FIRST AMENDMENT TO LOAN AND SUBORDINATED DEBENTURE PURCHASE AGREEMENT

Exhibit 10.14

Execution Copy

FIRST AMENDMENT

TO

LOAN AND SUBORDINATED DEBENTURE PURCHASE

BETWEEN

LASALLE BANK NATIONAL ASSOCIATION

AND

PRIVATEBANCORP, INC.

First Amendment dated as of December 12, 2006
Original Loan Agreement dated as of September 29, 2005

Exhibit A — Form of Amended and Restated Revolving Note

Exhibit B — Form of Amended and Restated Subordinated Debenture

Exhibit C — Form of First Amendment to Amended and Restated Pledge Agreement

Exhibit D — Form of First Amendment to Collateral Safekeeping Agreement

Exhibit E — Form of Legal Opinion

FIRST AMENDMENT TO LOAN AND SUBORDINATED DEBENTURE PURCHASE AGREEMENT

     This FIRST AMENDMENT TO LOAN AND SUBORDINATED DEBENTURE PURCHASE AGREEMENT (“First Amendment” ), dated as of December 12, 2006, is entered into by and between PRIVATEBANCORP, INC., a Delaware corporation ( “Borrower”) , and LASALLE BANK NATIONAL ASSOCIATION, a national banking association ( “Lender” ).

R E C I T A L S :

     A. The parties hereto have entered into that certain Loan and Subordinated Debenture Purchase Agreement, dated as of September 29, 2005, as previously amended, restated, supplemented or modified from time to time (the “2005 Loan Agreement” ).

     B. The parties hereto desire to amend and modify the 2005 Loan Agreement in accordance with the terms and subject to the conditions set forth in this First Amendment. As amended and modified by this First Amendment, the 2005 Loan Agreement may be referred to as the “Agreement.”

     C. The parties desire to amend the terms of the 2005 Loan Agreement to (i) extend the Revolving Loan Maturity Date, (ii) increase the Revolving Loan Amount, (iii) extend the Term Loan Maturity Date, (iv) extend the Subordinated Debt Maturity Date, (v) increase and extend the Subordinated Debt Amount, (vi) extend the Sub Debt Funding Expiration Date, and (vii) reflect the pending merger of Borrower with Piedmont Bancshares, Inc. and the resulting acquisition by Borrower of the outstanding capital stock of Piedmont Bank of Georgia. The parties agree to undertake such modifications, and the other modifications described in this First Amendment, in accordance with the terms, subject to the conditions, and in reliance upon the recitals, representations, warranties and covenants set forth herein, in the Agreement, and in the other Loan Documents, irrespective of whether entered into or delivered on or after September 29, 2005.

     D. Capitalized terms used but not otherwise defined in this First Amendment shall have the meanings respectively ascribed to them in the 2005 Loan Agreement.

     NOW, THEREFORE, in consideration of the mutual representations, warranties, covenants, and agreements hereinafter set forth, and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereto hereby agree as follows:

A G R E E M E N T :

      A.  Amendment to Recital “A” of the 2005 Loan Agreement . Recital “A” to the 2005 Loan Agreement is hereby deleted and replaced in its entirety with the following:

     “A. Borrower is a bank holding company that owns 100% of the issued and outstanding capital stock of The PrivateBank and Trust Company, an Illinois state-chartered, non-member bank with its main office located in Chicago, Illinois ( “PrivateBank” ), The PrivateBank, a federal savings bank with its main office located in St. Louis, Missouri ( “PrivateBank St. Louis” ), and The PrivateBank, a Michigan state-chartered, non-member bank with its main office located in Bloomfield Hills, Michigan ( “PrivateBank Michigan" ). Subject to the last sentence of this recital, the banks identified in the immediately preceding sentence may be referred to herein collectively as the “Subsidiary Banks” and individually as a “Subsidiary Bank.” Subject to the last sentence of this recital, the issued and outstanding capital stock of PrivateBank, PrivateBank St. Louis and PrivateBank Michigan may be referred to as the “Pledged Subsidiary Bank Shares” Borrower is a party to that certain Agreement and Plan of Merger, dated as of August 2, 2006, with Piedmont Bancshares, Inc. (as amended, restated, modified or supplemented from time to time, the “Piedmont Merger

      Agreement” ). Upon consummation of the transactions described in the Piedmont Merger Agreement (the “Piedmont Merger” ), Piedmont Bank of Georgia, a Georgia state-chartered, non-member bank with its main office located in Atlanta, Georgia ( “Piedmont Bank” ), wilt be a wholly-owned subsidiary of Borrower. Effective upon consummation of the Piedmont Merger, Piedmont Bank shall be included in the definition “Subsidiary Banks” for all purposes hereunder, and its issued and outstanding capital stock shall be included in the definition of “Pledged Subsidiary Bank Shares” for all purposes hereunder.”

      B.  Amendment to Recital “C of the 2005 Loan Agreement . Recital “C” to the 2005 Loan Agreement is hereby deleted and replaced in its entirety with the following:

     “C. Borrower has requested that Lender provide it with three credit facilities in the aggregate principal amount of $115,000,000 consisting of (a) a term loan (the “Term Loan” ) in the principal amount of $250,000 (the “Term Loan Amount” ), (b) a revolving line-of-credit (the “Revolving Loan” ) in the principal amount of up to $64,750,000 (the “Revolving Loan Amount” ), and (c) subordinated debt (the “Subordinated Debt” ) in the principal amount of up to $50,000,000. The Term Loan and the Revolving Loan may be referred to collectively as the “Senior Loans” and the Senior Loans and the Subordinated Debt may be referred to collectively as the “Loans.”

      C.  Amendments to Section 1.1 of the 2005 Loan Agreement .

     (i) The term “Indentures” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

      “Indenture(s)” means, either collectively or individually, as applicable (a) that certain indenture dated as of December 5, 2005, between Borrower and Wilmington Trust Company, as indenture trustee, (b) that certain indenture dated June 20, 2005, between Borrower and Wilmington Trust Company, and (c) that certain indenture dated May 12, 2004 between Borrower, as successor to BHB, and Wilmington Trust Company, as trustee.”

     (ii) The term “Junior Subordinated Debentures” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

      “Junior Subordinated Debentures” means, either collectively or individually, as applicable (a) the fixed/floating rate junior subordinated debentures, dated December 5, 2005 and due 2035, issued by Borrower, (b) the fixed/floating rate junior subordinated debentures, dated June 20, 2005 and due 2035, issued by Borrower, and (c) the floating rate junior subordinated debentures due 2034 issued by BHB, in each case pursuant to the applicable Indenture.”

     (iii) The term “Revolving Loan Maturity Date” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

“Revolving Loan Maturity Date” means December 31, 2007.”

     (iv) The term “Sub Debt Funding Expiration Date” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

      “Sub Debt Funding Expiration Date” means December 31, 2007.”

     (iv) The term “Subordinated Debt Amount” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

      “Subordinated Debt Amount” means $50,000,000.”

     (v) The term “Subordinated Debt Maturity Date” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

      “Subordinated Debt Maturity Date” means December 31, 2017.”

     (vi) The term “Term Loan Maturity Date” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

      “Term Loan Maturity Date” means December 31, 2017.”

     (vii) The term “Trust(s)” is hereby deleted from Section 1.1 of the 2005 Loan Agreement and replaced in its entirety with the following:

      “Trust(s)” means, collectively or individually, as applicable (a) that certain Delaware statutory business trust known as “PrivateBancorp Stautory Trust III,” which is maintained by Borrower in accordance with that certain Amended and Restated Trust Agreement dated as of December 5, 2005, (b) that certain Delaware statutory business trust known as “PrivateBancorp Statutory Trust II,” which is maintained by Borrower in accordance with that certain Amended and Restated Declaration of Trust dated June 20, 2005, and (c) that certain Delaware statutory business trust known as “Bloomfield Hills Statutory Trust I,” which is maintained by Borrower, as successor to BHB, in accordance with that certain Amended and Restated Declaration of Trust dated May 12, 2004.”

     (viii) Each of the following provisions is hereby added to Section 1.1, and deemed placed in the appropriate alphabetical order:

      “Piedmont Bank” has the meaning ascribed to such term in the recitals hereto.

      “Piedmont Merger” has the meaning ascribed to such term in the recitals hereto.

      “Piedmont Merger Agreement” has the meaning ascribed to such term in the recitals hereto.

      D.  Amendment to Section 4.3.1 of the 2005 Loan Agreement . Section 4.3.1 of the 2005 Loan Agreement is hereby deleted and replaced in its entirety with the following:

“ 4.3.1 The proceeds of the Loans shall be used by the Borrower to fund the cash consideration to be paid by Borrower in connection with the consummation of the Piedmont Merger, for working capital and for general corporate purposes.”

      E.  Representations and Warranties . The Borrower hereby represents and warrants to the Lender as follows:

     (i) No Event of Default or Potential Event of Default has occurred and is continuing (or would result from the amendments contemplated hereby).

     (ii) The execution, delivery and performance by the Borrower of this First Amendment have been duly authorized by all necessary corporate and other action and do not and will not

require any registration with, consent or approval of, or notice to or action by any Person (including any Governmental Agency) in order to be effective and enforceable.

     (iii) This First Amendment and the other Loan Documents (as amended by this First Amendment) constitute the legal, valid and binding obligations of the Borrower, enforceable against the Borrower in accordance with their respective terms.

     (iv) All representations and warranties of the Borrower in the 2005 Loan Agreement (as modified by this First Amendment) are true and correct, except, for the purposes of this First Amendment only, all references in Section 4.4 of the 2005 Loan Agreement to (x) the term “Financial Statements” shall be deemed to refer to “the consolidated financial statements as of and for the year ending December, 31, 2005, and as of and for the nine months ending September 30, 2006, audited in the case of Borrower’s year end financial statements by the Borrower’s certified public accountants.”

     (v) The Borrower’s obligations under the Agreement and under the other Loan Documents are not subject to any defense, counterclaim, set-off, right to recoupment, abatement or other claim.

     (vi) The Piedmont Merger Agreement remains in full force and effect and is identical to the agreement included as Annex A to the proxy statement/prospectus included as part of the Form S-4 filed by Borrower with the SEC. Borrower has not breached, and to the best of Borrower’s knowledge Piedmont has not breached, its obligations under the Piedmont Merger Agreement. All approvals and consents from Governmental Agencies required to be obtained in order for the transactions that are contemplated by the Piedmont Merger Agreement to be consummated have been obtained. The Piedmont Merger is scheduled to be consummated on or before December 31, 2006.

      F.  Conditions . Notwithstanding anything to the contrary contained elsewhere in the Agreement, the obligation of the Lender to extend the Revolving Loan Maturity Date, Term Loan Maturity Date and Subordinated Debt Maturity Date; increase the Revolving Loan Amount and Subordinated Debt Amount, and agree to the other modifications contemplated by this First Amendment, shall be subject to the performance by the Borrower prior to the date on which this First Amendment is executed (the “Amendment Closing Date”) of all of its agreements theretofore to be performed under the Agreement and to the satisfaction of the following conditions precedent. The obligations to continue to make disbursements of proceeds under the Loans are, and shall remain, subject to the conditions precedent in the 2005 Loan Agreement and to the receipt by the Lender of all the following in form and substance satisfactory to the Lender and its counsel, and, where appropriate, duly executed and dated the Amendment Closing Date:

     (i) an amended and restated Revolving Note, substantially in the form of Exhibit A attached hereto;

     (ii) an amended and restated Subordinated Debenture, substantially in the form of Exhibit B attached hereto;

     (iii) an amendment to the Pledge Agreement, substantially in the form of Exhibit C attached hereto;

     (iv) an amendment to the Collateral Safekeeping Agreement, substantially in the form of Exhibit D attached hereto;

     (v) a certificate of good standing of the Borrower, certified by the appropriate governmental official in its jurisdiction of incorporation and dated within the five business days preceding the date hereof;

     (vi) (a) copies, certified by the Secretary or Assistant Secretary of the Borrower, of the (I) resolutions duly adopted by the board of directors of the Borrower (or the appropriate committee thereof) authorizing the execution, delivery and performance of this First Amendment and the other documents to be delivered by the Borrower pursuant to this First Amendment (including the First Amendment, the “Amendment-Related Documents”), and (II) the Bylaws of the Borrower as currently in effect; and (b) a certification by the Secretary or Assistant Secretary of the Borrower that there has been no amendment to the articles of incorporation of the Borrower from and after September 29, 2005, and that the articles of incorporation delivered by the Borrower to the Lender on September 29, 2005, remain in full force and effect; and

     (vii) a written opinion of Vedder, Price, Kaufman & Kammholz, P.C., counsel to the Borrower, addressed to the Lender, substantially in the form of Exhibit E attached hereto.

      G.  Additional Terms .

          (i) Acknowledgment of Indebtedness under Agreement . The Borrower acknowledges and confirms that, as of the date hereof, the Borrower is indebted to the Lender, without defense, setoff, or counterclaim, in the aggregate principal amount of (i) Two Hundred Fifty Thousand and No/100 Dollars ($250,000) under the Term Loan, (ii) Nineteen Million and 00/100 Dollars ($19,000,000) under the Revolving Loan and (iii) Twenty-One Million and No/100 Dollars ($21,000,000) under the Subordinated Debt.

          (ii) The Agreement . All references in the 2005 Loan Agreement to the term “Agreement” shall be deemed to refer to the Agreement referenced in this First Amendment.

          (iii) First Amendment and 2005 Loan Agreement to be Read Together . This First Amendment supplements and is hereby made a part of the 2005 Loan Agreement, and the 2005 Loan Agreement and this First Amendment shall from and after the date hereof be read together and shall constitute the Agreement. Except as otherwise set forth herein, the 2005 Loan Agreement shall remain in full force and effect. :

          (iv) Loan Documents . The term “Loan Documents,” as used in the Agreement, shall from and after the date hereof include the Amendment-Related Documents.

          (v) Counterparts . This First Amendment may be executed by facsimile and in one or more counterparts, each of which shall be deemed an original and all of which taken together shall constitute one and the same document.

          (vi) Acknowledgments . The Borrower acknowledges that (i) it has been advised by counsel of its choice with respect to this First Amendment, the Loan Documents and the transactions contemplated thereby, (ii) each of the waivers set forth herein was knowingly and voluntarily made, and (iii) the obligations of the Lender hereunder shall be strictly construed and shall be expressly subject to the Borrower’s compliance in all respects with the terms and conditions of the Agreement.

          (vii) Delivery of Outstanding Capital Stock of Piedmont Bank: Change of Name . No later than one Business Day following the consummation of the Piedmont Merger, Borrower shall deliver to the Custodian (as defined in the Collateral Safekeeping Agreement) stock certificates issued by Piedmont Bank to Borrower and evidencing all of the outstanding capital stock of Piedmont Bank, together with irrevocable stock powers for each such certificate endorsed by Borrower in blank. Lender acknowledges and agrees that as of (or shortly after) the consummation of the Piedmont Merger, Piedmont Bank will change its name to “The Private Bank.”

          (viii) No Novation . The terms and conditions of the 2005 Loan Agreement and the Notes issued in favor of the Lender thereunder (the “Original Notes”) are amended as set forth in, and superceded and, with respect to the Revolving Note, and Subordinated Debenture, restated in their entirety by, the Agreement as modified by this First Amendment and the Revolving Note and

Subordinated Debenture issued hereunder in favor of the Lender. It is expressly understood and acknowledged that nothing in this First Amendment shall be deemed to cause or otherwise give rise to a novation of the Original Notes. Notwithstanding any provision of this First Amendment, any Amendment-Related Document or any Loan Document to the contrary, the execution and delivery of the restated Revolving Note and Subordinated Debenture pursuant to this First Amendment in favor of the Lender shall be in substitution for, but not in payment of, the Revolving Note and Subordinated Debenture that constitute a part of the Original Notes, respectively. All “Borrower’s Liabilities” under the 2005 Loan Agreement shall in all respects be continuing and this First Amendment shall not be deemed to evidence or result in a novation or repayment and re-borrowing of such “Borrower’s Liabilities.”

[Remainder of Page Intentionally Left Blank]

     IN WITNESS WHEREOF, the parties have executed this First Amendment as of the date first written above.

S-1

EXHIBIT A

FORM OF AMENDED AND RESTATED REVOLVING NOTE

AMENDED AND RESTATED REVOLVING NOTE

      FOR VALUE RECEIVED , the undersigned, PRIVATEBANCORP, INC., a Delaware corporation ( “Borrower” ), promises to pay to the order of LASALLE BANK NATIONAL ASSOCIATION, a national banking association, or the holder hereof from time to time ( “Lender” ), at such place as may be designated in writing by Lender, the principal sum of SIXTY-FOUR MILLION SEVEN HUNDRED FIFTY THOUSAND AND NO/100THS DOLLARS ($64,750,000.00) (or so much thereof that has been advanced and remains outstanding), with interest thereon as hereinafter provided. It is contemplated that there will be advances and payments under this note (this “Note” ) from time to time, but no advances or payments under this Note (including payment in full of the unpaid balance of principal hereof prior to maturity) shall affect or impair the validity or enforceability of this Note as to future advances hereunder. This Note is issued pursuant to the terms of an Amended and Restated Loan and Subordinated Debenture Purchase Agreement of even date herewith by and between Borrower and Lender (said Amended and Restated Loan and Subordinated Debenture Purchase Agreement together with the Agreed Upon Terms and Procedures, as each may be amended, restated, supplemented or modified from time to time, is referred to hereinafter as the “Loan Agreement” ). All capitalized terms used but not defined herein shall have the respective meanings ascribed to them in the Loan Agreement.

     This Note represents a continuation of the indebtedness represented by that certain Revolving Note dated February 11, 2000 made by Borrower to Lender in the original principal amount of $18,000,000, as such note has been amended prior to the date hereof (the “Original Revolving Note”). The Original Revolving Note is amended, restated and replaced by this Note. This Note does not constitute a novation, discharge or satisfaction of the Original Revolving Note replaced hereby or of the indebtedness evidenced by said Original Revolving Note.

     Interest shall accrue on all sums as advanced and outstanding from time to time under this Note and Loan Agreement as set forth in the Loan Agreement. Such interest shall be due and payable, in arrears (i) for any LIBO Rate Tranche, on the last day of each LIBOR Period, and (ii) for any Base Rate Tranche, on the last day of each September, December, March and June, beginning September 30, 2005, and as otherwise set forth in the Loan Agreement.

     The outstanding principal balance of this Note, together with all accrued and unpaid interest, shall be due and payable on the Revolving Loan Maturity Date. Additional principal payments shall be made in accordance with the provisions of the Loan Agreement.

     This Note is issued pursuant to the terms of the Loan Agreement and is secured by and entitled to the benefits of, among other things, the Collateral Documents. In case an Event of Default shall occur and be continuing, the principal of this Note together with all accrued interest thereon may, at the option of the holder hereof, immediately become due and payable on demand; provided, however, that if any document related to this Note provides for automatic acceleration of payment of sums owing hereunder, all sums owing hereunder shall be automatically due and payable in accordance with the terms of that, document.

     Unless otherwise provided in the Loan Agreement, all payments on account of the indebtedness evidenced by this Note shall be first applied to the payment of costs and expenses of Lender which are due and payable, then to past-due interest on the unpaid principal balance and the remainder to principal.

     Provided that no Event of Default then exists, this Note may be prepaid only upon those terms and conditions set forth in the Loan Agreement.

     If any interest payment required hereunder is not received by Lender on or before the tenth day following the date it becomes due, Borrower shall pay, at Lender’s option, a late or collection charge equal to 4% of the amount of such unpaid interest payment.

     From and after the Revolving Loan Maturity Date, or such earlier date as all sums owing on this Note become due and payable by acceleration or otherwise, or after the occurrence of an Event of Default, interest shall be computed on all amounts then due and payable under this Note at a “Default Rate” equal to 2% per annum (based on a 360-day year and charged on the basis of actual days elapsed) in excess of the interest rate otherwise accruing under this Note.

     If any attorney is engaged by Lender to enforce or defend any provision of this Note or any of the other Loan Documents, or as a consequence of any Event of Default, with or without the filing of any legal action or proceeding, then Borrower shall pay to Lender immediately upon demand all attorneys’ fees and expenses, together with interest thereon from the date of such demand until paid at the rate of interest applicable to the principal balance owing hereunder as if such unpaid attorneys’ fees and expenses had been added to the principal.

     No previous waiver and no failure or delay by Lender in acting with respect to the terms of this Note or any of the other Loan Documents shall constitute a waiver of any breach, default or failure of condition under this Note, the Loan Agreement or any of the other Loan Documents or the obligations secured thereby. A waiver of any term of this Note or any of the other Loan Documents or of any of the obligations secured thereby must be made in writing and shall be limited to the express written terms of such waiver. In the event of any inconsistencies between the terms of this Note and the terms of any other document related to the Loan evidenced by this Note, the terms of this Note shall prevail.

     Except as otherwise provided in the Loan Agreement, Borrower expressly waives presentment, demand, notice of dishonor, notice of default or delinquency, notice of acceleration, notice of protest and nonpayment, notice of costs, expenses or losses and interest thereon, notice of late charges, and diligence in taking any action to collect any sums owing under this Note or in proceeding against any of the rights or interests in or to properties securing payment of this Note. In addition, Borrower expressly agrees that this Note and any payment coming due hereunder may be extended from time to time witho