Document:

AMENDED AND RESTATED

    SHAREHOLDER AGREEMENT

    

    

    THIS AMENDED AND RESTATED SHAREHOLDER AGREEMENT (the “Agreement”), dated this 27th day of December, 2019, by and between Berkshire Hills
      Bancorp, Inc. (“Berkshire Hills”), and the Estate of David G. Massad (the “Shareholder”), amends and restates in its entirety that certain Agreement, dated May 22, 2017 (the “Shareholder Agreement”), by and between Berkshire Hills Bancorp, Inc.
      (“Berkshire Hills”), a Delaware corporation, and David G. Massad, an individual (“Massad”).  Any capitalized term used and not otherwise defined in this Agreement has the meaning set forth in Section 12 hereof.

    

    

    RECITALS

    

    

    WHEREAS, the Effective Time (as
      defined in the Merger Agreement) occurred on October 13, 2017;

    

    

    WHEREAS, Massad died on December 28,
      2018 and his daughter Pamela A. Massad (the “Representative”) was appointed as the personal representative of the Shareholder effective January 11, 2019; and

    

    

    WHEREAS, Berkshire Hills and the
      Representative mutually desire to amend and restate the Shareholder Agreement as set forth herein.

    

    

    NOW THEREFORE, in consideration of
      the recitals and the representations, warranties, covenants and agreements contained herein and other good and valuable consideration, and intending to be legally bound hereby, the parties hereto agree as follows:

    

    

    1. Representations and Warranties of the
          Shareholder and Representative.  The Shareholder and the Representative severally but not jointly represent and warrant to Berkshire Hills, as follows:

    

    

    (a) The Shareholder is the record owner of 3,757,344 shares of Berkshire Hills Bancorp, Inc. common stock, par value $0.01 per share (“Berkshire Hills Common Stock”);

    

    

    (b) The Representative has full power and authority to enter into this Agreement on behalf of the Shareholder and to cause the Shareholder to perform its obligations under this
        Agreement.  This Agreement constitutes a valid and binding obligation of the Shareholder, and the performance of its terms will not constitute a violation of any agreement or any instrument to which the Shareholder is a party.

    

    

    2. Representations and Warranties of Berkshire Hills.

    

    

    Berkshire Hills hereby represents and warrants to the Shareholder that Berkshire Hills has full power and authority to enter into and
      perform its obligations under this Agreement and that the execution and delivery of this Agreement by Berkshire Hills has been duly authorized by the Board of Directors of Berkshire Hills.  This Agreement constitutes a valid and binding obligation

     

    

    
      
        

    

    of Berkshire Hills, and the performance of its terms will not constitute a violation of any agreement or instrument to which Berkshire Hills is a party.

    

    

    3. Covenants.

    

    

    (a) The Shareholder covenants and agrees not to do the following, directly or indirectly, alone or in concert the Acting in Concert Group (as defined in the Series B Non-Voting
        Preferred Stock Certificate of Designations of Berkshire Hills from the date of this Agreement through the date that this Agreement terminates in accordance with Section 5):

    

    

    (i) acquire, offer or propose to acquire or agree to acquire, whether by purchase, tender or exchange offer, or through the acquisition of control of another person or entity
        (including by way of merger or consolidation) any shares of Berkshire Hills Common Stock or any other class of Berkshire Hills Bancorp, Inc. stock that has voting rights (“Berkshire Hills Voting Stock”), any rights to vote or direct the voting of
        any additional shares of Berkshire Hills Common Stock or Berkshire Hills Voting Stock, or any securities convertible into, Berkshire Hills Common Stock or Berkshire Hills Voting Stock (except (A) by way of stock splits, stock dividends, stock
        reclassifications or other distributions or offerings made available and, if applicable, exercised on a pro rata basis, to holders of the Berkshire Hills Common Stock generally, or (B) that number of shares of Berkshire Hills Common Stock, the
        purchase by the Shareholder of which would cause the Shareholder to beneficially own, in the aggregate with the Acting in Concert Group, no more than 9.9% of the then-outstanding shares of Berkshire Hills Common Stock, as calculated pursuant to 12
        C.F.R. § 225.41 of Regulation Y;

    

    

    (ii) convert the Berkshire Hills Preferred Stock Consideration received pursuant to the Merger Agreement to Berkshire Hills Common Stock pursuant to the terms of the Series B
        Non-Voting Preferred Stock Certificate of Designation, except that nothing in this sentence shall (A) prohibit one or more of the following transfers by the Shareholder to effectuate a conversion of the Berkshire Hills Preferred Stock Consideration
        to Berkshire Hills Common Stock: (i) to an affiliate of the Shareholder or to Berkshire Hills, provided that the affiliate would not be deemed part of the Shareholder’s Acting in Concert Group; (ii) in a widespread public distribution with the
        prior written consent of Berkshire Hills; (iii) in transfers in which no transferee (or group of associated transferees) would receive two percent (2%) or more of any class of voting securities of Berkshire Hills; or (iv) to a transferee that would
        control more than fifty percent (50%) of the voting securities of Berkshire Hills without any transfer from the Shareholder; and (B) prohibit the Shareholder from initiating a conversion of the Berkshire Hills Preferred Stock Consideration to
        Berkshire Hills Common Stock if after giving effect to such conversion, the Shareholder would beneficially own, in the aggregate with the Acting in Concert Group, no more than 9.9% of the then-outstanding shares of Berkshire Hills Common Stock, as
        calculated pursuant to 12 C.F.R. § 225.41 of Regulation Y;

    

    

    (iii) without Berkshire Hills’ prior written consent and Berkshire Hills’ review of the Shareholder’s proposed sale or transfer of such shares, which consent and review shall not be
        unreasonably withheld or delayed, directly or indirectly sell or transfer any Shareholder’s shares of Berkshire Hills Common Stock; additionally, any proposed sale by Shareholder of Berkshire Hills Common Stock shall first be offered to Berkshire
        Hills under the same terms and 

     

      

    
      
        

    

    conditions as the proposed sale, which Berkshire Hills shall have five (5) business days following the date Shareholder first presents in writing
        the terms of such proposed sale to Berkshire Hills, to accept such offer, except that nothing in this sentence shall prohibit one or more of the following transfers by the Shareholder or any Permitted Transferee (as defined below) that continues to
        be subject to this Agreement: (A) a transfer between members of the Acting in Concert Group; (B) a transfer by will or by operation of law; (C) a transfer in connection with estate or charitable planning purposes, including any transfer to one or
        more relatives of the Shareholder or any transfer to one or more trusts or other entities that are beneficially owned exclusively by the Shareholder, one or more relatives of the Shareholder, or any combination of them; and (D) a transfer to a
        charitable organization that is not controlled by the Shareholder or one or more affiliates or relatives; provided that as a condition to each permitted transfer under (A)-(D) of this clause (iii), each transferee (each a “Permitted Transferee”)
        shall deliver a written instrument to Berkshire Hills, in a form reasonably acceptable to Berkshire Hills, agreeing to be bound by the restrictions set forth in this Agreement. Notwithstanding the first sentence of this subsection, Shareholder may
        sell up to the Monthly Limit (as defined below) of Berkshire Hills Common Stock on a monthly basis without Berkshire’s prior review and written consent solely to the extent those shares of Berkshire Hills Common Stock are sold either (X) through a
        registered broker dealer on the open market and not through privately negotiated transactions (an “Open Market Sale”), or (Y) as part of one or more “blocks” (as defined in Rule 10b-18 promulgated under the Securities Exchange Act of 1934, as
        amended) of Berkshire Hills Common Stock through privately negotiated transactions (a “Block Sale”); provided that during any calendar month the aggregate number of shares of Berkshire Hills Common Stock that may be sold under this (Y) may not
        exceed two percent (2%) (the “Block Limit Percentage”) of the Reported Shares Outstanding.  For avoidance of doubt, shares of Berkshire Hills Common Stock covered by Hedging Transactions will be counted toward the Monthly Limit.  Berkshire Hills
        agrees that it will not unreasonably withhold or delay a request by the Shareholder to waive this clause (iii) with respect to a distribution in a firm commitment underwriting to (or a placement facilitated by) one or more broker-dealers reasonably
        acceptable to Berkshire Hills (a “Permitted Offering”); provided that the distribution is structured as or is similar in all material respects to a confidentially marketed public offer primarily to institutional accredited investors, and the number
        of shares of Berkshire Hill Common Stock offered and sold in such distribution does not exceed seven and 5/10 percent (7.5%) of the shares of Berkshire Hills Common Stock then outstanding.  The sale of shares by the Shareholder and each Permitted
        Transferee that continues to be subject to this Agreement shall be aggregated for purposes of the Monthly Limit and the Block Limit Percentage.  Notwithstanding any other provision of this Agreement, this Section 3(a)(iii) shall not apply to any
        Permitted Transferee that beneficially owns less than three and 5/10 percent (3.5%) of the Reported Shares Outstanding.

    

    

    (iv) (A) propose or seek to effect a merger, consolidation, recapitalization, reorganization, sale, lease, exchange or other disposition of a majority of the assets of, or other
        business combination involving, or a tender or exchange offer for securities of, Berkshire Hills or any material portion of Berkshire Hills’ business or assets or any type of transaction that would result in a change in control of Berkshire Hills
        (any such transaction described in this clause (A) is a “Company Transaction” and any proposal or other action seeking to effect a Company Transaction as described in this clause (A) is defined as a “Company Transaction Proposal”), (B) seek to
        exercise any control or influence over the management of Berkshire Hills or the Board of Directors of Berkshire Hills or any of the businesses, operations or policies of Berkshire Hills; provided that the Shareholder shall not be prohibited from
        communicating with the executive officers and directors of Berkshire Hills in the Shareholder’s capacity as a shareholder of Berkshire Hills, (C) present to Berkshire Hills, its shareholders or any third party any proposal constituting or that
        could reasonably be expected to result in a Company Transaction, or (D) seek to effect a change in control of Berkshire Hills;

    

    

    (v) publicly suggest or announce the Shareholder’s willingness or desire to engage in a transaction or group of transactions or have another person engage in a transaction or group
        of transactions that would constitute or could reasonably be expected to result in a Company Transaction or take any action that might require Berkshire Hills to make a public announcement regarding any such Company Transaction;

    

    

    (vi) initiate, request, induce, encourage or attempt to induce or give encouragement (publicly or otherwise) to any other person to initiate any proposal constituting or that can
        reasonably be expected to result in a Company Transaction Proposal, or otherwise provide assistance to any person who has made or is contemplating making, or enter into discussions or negotiations with respect to, any proposal constituting or that
        would reasonably be expected to result in a Company Transaction Proposal;

    

    

    (vii) solicit proxies or written consents or assist or participate in any other way, directly or indirectly, in any solicitation of proxies or written consents, or otherwise become a
        “participant” in a “solicitation,” or assist any “participant” in a “solicitation” (as such terms are defined in Rule 14a-1 of Regulation 14A and Instruction 3 of Item 4 of Schedule 14A, respectively, under the Securities Exchange Act of 1934, as
        amended (the “Exchange Act”)) in opposition to any recommendation or proposal of Berkshire Hills’ Board of Directors, or recommend or request or induce or attempt to induce any other person to take any such actions, or seek to advise, encourage or
        influence any other person with respect to the voting of (or the execution of a written consent in respect of) the Berkshire Hills Common Stock, or execute any written consent in lieu of a meeting of the holders of the Berkshire Hills Common Stock
        or grant a proxy with respect to the voting of the capital stock of Berkshire Hills to any person or entity other than the Board of Directors of Berkshire Hills; provided that the Shareholder shall be permitted to grant a proxy to a representative
        of the Shareholder for the purpose of such representative voting the Shareholder’s shares of Berkshire Hills Common Stock in accordance with the Shareholder’s instructions at a meeting of the Berkshire Hills shareholders wherein such proxy is voted
        the manner required by this Agreement;

    

    

    (viii) initiate, propose, submit, encourage or otherwise solicit shareholders of Berkshire Hills for the approval of one or more shareholder proposals or induce or attempt to induce
        any other person to initiate any shareholder proposal, or seek election to, or seek to place a representative or other affiliate of Shareholder on, Berkshire Hills’ Board of Directors or seek removal of any member of Berkshire Hills’ Board of
        Directors or any executive officer of Berkshire Hills;

    

    

    (ix) form, join in or in any other way (including by deposit of Berkshire Hills’ capital stock) participate in a partnership, pooling agreement, syndicate, voting trust or other 

     

      

    
      
        

    

    group with respect to Berkshire Hills Common Stock, or enter into any agreement or arrangement or otherwise act in concert with any other person,
        for the purpose of acquiring, holding, voting or disposing of Berkshire Hills Common Stock;

    

    

    (x) (A) join with or assist any person or entity, directly or indirectly, in opposing, or make any statement in opposition to, any proposal or director nomination submitted by
        Berkshire Hills’ Board of Directors to a vote of Berkshire Hills’ shareholders, or (B) join with or assist any person or entity, directly or indirectly, in supporting or endorsing (including supporting, requesting or joining in any request for a
        meeting of shareholders in connection with), or make any statement in favor of, any proposal submitted to a vote of Berkshire Hills’ shareholders that is opposed by Berkshire Hills’ Board of Directors;

    

    

    (xi) vote for any proposal or any individual for election to the Board of Directors of Berkshire Hills, other than those proposals or nominations recommended or supported by
        Berkshire Hills’ Board of Directors;

    

    

    (xii) except in connection with the enforcement of this Agreement, initiate, participate as a named plaintiff, finance or otherwise encourage any litigation against Berkshire Hills or
        any of its respective officers and directors, or any derivative litigation on behalf of Berkshire Hills, based upon any act or omission relating to Berkshire Hills that occurs or is alleged to have occurred after the Effective Time; provided, this
        clause shall not preclude or in any way restrict the Shareholder from (A) electing to participate in any settlement or judgment resulting from a class action, or (B) submitting to witness interviews or providing testimony or documentary evidence,
        whether voluntarily or in response to a subpoena;

    

    

    (xiii) request, or induce or encourage any other person to request, that Berkshire Hills amend or waive any of the provisions of this Agreement; and

    

    

    (xiv) advise, assist, encourage or finance (or arrange, assist or facilitate financing to or for) any other person in connection with any of the matters restricted by, or otherwise
        seek to circumvent the limitations of, this Agreement.

    

    

    Notwithstanding any other provision in this Agreement, Shareholder shall not convert any shares of Series B Non-Voting Preferred Stock if,
      after giving effect to such conversion, the Acting in Concert Group beneficially would own more than 9.9% of the then-outstanding shares of Berkshire Hills Common Stock and Berkshire Hills Voting Stock, if any, as calculated pursuant to 12 C.F.R.
      225.41 of Regulation Y.

    

    

    (b) Shareholder agrees that upon Berkshire Hills’s reasonable request from time to time, Shareholder will determine, based on the definition of “Acting in Concert” of Regulation Y,
        which individuals and entities constitute the Acting in Concert Group, and provide written confirmation to Berkshire Hills that, to the knowledge of the Shareholder after reasonable inquiry, the Acting in Concert Group beneficially owns no more
        than 9.9% of the then-outstanding shares of Berkshire Hills Common Stock and Berkshire Hills Voting Stock, if any, as calculated pursuant to 12 C.F.R. § 225.41 of Regulation Y.

    

    

    
      
        

    

    (c) During the term of this Agreement, the Shareholder agrees not to disparage Berkshire Hills or any of its directors (including shareholders supported by Berkshire Hills’ Board of
        Directors), officers or employees in any public or quasi-public forum, and Berkshire Hills agrees not to disparage the Shareholder in any public or quasi-public forum.

    

    

    (d) During the term of this Agreement, at any Annual or Special Meeting of Shareholders of Berkshire Hills, to the extent that Shareholder beneficially owns more than five percent
        (5.0%) of the then-outstanding shares of Berkshire Hills Common Stock, the Shareholder covenants and agrees to vote all the shares of Berkshire Hills Common Stock beneficially owned by the Shareholder in excess of five percent (5.0%) of the
        then-outstanding shares of Berkshire Hills Common Stock (i) in favor of the nominees for election or re-election as directors of Berkshire Hills selected by the Board of Directors of Berkshire Hills; (ii) in favor of any proposal which the Board of
        Directors of Berkshire Hills recommends a vote in favor to its shareholders; and (iii) against any proposal which the Board of Directors of Berkshire Hills recommends a vote against to its shareholders. The Shareholder may vote up to five percent
        (5.0%) of the then-outstanding shares of Berkshire Hills Common Stock in the Shareholder’s discretion.

    

    

    (e) During the term of this Agreement, the Shareholder either individually or collectively with the Acting in Concert Group, and no member of the Acting in Concert Group will,
        directly or indirectly:

     

      

    	 	 (i)	
            Exercise or attempt to exercise a controlling influence over the management or policies of Berkshire Hills, Berkshire Bank or any of their
              subsidiaries;

             

            

          
	 	 (ii)	
            Have or seek to have the Shareholder or any representative of Shareholder serve on the board of directors of Berkshire Hills, Berkshire Bank or any of
              their subsidiaries;

             

            

          
	 	 (iii)	
            Have or seek to have any employee or representative of the Shareholder serve as an officer, agent, or employee of Berkshire Hills, Berkshire Bank or
              any of their subsidiaries;

             

            

          
	 	 (iv)	
            Take any action that would cause Berkshire Hills, Berkshire Bank or any of their subsidiaries to become a subsidiary of Shareholder; 

             

            

          
	 	 (v)	
            Own, control, or hold with power to vote securities that represent twenty-five percent (25%) or more of any class of voting securities of Berkshire
              Hills, Berkshire Bank or any of their subsidiaries;

             

            

          
	 	 (vi)	
            Propose a director or slate of directors in opposition to a nominee or slate of nominees proposed by the management or board of directors of Berkshire
              Hills, Berkshire Bank or any of their subsidiaries;

             

            

          
	 	 (vii)	
            Enter into any agreement with Berkshire Hills or any of its subsidiaries that substantially limits the discretion of Berkshire Hills’ management over
              major policies and decisions, including, but not limited to, policies or decisions about employing and compensating executive officers; engaging in new business lines; raising additional debt or equity capital; merging or consolidating with
              another firm; or acquiring, selling, leasing, transferring, or disposing of material assets, subsidiaries, or other entities;

          

    

    

    

  

  
    
      

  

  
    

    

    	 	 (viii)	
            Solicit or participate in soliciting proxies with respect to any matter presented to the shareholders of Berkshire Hills, Berkshire Bank or any of
              their subsidiaries; or

             

            

          
	 	 (ix)	
            Dispose or threaten to dispose (explicitly or implicitly) of equity interests of Berkshire Hills, Berkshire Bank or any of their subsidiaries in any
              manner as a condition or inducement of specific action or non-action by Berkshire Hills, Berkshire Bank or any of their subsidiaries; provided that the Shareholder shall not be prohibited from communicating with the executive officers and
              directors of Berkshire Hills in the Shareholder’s capacity as a shareholder of Berkshire Hills.

          

    

    

    (f) Until October 13, 2020, and in the event that either or both of the New Board Members (as defined
          by the Merger Agreement) no longer serves as a member of the Berkshire Hills and Berkshire Bank Board of Directors, the Shareholder shall have the right to
          consult with Berkshire Hills’ Corporate Governance and Nominating Committee in its selection of a qualified nominee to serve on the Boards of Berkshire Hills and Berkshire Bank. Such consultation shall include the then chair of the Berkshire
          Hills Corporate Governance and Nominating Committee consulting with the Representative (or, at the Representative’s election, one or more Permitted Transferees) regarding the relative strengths of the leading candidates to be nominated to serve
          on the Boards of Berkshire Hills and Berkshire Bank.  Each such nominee shall, if elected or appointed to the Board of Berkshire Hills, qualify as an “independent director” under then applicable rules of the New York Stock Exchange.

    

    

    (g) After Berkshire Hills files with the SEC the Berkshire Hills Annual Report on Form 10-K for the year ending December 31, 2019 (the “2019 Form
        10-K”), if (i) in the reasonable opinion of counsel to the Shareholder, the Shareholder may not reasonably rely on the exemption from registration under the Securities Act of 1933 (the “Securities Act”) provided by Rule 144 for sales by
        non-affiliates of Berkshire Hills of shares of Berkshire Hills Common Stock that are not “restricted” within the meaning of such rule, and (ii) Berkshire Hills then is eligible to file with the SEC a so-called “automatic shelf registration
        statement” on Form S-3 within the meaning of Rule 462(e) under the Securities Act (a “Resale Shelf Registration Statement”), then Berkshire Hills, upon the written request of the Shareholder, will file with the SEC, at the expense of Berkshire
        Hills, a Resale Shelf Registration Statement registering with the SEC the offer and resale of all shares of Berkshire Hills Common Stock then beneficially owned by the Shareholder and each Permitted Transferee who continues to be bound by this
        Agreement.  Without limiting the scope of the immediately preceding sentence, Berkshire Hills agrees that, unless the Shareholder otherwise directs Berkshire Hills in writing, Berkshire Hills shall use its best efforts to file with the SEC, as soon
        as possible after Berkshire Hills files its 2019 Form 10-K, a Resale Shelf Registration Statement registering the offer and resale of all shares of Berkshire Hills Common Stock then beneficially owned by the Shareholder and each Permitted
        Transferee who continues to be bound by this Agreement, including all shares of Berkshire Hills Common Stock

    
      
        

    

    issuable upon the conversion of all shares of Series B Non-Voting Preferred Stock then issued and outstanding.

    4. Notice of Breach and Remedies.

    

    

    The parties expressly agree that an actual or threatened breach of this Agreement by any party will give rise to irreparable injury that
      cannot adequately be compensated by damages.  Accordingly, in addition to any other remedy to which it may be entitled, each party shall be entitled to seek a temporary restraining order or injunctive relief to prevent a breach of the provisions of
      this Agreement or to secure specific enforcement of its terms and provisions.

    

    

    The Shareholder expressly agrees that the Shareholder will not be excused or claim to be excused from performance under this Agreement as a
      result of any material breach by Berkshire Hills unless and until Berkshire Hills is given written notice of such breach and allowed thirty (30) business days either to cure such breach or seek relief in court.  If Berkshire Hills seeks relief in
      court, the Shareholder irrevocably stipulates that any failure to perform by the Shareholder or any assertion by the Shareholder that the Shareholder is excused from performing the Shareholder’s obligations under this Agreement because it would cause
      Berkshire Hills irreparable harm, then Berkshire Hills shall not be required to provide further proof of irreparable harm in order to obtain equitable relief and that the Shareholder shall not deny or contest that such circumstances would cause
      Berkshire Hills irreparable harm.  If, after such thirty (30) business day period, Berkshire Hills has not either reasonably cured such material breach or obtained relief in court, the Shareholder may terminate this Agreement by delivery of written
      notice to Berkshire Hills.

    

    

    Berkshire Hills expressly agrees that it will not be excused or claim to be excused from performance under this Agreement as a result of
      any material breach by the Shareholder unless and until the Shareholder is given written notice of such breach and allowed thirty (30) business days either to cure such breach or seek relief in court.  If the Shareholder seeks relief in court,
      Berkshire Hills irrevocably stipulates that any failure to perform by Berkshire Hills or any assertion by Berkshire Hills that it is excused from performing its obligations under this Agreement because it would cause the Shareholder irreparable harm,
      then the Shareholder shall not be required to provide further proof of irreparable harm in order to obtain equitable relief and that Berkshire Hills shall not deny or contest that such circumstances would cause the Shareholder irreparable harm.  If,
      after such thirty (30) business day period, the Shareholder has not either reasonably cured such material breach or obtained relief in court, Berkshire Hills may terminate this Agreement by delivery of written notice to the Shareholder.

    

    

    5. Term.  This Agreement shall be
        effective upon the execution of this Agreement and will remain in effect until such time that the Acting in Concert Group beneficially owns fewer than five percent (5%) of the shares of Berkshire Hills Common Stock then outstanding for a period of
        120 consecutive calendar days; provided that any Permitted Transferee may elect to terminate this Agreement as to that Permitted Transferee if the Permitted Transferee beneficially owns less than one percent (1%) of the Reported Shares Outstanding,
        and if a Permitted Transferee so terminates this Agreement, such Permitted Transferee shall not be included in the Acting in Concert Group.  Any transferee or assign in an Open Market Sale, a Block Trade, or a 

     

      

    
      
        

    

    Permitted Offering shall not be considered a “successor” or “assign” for purposes of this Section and shall have no obligation under this
        Agreement.

    

    

    6. Publicity.  The Shareholder
        acknowledges that Berkshire Hills may be required to disclose the existence and terms of this Agreement pursuant to securities and banking laws.  In addition, during the term of this Agreement, the Shareholder shall provide to Berkshire Hills for
        Berkshire Hills’ prior review and approval any disclosure proposed to be made by the Shareholder concerning this Agreement, which review and approval shall not be unreasonably delayed or withheld; provided that the Shareholder may make any
        disclosure which the Shareholder determines in good faith, based upon the advice of counsel, is required under applicable law.

    

    

    7. Notices.  All notices, communications
        and deliveries required or permitted by this Agreement shall be made in writing signed by the party making the same, shall specify the section of this Agreement pursuant to which it is given or being made and shall be deemed given or made (a) on
        the date delivered if delivered by telecopy, by facsimile or in person, (b) on the third Business Day after it is mailed if mailed by registered or certified mail (return receipt requested) (with postage and other fees prepaid) or (c) on the day
        after it is delivered, prepaid, to an overnight express delivery service that confirms to the sender delivery on such day, as follows:

    

    

    	
            Shareholder:

          	
            Estate of David G. Massad

          
	 	
            c/o Pamela A. Massad, Esq.

          
	 	
            Tilton Fletcher PC

          
	 	
            The Guarantee Building

          
	 	
            370 Main Street

          
	 	
            12th Floor

          
	 	
            Worcester, Massachusetts 01608

          

    

    

    	
            With a copy (which shall

          	 
	
             not constitute notice) to:

          	
            Michael K. Krebs

          
	 	
            Nutter McClennen & Fish LLP

          
	 	
            155 Seaport Boulevard

          
	 	
            Boston, Massachusetts 02210

          

    

    

    	
            Berkshire Hills

          	 
	
            Bancorp, Inc.

          	
            Richard M. Marotta

          
	 	
            Chief Executive Officer

          
	 	
            Berkshire Hills Bancorp, Inc.

          
	 	
            60 State Street

          
	 	
            Boston, Massachusetts 02109

          

    

    

    
      
        

    

    

    

    

    

    	
            With copies (which shall

          	 
	
             not constitute notice) to:

          	
            Wm. Gordon Prescott

          
	 	
            Executive Vice President and General Counsel

          
	 	
            Berkshire Hills Bancorp, Inc.

          
	 	
            24 North Street

          
	 	
            Pittsfield, Massachusetts 01201

          
	 	 
	 	
            Lawrence Spaccasi, Esq.

          
	 	
            Marc Levy, Esq.

          
	 	
            Luse Gorman, PC

          
	 	
            5335 Wisconsin Avenue, NW

          
	 	
            Suite 780

          
	 	
            Washington, DC 20015

          

    

    

    8. Governing Law and Choice of Forum. 
        Unless applicable federal law or regulation is deemed controlling, Delaware law shall govern the construction and enforceability of this Agreement.  Any and all actions concerning any dispute arising hereunder shall be filed and maintained in the
        Business Litigation Session of the Superior Court of the Commonwealth of Massachusetts or, if under applicable law, exclusive jurisdiction over such matters is vested in the Federal courts, the United States District Court for the District of
        Massachusetts.  Each of the parties to this Agreement, including each Permitted Transferee who becomes a party to this Agreement, agrees that the Business Litigation Session of the Superior Court of the Commonwealth of Massachusetts and the United
        States District Court for the District of Massachusetts may exercise personal jurisdiction over such parties in any such action.

    

    

    9. Severability.  If any term, provision,
        covenant or restriction of this Agreement is held by any governmental authority or a court of competent jurisdiction to be invalid, void or unenforceable, the remainder of the terms, provisions, covenants and restrictions of this Agreement shall
        remain in full force and effect and shall in no way be affected, impaired or invalidated.

    

    

    10. Successors and Assigns.  This
        Agreement shall be binding upon and shall inure to the benefit of the parties to this Agreement, as well as their respective representatives, successors, permitted assigns, heirs and estates.

    

    

    11. Amendments.  This Agreement may not be
        modified, amended, altered or supplemented except by a written agreement executed by all of the parties.

    

    

    12. Definitions.  As used in this
        Agreement, the following terms shall have the meanings indicated, unless the context otherwise requires:

    

    

    (a) The term “acquire” means every type of acquisition, whether effected by purchase, exchange, operation of law or otherwise.

    (b) The term “affiliate” means, with respect to any person, a person or entity that directly, or indirectly through one or more intermediaries, controls or is controlled by, or is
        under common control with such other person.

    

    

    
      
        

    

    (c) The terms “beneficial owner” and “beneficially own” have the meanings ascribed to them in, and shall be determined in accordance with, Rule 13d-3 of the SEC’s Rules and
        Regulations under the Exchange Act.

    

    

    (d) The term “Berkshire Hills Preferred Stock Consideration” means the shares of non-voting, participating Berkshire Hills preferred stock as defined by the Series B Non-Voting
        Preferred Stock Certificate of Designation.

    

    

    (e) The term “change in control” denotes circumstances under which: (i) any person or group becomes the beneficial owner of shares of capital stock of Berkshire Hills representing
        twenty-five percent (25%) or more of the total number of votes that may be cast for the election of the Board of Directors of Berkshire Hills, (ii) the persons who were directors of Berkshire Hills cease to be a majority of the Board of Directors,
        in connection with any tender or exchange offer (other than an offer by Berkshire Hills), merger or other business combination, sale of assets or contested election, or combination of the foregoing, or (iii) shareholders of Berkshire Hills approve
        a transaction pursuant to which substantially all of the assets of Berkshire Hills will be sold.

    

    

    (f) The term “control” (including the terms “controlling,” “controlled by,” and “under common control with”) means the possession, direct or indirect, of the power to direct or
        cause the direction of the management, activities or policies of a person or organization, whether through the ownership of capital stock, by contract, or otherwise.

    

    

    (g) The term “group” has the meaning as defined in Section 13(d)(3) of the Exchange Act.

    

    

    (h) The term “Hedging Transaction” means any short sale (whether or not against the box) and any sale or grant of any put option or with respect to Berkshire Hills Common Stock but
        shall not include a broad-based market basket or index, including the Nasdaq Bank Index and the KBW Regional Banking Index (or any successor index), that includes, relates to or derives a portion of its value from Berkshire Hills Common Stock) that
        is conducted by the Shareholder from the Effective Time and through the date this Agreement terminates in accordance with Section 5 hereto.

    

    

    (i) The term “Merger Agreement” means the Agreement and Plan of Merger by and between the Berkshire Hills and Commerce Bancshares Corp., dated as of May 22, 2017.

    

    

    (j) The term “Monthly Limit” means 600,000 shares of Berkshire Hills Common Stock.

    

    

    (k) The term “person” includes an individual, group acting in concert, corporation, partnership, association, joint stock company, trust, unincorporated organization or similar
        company, syndicate, or any other group formed for the purpose of acquiring, holding or disposing of the equity securities of Berkshire Hills.

    

    

    
      
        

    

    (l) The term “Reported Shares Outstanding” means the number of shares of Berkshire Hills Common Stock reported as issued and outstanding on the cover page of the Form 10-K or Form
        10-Q most recently filed by Berkshire Hills with the SEC.

    

    

    (m) The term “SEC” means the U.S. Securities and Exchange Commission.

    

    

    (n) The term “Series B Non-Voting Preferred Stock” has the meaning set forth in the Series B Non-Voting Preferred Stock Certificate of Designation.

    

    

    (o) The term “Series B Non-Voting Preferred Stock Certificate of Designation” means the Certificate of Designations of Series B Non-Voting Preferred Stock of Berkshire Hills
        Bancorp, Inc. dated October 12, 2017.

    

    

    (p) The term “transfer” means, directly or indirectly, to sell, gift, assign, pledge, encumber, hypothecate or similarly dispose of (by operation of law or otherwise), either
        voluntarily or involuntarily, or to enter into any contract, option or other arrangement or understanding with respect to the sale, gift, assignment, pledge, encumbrance, hypothecation or similar disposition of (by operation of law or otherwise),
        any Berkshire Hills Common Stock or any interest in any Berkshire Hills Common Stock; provided, however, that a merger or consolidation in which Berkshire Hills or any of its Subsidiaries is a constituent corporation shall not be deemed to be the
        transfer of any common stock beneficially owned by the Shareholder. The term “transfer” shall not include a transfer of record (but not beneficial) ownership to transfer shares of Berkshire Hills Common Stock into “street name” as part of a
        customary custody arrangement.

    

    

    (q) The term “vote” means to vote in person or by proxy, or to give or authorize the giving of any consent as a shareholder on any matter.

    

    

    13. Termination.  This Agreement shall
        cease, terminate and have no further force and effect upon the expiration of the term as set forth in Section 5, unless earlier terminated pursuant to Section 4 or Section 5 hereof or by mutual written agreement of the parties.

    

    

    14. Counterparts; Facsimile.  This
        Agreement may be executed in any number of counterparts and by the parties in separate counterparts, and signature pages may be delivered by facsimile, each of which when so executed shall be deemed to be an original and all of which taken together
        shall constitute one and the same agreement.

    

    

    15. Duty to Execute.  Each party agrees to
        execute any and all documents, and to do and perform any and all acts and things necessary or proper to effectuate or further evidence the terms and provisions of this Agreement.

    

    

    [Remainder of this page intentionally left blank.]

    
      
        

    

    

    

    IN WITNESS WHEREOF, this Agreement has been duly executed by the undersigned and is effective as of the day and year first above written.

    

    

    BERKSHIRE HILLS BANCORP, INC.

    

    

    

    

    

    

    By:  /s/ Richard M. Marotta

         Richard M. Marotta

         Chief Executive Officer

    

    

    

    

    SHAREHOLDER

    

    

    ESTATE OF DAVID G. MASSAD

    

    

    

    

    

    

    
      By:  /s/ Pamela A. Massad

          

           Pamela A. Massad

           Personal RepresentativeExhibit 10.1

 

SEPARATION
AGREEMENT

 

This Separation
Agreement (“Agreement”) is entered into as of this 5th day of December, 2019, by and between TAILORED SHARED
SERVICES, LLC (“SSU”), a wholly owned subsidiary of Tailored Brands, Inc. (“TBI”) (collectively, SSU and
TBI shall be referred to as “TAILORED BRANDS” or the “Company”), and MARY BETH BLAKE (“Blake”).

 

Recitals

 

i.         
In consideration of Blake’s acceptance of this Agreement and, pursuant to it, TAILORED BRANDS is agreeable to paying to Blake
the payments and benefits under this Agreement.

 

ii.        
In consideration of TAILORED BRANDS’
acceptance of this Agreement and its agreement
to pay Blake the payments and benefits under this Agreement, Blake is willing to execute this Agreement and any and all releases
of claims described under this Agreement.

 

Based
on these recitals and in consideration of the mutual promises and agreements set forth in this Agreement, Blake and the Company
agree as follows:

 

Terms

1.        Termination
of Employment.

 

a.        Termination.
By executing this Agreement, Blake acknowledges that her employment shall continue through December 31, 2019 and be terminated
on such date (“the Termination Date”). If Blake executes and does not revoke this Agreement, and continues as an active
and engaged employee of the Company then she shall continue to receive the salary and benefits she is now receiving. Blake acknowledges
and agrees that as of the Termination Date she shall cease to serve as an employee, officer, agent or representative of TAILORED
BRANDS and its direct and indirect parent(s), subsidiaries and affiliates and shall not represent herself as being any of the
foregoing. As of the Termination Date, Blake will receive a lump sum payment in cash, less applicable taxes and withholdings,
to be paid in the Company’s customary payroll cycle immediately following the Termination Date, equal to (i) Blake’s
annual salary earned, through the Termination Date; (ii) any accrued time off pay earned by Blake; and (iii) any unreimbursed
business expenses of Blake, in each case, to the extent not theretofore paid.

 

b.       Separation
Payments. Conditioned upon Blake’s not terminating her employment prior to the Termination Date, her execution of a
release of claims satisfactory to the Company effective through the Termination Date (the “Second Release”), and her
continued compliance with the covenants contained in Sections 4 and 5 of this Agreement, the Company shall provide the following
payments and benefits to Blake, less applicable taxes and withholdings:

 

i.                   
$600,000.00, calculated in accordance with the customary payroll practices of the Company to be paid through the first anniversary
of the Termination Date in substantially equal installments in accordance with the customary payroll practices of the Company;

 

ii.                 
A lump sum payment in cash equal to $42,000.00, representing the Bonus earned by Blake under the Company’s annual cash
bonus program for executive officers for the fiscal year of the Company ending following the Termination Date, to be paid no
later than April 15, 2020.

 

     

     

    

 

iii.               
A lump sum payment in cash equal to $40,000.00, payable within 15 days of the Termination Date, in consideration of certain equity
that would have vested in April 2020.

 

iv.                
A lump sum payment in cash equal to $12,000.00 for health insurance premiums. Blake understands and agrees that the Company provided
health care coverage ends on the Termination Date and Blake is responsible for enrolling in health insurance through the marketplace
or COBRA in order to obtain coverage.

 

v.                  
Up to $10,000.00 for outplacement services upon the Company’s receipt of appropriate invoices from Blake for such services.

 

vi.                
Any other benefits to which Blake is entitled under the terms and conditions of the Company’s plans and policies including,
without limitation, reimbursement of expenses related to Company requested travel from Blake’s home in St. Louis, MO. 

 

2.        
Release of Claims by Blake.

 

a.        
In consideration for the payments and benefits provided for in Section 1(b) and other good and valuable consideration, Blake
hereby releases TAILORED BRANDS, its parent companies, subsidiaries, and affiliates and all of
their respective officers, directors, employees, insurers and agents (collectively, the “Released Parties”) from any
and all claims, arising on or before the date of execution of this Agreement, whether known or unknown, foreseen or unforeseen,
asserted or unasserted, including but not limited to those claims asserted or that could have been asserted arising from or in
any way related to her employment with and/or separation from TAILORED BRANDS or any of its subsidiaries or affiliates, and this
release includes any claims she might have for re-employment or for additional compensation or benefits, including claims for violations
of the California Labor Code and the federal Equal Pay Act, as amended, and applies to claims under federal law, state law, contract
or tort, including but not limited to applicable state civil rights laws, the California Fair Employment & Housing Act, Cal.
Govt. Code § 12940 et. seq. (“FEHA”), the California Family Rights Act, Title VII of the Civil Rights Act of 1964,
as amended, the Post-Civil War Civil Rights Acts (42 U.S.C. Sections 1981-88), the Americans With Disabilities Act, the Rehabilitation
Act of 1973, Executive Order 11246, the Sarbanes-Oxley Act of 2002, Pub. L. No. 107-204, 116 Stat. 745, Family and Medical Leave
Act, the Age Discrimination in Employment Act (29 U.S.C. Section 621 et seq.) (“ADEA”), the Older Workers Benefit Protection
Act, and any regulations under such laws. Further, Blake acknowledges that she is receiving consideration for her release
of any claim under the ADEA in addition to anything of value to which she was already entitled.

 

b.         Nothing
in this Agreement is intended to waive claims (i) for unemployment or workers’ compensation benefits, (ii) for vested
rights under any employee benefit plan covered under the provisions of the Employee Retirement Income Security Act of 1974,
as amended (“ERISA”) as applicable on the date this Agreement is signed, (iii) that may arise after
this Agreement is signed, or (iv) which cannot be released as a matter of law by private agreement. In addition, nothing
contained in this Agreement shall prevent Blake from filing a charge or complaint with or from participating in an
investigation or proceeding conducted by the EEOC, NLRB, or any other any federal, state or local agency charged with the
enforcement of any laws, or from exercising rights under Section 7 of the NLRA to engage in joint activity with other
employees, although, by signing this release, Blake hereby waives rights to individual relief based on claims asserted in
such a charge or complaint, except where such a waiver of individual relief is prohibited (provided, however, that nothing
herein limits her right to receive an award for information submitted pursuant to Section 21F of the Securities Exchange Act
of 1934).

 

    -2-

     

    

 

c.        
Blake understands and agrees that claims or facts in addition to or different from those which are now known or believed
by her to exist may hereafter be discovered, but it is her intention to fully and forever release, remise and discharge all claims
which she had, may have had, or now have against the Released Parties, whether known or unknown, suspected or unsuspected, asserted
or unasserted, contingent or non-contingent, without regard to the subsequent discovery or existence of such additional or different
facts.

 

3.        
No Suit. Blake represents and warrants that she
has not previously filed, and to the maximum extent permitted by law agrees that she will not file, a complaint, charge, or lawsuit
against any of the Released Parties regarding any of the claims released herein. If, notwithstanding this representation and warranty,
Blake filed or files such a complaint, charge, or lawsuit, Blake agrees that she shall cause such complaint, charge, or lawsuit
to be dismissed with prejudice and shall pay any and all costs required in obtaining dismissal of such complaint, charge, or lawsuit,
including without limitation the attorneys’ fees of any member of the Released Parties against whom she has filed such a
complaint, charge, or lawsuit.

 

4.        Cooperation
Clause. After the Termination Date, Blake agrees to exercise her best, good faith efforts to (a) cooperate fully with the Company
and its affiliates and their respective counsel in connection with any pending or future litigation, arbitration, administrative
proceedings, or investigation relating to any matter that occurred during her employment in which she was involved or of which
she has knowledge; and (b) respond in good faith to any telephone calls and/or information requests from the Company or its representatives
within a reasonable period of time. Blake further agrees that, in the event she is subpoenaed by any person or entity (including,
but not limited to, any government agency) to give testimony or provide documents (in a deposition, court proceeding or otherwise),
which in any way relates to her employment by TAILORED BRANDS, she will give prompt notice of such request to the General Counsel
of the Company and, unless legally required to do so, will make no disclosure until the Company and/or its affiliates have had
a reasonable opportunity to contest the right of the requesting person or entity to such disclosure. Failure to cooperate or respond
in a timely fashion will be considered a material breach of this Agreement. If Blake is required to travel or incur other expenses
as a result of any requests made to her by the Company pursuant to this Cooperation Clause, the Company shall bear, and reimburse
Blake for, all reasonable out of pocket costs of any such expenses.

 

5.        Restrictive
Covenants.

 

a.    
    Non-Competition. Blake acknowledges that she has, while employed, acquired unique and valuable
experience with respect to the businesses, operations, plans and strategies of the Company and its subsidiaries. Blake hereby
covenants and agrees that, for a period equal to twelve months
following the Termination Date, she will not, directly or indirectly, work in any capacity for the following retailers that compete
with the Company: Macy’s, Indochino, Nordstrom, Proper Cloth, Bonobos, Brooks Brothers, Black Tux, Dillard’s, DXL,
and Kohl’s (collectively the “Named Competitors”). This restriction shall include Blake’s participation
in any operations of the Named Competitors with respect to which Blake devoted time as part of her employment on behalf of the
Company or one or more of its subsidiaries. This non-competition covenant shall be applicable with respect to the United States,
Canada, the United Kingdom and any other country in which Blake would be competing with the business of the Company or its subsidiaries
as set forth in this Section 5(a).

 

    -3-

     

    

 

b.       
Non-Solicitation. For a period equal to twelve months
following the Termination Date, Blake shall not directly or indirectly cause, solicit, induce or encourage any employee of the
Company or its subsidiaries to terminate his/her employment with the Company or such subsidiary.

 

c.        
Non-Disparagement. Blake agrees not to engage at any time in any form of conduct or make any statements, or direct any
other person or entity to engage in conduct or make any statements, that disparage, criticize or otherwise impair the reputation
of the Company, its affiliates, and their respective past and present officers, directors, shareholders, partners, members and
agents. The Company agrees not to engage at any time in any form of conduct or make any statements or direct any person or entity
to engage in conduct or make any statements, that disparage, criticize or otherwise impair the reputation of Blake. Nothing contained
in this Section 5(c) shall preclude Blake or the Company from providing truthful testimony or statements pursuant to subpoena
or other legal process or in response to inquiries from any government agency or entity. 

 

d.        
Proprietary Information. Blake acknowledges and agrees that she has acquired as a result of her employment with the Company
or otherwise, Proprietary Information (as defined below) of the Company, which is of a confidential or trade secret nature, and
all of which has a great value to the Company and is a substantial basis and foundation upon which the Company’s business
is predicated. Accordingly, Blake agrees to regard and preserve as confidential at all times all Proprietary Information and to
refrain from publishing or disclosing any part of it to any person or entity and from using, copying or duplicating it in any
way by any means whatsoever, except in furtherance of the business of the Company or as required by applicable law or legal process.
“Proprietary Information” includes all information and data in whatever form, tangible or intangible, pertaining
in any manner to pricing policy, marketing programs, advertising, executive training and specific inventory purchase pricing and
any written information, including customer lists, of the Company or any affiliate thereof, unless the information is or becomes
publicly known through lawful means. 

 

e.        
Covenant Exceptions. Notwithstanding the foregoing covenant obligations of this
Section 5, Blake understands that nothing in this Agreement shall (i) prohibit her from making reports of possible violations
of federal law or regulation to any governmental agency or entity in accordance with the provisions of and rules promulgated under
Section 21F of the Securities Exchange Act of 1934 or Section 806 of the Sarbanes-Oxley Act of 2002, or of any other whistleblower
protection provisions of state or federal law or regulation, or (ii) require notification or prior approval by the Company. Moreover,
pursuant to 18 USC § 1833(b), Blake is hereby notified that she may be entitled to immunity and protection from liabilities
under the Defend Trade Secrets Act of 2016 (18 U.S.C. §§ 1831-39) for disclosing a trade secret under the following
limited circumstances: (i)  Blake shall not be held criminally or civilly liable under any federal or state trade secret
law for the disclosure of a trade secret that is made: (A) in confidence to a federal, state, or local government official, either
directly or indirectly, or to an attorney, and solely for the purpose of reporting or investigating a suspected violation of law;
or (B) in a complaint or other document filed in a lawsuit or other proceeding, if such filing is made under seal; and (ii) if
Blake files a lawsuit for retaliation by the Company for reporting a suspected violation of law, she may disclose the Company’s
trade secrets to her attorney and use the trade secret information in the court proceeding if any document containing the trade
secret is filed under seal and the trade secret is not disclosed except pursuant to court order.

 

    -4-

     

    

 

f.         
Remedy. Blake and the Company agree that a monetary remedy for a breach of this Section 5 will be inadequate and will be
impracticable and extremely difficult to prove, and further agree that such a breach would cause the non-breaching party irreparable
harm, and that the non-breaching party shall be entitled to specific performance and/or temporary and permanent injunctive relief
without the necessity of proving actual damages. Blake and the Company agree that the non-breaching party shall be entitled to
such specific performance and/or injunctive relief, including temporary restraining orders, preliminary injunctions and permanent
injunctions, without the necessity of posting bond or other undertaking in connection therewith. Any such requirement of bond
or undertaking is hereby waived by Blake and the Company and both acknowledge that in the absence of such a waiver, a bond or
undertaking may be required by the court. In the event of litigation to enforce any of these covenants, the courts are hereby
specifically authorized to reform such covenant as and to the extent, but only to such extent, necessary in order to give full
force and effect hereto to the maximum degree permitted by law. Blake also agrees that if she is in breach of this Section 5,
the Company shall cease all payments and other benefits payable under this Agreement and Blake will be required to repay all amounts
paid to her by the Company pursuant to Section 1(b) of this Agreement prior to the time of such breach. 

 

6.        Return
of Company Property.  Blake must return to the Company all Company property in her possession, custody or control, including,
but not limited to, Proprietary Information, computer equipment, software, laptop, iPad, and credit cards. It is understood and
agreed that all paper and electronic files, documents, memoranda, letters, handbooks and manuals, facsimile and/or other communications
concerning TAILORED BRANDS and its business that were written, authorized, signed, received and/or transmitted prior or during
Blake’s employment are and remain Company property. Blake further agrees that she has not and will not (a) copy any computer
files, documents or electronic messages to disks or compact disks; (b) forward computer files, documents or electronic messages
to personal e-mail accounts or any other e-mail accounts; or (c) delete or destroy any documents, computer files, or electronic
messages contained on her computer or the Company’s server.

 

7.        
Voluntary Waiver. TAILORED BRANDS hereby advises Blake to consult with an attorney regarding this Agreement and the
release of claims contained herein. By signing below, Blake acknowledges that she has been advised by TAILORED BRANDS to consult
with an attorney, and Blake agrees that she has had an opportunity to have an attorney of her choice review this Agreement and
the release contained herein before signing this Agreement. Blake acknowledges that she has carefully read and understands all
of the provisions of this Agreement and that she is executing this Agreement of her own free will and without duress. Blake also
acknowledges receipt of the Agreement on December 5, 2019 and that
she has been given at least 21 days to consider it, and that Blake voluntarily signs it and agrees to be bound by its terms.
Blake also understands and agrees that this Agreement must be signed between December 5, 2019 and December 26,
2019 and if she does not terminate her employment prior to the Termination Date, she must execute the Second Release in
order for her to be entitled to the benefits given under it. Blake also understands she may revoke the Agreement within 7 days
after signing it, and unless so revoked, the Agreement will be fully effective upon expiration of the revocation period. Blake
understands and agrees that to revoke this Agreement, written notice of the revocation must be received by the following person
no later than 11:59 p.m. Pacific Time on the seventh (7th) day from the date this Agreement is signed:

 

    -5-

     

    

 

A. Alexander Rhodes, Esq.

Executive Vice President, General Counsel,

Chief Compliance Officer and Corporate Secretary

Tailored Brands, Inc.

6100 Stevenson Boulevard

Fremont, CA 94538

Phone: 510.723.8669

 

8.         No
Further Entitlements. Blake acknowledges and agrees that the payment(s), benefits, and obligations of the Company to Blake
provided for in this Agreement are in full discharge of any and all liabilities and obligations of the Company or any of its affiliates
to her, monetarily or with respect to employee benefits or otherwise, including but not limited to any and all obligations arising
under any alleged additional written or oral employment agreement, policy, plan or procedure of TAILORED BRANDS or any of its affiliates
and/or any alleged understanding or arrangement between Blake and TAILORED BRANDS or any of its affiliates other than claims for
accrued and vested benefits under an employee benefit, insurance, or pension plan of TAILORED BRANDS or any of its affiliates (but
excluding any employee benefit plan providing severance or similar benefits), subject to the terms and conditions of such plan(s).

 

9.        Taxes.
The payments and provision of benefits referenced in this Agreement shall be subject to withholding for all applicable taxes, including
but not limited to income, employment, and social insurance taxes, as shall be required by law.

 

10.
      Entire agreement. This
Agreement contains the entire agreement between Blake and the Company regarding Blake’s termination of employment, and supersedes
any prior or contemporaneous agreement, understanding, or representation concerning that subject matter.

 

11.       Civil
Code Section 1542. This Agreement constitutes a waiver and release of any and all claims which would otherwise be preserved
by operation of Section 1542 of the Civil Code of the State of California, and under any and all similar laws of any governmental
entity. Section 1542 of the Civil Code provides as follows:

 

A general release does not extend to claims which
the creditor does not know or suspect to exist in his or her favor at the time of executing the release, which if known by him
or her must have materially affected his or her settlement with the debtor.

 

12.        Binding
on Successors. This Agreement shall be binding upon the successors
and/or assigns, if any, of TAILORED BRANDS. In light of the payment by TAILORED BRANDS of all amounts due to Blake, she
acknowledges and agrees that California Labor Code Section 206.5 is not applicable. That section provides in pertinent part as
follows:

 

No employer shall require the execution of any release
of any claim or right on account of wages due, or to become due, or made as an advance on wages to be earned, unless payment of
such wages has been made.

 

13.       Reimbursement
of Reasonable Business Expenses. By executing this Agreement, Blake is not releasing any claims for reimbursement of
business-related expenses under Labor Code Section 2802. Blake is hereby advised of her right to consult with an attorney of
her choosing about this business-related expenditures acknowledgement. Blake hereby
affirms that she has received full and adequate reimbursement for any necessary business-related expenditures or
losses incurred in the course of employment with TAILORED BRANDS and any of its parent companies or affiliates. 

 

    -6-

     

    

 

14.      
Governing Law. This Agreement will be governed by California law without resort to conflict of law principles.

 

15.      
Jointly Drafted. The parties understand and agree that this Agreement is deemed to have been drafted jointly by the
parties. Any uncertainty or ambiguity will not be construed for or against any party based on attribution of drafting to any party.

 

16.      
Non-Admission. Nothing contained in this Agreement will be deemed or construed as an admission of wrongdoing or liability
on the part of Blake or the Company or any of its affiliates.

 

17.      
Compliance with Section 409A. This Agreement and the payments hereunder are intended to be exempt, to the
greatest extent possible, from the requirements of Section 409A of the Internal Revenue Code of 1986, as amended (“Section
409A”) and to the extent not so exempt, to comply with the requirements of Section 409A, and the terms of this Agreement
shall be construed and administered to give full effect to such intent, and if necessary, any provision shall be held null and
void to the extent such provision (or part thereof) fails to comply with Section 409A or the Treasury Regulations thereunder. For
purposes of Section 409A, each payment of compensation under the Agreement shall be treated as a separate payment of compensation.
Any amounts payable solely on account of an involuntary termination shall be excludible from the requirements of Section 409A,
either as separation pay or as short-term deferrals to the maximum possible extent. Notwithstanding anything in this Agreement
to the contrary, any reimbursements or in-kind benefits provided under this Agreement shall be made or provided in accordance with
the requirements of Section 409A, including, where applicable, the requirements that (a) any reimbursement is for expenses
incurred during the period of time specified in this Agreement, (b) the amount of expenses eligible for reimbursement, or
in-kind benefits provided, during any taxable year of Blake may not affect the expenses eligible for reimbursement, or in-kind
benefits to be provided, in any other taxable year of Blake, (c) the reimbursement of an eligible expense will be made no
later than the last day of Blake’s taxable year following the year in which the expense is incurred, and (d) the right
to reimbursement or in-kind benefits is not subject to liquidation or exchange for another benefit. Nothing herein shall be construed
as the guarantee of any particular tax treatment to Blake,
and neither TAILORED BRANDS nor any of its affiliates shall have any liability with respect to any failure to comply with the requirements
of Section 409A

 

    -7-

     

    

 

Execution
by Parties

 

The Company
and Blake acknowledge and represent that they have read this Agreement, understand its terms, and enter into it knowingly and voluntarily.

 

	TAILORED SHARED SERVICES, LLC	 	MARY BETH BLAKE
	 	 	 
	By:	/s/ Dinesh
Lathi	 	/s/ Mary Beth Blake
	Dinesh Lathi	 	 
	President and Chief Executive	 	 
	Officer Dated: Dec, 27, 2019    	 	Dated: Dec, 26, 2019

 

    -8-

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