Document:

Officer and Employee 2008 Non-Qualified Stock Option Agreement

 Exhibit 10.52 
 TAYLOR CAPITAL GROUP, INC. 
 OFFICER AND EMPLOYEE 
 2008 NON-QUALIFIED STOCK OPTION AGREEMENT 
 NOTICE OF OPTION GRANT 
 Name of Optionee: Hoppe, Mark A. 
 You have been granted an option to
purchase shares of Common Stock (“Shares”) of Taylor Capital Group, Inc. (the “Company”) as follows (the “Option”): 
  

					
	Date of Award:	 	February 4, 2008	 	
			
	Exercise Price per Share:	 	$19.99	 	
			
	Total Number of Options Granted:	 	50,000	 	

 Expiration Date: 8 years from the Date of the Option Grant/ February 4, 2016 
 Vesting Schedule: This option may not be exercised prior to the first anniversary of the Date of Grant. Thereafter, this option may be exercised to a
maximum cumulative extent of 25% of the total shares covered by this option on and after the first anniversary of the Date of Grant, 50% of the total shares on and after the second anniversary of the Date of Grant, 75% of the total shares on and
after the third anniversary of the Date of Grant, and 100% of the total shares on and after the fourth anniversary of the Date of Grant. 
 The Optionee and
the Company hereby agree that this Option is granted under and governed by the terms and conditions of the 2008 Non-Qualified Stock Option Agreement, which is attached hereto and made an integral part hereof, and the Taylor Capital Group, Inc. 2002
Incentive Compensation Plan. The Company and Optionee each agree to be bound by all of the terms and conditions set forth in the 2008 Non-Qualified Stock Option Agreement. 
  

			
	Taylor Capital Group, Inc.
		
	By:	 	 /s/ BRUCE W. TAYLOR

		
	Its:	 	Chief Executive Officer

 TAYLOR CAPITAL GROUP, INC.  
 NON-QUALIFIED STOCK OPTION 
 In consideration of the premises, mutual covenants
and agreements herein, the Company and the Optionee agree as follows: 
 GRANT OF OPTION 
 Grant of Option. Taylor Capital Group, Inc. (the “Company”) hereby grants to Mark A. Hoppe (the “Optionee”) an option (the “Option”) to purchase that number of shares of
Common Stock of the Company (“Shares”) set forth under the heading “Total Number of Options Granted” in the Optionee’s Notice of Option Grant (the “Notice”), and at the Exercise Price per Share set forth in the
Notice, subject to the provisions of the Notice and this 2008 Non-Qualified Stock Option Agreement (both documents collectively referred to as the “Agreement”). 
 Tax Status. This Option is not intended to qualify as an incentive stock option within the meaning of Section 422 of the Internal Revenue Code of 1986, as amended (the “Code”). 

Subject to Plan. This Option is subject to all of the terms and conditions of the Taylor Capital Group, Inc. 2002 Incentive Compensation Plan, as
amended and restated as of April 26, 2007 (the “Plan”), as the same may be further amended from time to time. 
 VESTING 
 Vesting Schedule. Subject to the terms of Section 2.3, the Option shall become vested and exercisable, if at all, at the time or times and as to that
number of Shares determined in accordance with the Vesting Schedule set forth in the Notice. 
 Termination of Vesting. Subject to
Section 2.3, in the event the Optionee’s employment with the Company or the Bank (or any other employment, consulting, advisory or service relationship or arrangement with the Company, the Bank or any Subsidiary (as defined below)) is
terminated for any reason, (i) no further vesting (pro rata or otherwise) shall occur from and after the occurrence of such event, and (ii) the Option shall terminate in accordance with Article 4 hereof. 
 Acceleration of Vesting. Notwithstanding the Vesting Schedule set forth in the Notice, this Option shall accelerate and become immediately vested and
exercisable as to any Shares that have not otherwise vested as of the termination of the Optionee’s employment with the Company, the Bank or any Subsidiary by reason of the Optionee’s death, Disability or Retirement, by the Company without
Cause, as a result of the 

 
Company’s delivery of a notice of its intent not to renew the term of the Employment Agreement without Cause, or by the Optionee for Good Reason (as
those terms are defined below). 
 Definitions. For purposes of this Option, the following terms shall have the following meanings: 

“Bank” means Cole Taylor Bank. 
 “Cause” means: (a) Optionee has committed an act of dishonesty that results, or is intended to result, in material gain or personal enrichment of Optionee or has, or is intended to have, a material detrimental effect on the
reputation or business of the Bank or the Company; (b) Optionee has committed an act or acts of fraud, moral turpitude or constituting a felony (other than relating to the operation of a motor vehicle); (c) any material breach by Optionee
of any provision of the Employment Agreement that, if curable, has not been cured by Optionee within thirty (30) days of written notice of such breach from the Bank or the Company; (d) an intentional act or willful gross negligence on the
part of Optionee that has, or is intended to have, a material, detrimental effect on the reputation or business of the Bank or the Company; (e) Optionee’s refusal, after thirty (30) days written notice thereof, to perform specific
reasonable directives from the board of directors of the Bank or the Company that are reasonably consistent with the scope and nature of his duties and responsibilities, as set forth in the Employment Agreement; or (f) Optionee being barred or
prohibited by any governmental authority or agency from holding the position of Chief Executive Officer of the Bank or the Company. The decision to terminate Optionee’s employment for Cause, to take other action or to take no action in response
to any occurrence shall be in the sole and exclusive discretion of the board of directors of the Company. No act or failure to act shall be considered “intentional” unless it is done, or omitted to be done, by the Optionee in bad faith or
without reasonable belief that Optionee’s action or omission was in the best interests of the Bank or the Company; and provided further that no act or omission shall constitute Cause hereunder absent such a finding by the board of directors of
the Company. 
 “Disability” for the purposes of this Agreement, shall be deemed to have occurred if the Company determines that
Optionee has a physical or mental impairment, as confirmed by a licensed physician selected by the Company, which renders Optionee unable to engage in any substantial gainful activity, and is expected to result in death or is expected to last for a
continuous period of not less than twelve (12) months. This definition of “Disability” is intended to comply with section 409A of the Code, and the regulations promulgated thereunder, and shall be interpreted and administered in
accordance with said provisions. Termination due to disability shall be deemed to have occurred upon the first day of the month following the determination of Disability as defined in the preceding sentence. 

 “Employment Agreement” means the Executive Employment Agreement dated as of January 30,
2008 by and among Optionee, the Company and the Bank. 
 “Good Reason” shall mean the occurrence of any of the following events
unless, (A) such event occurs with the Optionee’s express prior written consent, (B) the event is an isolated, insubstantial or inadvertent action or failure to act which is remedied by the Company or the Bank promptly after receipt
of notice thereof given by the Optionee, (C) the event occurs in connection with the termination of the Optionee’s employment for Cause, Disability or death or (D) the event occurs in connection with the Optionee’s voluntary
termination of employment other than due to the occurrence of one of the following events: 
 (1) a material adverse change in
the nature or scope of the authorities, powers, functions, duties or responsibilities attached to Optionee’s position (including, but not limited to, Optionee not being re-elected or removed from his positions with the Bank or the Company); or

 (2) a change in the Optionee’s principal office to a location outside of Cook County, DuPage County or Lake County; or

 (3) any material reduction in Optionee’s base salary and bonus opportunity (other than permitted proportionate
reductions applicable to all similarly situated senior executives of the Bank, unless such reduction occurs during the two year period commencing upon a Change in Control); or 
 (4) a material breach of the Employment Agreement by the Company or the Bank. 
 Anything herein to the contrary notwithstanding, the Optionee shall be required to give written notice to the Board of Directors of the Company that the Optionee
believes an event has occurred that constitutes a Good Reason event within ninety (90) days of the initial occurrence, which written notice shall specify the particular act or acts, on the basis of which the Optionee intends to so terminate the
Optionee’s employment, and the Company shall then be given the opportunity, within thirty (30) days of its receipt of such notice, to cure said event. Optionee’s termination shall not be considered to be a termination for Good Reason
unless such termination occurs within one hundred twenty (120) days after the occurrence of the Good Reason event. 
 “Retirement” shall mean the termination of the Optionee’s employment with the Company, the Bank or any Subsidiary for any reason other than for Cause at or after Optionee reaches age 65 with 5 years of service. 
 “Subsidiary” or “Subsidiaries” shall mean any corporation or other entity of which outstanding shares or ownership interests
representing 50% or more of the combined voting power of such corporation or other entity entitled to elect the management thereof, or such lesser percentages may be approved by the Compensation Committee, are owned, directly or indirectly, by the
Company. 

 Any capitalized terms not otherwise defined in this Agreement shall have the meaning set forth in the Plan. 

EXERCISE OF OPTION 
 Right to Exercise. The Option may be
exercised, to the extent then exercisable, at any time and from time to time prior to the Expiration Date stated in the Notice. Subject to Section 6.6 hereof, this Option shall be exercisable, during the Optionee’s lifetime, only by the
Optionee or, in the event of the Optionee’s Disability, by the Optionee’s legal representative or guardian, as the case may be. In the event of the Optionee’s death, to the extent this Option remains exercisable thereafter, this
Option may be exercised by the Optionee’s estate or the person or persons to whom the Option passes by will or the laws of descent and distribution. 
 Manner of Exercise. The Option may be exercised, to the extent then exercisable, by delivering written notice to the Secretary of the Company, in such form as the Company may require from time to time; provided, however, that
the Option may not be exercised at any one time other than in multiples of twenty-five (25) Shares (unless the exercise is with respect to the remaining number of Shares as to which the Option is then exercisable). Such notice of exercise shall
specify the number of Shares as to which the Option is being exercised, and shall be accompanied by full payment of the Exercise Price for such Shares. 
 Payment of Exercise Price. Payment of the Exercise Price shall be made (i) in cash or check made payable to the Company, (ii) by tendering (or certifying as to ownership of) previously acquired Shares held for at
least six (6) months by the Optionee (or such longer period as may be required to avoid a charge to the Company’s earnings for financial accounting purposes) valued at Fair Market Value as of the date of delivery, or (iii) any
combination of the above. 
 In addition, in the event that shares of common equity securities of the Company are registered under the
Securities Exchange Act of 1934, payment of the Exercise Price hereunder may, in the sole discretion of the Compensation Committee, also be made by delivering a properly executed exercise notice to the Company together with a copy of irrevocable
instructions to a broker to promptly deliver to the Company the amount of sale or loan proceeds to pay the exercise price. To facilitate the foregoing, the Company may enter into agreements for coordinated procedures with one or more brokerage
firms. 
 Compliance with Employment Agreement. The Optionee’s right to exercise any unexercised Options shall terminate and such Options
shall be forfeited in the event that Optionee breaches any of his obligations set forth in Sections 8, 9, 10, 11, 12 and 13 of the Employment Agreement. 

 Withholding Taxes. The Company shall have the right to deduct from any compensation or any other payment of
any kind (including withholding the issuance of Shares) due the Optionee, the amount of any federal, state or local taxes required by law to be withheld as the result of any exercise of this Option; provided, however, that the value of any Shares
withheld by the Company upon the exercise of the Option may not exceed the statutory minimum withholding amount required by law. In lieu of such deduction, the Company may require the Optionee to make a cash payment to the Company equal to the
amount of taxes required to be withheld. If the Optionee does not make such payment when requested, the Company may refuse to issue any Shares under this Option until arrangements satisfactory to the Company for such payment have been made.

 Issuance of Shares. Subject to Section 3.7 hereof, upon exercise of the Option in accordance with the terms of this Agreement, the
Company shall issue in the name of the Optionee the number of Shares so paid for in such exercise, in the form of fully paid and nonassessable Shares. 
 Securities Law Considerations. If at any time during the term of the Option, the Company shall be advised by its counsel that Shares issuable upon exercise of the Option are required to be registered under the Federal
Securities Act of 1933, as amended (the “1933 Act”), or under applicable state securities laws, or that delivery of such Shares must be accompanied or preceded by a prospectus meeting the requirements of the 1933 Act or of any applicable
state securities laws, issuance of Shares by the Company may be deferred until such registration is effected or a prospectus available or an appropriate exemption from registration is secured. The Optionee shall have no interest in the Shares
covered by this Option unless and until such Shares are issued. The Optionee agrees and acknowledges that the Option may not be exercised unless the foregoing conditions are satisfied. 
 TERMINATION OF OPTION 
 Lapse of Option. Unless earlier terminated as provided in this Article 4 or in Article
5, the Option shall terminate, and be of no force or effect after 5:00 p.m. (Central Standard or Daylight Time, which ever is in effect), on the Expiration Date specified in the Notice. 
 Termination of Employment. Except as provided in Article 5, the Option shall, unless otherwise provided in the Notice of Option Grant, terminate and lapse upon a termination of Optionee’s employment
or service relationship with the Company, the Bank or the Company’s Subsidiaries as follows: 
 immediately upon a termination of Optionee’s
employment or service relationship for Cause; 

 ninety (90) days following the termination of Optionee’s employment or service relationship for any reason,
including but not limited to the delivery by the Company of a notice of its intent not to renew the term of the Employment Agreement without Cause, other than a termination by the Company for Cause, by the Optionee for Good Reason, or by reason of
Optionee’s death, Permanent Disability, or Retirement; or 
 one (1) year following a termination of the Optionee’s employment or service
relationship by Optionee for Good Reason, or by reason of Optionee’s death, Disability, or Retirement, provided however that in no event shall this Option remain exercisable beyond the Expiration Date. 
 Leave of Absence. For purposes of this Agreement, the Optionee’s employment or service with the Company, the Bank or any Subsidiary shall not be
deemed to terminate if the Optionee takes any military leave, sick leave, maternity leave, or other bona fide leave of absence approved by the Company of ninety (90) days or less. In the event of a leave in excess of ninety (90) days,
solely for purposes of this Agreement and the Option, the Optionee’s employment or service shall be deemed to terminate on the ninety-first (91st) day of the leave unless the Optionee’s right to re-employment with the Company, the
Bank or any Subsidiary remains guaranteed by statute or contract, unless the Compensation Committee, in its sole discretion, shall provide for a longer leave of absence. Notwithstanding the foregoing, unless otherwise determined by the Compensation
Committee (or required by law), any leave of absence shall not be considered as continuing employment or service with the Company, the Bank or any Subsidiary for purposes of vesting in additional Shares during such leave pursuant to Section 2.1
of this Agreement. 
 CHANGE IN CONTROL; ADJUSTMENTS 
 Consequences of a Change in Control. 
 Notwithstanding any other provision of this Option to the contrary, whether
express or implied, the Compensation Committee may, in its sole discretion, by providing at least 30-days prior written notice to the Optionee, elect to (i) accelerate the Expiration Date of the Option to the effective date of the Change in
Control and (ii) require that in lieu of the exercise of the Option, the Optionee be provided with a net payment as set forth in this Section 5.1. Any payments to be made to Optionee under this Section 5.1 shall be in an amount equal
to the excess, if any, of (i) the Fair Market Value of a share of Common Stock on the 

 
effective date of the Change in Control over (ii) the Exercise Price per Share, multiplied by the number of Shares remaining available under this
Option, less any required withholding taxes. Payments under this Section 5.1 shall be made, in the sole discretion of the Company, (i) in cash, (ii) in the form of the consideration being paid to holders of shares of Common Stock in
connection with such Change in Control, or (iii) any combination of the foregoing. 
 Change in Control. For purposes of this Agreement, a
“Change in Control” shall mean any of the following: 
 a change in the ownership of the Company or the Bank (as defined in Treasury Regs.
Section 1.409A-3(i)(5)(v)) (other than a transfer to a group comprised of members of the Taylor Family or an Employee Stock Ownership Plan established by the Company); or 
 a change in effective control of the Company or the Bank (as defined in Treasury Regs. Section 1.409A-3(i)(5)(vi)), or 
 a change in the ownership of a substantial portion of the assets of the Company or the Bank (as defined in Treasury Regs. Section 1.409A-3(i)(5)(vii)). 
 However, a Change in Control shall not occur under Subparagraphs (a), (b) or (c) if the Taylor Family continues to be the beneficial owner, directly or indirectly, of more than 30% of the combined voting
power of the then outstanding securities of the Company (or of the Bank for a Change in Control under Subparagraph (c) involving the Bank), and no other person or group is or becomes the beneficial owner, directly or indirectly, of securities
of the Company (or the Bank for a Change in Control under Subparagraph (c) involving the Bank) having combined voting power greater than that beneficially owned, directly or indirectly, by the Taylor Family. 
 For purposes of this definition of Change in Control, the Taylor Family means (i) Iris Taylor and the Estate of Sidney J. Taylor, (ii) a descendant (or a
spouse of a descendant) of Sidney J. Taylor and Iris Taylor, (iii) any estate, trust, guardianship or custodianship for the primary benefit of any individual described in (i) or (ii) above, or (iv) a proprietorship, partnership,
limited liability company, or corporation controlled directly or indirectly by one or more individuals or entities described in (i), (ii), or (iii) above. 
 For purposes of this definition of Change in Control, Employee Stock Ownership Plan means a retirement plan that is qualified under Section 401(a) of the Internal Revenue Code and is sponsored by the Company (or a member of its
controlled group, as determined under Section 414(b) of the Internal Revenue Code). 

 The term “Exchange Act” means the Securities Exchange Act of 1934. The terms “beneficial owner” and
“beneficially owned” shall have the meaning set forth in Rule 13d-3 under the Exchange Act. 
 The term “outstanding securities” when
used in the context of the “combined voting power of the Company’s then outstanding securities” shall mean only the common stock of the Company and securities convertible into such common stock. 
 Adjustments. This Option shall be subject to adjustment as provided in Section 10 of the Plan. Such adjustments shall be final, binding and conclusive. No
fractional shares will be issued pursuant to the Option on account of any such adjustments. 
 MISCELLANEOUS 
 Administration. This Option shall be administered by the Compensation Committee or its delegate as provided in Section 3 of the Plan. 
 No Guarantee of Employment or Service; Compensation. Nothing in this Agreement shall be construed as an employment, consulting or similar contract for
services between the Company, the Bank or any Subsidiary and the Optionee. Any benefit derived under the Agreement shall not be considered normal or expected compensation for purposes of calculating any severance, resignation, bonus, pension,
retirement or similar payments or benefits. 
 No Rights of a Shareholder. The Optionee shall not have any of the rights of a shareholder of
the Company with respect to the Shares that may be issued upon the exercise of the Option unless and until such time as the Shares are issued to the Optionee following an exercise. No adjustment shall be made for dividends or other distributions
made by the Company to its shareholders or other rights for which the record date is prior to the date on which the Optionee is admitted as a shareholder with respect to Shares that may be issued upon the exercise of the Option. 
 The Company’s Rights. The existence of the Option shall not affect in any way the right or power of the Company or its shareholders to make or
authorize any or all adjustments, recapitalizations, reorganizations or other changes in the Company’s capital structure or its business, or any merger or consolidation of the Company, or any issue of bonds, debentures, preferred or other
securities with preference ahead of or convertible into, or otherwise affecting the Shares or the rights thereof, or the dissolution or liquidation of the Company, or any sale or transfer of all or any part of the Company’s assets or business,
or any other act or proceeding, whether of a similar character or otherwise. 
 Optionee. Whenever the word “Optionee” is used in any
provision of this Agreement, 

 
under circumstances where the provision should logically be construed to apply to the estate, personal representative or beneficiary to whom this Option may
be transferred by will or by the laws of descent and distribution, the word “Optionee” shall be deemed to include such person. 
 Nontransferability of Option. Except as provided in Section 3.1 and in this Section 6.6, this Option is not transferable by the Optionee otherwise than by will or the laws of descent and distribution, and is
exercisable, during the Optionee’s lifetime, only by him. Subject to the prior written consent of the Compensation Committee, this Option may transferred, in whole or in part, to a spouse or lineal descendant of the Optionee (a “Family
Member”), a trust for the exclusive benefit of Family Members, a partnership or other entity in which all the beneficial owners are the Optionee and/or Family Members, or any other entity affiliated with the Optionee that may be approved by the
Compensation Committee. Subsequent transfers of this Option shall be prohibited except in accordance with this Section 6.6. All terms and conditions of this Option, including provisions relating to the termination of the Optionee’s
employment or service with the Company, shall continue to apply following a transfer made in accordance with this Section 6.6. 
 Entire
Agreement; Modification. Except as provided in the Plan and the Notice, this Agreement contains the entire agreement between the parties with respect to the subject matter contained herein, and may not be modified, except as provided in a
written document signed by each of the parties hereto. Any oral or written agreements, representations, warranties, written inducements, or other communications made prior to the execution of this Agreement shall be void and ineffective for all
purposes. 
 Severability. In the event that any term or provision of this Agreement shall be finally determined to be superseded, invalid,
illegal or otherwise unenforceable pursuant to applicable law by a governmental authority having jurisdiction and venue, that determination shall not impair or otherwise affect the validity, legality or enforceability, to the maximum extent
permissible by law, (a) by or before that authority of the remaining terms and provisions of this Agreement, which shall be enforced as if the unenforceable term or provision were deleted, or (b) by or before any other authority of any of
the terms and provisions of this Agreement. 
 Code Section 409A. This Option is intended to be exempt from Section 409A of the Code,
and the regulations and guidance promulgated thereunder (“Section 409A”). Notwithstanding the foregoing or any provision of the Plan or this Option to the contrary, if any provision of this Option or the Plan contravenes Section 409A
or could cause the Optionee to incur any tax, interest or penalties under Section 409A, the Committee may, in its sole discretion and without the Optionee’s consent, modify such provision to comply with, or avoid being subject to,
Section 409A, or to avoid the incurrence of taxes, interest and penalties under Section 409A. 

 Conflicts. In the event of any conflict between the terms of this Agreement and the Optionee’s Notice
of Option Grant, the terms of such Notice of Option Grant shall control. 
 Governing Law. This Agreement shall be governed and construed in
accordance with the laws of the State of Illinois (regardless of the law that might otherwise govern under applicable Illinois principles of conflict of laws).Officer and Employee Restricted Stock Award

 Exhibit 10.53 
 TAYLOR CAPITAL GROUP, INC. 
 OFFICER AND EMPLOYEE 
 RESTRICTED STOCK AWARD 
 NOTICE OF RESTRICTED STOCK GRANT 
 Name of Employee: Hoppe, Mark A. 
 You have been awarded restricted shares
of Common Stock (“Shares”) of Taylor Capital Group, Inc. (the “Company”) as follows (the “Award”): 
  

					
	Date of Award:	 	February 4, 2008	 	
			
	Total Number of Shares Awarded:	 	60,030	 	

 Vesting Schedule: The Restrictions shall
lapse as to twenty-five percent (25%) of the Restricted Shares on the first (1st) anniversary of the Date of Award, fifty percent
(50%) of the Restricted Shares on the second (2nd) anniversary of the Date of Award, seventy-five percent (75%) of the Restricted
Shares on the third (3rd) anniversary of the Date of Award and one hundred percent (100%) of the Restricted Shares on the fourth
(4th) anniversary of the Date of Award, provided that Employee remains in the continuous employment of the Company, the Bank or a Subsidiary at
all times from the Date of Award through and including each such anniversary of the Date of Award. 
 The Employee and the Company hereby agree that this
Award is granted under and governed by the terms and conditions of the 2008 Restricted Stock Award, which is attached hereto and made an integral part hereof, and the Taylor Capital Group, Inc. 2002 Incentive Compensation Plan. The Company and
Employee each agree to be bound by all of the terms and conditions set forth in the 2008 Restricted Stock Award. 
  

			
	Taylor Capital Group, Inc.
		
	By:	 	 /s/ BRUCE W. TAYLOR

		
	Its:	 	Chief Executive Officer

 TAYLOR CAPITAL GROUP, INC. 
 RESTRICTED STOCK AWARD 
 In consideration of the premises, mutual
covenants and agreements herein, the Company and the Employee agree as follows: 
 AWARD 
 Award of Shares. Subject to all of the terms and conditions set forth in this 2008 Restricted Stock Award and the accompanying Notice of Restricted Stock Grant (the “Notice”) (both documents
collectively referred to as the “Agreement”), Taylor Capital Group, Inc. (the “Company”) hereby grants to Mark A. Hoppe (the “Employee”) that number of restricted shares of Common Stock (the “Restricted
Shares”) set forth under the heading “Total Number of Shares Awarded” in the Notice. 
 Conditions to Award. The Award of
Restricted Shares to Employee is conditioned upon Employee delivering to the Company: (1) if requested by the Company, a duly signed stock power, endorsed in blank, relating to the Restricted Shares as required under Section 2.7 hereof,
(2) a duly signed Section 83(b) Election, if the Employee makes such election, within ten (10) days of filing the Section 83(b) Election along with any other filing and notification required pursuant to regulations issued under
Section 83(b) of the Code, and (3) such other documents or agreements as the Company may request. 
 Voting and Other Rights. As of
February 4, 2008 (“Date of Award”), Employee shall have all of the rights and status as a shareholder of the Company in respect of the Restricted Shares, including the right to vote such shares and to receive dividends or other
distributions thereon. Any cash dividends paid on any Restricted Shares shall be paid to the Employee. In the event any non-cash dividends or other distributions, whether in property, or stock of another company, are paid on any Restricted Shares,
such non-cash dividends or other distributions payable to the Employee shall be retained by the Company and not delivered to the Employee until such time as the Restrictions on the Restricted Shares with respect to which such non-cash dividends or
other distributions have been paid shall have lapsed and such shares shall have become Vested Shares. Such non-cash dividends or distributions with respect to the Restricted Shares shall be retained by the Company in the event the corresponding
Restricted Shares on which such non-cash dividends or other distributions were paid are forfeited to the Company under Section 2.1(b) hereof. 
 Subject to Plan. This 2008 Restricted Stock Award is subject to all of the terms and conditions of the Taylor Capital Group, Inc. 2002 Incentive Compensation Plan, as amended and restated as of April 26, 2007 (the
“Plan”), as the same may be further amended from time to time. Any capitalized terms not otherwise defined in this Agreement shall have the meaning set forth in the Plan. 

 RESTRICTIONS 
 Restrictions. The Restricted Shares are being awarded to Employee subject to the following transfer and forfeiture restrictions (collectively, the “Restrictions”). 
 Transfer. Prior to the date that the Restricted Shares become Vested Shares (as defined in Section 2.2 hereof), Employee may not directly or
indirectly, by operation of law or otherwise, voluntarily or involuntarily, anticipate, alienate, attach, sell, assign, pledge, encumber, charge or otherwise transfer all or any part of the Restricted Shares without the written consent of the
Company, which consent may be withheld by the Company in its sole discretion. 
 Forfeiture. Upon termination of Employee’s employment
with the Company, the Bank or any Subsidiary, all Restricted Shares which are not Vested Shares (or have not become Vested Shares under Section 2.2 or Section 2.3 hereof) at the effective time of such termination, shall immediately
thereafter be returned to or canceled by the Company, and shall be deemed to have been forfeited by Employee to the Company. Upon any forfeiture of Restricted Shares under this Section 2.1, the Company will not be obligated to pay Employee any
consideration whatsoever for the forfeited Restricted Shares, unless required by applicable law. 
 Lapse of Restrictions. Subject to the other
terms of this Agreement, the Restrictions shall lapse with respect to the Restricted Shares awarded hereunder only at the time or times and as to that number of Restricted Shares determined in accordance with the Vesting Schedule set forth in the
Notice. To the extent the Restrictions shall have lapsed with respect to Restricted Shares subject to this Award, those shares (the “Vested Shares”) will thereafter be free of the Restrictions. 
 Acceleration of Vesting. Notwithstanding the Vesting Schedule set forth in the Notice, the Restrictions shall lapse with respect to any Restricted Shares
that have not otherwise vested as of the termination of the Employee’s employment with the Company, the Bank or any Subsidiary (as defined below) if such termination is by reason of the Employee’s death, Disability or Retirement, by the
Company without Cause, as a result of the Company’s delivery of a notice of its intent not to renew the term of the Employment Agreement without Cause, or by the Employee for Good Reason (as those terms are defined below). 
 Termination of Vesting. Subject to Section 2.3, in the event the Employee’s employment with the Company or the Cole Taylor Bank (the
“Bank”) (or 

 
any other employment, consulting, advisory or service relationship or arrangement with the Company, the Bank or any Subsidiary) is terminated for any
reason, no further vesting (pro rata or otherwise) shall occur after the occurrence of such event. 
 Withholding Taxes. 
 The Award of the Restricted Shares to the Employee, and the lapse of Restrictions on the Restricted Shares, shall be conditioned on any applicable
federal, state or local withholding taxes having been paid by Employee at the appropriate time pursuant to a direct payment of cash or other readily available funds to the Company. The Committee may permit the Employee to satisfy all or any portion
of his obligations under this Section 2.5(a) by having the Company withhold from the Restricted Shares with respect to which the Restrictions will lapse, that number of shares of Common Stock having an aggregate Fair Market Value, determined as
of the date of the taxable event with respect to such shares, equal to the federal, state or local taxes required to be withheld by the Company with respect to such lapse of Restrictions; provided however, that the Fair Market Value of any shares of
Common Stock withheld under this Section 2.5(a) may not exceed the statutory minimum withholding amount required by law. 
 If the
Employee shall have elected to file a Section 83(b) Election with respect to the award of Restricted Shares hereunder, the award of the Restricted Shares shall be conditioned on the Employee providing the Company with a direct payment of cash
or other immediately available funds in an amount equal to the statutory minimum withholding taxes required to by withheld by the Company not later than 30 days after the date of the award. 
 Issuance of Shares; Restrictive Legend. Any such certificates issued by the Company with respect to the Restricted Shares shall be registered in
Employee’s name and shall be inscribed with a legend evidencing the Restrictions, and such additional legends as may be required to comply with the Securities Act of 1933, as amended, and other applicable federal or state securities laws.
Alternatively, the Company may issue Restricted Shares hereunder in uncertificated form. 
 Custody. All certificates representing the
Restricted Shares (other than Vested Shares) shall be deposited, together with stock powers executed by Employee, in proper form for transfer, with the Company. The Company shall provide Employee with a copy of any certificate representing the
Restricted Shares, or such other evidence thereof as may be determined by the Company, which shall contain the legends described in Section 2.6. The Company is hereby authorized to cause the transfer into 

 
its name of the Restricted Shares (and any non-cash distributions or other property described in Section 1.3 hereof) which are forfeited to the Company
pursuant to Section 2.1(b) hereof. At the request of Employee, certificates representing Vested Shares shall, subject to any applicable securities law restrictions, be delivered by the Company to Employee or Employee’s personal
representative. Certificates representing shares that have become Vested Shares in accordance with Section 2.2 or 2.3 shall be issued without the legend evidencing the Restrictions, but may contain such legends as may be required to comply with
the Securities Act of 1933, as amended, or any other applicable federal or state securities laws. 
 ADJUSTMENTS 
 Adjustments. Any Adjustments made under Section 10 of the Plan will be final, binding and conclusive. No fractional shares will be issued pursuant to the
Award on account of any such adjustments. The terms “Restricted Shares” and “Vested Shares” shall include any shares, securities, or other property that Employee receives or becomes entitled to receive as a result of
Employee’s ownership of the original Restricted Shares, and any such shares, securities or other property shall be subject to the same Restrictions and other terms and conditions that apply with respect to, and shall vest or be forfeited at the
same time as, the Restricted Shares with respect to which such shares, securities or other property are issued. 
 DEFINITIONS 
 Definitions. For purposes of this Agreement, the following terms shall have the following meanings: 
 “Cause” means: (a) Employee has committed an act of dishonesty that results, or is intended to result, in material gain or
personal enrichment of Employee or has, or is intended to have, a material detrimental effect on the reputation or business of the Company or the Bank; (b) Employee has committed an act or acts of fraud, moral turpitude or constituting a felony
(other than relating to the operation of a motor vehicle); (c) any material breach by Employee of any provision of the Employment Agreement that, if curable, has not been cured by Employee within thirty (30) days of written notice of such
breach from the Company or the Bank; (d) an intentional act or willful gross negligence on the part of Employee that has, or is intended to have, a material, detrimental effect on the reputation or business of the Company or the Bank;
(e) Employee’s refusal, after thirty (30) days written notice thereof, to perform specific reasonable directives from the board of directors of the Company or the 

 
Bank that are reasonably consistent with the scope and nature of his duties and responsibilities, as set forth in the Employment Agreement; or
(f) Employee being barred or prohibited by any governmental authority or agency from holding the position of Chief Executive Officer of the Company or the Bank. The decision to terminate Employee’s employment for Cause, to take other
action or to take no action in response to any occurrence shall be in the sole and exclusive discretion of the board of directors of the Company. No act or failure to act shall be considered “intentional” unless it is done, or omitted to
be done, by the Employee in bad faith or without reasonable belief that Employee’s action or omission was in the best interests of the Company or the Bank; and provided further that no act or omission shall constitute Cause hereunder absent
such a finding by the board of directors of the Company. 
 “Change In Control” shall mean any of the following: 
 (a) a change in the ownership of the Company or the Bank (as defined in Treasury Regs. Section 1.409A-3(i)(5)(v)) (other than a
transfer to a group comprised of members of the Taylor Family or an Employee Stock Ownership Plan established by the Company); or 
 (b) a change in effective control of the Company or the Bank (as defined in Treasury Regs. Section 1.409A-3(i)(5)(vi)), or 
 (c) a change in the ownership of a substantial portion of the assets of the Company or the Bank (as defined in Treasury Regs. Section 1.409A-3(i)(5)(vii)). 
 However, a Change in Control shall not occur under Subparagraphs (a), (b) or (c) if the Taylor Family continues to be the
beneficial owner, directly or indirectly, of more than 30% of the combined voting power of the then outstanding securities of the Company (or of the Bank for a Change in Control under Subparagraph (c) involving the Bank), and no other person or
group is or becomes the beneficial owner, directly or indirectly, of securities of the Company (or the Bank for a Change in Control under Subparagraph (c) involving the Bank) having combined voting power greater than that beneficially owned,
directly or indirectly, by the Taylor Family. 
 For purposes of this definition of Change in Control, the Taylor Family means
(i) Iris Taylor and the Estate of Sidney J. Taylor, (ii) a descendant (or a spouse of a descendant) of Sidney J. Taylor and Iris Taylor, (iii) any estate, trust, guardianship or custodianship for the primary 

 
benefit of any individual described in (i) or (ii) above, or (iv) a proprietorship, partnership, limited liability company, or corporation
controlled directly or indirectly by one or more individuals or entities described in (i), (ii), or (iii) above. 
 For
purposes of this definition of Change in Control, Employee Stock Ownership Plan means a retirement plan that is qualified under Section 401(a) of the Internal Revenue Code and is sponsored by the Company (or a member of its controlled group, as
determined under Section 414(b) of the Internal Revenue Code). 
 The term “Exchange Act” means the Securities
Exchange Act of 1934. The terms “beneficial owner” and “beneficially owned” shall have the meaning set forth in Rule 13d-3 under the Exchange Act. 
 The term “outstanding securities” when used in the context of the “combined voting power of the Company’s then
outstanding securities” shall mean only the common stock of the Company and securities convertible into such common stock. 
 “Disability” for the purposes of this Agreement, shall be deemed to have occurred if the Company determines that Employee has a physical or mental impairment, as confirmed by a licensed physician selected by the Company, which
renders Employee unable to engage in any substantial gainful activity, and is expected to result in death or is expected to last for a continuous period of not less than twelve (12) months. This definition of “Disability” is intended
to comply with section 409A of the Code, and the regulations promulgated thereunder, and shall be interpreted and administered in accordance with said provisions. Termination due to disability shall be deemed to have occurred upon the first day of
the month following the determination of Disability as defined in the preceding sentence. 
 “Good Reason” shall
mean the occurrence of any of the following events unless, (A) such event occurs with the Employee’s express prior written consent, (B) the event is an isolated, insubstantial or inadvertent action or failure to act which is remedied
by the Company or the Bank promptly after receipt of notice thereof given by the Employee, (C) the event occurs in connection with the termination of the Employee’s employment for Cause, Disability or death or (D) the event occurs in
connection with the Employee’s voluntary termination of employment other than due to the occurrence of one of the following events: 
 (1) a material adverse change in the nature or scope of the authorities, powers, functions, duties or 

 
responsibilities attached to Employee’s position (including, but not limited to, Employee not being re-elected or removed from his positions with the
Company or the Bank); or 
 (2) a change in the Employee’s principal office to a location outside of Cook County, DuPage
County or Lake County; or 
 (3) any material reduction in Employee’s base salary and bonus opportunity (other than
permitted proportionate reductions applicable to all similarly situated senior executives of the Company, unless such reduction occurs during the two year period commencing upon a Change in Control); or 
 (4) a material breach of the Employment Agreement by the Company or the Bank. 
 Anything herein to the contrary notwithstanding, the Employee shall be required to give written notice to the Board of Directors of the Company that the
Employee believes an event has occurred that constitutes a Good Reason event within ninety (90) days of the initial occurrence, which written notice shall specify the particular act or acts, on the basis of which the Employee intends to so
terminate the Employee’s employment, and the Company shall then be given the opportunity, within thirty (30) days of its receipt of such notice, to cure said event. Employee’s termination shall not be considered to be a termination
for Good Reason unless such termination occurs within one hundred twenty (120) days after the occurrence of the Good Reason event. 
 “Retirement” shall mean the termination of Employee’s employment with the Company, the Bank or any Subsidiary for any reason other than for Cause after Employee reaches age sixty-five (65) with 5
years of service. 
 “Section 83(b) Election” shall mean an election made pursuant to Section 83(b) of the
Internal Revenue Code of 1986, as amended, to be taxed with respect to the Restricted Shares at the time of grant rather than upon the lapse of the Restrictions. 
 “Subsidiary” or “Subsidiaries” shall mean any corporation or other entity of which outstanding shares or ownership
interests representing 50% or more of the combined voting power of such corporation or other entity entitled to elect the management thereof, or such lesser percentages may be approved by the Compensation Committee, are owned, directly or
indirectly, by the Company. 

 MISCELLANEOUS 
 Administration. This Award shall be administered by the Compensation Committee or its delegate as provided in Section 3 of the Plan. 
 No Guarantee of Employment or Service; Compensation. Nothing in this Agreement shall be construed as an employment, consulting or similar contract for services between the Company, the Bank or any Subsidiary and the Employee.
Any benefit derived under this Agreement shall not be considered compensation for purposes of calculating any severance, resignation, bonus, pension, retirement or similar payments or benefits. 
 The Company’s Rights. The existence of the Award shall not affect in any way the right or power of the Company or its shareholders to make or
authorize any or all adjustments, recapitalizations, reorganizations or other changes in the Company’s capital structure or its business, or any merger or consolidation of the Company, or any issue of bonds, debentures, preferred or other
securities with preference ahead of or convertible into, or otherwise affecting the Shares or the rights thereof, or the dissolution or liquidation of the Company, or any sale or transfer of all or any part of the Company’s assets or business,
or any other act or proceeding, whether of a similar character or otherwise. 
 Employee. Whenever the word “Employee” is used in any
provision of this Agreement, under circumstances where the provision should logically be construed to apply to the estate, personal representative or beneficiary to whom this Award may be transferred by will or by the laws of descent and
distribution, the word “Employee” shall be deemed to include such person. 
 Nontransferability of Award. This Award is not
transferable by the Employee otherwise than by will or the laws of descent and distribution. 
 Entire Agreement; Modification. Except as
provided in the Plan and the Notice, this Agreement contains the entire agreement between the parties with respect to the subject matter contained herein, and may not be modified, except as provided in a written document signed by each of the
parties hereto. Any oral or written agreements, representations, warranties, written inducements, or other communications made prior to the execution of this Agreement shall be void and ineffective for all purposes. 
 Severability. In the event that any term or provision of this Agreement shall be finally determined to be superseded, invalid, illegal or otherwise
unenforceable pursuant to applicable law by a governmental authority having jurisdiction and venue, that determination shall not impair or otherwise affect the validity, legality or enforceability, to the maximum extent permissible by law,
(a) by or before that authority of the remaining terms and provisions of this Agreement, which shall be enforced as if the unenforceable term or provision were deleted, or (b) by or before any other authority of any of the terms and
provisions of this Agreement. 

 Governing Law. This Agreement shall be governed and construed in accordance with the laws of the State of
Illinois (regardless of the law that might otherwise govern under applicable Illinois principles of conflict of laws).

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