "material" with respect to the Company means such fact, change, circumstance or effect is material in relation to the business, assets, results of operations or financial condition of the Company and the Company Subsidiaries taken as a whole. As used in this Agreement, the term " Material Adverse Effect " means any circumstance, event, change, development or effect that, individually or in the aggregate, (1) is material and adverse to the business, assets, results of operations or financial condition of the Company and Company Subsidiaries taken as a whole or (2) would materially impair the ability of the Company to perform its obligations under this Agreement or the Preferred Stock Certificate of Designations (collectively with this Agreement, the " Transaction Documents ") or to consummate the Closing; provided , however , that in determining whether a Material Adverse Effect has occurred, there shall be excluded any effect resulting from the following: (A) changes in U.S. generally accepted accounting principles (" GAAP ") or regulatory accounting principles generally applicable to banks, financial holding companies, mortgage originators, savings associations or their holding companies, (B) changes in applicable laws, rules and regulations or interpretations thereof by Governmental Entities, (C) actions or omissions of the Company required or expressly permitted by the terms of this Agreement or taken with the prior written consent of the Investor, (D) changes in general economic, monetary or financial conditions, including changes in prevailing interest rates, credit markets, secondary mortgage market conditions or housing price appreciation/depreciation trends, (E) changes in the market price or trading volumes of the Common Stock or the Company’s other securities (but not the underlying causes of such changes), (F) the failure of the Company to meet any internal or public projections, forecasts, estimates or guidance (including guidance as to "earnings drivers") (but not the underlying causes of such failure), (G) changes in global or national political conditions, including the outbreak or escalation of war or acts of terrorism, and (H) the identity of the Investor or

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the public disclosure of this Agreement or the transactions contemplated hereby except, with respect to clauses (D) and (G), to the extent that the effects of such changes have a disproportionate effect on the Company, taken as a whole, relative to other similarly situated banks, savings associations or their holding companies generally.      (c) " Previously Disclosed " with regard to (1) a party (including the Company) means information set forth on its Disclosure Schedule, provided , however , that disclosure in any section of such Disclosure Schedule shall apply only to the indicated section of this Agreement except to the extent that it is reasonably apparent from the face of such disclosure that such disclosure is relevant to another section of this Agreement, and (2) the Company means information publicly disclosed by the Company in (A) its Annual Report on Form 10-K for the fiscal year ended December 31, 2007, as filed by it with the Securities and Exchange Commission (" SEC ") on February 29, 2008, (B) its Definitive Proxy Statement on Schedule 14A, as filed by it with the SEC on April 25, 2008, (C) its Quarterly Reports on Form 10-Q for the quarterly periods ended March 31, 2008, as filed by it with the SEC on May 12, 2008, or June 30, 2008, as filed by it with the SEC on August 11, 2008 or (D) any Current Report on Form 8-K filed or furnished by it with the SEC since December 31, 2007 and publicly available on EDGAR prior to the date of this Agreement.      2.2 Representations and Warranties of the Company . Except as Previously Disclosed, the Company represents and warrants to the Investor, as of the date of this Agreement (except to the extent made only as of a specified date), that:      (a) Organization and Authority . (1) The Company is a corporation duly organized and validly existing under the laws of the State of Illinois, is duly qualified to do business and is in good standing in all jurisdictions where its ownership or leasing of property or the conduct of its business requires it to be so qualified and where failure to be so qualified would have or reasonably be expected to result in a Material Adverse Effect, and has the corporate power and authority to own its properties and assets and to carry on its business as it is now being conducted. The Company is duly registered as a bank holding company under the Bank Holding Company Act of 1956, as amended (" BHC Act "). The Company has furnished to the Investor true, correct and complete copies of the Articles of Incorporation and bylaws as in effect on the date of this Agreement. The Company is not in violation of any of the provisions of its Articles of Incorporation, bylaws or other organizational or charter documents.      (2) Each Company Significant Subsidiary is duly organized and validly existing under the laws of its jurisdiction of organization, is duly qualified to do business and is in good standing in all jurisdictions where its ownership or leasing of property or the conduct of its business requires it to be so qualified, except in each case where failure to be so qualified, in good standing or validly existing would not have or reasonably be expected to result in a Material Adverse Effect, and has the corporate power and authority to own its properties and assets and to carry on its business as it is being conducted. No Company Significant Subsidiary is in violation of any of the material provisions of its respective

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certificate or articles of incorporation, bylaws or other organizational or charter documents.      (3) The deposit accounts of each Company Bank are insured up to applicable limits by the Federal Deposit Insurance Corporation, and all premiums and assessments required to be paid in connection therewith have been paid when due. The Company does not control, as that term is used in section 2(a)(2) of the BHC Act, 12 U.S.C. s. 1841(a)(2), and defined and interpreted by the Federal Reserve Board under 12 C.F.R. Part 225, any bank, trust company, savings association, or depository institution that is not included as a Company Bank under Section 5.9(d) of this Agreement.      (b) Capitalization . The authorized capital stock of the Company consists of 60,000,000 shares of common stock, no par value per share (the " Common Stock "), and 20,000,000 shares of preferred stock, no par value, of the Company (the " Company Preferred Stock "), of which 100,000 shares have been designated as Junior Serial Preferred Stock A. As of the close of business on August 20, 2008 (the " Capitalization Date "), there were 23,637,725 shares of Common Stock outstanding and no shares of Company Preferred Stock outstanding. As of the close of business on the Capitalization Date, other than (i) issuances, awards or grants outstanding or issuable under the Company’s Directors Deferred Fee and Stock Plan, the Company’s 2007 Stock Incentive Plan and the Company’s 1997 Stock Incentive Plan or the Company’s Employee Stock Purchase Plan, each as amended in respect of which an aggregate of 3,337,607 shares of Common Stock have been reserved for issuance, and (ii) the warrant certificates issued pursuant to that certain Agreement and Plan of Merger by and among the Company, Wayne Hummer Asset Management Company and Lake Forest Capital Management Co., Robert L. Meyers, James P. Richter and S.A. Lincoln dated as of February 4, 2003 (the " Warrants "), in respect of which an aggregate of 19,000 shares of Common Stock have been reserved for issuance, no shares of Common Stock or Company Preferred Stock were reserved for issuance. All of the issued and outstanding shares of Common Stock have been duly authorized and validly issued and are fully paid, nonassessable and free of preemptive or similar rights. No bonds, debentures, notes or other indebtedness having the right to vote on any matters on which the stockholders of the Company may vote (" Voting Debt ") are issued and outstanding. As of the date of this Agreement, except (i) pursuant to any cashless exercise provisions of any Company stock options or pursuant to the surrender of shares to the Company or the withholding of shares by the Company to cover tax withholding obligations under the Benefit Plans, and (ii) as set forth elsewhere in this Section 2.2(b) , the Company does not have and is not bound by any outstanding subscriptions, options, warrants, calls, commitments or agreements of any character calling for the purchase or issuance of, or securities or rights convertible into or exchangeable for, any shares of Common Stock or Company Preferred Stock or any other equity securities of the Company or Voting Debt or any securities representing the right to purchase or otherwise receive any shares of capital stock of the Company (including any rights plan or agreement). The issue and sale of the Securities hereunder will not obligate the Company or any Subsidiary to issue shares of Common Stock or other securities to any person (other than the Investor) and will not result in a right of any holder of Company or Subsidiary securities to adjust or reset the exercise, conversion,

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exchange or purchase price of or under such securities. There are no persons entitled to registration rights or similar rights of the Corporation that would entitle such persons to pre-empt, "piggyback" or participate in the registration contemplated by Section 4.7 .      (c) Company’s Subsidiaries . The Company owns, directly or indirectly, all of the issued and outstanding shares of capital stock of and all other equity interests in each of the Company Significant Subsidiaries, free and clear of any material liens, charges, rights of first refusal, adverse rights or claims, pledges, covenants, title defects, security interests and other material encumbrances of any kind other than those accruing to the benefit of, or initiated by, the Investor or any of its Affiliates (" Liens "), and all of such shares or equity interests are duly authorized and validly issued and are fully paid, nonassessable and free of preemptive rights. No Company Subsidiary has or is bound by any outstanding subscriptions, options, warrants, calls, commitments or agreements of any character calling for the purchase or issuance of any shares of capital stock, any other equity security or any Voting Debt of such Company Subsidiary or any securities representing the right to purchase or otherwise receive any shares of capital stock, any other equity security or Voting Debt of such Company Subsidiary.      (d) Authorization . (1) The Company has the corporate power and authority to enter into this Agreement and to carry out its obligations under the Transaction Documents. The execution, delivery and performance of this Agreement by the Company and the consummation of the transactions contemplated by the Transaction Documents have been duly authorized by the board of directors of the Company (the " Board of Directors "). This Agreement has been duly and validly executed and delivered by the Company and, assuming due authorization, execution and delivery by the Investor, is a valid and binding obligation of the Company enforceable against the Company in accordance with its terms (except as enforcement may be limited by applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer and similar laws of general applicability relating to or affecting creditors’ rights or by general equity principles). No other corporate proceedings (including any shareholder approval) are necessary for the execution and delivery by the Company of this Agreement, the performance by it of its obligations under the Transaction Documents or the consummation by it of the transactions contemplated thereby.      (2) Neither the execution and delivery by the Company of the Transaction Documents, nor the consummation of the transactions contemplated thereby, nor compliance by the Company with any of the provisions thereof (including, without limitation, the conversion provisions of the Convertible Preferred Stock), will (A) violate, conflict with, or result in a breach of any provision of, or constitute a default (or an event which, with notice or lapse of time or both, would constitute a default) under, or result in the termination of, or result in the loss of any benefit or creation of any right on the part of any third party under, or accelerate the performance required by, or result in a right of termination or acceleration of, or result in the creation of any Lien upon any of the material properties or assets of the Company or any Company Subsidiary under any of the terms, conditions or provisions of (i) its Articles of Incorporation or bylaws (or similar governing documents) or the charter, bylaws or other

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governing instrument of any Company Significant Subsidiary or (ii) any note, bond, mortgage, indenture, deed of trust, license, lease, agreement or other instrument or obligation to which the Company or any Company Significant Subsidiary is a party or by which it may be bound, or to which the Company or any Company Significant Subsidiary or any of the properties or assets of the Company or any Company Subsidiary may be subject, or (B) subject to compliance with the statutes and regulations referred to in Section 2.2(e) , violate any law, statute, ordinance, rule, regulation, permit, concession, grant, franchise or any judgment, ruling, order, writ, injunction or decree applicable to the Company or any Company Subsidiary or any of their respective properties or assets except in the case of clauses (A)(ii) and (B) for such violations, conflicts and breaches as would not, individually or in the aggregate, have or reasonably be expected to result in a Material Adverse Effect.      (e) Governmental Consents . Other than the securities or blue sky laws of the various states, no material notice to, registration, declaration or filing with, exemption or review by, or authorization, order, consent or approval of, any Governmental Entity, or expiration or termination of any statutory waiting period, is necessary for the consummation by the Company of the transactions contemplated by the Transaction Documents.      (f) Financial Statements . Each of the consolidated balance sheets of the Company and the Company Subsidiaries and the related consolidated statements of income, stockholders’ equity and cash flows, together with the notes thereto (collectively, the " Company Financial Statements "), included in any Company Report filed with the SEC prior to the date of this Agreement, (1) have been prepared from, and are in accordance with, the books and records of the Company and the Company Subsidiaries, (2) complied, as of their respective date of filing with the SEC, in all material respects with applicable accounting requirements and with the published rules and regulations of the SEC with respect thereto, (3) have been prepared, in all material respects, in accordance with GAAP applied on a consistent basis during the periods involved and (4) present fairly, in all material respects, the consolidated financial position of the Company and the Company Subsidiaries as of and for the dates set forth therein and the consolidated results of operations, changes in stockholders’ equity and cash flows of the Company and the Company Subsidiaries for the periods stated therein, subject, in the case of any unaudited financial statements, to normal recurring year-end audit adjustments and the lack of footnotes. The independent auditors who examined or audited the Company Financial Statements are independent public accountants with respect to the Company and its Subsidiaries within the meaning of Rule 101 of the AICPA’s Code of Professional Conduct and its interpretations and rulings.      (g) Reports . (1) Since December 31, 2005, the Company and each Company Subsidiary has timely filed all material reports, registrations, documents, filings, statements and submissions, together with any amendments thereto, that it was required to file with any Governmental Entity (the foregoing, collectively, the " Company Reports ") and has paid all fees and assessments due and payable in connection therewith. As of their respective dates of filing, the Company Reports complied in all material

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respects with all statutes and applicable rules and regulations of the applicable Governmental Entities. To the knowledge of the Company, as of the date of this Agreement, there are no outstanding comments from the SEC or any other Governmental Entity with respect to any Company Report. In the case of each such Company Report filed with or furnished to the SEC, such Company Report did not, as of its date or if amended prior to the date of this Agreement, as of the date of such amendment, contain an untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary in order to make the statements made in it, in light of the circumstances under which they were made, not misleading and complied in all material respects with the applicable requirements of the Securities Act of 1933, as amended (the " Securities Act ") and the Securities Exchange Act of 1934, as amended (the " Exchange Act "). With respect to all other Company Reports, the Company Reports were complete and accurate in all material respects as of their respective dates. No executive officer of the Company or any Company Subsidiary has failed in any respect to make the certifications required of him or her under Section 302 or 906 of the Sarbanes-Oxley Act of 2002.      (2) The records, systems, controls, data and information of the Company and the Company Subsidiaries are recorded, stored, maintained and operated under means (including any electronic, mechanical or photographic process, whether computerized or not) that are under the exclusive ownership and direct control of the Company or the Company Subsidiaries or their accountants (including all means of access thereto and therefrom), except for any non-exclusive ownership and non-direct control that would not have or reasonably be expected to result in a material adverse effect on the system of internal accounting controls described below in this Section 2.2(g) . The Company (A) has implemented and maintains disclosure controls and procedures (as defined in Rule 13a-15(e) of the Exchange Act) to ensure that material information relating to the Company, including the consolidated Company Subsidiaries, is made known to the chief executive officer and the chief financial officer of the Company by others within those entities, and (B) has disclosed, based on its most recent evaluation prior to the date hereof, to the Company’s outside auditors and the audit committee of the Board of Directors (x) any significant deficiencies and material weaknesses in the design or operation of internal controls over financial reporting (as defined in Rule 13a-15(f) of the Exchange Act) that are reasonably likely to adversely affect the Company’s ability to record, process, summarize and report financial information and (y) any fraud, whether or not material, that involves management or other employees who have a significant role in the Company’s internal controls over financial reporting. Since December 31, 2006 and until the date of this Agreement, (A) neither the Company nor any Company Subsidiary nor, to the knowledge of the Company, any director, officer, employee, auditor, accountant or representative of the Company or any Company Subsidiary has received or otherwise had or obtained knowledge of any material complaint, allegation, assertion or claim, whether written or oral, regarding the accounting or auditing practices, procedures, methodologies or methods of the Company or any Company Subsidiary or their respective internal accounting controls, including any material complaint, allegation, assertion or claim that the

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Company or any Company Subsidiary has engaged in questionable accounting or auditing practices and (B) no attorney representing the Company or any Company Subsidiary, whether or not employed by the Company or any Company Subsidiary, has reported evidence of a material violation of securities laws, breach of fiduciary duty or similar violation by the Company or any of its officers, directors, employees or agents to the Board of Directors or any committee thereof or to any director or officer of the Company.      (h) Properties and Leases . Except as (1) would not have or (2) would not reasonably be expected to have a Material Adverse Effect, the Company and the Company Subsidiaries have good and marketable title to all real properties and all other properties and assets owned by them, in each case free from Liens that would affect the value thereof or interfere with the use made or to be made thereof by them. Except as (1) would not have or (2) would not reasonably be expected to have a Material Adverse Effect, the Company and the Company Subsidiaries hold all leased real or personal property under valid and enforceable leases, of which they are in compliance, and with no exceptions that would interfere with the use made or to be made thereof by them.      (i) Taxes . (1) Each of the Company and the Company Subsidiaries has (x) duly and timely filed (including pursuant to applicable extensions granted without penalty) all material Tax Returns required to be filed by it and (y) paid in full all material Taxes due or made adequate provision in the financial statements of the Company (in accordance with GAAP) for any such Taxes, whether or not shown as due on such Tax Returns; (2) no material deficiencies for any Taxes have been proposed, asserted or assessed in writing against or with respect to any Taxes due by or Tax Returns of the Company or any of the Company Subsidiaries which deficiencies have not since been resolved, except for Taxes proposed, asserted or assessed that are being contested in good faith by appropriate proceedings and for which reserves adequate in accordance with GAAP have been provided; and (3) there are no material Liens for Taxes upon the assets of either the Company or the Company Subsidiaries except for statutory Liens for current Taxes not yet due or Liens for Taxes that are being contested in good faith by appropriate proceedings and for which reserves adequate in accordance with GAAP have been provided. None of the Company or any of the Company Subsidiaries has been a "distributing corporation" or a "controlled corporation" in any distribution occurring during the last two years in which the parties to such distribution treated the distribution as one to which Section 355 of the Internal Revenue Code of 1986, as amended (the " Code ") is applicable. None of the Company or any Company Subsidiary has engaged in any transaction that is a "listed transaction" for federal income tax purposes within the meaning of Treasury Regulations section 1.6011-4, which has not yet been the subject of an audit. For purposes of this Agreement, " Taxes " shall mean all taxes, charges, levies, penalties or other assessments imposed by any United States federal, state, local or foreign taxing authority, including any income, excise, property, sales, transfer, franchise, payroll, withholding, social security or other taxes, together with any interest or penalties attributable thereto, and any payments made or owing to any other person measured by such taxes, charges, levies, penalties or other assessment, whether pursuant to a tax indemnity agreement, tax sharing payment or otherwise (other than pursuant to commercial agreements or Benefit Plans). For purposes of this Agreement, " Tax Return "

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shall mean any return, report, information return or other document (including any related or supporting information) required to be filed with any taxing authority with respect to Taxes, including without limitation all information returns relating to Taxes of third parties, any claims for refunds of Taxes and any amendments or supplements to any of the foregoing.      (j) Absence of Certain Changes . Since December 31, 2007 until the date hereof, (1) the Company and the Company Subsidiaries have conducted their respective businesses in all material respects in the ordinary course, consistent with prior practice, (2) except (A) for any publicly disclosed ordinary dividends on the Common Stock, (B) pursuant to any cashless exercise provisions of any Company stock options or pursuant to the surrender of shares to the Company or the withholding of shares by the Company to cover tax withholding obligations under the Benefit Plans, and (C) for any repurchases of Common Stock under announced repurchase programs, the Company has not made or declared any distribution in cash or in kind to its stockholders or issued or repurchased any shares of its capital stock or other equity interests and (3) no event or events have occurred that has had or would reasonably be expected to result in a Material Adverse Effect.      (k) No Undisclosed Liabilities . Neither the Company nor any of the Company Subsidiaries has any material liabilities or obligations of any nature (absolute, accrued, contingent or otherwise) which are not properly reflected or reserved against in the Company Financial Statements to the extent required to be so reflected or reserved against in accordance with GAAP, except for (1) liabilities that have arisen since December 31, 2007 in the ordinary course of business or of a nature and amount consistent with past practice and (2) contractual liabilities under (other than liabilities arising from any breach or violation of) agreements Previously Disclosed or not required by this Agreement to be so disclosed.      (l) Commitments and Contracts . The Company has Previously Disclosed or provided or made available to the Investor or its representatives true, correct and complete copies of, each contract or agreement that is a "material contract" (as such term is defined in Item 601(b)(10) of Regulation S-K under the Securities Act) to which the Company or any Company Significant Subsidiary is a party or subject (each, a " Company Significant Agreement "). (i) Each of the Company Significant Agreements is valid and binding on the Company and the Company Significant Subsidiaries, as applicable, and in full force and effect; (ii) the Company and each of the Company Significant Subsidiaries, as applicable, are in all material respects in compliance with and have in all material respects performed all obligations required to be performed by them to date under each Company Significant Agreement; and (iii) as of the date hereof, to the Company’s knowledge, neither the Company nor any of the Company Significant Subsidiaries has received notice of any material violation or default (or any condition which with the passage of time or the giving of notice would cause such a violation of or a default) by any party under any Company Significant Agreement.      (m) Offering of Securities . Neither the Company nor any person acting on its behalf has taken any action (including any offering of any securities of the Company

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under circumstances which would require the integration of such offering with the offering of any of the Securities to be issued pursuant to this Agreement under the Securities Act, and the rules and regulations of the SEC promulgated thereunder) which might subject the offering, issuance or sale of any of the Securities to the Investor pursuant to this Agreement to the registration requirements of the Securities Act.      (n) Status of Securities . The Preferred Stock Certificate of Designations is being concurrently filed with the Secretary of State of the State of Illinois in accordance with the Illinois Business Corporation Act. The shares of Convertible Preferred Stock have been duly authorized by all necessary corporate action. When issued and sold against receipt of the consideration therefor as provided in this Agreement, such shares of Convertible Preferred Stock will be validly issued, fully paid and nonassessable and will not be subject to any Liens or preemptive or similar rights of any other stockholder of the Company. The shares of Common Stock issuable upon the conversion of the Convertible Preferred Stock have been duly authorized by all necessary corporate action and when so issued upon such conversion or exercise will be validly issued, fully paid and nonassessable, will not be subject to any Liens or subject the holders thereof to personal liability and will not be subject to preemptive or similar rights of any other stockholder of the Company.      (o) Litigation and Other Proceedings . There is no pending or, to the knowledge of the Company, threatened, claim, action, suit, investigation or proceeding, against the Company or any Company Subsidiary or to which any of their assets are subject, nor is the Company or any Company Subsidiary subject to any order, judgment or decree, in each case except as are disclosed in the Company reports filed with the SEC or which are not required to be disclosed pursuant to the Securities Act or the Exchange Act, or the rules and regulations promulgated thereunder. Except as are disclosed in the Company reports filed with the SEC or which are not required to be disclosed pursuant to the Securities Act or the Exchange Act, or the rules and regulations promulgated thereunder, there is no unresolved violation, criticism or exception by any Governmental Entity with respect to any report or relating to any examinations or inspections of the Company or any Company Subsidiaries.      (p) Compliance with Laws. The Company and each Company Subsidiary have all material permits, licenses, franchises, authorizations, orders and approvals of, and have made all filings, applications and registrations with, Governmental Entities that are required in order to permit them to own or lease their properties and assets and to carry on their business as presently conducted and that are material to the business of the Company or such Company Subsidiary. The Company and each Company Subsidiary has complied in all material respects and is not in default or violation in any respect of, and none of them is, to the knowledge of the Company, under investigation with respect to or, to the knowledge of the Company, has been threatened to be charged with or given notice of any material violation of, any applicable material domestic (federal, state or local) or foreign law, statute, ordinance, license, rule, regulation, policy or guideline, order, demand, writ, injunction, decree or judgment of any Governmental Entity, other than such noncompliance, defaults or violations that would not have or reasonably be expected to result in a Material Adverse Effect. Except for statutory or regulatory

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restrictions of general application, no Governmental Entity has placed any material restriction on the business or properties of the Company or any Company Subsidiary.      (q) Risk Management Instruments . Except as has not had or would not reasonably be expected to result in a Material Adverse Effect, all material derivative instruments, including, swaps, caps, floors and option agreements, whether entered into for the Company’s own account, or for the account of one or more of the Company Subsidiaries, were entered into (1) only in the ordinary course of business, (2) in accordance with prudent practices and in all material respects with all applicable laws, rules, regulations and regulatory policies and (3) with counterparties believed to be financially responsible at the time; and each of them constitutes the valid and legally binding obligation of the Company or one of the Company Subsidiaries, enforceable in accordance with its terms, except as may be limited by applicable bankruptcy, insolvency, fraudulent transfer, moratorium or other laws relating to or affecting the enforcement of creditors’ rights generally or by general equitable principles. Neither the Company or the Company Subsidiaries, nor, to the knowledge of the Company, any other party thereto, is in material breach of any of its obligations under any such agreement or arrangement.      (r) Anti-takeover Provisions Not Applicable . The Board of Directors has taken all necessary action to ensure that the transactions contemplated by the Transaction Documents and any of the transactions contemplated thereby will be deemed to be exceptions to the provisions of Section 11.75 of the Illinois Business Corporation Act, and that any other similar "moratorium," "control share," "fair price," "takeover" or "interested stockholder" law does not and will not apply to this Agreement or to any of the transactions contemplated by the Transaction Documents.      (s) Brokers and Finders . Neither the Company nor any Company Subsidiary nor any of their respective officers, directors, employees or agents has employed any broker or finder or incurred any liability for any financial advisory fees, brokerage fees, commissions or finder’s fees, and no broker or finder has acted directly or indirectly for the Company or any Company Subsidiary, in connection with this Agreement or the transactions contemplated hereby.      (t) Registration Exemption . Based, in part, upon the representations and warranties of the Investor contained in Section 2.3(c) , the Company is not required by applicable law or regulation in connection with the offer, sale and delivery of the Securities to the Investor in the manner contemplated by this Agreement to register the Securities under the Securities Act or any state securities laws.      (u) Agreements with Regulatory Agencies . Neither the Company nor any Company Subsidiary is subject to any cease-and-desist or other similar order or enforcement action issued by, or is a party to any written agreement, consent agreement or memorandum of understanding with, or is a party to any commitment letter or similar undertaking to, or is subject to any capital directive by, or since December 31, 2006, has adopted any board resolutions at the request of, any Governmental Entity that currently restricts in any material respect the conduct of its business or that in any material manner

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relates to its capital adequacy, its liquidity and funding policies and practices, its ability to pay dividends, its credit, risk management or compliance policies, its internal controls, its management or its operations or business (each item in this sentence, a " Regulatory Agreement "), nor has the Company or any Company Subsidiary been advised since December 31, 2006 and until the date hereof by any Governmental Entity that it is considering issuing, initiating, ordering, or requesting any such Regulatory Agreement. The Company and each Company Subsidiary are in compliance in all material respects with each Regulatory Agreement to which it is party or subject, and neither the Company nor any Company Subsidiary has received any notice from any Governmental Entity indicating that either the Company or any Company Subsidiary is not in compliance in all material respects with any such Regulatory Agreement. Neither the Company nor any of the Company Banks have, during the Company’s ownership of such Company Banks, been notified by any Governmental Authority that it is in "Troubled Condition" as defined in 12 C.F.R. 225.71(d); 12 C.F.R. 5.51(c)(6); or 12 C.F.R. 303.101(c). The Company and each Company Bank is "Well Managed" as defined in 12 C.F.R. 5.34(d)(3); 12 C.F.R. 225.2(s); 12 C.F.R. 208.77(h); and 12. C.F.R. 362.17(e), respectively.      (v) Mortgage Banking Business . To the knowledge of the Company (which solely for purposes of this Section 2.2(v) shall include the officer of the Company in charge of the Company’s mortgage banking business), and except as has not had and would not reasonably be expected to have a Material Adverse Effect: (1) The Company and each Company Subsidiary has complied with, and all documentation in connection with the origination, processing, underwriting and credit approval of any mortgage loan originated, purchased or serviced by the Company or any Company Subsidiary satisfied, (A) all applicable federal, state and local laws, rules and regulations with respect to the origination, insuring, purchase, sale, pooling, servicing, subservicing, or filing of claims in connection with mortgage loans, including all laws relating to real estate settlement procedures, consumer credit protection, truth in lending laws, usury limitations, fair housing, transfers of servicing, collection practices, equal credit opportunity and adjustable rate mortgages, (B) the responsibilities and obligations relating to mortgage loans set forth in any agreement between the Company or any Company Subsidiary and any Agency, Loan Investor or Insurer, (C) the applicable rules, regulations, guidelines, handbooks and other requirements of any Agency, Loan Investor or Insurer and (D) the terms and provisions of any mortgage or other collateral documents and other loan documents with respect to each mortgage loan; and (2) Except as Previously Disclosed, no Agency, Loan Investor or Insurer has (A) claimed in writing that the Company or any Company Subsidiary has violated or has not complied with the applicable underwriting standards with respect to mortgage loans sold by the Company or any Company Subsidiary to a Loan Investor or Agency, or with respect to any sale of mortgage servicing rights to a Loan Investor, (B) imposed in writing restrictions on the activities (including commitment authority) of the Company or any Company Subsidiary or (C)

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indicated in writing to the Company or any Company Subsidiary that it has terminated or intends to terminate its relationship with the Company or any Company Subsidiary for poor performance, poor loan quality or concern with respect to the Company’s or any Company Subsidiary’s compliance with laws. For purposes of this Section 2.2(v) : (A) " Agency " shall mean the Federal Housing Administration, the Federal Home Loan Mortgage Corporation, the Federal National Mortgage Association, the Government National Mortgage Association, or any other federal or state agency with authority to (i) authority to determine any investment, origination, lending or servicing requirements with regard to mortgage loans originated, purchased or serviced by the Company or any Company Subsidiary or (ii) originate, purchase, or service mortgage loans, or otherwise promote mortgage lending, including without limitation state and local housing finance authorities. (B) " Loan Investor " shall mean any person (including an Agency) having a beneficial interest in any mortgage loan originated, purchased or serviced by the Company or any Company Subsidiary or a security backed by or representing an interest in any such mortgage loan; and (C) " Insurer " means a person who insures or guarantees for the benefit of the mortgagee all or any portion of the risk of loss upon borrower default on any of the mortgage loans originated, purchased or serviced by the Company or any Company Subsidiary, including, the Federal Housing Administration, the United States Department of Veterans’ Affairs, the Rural Housing Service of the U.S. Department of Agriculture and any private mortgage insurer, and providers of hazard, title or other insurance with respect to such mortgage loans or the related collateral. (w) Credit Reporting . (1) The Company has provided Investor with a true and complete list of (A) all Past Due, nonaccrual, and restructured loans of $5 million or more made by the Company or any Company Bank as of June 30, 2008, and (B) any loan of $5 million or more that would be graded "substandard," "doubtful" or "loss" in connection with a state or federal bank inspection or bank holding company inspection, and have duly reported all Past Due loans, nonaccrual loans, and restructured loans on Schedule RC-N of form FFIEC 031 or 041, as applicable, as of June 30, 2008. (2) Neither the Company nor any of the Company Banks are under an order, directive, or request in any form from any federal or state banking agency to increase the provision to the ALLL for any current reporting period or any other or reporting period ended during the previous twelve (12) months. (3) The Company and the Company Banks have developed and implemented a loan review system that meets in all material respects the applicable standards of

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the federal banking agencies that are the primary regulators for each of them as defined in the Interagency Policy Statement on the Allowance for Loan and Lease Losses, Attachment 1.      2.3 Representations and Warranties of the Investor . Except as Previously Disclosed, the Investor hereby represents and warrants to the Company, as of the date of this Agreement, that:      (a) Organization and Authority . The Investor is duly organized, validly existing and in good standing under the laws of the jurisdiction of its organization, is duly qualified to do business and is in good standing in all jurisdictions where its ownership or leasing of property or the conduct of its business requires it to be so qualified and where failure to be so qualified would be reasonably expected to materially and adversely affect the Investor’s ability to perform its obligations under this Agreement or consummate the transactions contemplated hereby on a timely basis, and the Investor has the corporate or other power and authority and governmental authorizations to own its properties and assets and to carry on its business as it is now being conducted.      (b) Authorization . (1) The Investor has the corporate or other power and authority to enter into this Agreement and to carry out its obligations hereunder. The execution, delivery and performance of this Agreement by the Investor and the consummation of the transactions contemplated hereby have been duly authorized by the Investor’s board of directors, general partner or managing members, as the case may be, and no further approval or authorization by any of its partners or other equity owners, as the case may be, is required. This Agreement has been duly and validly executed and delivered by the Investor and assuming due authorization, execution and delivery by the Company, is a valid and binding obligation of the Investor enforceable against the Investor in accordance with its terms (except as enforcement may be limited by applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer and similar laws of general applicability relating to or affecting creditors’ rights or by general equity principles).      (2) Neither the execution, delivery and performance by the Investor of this Agreement, nor the consummation of the transactions contemplated hereby, nor compliance by the Investor with any of the provisions hereof, will (A) violate, conflict with, or result in a breach of any provision of, or constitute a default (or an event which, with notice or lapse of time or both, would constitute a default) under, or result in the termination of, or accelerate the performance required by, or result in a right of termination or acceleration of, or result in the creation of any Lien upon any of the properties or assets of the Investor under any of the terms, conditions or provisions of (i) its certificate of limited partnership or partnership agreement or similar governing documents or (ii) any note, bond, mortgage, indenture, deed of trust, license, lease, agreement or other instrument or obligation to which the Investor is a party or by which it may be bound, or to which the Investor or any of the properties or assets of the Investor may be subject, or (B) subject to compliance with the statutes and regulations referred to in the next paragraph, violate any law, statute, ordinance, rule or regulation,

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permit, concession, grant, franchise or any judgment, ruling, order, writ, injunction or decree applicable to the Investor or any of its properties or assets except in the case of clauses (A)(ii) and (B) for such violations, conflicts and breaches as would not reasonably be expected to materially and adversely affect the Investor’s ability to perform its respective obligations under this Agreement or consummate the transactions contemplated hereby on a timely basis.      (3) Other than the securities or blue sky laws of the various states, no notice to, registration, declaration or filing with, exemption or review by, or authorization, order, consent or approval of, any Governmental Entity, nor expiration or termination of any statutory waiting period, is necessary for the consummation by the Investor of the transactions contemplated by this Agreement.      (c) Purchase for Investment . The Investor acknowledges that the Securities have not been registered under the Securities Act or under any state securities laws and are "restricted securities" within the meaning of Rule 144 and may not be sold, transferred or otherwise disposed of without registration under the Securities Act or an exemption therefrom and acknowledges that each certificate evidencing the Convertible Preferred Stock and shares of Common Stock issuable upon conversion thereof will bear a legend to the effect set forth in Section 4.3 . The Investor (1) is acquiring the Securities pursuant to an exemption from registration under the Securities Act solely for investment with no present intention to distribute any of the Securities to any person, without prejudice, however, to the Investor’s right at all times to sell or otherwise dispose of all or any part of such Securities in compliance with applicable federal and state securities laws (and, subject to this sentence and the provisions of Section 4.2 , nothing contained herein shall be deemed a representation or warranty by the Investor to hold any Securities for any period of time), (2) will not sell or otherwise dispose of any of the Securities, except in compliance with the registration requirements or exemption provisions of the Securities Act and any other applicable securities laws, (3) has such knowledge and experience in financial and business matters and in investments of this type that it is capable of evaluating the merits and risks of its investment in the Securities and of making an informed investment decision, and (4) is an "accredited investor" (as that term is defined by Rule 501 of the Securities Act).      (d) Ownership . As of the date of this Agreement, neither the Investor nor any of its Affiliates are the owners of record or the Beneficial Owners of shares of Common Stock or securities convertible into or exchangeable for Common Stock other than as specified in Schedule 2.3(d).      (e) Brokers and Finders . Neither the Investor nor its Affiliates, any of their respective officers, directors, employees or agents has employed any broker or finder or incurred any liability for any financial advisory fees, brokerage fees, commissions or finder’s fees, and no broker or finder has acted directly or indirectly for the Investor, in connection with this Agreement or the transactions contemplated hereby.

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ARTICLE III COVENANTS      3.1 Other Actions .      The Investor, on the one hand, and the Company, on the other hand, will cooperate and consult with the other and use reasonable best efforts to perform the covenants contemplated by this Agreement. Each party shall execute and deliver both before and after the Closing such further certificates, agreements and other documents and take such other actions as the other parties may reasonably request to consummate or implement such transactions or to evidence such events or matters.      3.2 Access, Information and Confidentiality .      (a) From the date hereof, until the date when the Investor holds less than 50% of the Convertible Preferred Stock or Common Stock into which shares of Convertible Preferred Stock owned by the Investor are convertible (the " Qualifying Ownership Interest "), the Company will permit the Investor to visit and inspect, at the Investor’s expense, the prope