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EXHIBIT 10.10




AMENDED AND RESTATED

PLEDGE AND SECURITY AGREEMENT




     This
AMENDED AND RESTATED PLEDGE AND SECURITY AGREEMENT (the
“Pledge Agreement”) dated as of
May 29, 2005, is made by WINTRUST FINANCIAL CORPORATION, an Illinois corporation (the “Pledgor”),
whose address is 727 North Bank Lane, Lake Forest, Illinois 60045, for the benefit of LASALLE BANK
NATIONAL ASSOCIATION, a national banking association (the “Bank”), whose address is 135 South
LaSalle Street, Chicago, Illinois 60603.



RECITALS:




     WHEREAS
the Pledgor is the owner of the capital stock of each subsidiary listed on Exhibit A
hereto (each is referred to herein as a “Subsidiary” and collectively as the “Subsidiaries”);



     WHEREAS, the capital stock of the Subsidiaries owned by the Pledgor constitutes 100% of the
issued and outstanding capital stock of the Subsidiaries;



     WHEREAS, the Pledgor has had a continuing borrowing relationship with the Bank, has heretofore
pledged the capital stock of the Subsidiaries, is about to enter into a Third Amendment to Second
Amended and Restated Loan Agreement (the “Loan Agreement”) and desires to amend and restate the
Pledge and Security Agreement;



     WHEREAS, the Pledgor has agreed to continue to provide security for, the loan contemplated in
the Loan Agreement in accordance with the terms of this Pledge Agreement.



     NOW, THEREFORE, in order to induce the Bank to make the loan contemplated in the Loan Agreement and
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:



AGREEMENT




     1. Grant of Security Interest. To secure the Obligations (as defined below), the
Pledgor hereby pledges and grants to the Bank a security interest in and transfers and delivers to
the Bank the following: (a) the number of shares of capital stock of each of the Subsidiaries set
forth on Exhibit A hereto, which constitute one hundred percent (100%) of the issued and
outstanding capital stock of the Subsidiaries, including all substitutions of, and additions to,
such stock; (b) executed and undated stock powers for the capital stock described in (a) above, in
form and content satisfactory to the Bank duly executed in blank, containing all requisite federal
and state stock transfer tax stamps, if any (the items described in (a) and (b) above may
collectively be referred to as the “Pledged Stock”); (c) all income and profits therefrom, all
distributions thereon, all other proceeds therefrom and all rights, benefits and privileges
pertaining to or arising from the Pledged Stock; and (d) such other collateral that may be provided
after the date hereof to secure the Obligations. All property at any time pledged to the Bank
hereunder or in which the Bank is granted a security interest hereunder (whether described herein
or not, subject to the provisions of



 









 




Paragraph 3(c)
below) all income therefrom and proceeds therefrom, may be referred to
collectively as the “Pledged Security”.




     2. Obligations. The obligations secured by this Pledge Agreement are the following
(referred to collectively hereafter as the “Obligations”);



          (a) all obligations and agreements of Pledgor contained in (including, without limitation, the
payment of all indebtedness of the Pledgor in respect of) the Loan Agreement, and any and all
amendments, modifications or renewals thereof;




          (b) all sums advanced by, or on behalf of, the Bank in connection with, or relating to, the
Loan Agreement, the Note or the Pledged Security including, but not limited to, any and all sums
advanced to preserve the pledged security, or to perfect the Bank’s security interest in the
Pledged Security;




          (c) in the event of any proceeding to enforce the satisfaction of the Obligations, or any of
them, or to preserve and protect the Bank’s rights under the Loan Agreement, the Notes referred to
in the Loan Agreement, this Pledge Agreement or any other agreement, document or instrument
relating to the transactions contemplated in the Loan Agreement, the reasonable expenses of
retaking, holding, preparing for sale, selling or otherwise disposing of or realizing on the
Pledged Security, or of any exercise by the Bank of its rights,
together with reasonable attorney’s
fees, expenses and court costs; and




          (d) any indebtedness, obligation or liability of the Pledgor or the Subsidiaries to the Bank,
whether direct or indirect, joint or several, absolute or contingent, now or hereafter existing,
however created or arising and however evidenced.




     NOTWITHSTANDING ANYTHING TO THE CONTRARY CONTAINED IN THIS PLEDGE AGREEMENT, THE PARTIES HERETO
AGREE THAT THE PLEDGED SECURITY SHALL IN NO EVENT BE CONSIDERED AS COLLATERAL FOR ANY SUBORDINATED
NOTE OR SUBORDINATED DEBENTURE ISSUED BY BORROWER WHICH IS INTENDED TO QUALIFY AS TIER 2 CAPITAL
UNDER 12 CFR 3.



     3. Additional Terms.



          (a) The Pledgor agrees that the Bank shall have full and irrevocable right, power and
authority, to collect, withdraw or receipt for all amounts due or to become due and payable upon,
in connection with, or relating to, the Pledged Security, to execute any withdrawal receipts
respecting the Pledged Security, and to endorse the name of the Pledgor on any or all documents,
instruments or commercial paper given in payment thereof, and at the Bank’s discretion to take any
other action, including, without limitation, the transfer of any Pledged Security into the Bank’s
own name or the name of any nominee for the Bank, which the Bank may deem necessary or appropriate
to preserve or. protect the Bank’s interest in any of the Pledged Security.




          (b) Unless a Default (as hereinafter defined) shall have occurred, the Pledgor shall be
entitled to vote any and all shares of the Pledged Stock and to give consents, waivers and
ratifications in respect thereof, provided that no vote shall be cast, no consent, waiver or
ratification shall be given and no action shall be taken by the
Pledgor which would violate or be





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inconsistent with any of the terms of the Loan Agreement, the Notes or this Pledge Agreement,
or which would have the effect of impairing the position or interests of the Pledgor or any holder
of the Notes. All such rights of the Pledgor to vote and to give consents, waivers and
ratifications shall cease upon the occurrence of a Default.




          (c) Unless a Default shall have occurred, all dividends and other distributions payable in
respect of the Pledged Security shall be paid to the Pledgor. Upon the occurrence of a Default, all
such dividends and other distributions and payments shall be paid to the Bank. After a Default
shall have occurred, all such amounts paid in respect of the Pledged Security shall, until paid or
delivered to the Bank, be held in trust for the benefit of the Bank as additional Pledged Security
to secure the Obligations.




     4. Representations, Warranties and Covenants. The Pledgor further represents,
warrants and agrees that:



          (a) The Pledgor is the legal, record and beneficial owner of, and has good and marketable title
to, the Pledged Security, subject to no lien, claim, security interest or other encumbrance, except
the security interest created by this Pledge Agreement.




          (b) Without the prior written consent of the Bank, the Pledgor will not sell, assign, transfer,
exchange, or otherwise dispose of, or grant any option with respect to, the Pledged Security, nor
will it create, incur or permit to exist any lien, claim, security interest or other encumbrance
with respect to any of the Pledged Security, or any interest therein, or any proceeds thereof,
except for the security interest provided for by this Pledge Agreement. Without the prior written
consent of the Bank, the Pledgor agrees that it will not, and it will not permit any Subsidiary *
to: (i) issue or reissue any capital stock or other securities (or warrants therefor or other
rights with respect thereto) in addition to or issue other securities of any nature in exchange or
substitution for any of the Pledged Security; (ii) redeem any of the Pledged Security, or (iii)
declare any stock dividend or split or otherwise change the capital structure of any Subsidiary.




          (c) The Pledged Security is genuine and in all respects, represents what it purports to be and
all the shares of the Pledged Stock have been duly and validly issued, and are fully paid and
non-assessable.




          (d) The pledge, assignment and delivery of the Pledged Security pursuant to this Pledge
Agreement creates a valid perfected security interest in the Pledged Security, and the proceeds
thereof, subject to no prior lien, claim, security interest or other encumbrance or to any
agreement purporting to grant to any third party a perfected security interest in the assets of the
Pledgor which would include any of the Pledged Security. The Pledgor will at all times defend the
Bank’s right, title and security interest in and to the Pledged security and the proceeds thereof
against any and all claims and demands of any person adverse to the claims of the Bank.




          (e) The
Pledgor will take, and will cause the Subsidiaries to take, such action  and to
execute such documents as the Bank may from time to time reasonably request relating to the Pledged
Security or the proceeds thereof.




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          (f) The
Pledgor has full right, power and authority to enter into, to execute and to deliver
this Pledge Agreement and this Pledge Agreement is binding upon, and enforceable against the
Pledgor in accordance with its terms.




          (g) The Pledgor shall pay any fees, assessments, charges or taxes arising with respect to the
Pledged Security. In case of failure by the Pledgor to pay any such taxes, assessments, charges
or taxes, the Bank shall have the right, but shall not be obligated, to pay such fees, assessments,
charges or taxes, as the case may be, and, in that event, the cost thereof shall be payable by the
Pledgor to the Bank immediately upon demand together with interest at the rate equal to the Prime
Rate (or, after the occurrence at a Default, the Prime Rate plus 2%) (Prime Rate shall have the
meaning provided in the Loan Agreement) from the date of disbursement by the Bank to the date of
payment by the Pledgor.




          (h) None of the Pledged Stock constitutes margin stock, as defined in Regulation U of the
Board of Governors of the Federal Reserve System.




     5. 
Events of Default. The Pledgor shall be in default under this Pledge Agreement
upon the occurrence of any one or more of the following events or conditions (each, a “Default”):



          (a) nonpayment of any of the Obligations when due, whether by acceleration or otherwise;




          (b) the nonperformance of any obligation or any breach of any warranty, representation or
covenant made by the Pledgor in this Pledge Agreement, and the same
is not cured within fifteen
(15) days after notice thereof by the Bank; .




          (c) the nonperformance of any obligation in any other instrument, document or agreement
relating to the Obligations, including, without limitation, the Loan Agreement and the Notes, which
nonperformance continues beyond the applicable cure period, if any, specifically provided therefor;




          (d) any breach of any warranty, representation or covenant made by the Pledgor in any other
instrument, document or agreement between the Pledgor and Bank which breach remains uncured beyond
any applicable time period, if any, specifically provided therefor,




          (e) any oral or written misrepresentation is made by the Pledgor in this Pledge Agreement or
in any document furnished by the Pledgor, or on the Pledgor’s behalf, to the Bank in connection
with this Pledge Agreement or the Pledged Security;




          (f) the claim or creation of any lien, claim, security interest or other encumbrance upon any
of the Pledged Security or the making of any levy, judicial seizure, or attachment thereof; or




          (g) The dissolution, bankruptcy, insolvency or failure of the Pledgor or any Subsidiary.






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6.
Rights of Parties upon Default.




          (a) Upon the occurrence of a Default, in addition to all the rights, power and remedies the
Bank shall be entitled to exercise, whether vested in the Bank by the terms of this Pledge
Agreement, the terms of the Loan Agreement, the terms of the Notes, by law, in equity, by
statute (including, without limitation, Article 9 of the Illinois Uniform Commercial Code) or
otherwise, for the protection and enforcement of the Bank’s rights in respect of the Pledged
Security, the Bank may be entitled to, without limitation (but is under no obligation to the
Pledgor so to do):





     (i) transfer all or any part of the Pledged Security into the Bank’s name or
the name of its nominee or nominees;




     (ii) after first obtaining all necessary regulatory approvals, vote all or any
part of the Pledged Security (whether or not transferred into the name of the Bank
or any nominee) and give all consents, waivers and ratifications in respect of the
Pledged Security and otherwise act with respect thereto as though it were the
outright owner thereof;




     (iii) at any time or from time to time to sell, assign and deliver, or grant
options to purchase, all or any part of the Pledged Security, or any interest
therein, at any public or private sales, without demand of performance,
advertisement or notice of intention to sell or of the time or place of sale or
adjournment thereof or to redeem or otherwise (all of which are hereby waived by
the Pledgor), for cash, on credit or for other property, for immediate or future
delivery without any assumption of credit risk and for such price or prices and on
such terms as the Bank in its absolute discretion may determine, provided that
unless, in the sole discretion of the Bank, any of the Pledged Security threatens
to decline in value or is or becomes a type sold on a recognized market, the Bank
will give the Pledgor reasonable notice of the time and place of any public sale
thereof, or of the time after which any private sale or other intended disposition
is to be made. Any requirements of reasonable notice shall be met if such notice is
mailed to the Pledgor as provided in Paragraph 14 below, at least fifteen
(15) days before the time of the sale or disposition. Any sale of any of the
Pledged Security conducted in conformity with customary practices of banks;
insurance companies or other financial institutions disposing of property similar
to the Pledged Security shall be deemed to be commercially reasonable. Any
remaining Pledged Security shall remain subject to the terms of this Pledge
Agreement; and




     (iv) collect any and all money due or to become due and enforce in the
Pledgor’s name all rights with respect to the Pledged Security.



          (b) Pledgor agrees to cause each Subsidiary to give the Bank, any prospective purchaser of the
Pledged Security (pursuant to paragraph 6(a)(iii)) and their respective representatives,
reasonable access to further information (including, but not limited to, records, files,
correspondence, tax work papers and audit work papers) relating to or concerning the Pledgor or
such Subsidiary.





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     7. Remedies Cumulative. Each right, power and remedy of the Bank provided in this
Pledge Agreement or now or hereafter existing at law or in equity or by statute or otherwise shall
be cumulative and concurrent and shall be in addition to every other right, power or remedy
provided for in this Pledge Agreement or now or hereafter existing at law or in equity or by
statute or otherwise. The exercise or partial exercise by the Bank at any one or more of such
rights, powers or remedies shall not preclude the simultaneous or later exercise by the Bank of all
such other rights, powers or remedies, and no failure or delay on the part of the Bank to exercise
any such right, power or remedy shall operate as a waiver thereof.



     8. Waiver or Defenses. No renewal or extension of the time of payment of the
Obligations, nor any release, surrender of, or failure to perfect or enforce any security interest
for the Obligations; no release of any person primarily or secondarily liable on the Obligations
(including any maker, endorser, or guarantor); no delay in enforcement of payment of the
Obligations; and no delay or omission in exercising any right or power with respect of the
Obligations or any security agreement securing the Obligations shall affect the rights of the Bank
in the Pledged Security.



     9. Waiver. Waiver by the Bank of any Default hereunder, or of any breach of
the provisions of this Pledge Agreement by the Pledgor, or any right of the Bank hereunder, shall
not constitute a waiver of any other Default or breach or right, nor the same Default or breach or
right on a future occasion.



     10. Law Governing. This Pledge Agreement and the rights and obligations of the
parties hereunder shall be construed and interpreted in accordance with the law of the State of
Illinois applicable to agreements made and to be wholly performed in such state. Whenever
possible, each provision or this Pledge Agreement shall be interpreted in such manner as to be
effective and valid under applicable law; provided, if any provision of this Pledge Agreement shall
be held to be prohibited or invalid under applicable law, such provision shall be ineffective only
to the extent of such prohibition or invalidity, without invalidating the remainder of such
provision or the remaining provisions of this Pledge Agreement.



     11. The Pledgor’s Obligations Absolute. The Obligations of the Pledgor under
this Pledge Agreement shall be absolute and unconditional and shall remain in full force and effect
without regard to, and shall not be released, discharged or in any way impaired by any
circumstance whatsoever, including without limitation: (a) any amendment or modification of the
Notes, the Loan Agreement or any other document or instrument provided for herein or therein or
related thereto, or any assignment, transfer or other disposition of any thereof; (b) any waiver,
consent, extension, indulgence or other action or inaction under or in respect of any such document
or instrument or any exercise or non-exercise of any right, remedy, power or privilege under or in
respect of any such document or instrument or this Pledge Agreement; (c) any bankruptcy,
insolvency, reorganization, arrangement, readjustment, composition, liquidation, or similar
proceeding with respect to the Pledgor or any of its properties or creditors; or (d) any limitation
on the Pledgor’s liabilities or obligations under any such instrument or any invalidity ‘or lack
of enforceability, in whole or in part, of any such document or instrument or any term thereof;
whether or not the Pledgor shall have notice or knowledge of the foregoing.



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     12. Termination.
This Pledge Agreement shall terminate upon the receipt by
the Bank of evidence satisfactory to the Bank, in the Bank’s sole and absolute discretion, of the
payment in full of the Obligations. At the time of such termination, the Bank, at the request and
expense of the Pledgor, will execute and deliver to the Pledgor a proper instrument or instruments
acknowledging the satisfaction and termination of this Pledge Agreement, and will duly assign,
transfer and deliver to the Pledgor such of the Pledged Security as has not yet theretofore been
sold or otherwise applied or released pursuant to this Pledge Agreement.



     13. Further Assurances. The Pledgor shall, at its expense, duly execute,
acknowledge and deliver all such instruments and take all such action as the Bank from time to time
may request in order to further effectuate the purposes of this Pledge Agreement and to carry out
the terms hereof. The Pledgor, at its expense, at all times, shall cause this Pledge Agreement (or
a proper notice or statement, in respect hereof) to be duly recorded, published and filed and
rerecorded, republished and refiled in such manner and in such places, if any, and shall pay or
cause to be paid all such recording, filing and other taxes, fees and charges, if any, and will
comply with all such statutes and regulations, if any, as may be required by law in order to
establish, perfect, preserve and protect the rights and security interests of the Bank hereunder.



     14. Notices. All communications provided for or related hereto shall be given
in accordance with Paragraph 10(c) of the Loan Agreement.



     15. Amendments. Any term of this Pledge Agreement may be amended only with the
written consent of the Pledgor and the Bank. Any amendment effected in accordance with this
Paragraph 15 shall be binding upon (i) each holder of the Notes at the time outstanding;
(ii) each future holder of the Notes; and (iii) the Pledgor.



     16. Assigns. This Pledge Agreement and all rights and liabilities hereunder and
in and to any and all Pledged Security shall inure to the benefit of the Bank and its successors
and assigns, and shall be binding on the Pledgor and the Pledgor’s successors and assigns;
provided, however, the Pledgor may not assign its rights or liabilities hereunder or to any of the
Pledged Security without the written consent of the Bank.



     17. Miscellaneous. This Pledge Agreement embodies the entire agreement and
understanding between the Bank and the Pledgor and supersedes all prior agreements and
understandings relating to the subject matter hereof. The headings in this Pledge Agreement are for
purposes of reference only and shall not limit or otherwise affect the meaning hereof.



     The Pledgor acknowledges that this Pledge Agreement is and shall be effective upon execution
by the Pledgor and delivery to and acceptance hereof by the Bank, and it shall not be necessary for
the Bank to execute any acceptance hereof or otherwise to signify or express its acceptance hereof
to the Pledgor.



	 	 	 	 	 	 	 
	 	 	WINTRUST FINANCIAL CORPORATION	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ DAVID A. DYKSTRA 8/26/2005
 

	 	 
	 

	 	Its:
	 	Senior Executive Vice President
&
Chief Operating Officer	 	 






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