As filed with the Securities and Exchange Commission on March 24, 2025

Registration No. 333-      ​

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM S-4

REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933

BERKSHIRE HILLS BANCORP, INC.
(Exact Name of Registrant as Specified in Its Charter)

60 State Street
Boston, Massachusetts 02109
(800) 773-5601 ext. 133773

(Address, Including Zip Code, and Telephone Number, Including Area Code, of Registrant’s Principal Executive Offices)​

Nitin J. Mhatre
President and Chief Executive Officer
60 State Street
Boston, Massachusetts 02109
(800) 773-5601 ext. 133773

(Name, Address, Including Zip Code, and Telephone Number, Including Area Code, of Agent For Service)​

Copies to:

Approximate date of commencement of proposed sale to the public: As soon as practicable after this registration statement becomes effective.

If the securities being registered on this form are to be offered in connection with the formation of a holding company and there is compliance with General Instruction G, check the following box: ☐

If this form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ☐

If this form is a post-effective amendment filed pursuant to Rule 462(d) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 7(a)(2)(B) of the Securities Act. ☐

If applicable, place an X in the box to designate the appropriate rule provision relied upon in conducting this transaction:

Exchange Act Rule 13e-4(i) (Cross-Border Issuer Tender Offer) ☐

Exchange Act Rule 14d-1(d) (Cross-Border Third-Party Tender Offer) ☐

The registrant hereby amends this registration statement on such date or dates as may be necessary to delay its effective date until the registrant shall file a further amendment which specifically states that this registration statement shall thereafter become effective in accordance with Section 8(a) of the Securities Act of 1933 or until the registration statement shall become effective on such date as the Securities and Exchange Commission, acting pursuant to said Section 8(a), may determine.

Information contained in this Joint Proxy Statement/Prospectus is subject to completion or amendment. A registration statement relating to the securities of Berkshire Hills Bancorp, Inc. to be issued in the merger has been filed with the Securities and Exchange Commission. These securities may not be sold nor may offers to buy be accepted prior to the time the registration statement becomes effective. This Joint Proxy Statement/Prospectus shall not constitute an offer to sell or the solicitation of an offer to buy nor shall there be any sale of these securities in any jurisdiction in which such offer, solicitation or sale is not permitted or would be unlawful prior to registration or qualification under the securities laws of any such jurisdiction.

SUBJECT TO COMPLETION, DATED MARCH 24, 2025

To the Stockholders of Brookline Bancorp, Inc. and
the Stockholders of Berkshire Hills Bancorp, Inc.

MERGER PROPOSED  —  YOUR VOTE IS VERY IMPORTANT

On behalf of the boards of directors of Berkshire Hills Bancorp, Inc. (“Berkshire”) and Brookline Bancorp, Inc. (“Brookline”), we are pleased to enclose the accompanying Joint Proxy Statement/Prospectus relating to the proposed merger of equals of Berkshire and Brookline. We are requesting that you take certain actions as a holder of Berkshire common stock or as a holder of Brookline common stock.

On December 16, 2024, Berkshire, Commerce Acquisition Sub, Inc., a direct, wholly-owned subsidiary of Berkshire (“Merger Sub”), and Brookline entered into a merger agreement (the “Merger Agreement”) pursuant to which Berkshire and Brookline have agreed to combine their respective businesses in a merger of equals.

Under the Merger Agreement, Merger Sub will merge with and into Brookline, with Brookline as the surviving corporation (the “Merger”), immediately followed by the merger of Brookline with and into Berkshire, with Berkshire as the surviving corporation (the “Holdco Merger”). Immediately following the Merger and the Holdco Merger (collectively, the “Mergers”), Berkshire Bank, the wholly-owned subsidiary of Berkshire, and two of Brookline’s wholly-owned banking subsidiaries, PCSB Bank and Bank Rhode Island, will merge with and into Brookline Bank, the wholly-owned subsidiary of Brookline, with Brookline Bank as the surviving bank (the “Bank Merger”). Each of Brookline and Berkshire will have equal representation on the board of directors of the surviving corporation and the surviving bank.

If the Mergers are completed, Brookline stockholders will be entitled to receive 0.42 shares of Berkshire common stock, $0.01 par value, for each share of Brookline common stock, $0.01 par value, that they own. The maximum number of shares of Berkshire common stock estimated to be issuable upon completion of the Mergers is 37,882,325. The value of the Merger Consideration will depend on the market price of Berkshire common stock on the effective date of the Mergers. Based on Berkshire’s closing price of $30.20 on December 13, 2024, which was the last trading date preceding the public announcement of the proposed merger, each share of Brookline common stock exchanged for 0.42 shares of Berkshire common stock would have had a value of $12.68, or approximately $1.1 billion in aggregate Merger Consideration. Based on Berkshire’s closing price of $      on            , 2025, which is the most recent practicable trading day prior to the printing of this document, each share of Brookline common stock exchanged for 0.42 shares of Berkshire common stock would have a value of $      . We urge you to obtain current market quotations for both Berkshire common stock and Brookline common stock.

The common stock of Berkshire trades on the New York Stock Exchange under the symbol “BHLB.” The common stock of Brookline trades on the Nasdaq Global Select Market under the symbol “BRKL.” Following the Mergers, the common stock of the surviving corporation will be listed on the New York Stock Exchange under the symbol “BHLB.”

Berkshire will hold a virtual annual meeting of its stockholders (the “Berkshire Annual Meeting”) on            , 2025, at            , Eastern time, where the Berkshire stockholders will be asked to vote on a proposal to approve the issuance of Berkshire common stock pursuant to the Merger Agreement (the “Berkshire Share Issuance Proposal”), a proposal to amend Berkshire’s Certificate of Incorporation to increase the number of authorized shares of common stock of the surviving corporation (the “Berkshire Certificate of Incorporation Amendment Proposal”), a proposal to approve the Berkshire Hills Bancorp, Inc. 2025 Stock Option and Incentive Plan (the “Berkshire Equity Plan Proposal”), the election of directors, an advisory vote on executive compensation practices, and the ratification of Crowe LLP as Berkshire’s independent registered public accountants for 2025. The approval by Berkshire stockholders of the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, and the Berkshire Equity Plan Proposal are required to complete the Mergers.

Brookline will hold a virtual special meeting of its stockholders (the “Brookline Special Meeting”) on            , 2025, at            , Eastern time, where the Brookline stockholders will be asked to vote on

a proposal to adopt the Merger Agreement (the “Brookline Merger Proposal”) and a proposal to approve, on a non-binding advisory basis, the compensation that may become payable to the named executive officers of Brookline in connection with the Mergers (the “Brookline Merger-Related Compensation Proposal”). The approval by Brookline stockholders of the Brookline Merger Proposal is required to complete the Mergers.

Information about the Berkshire Annual Meeting, the Brookline Special Meeting, and the Mergers is contained in the accompanying Joint Proxy Statement/Prospectus.

Each of the boards of directors of Berkshire and Brookline unanimously recommends that holders of common stock vote “FOR” each of the proposals to be considered at the respective stockholder meetings. We strongly support this combination of our companies and join our boards in their recommendations.

The accompanying Joint Proxy Statement/Prospectus provides you with detailed information about the Merger Agreement and the Mergers. It also contains or references information about Berkshire and Brookline and certain related matters. You are encouraged to read the accompanying Joint Proxy Statement/​Prospectus carefully. In particular, you should read the section entitled “Risk Factors” beginning on page [  ] for a discussion of the risks you should consider in evaluating the proposed merger and how it will affect you. You can also obtain information about Berkshire and Brookline from documents that have been filed with the Securities and Exchange Commission that are incorporated into this Joint Proxy Statement/Prospectus by reference.

We look forward to your participation in the annual meeting and the special meeting and we appreciate your continued support.

The securities of Berkshire to be issued in the Merger are not deposits or savings accounts or other obligations of any bank or savings association subsidiary of Berkshire or Brookline and are not insured by the Federal Deposit Insurance Corporation or any other governmental agency.

Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved the Mergers described in this document or the Berkshire securities to be issued in connection with the Mergers or passed upon the adequacy or accuracy of this document. Any representation to the contrary is a criminal offense.

The accompanying Joint Proxy Statement/Prospectus is dated            , 2025, and it is first being mailed or otherwise delivered to stockholders of Berkshire and Brookline on or about            , 2025.

 

ABOUT THIS DOCUMENT

This Joint Proxy Statement/Prospectus, which we also refer to as “this document,” forms part of a registration statement on Form S-4 (Registration Statement No. 333-      ) filed with the Securities and Exchange Commission (the “SEC”) by Berkshire, and constitutes a prospectus of Berkshire under the Securities Act of 1933, as amended (the “Securities Act”), with respect to the shares of Berkshire securities to be issued to Brookline stockholders, as required by the Merger Agreement. This document also constitutes a proxy statement for Berkshire and for Brookline. In addition, it constitutes a notice of meeting with respect to the annual meeting of stockholders of Berkshire and the special meeting of stockholders of Brookline.

You should rely only on the information contained in this document. No one has been authorized to provide you with information that is different from the information contained in this document. This document is dated            , 2025. You should not assume that the information contained in this document is accurate as of any date other than that date. Neither the mailing of this document to either Berkshire stockholders or Brookline stockholders nor the issuance by Berkshire of its common stock in connection with the Mergers will create any implication to the contrary.

This document does not constitute an offer to sell, or a solicitation of an offer to buy, any securities, or the solicitation of a proxy, in any jurisdiction to or from any person to whom it is unlawful to make any such offer or solicitation in such jurisdiction. Information contained in this document regarding Berkshire has been provided by Berkshire and information contained in this document regarding Brookline has been provided by Brookline.

 

 

BERKSHIRE HILLS BANCORP, INC.
60 State Street
Boston, Massachusetts 02109

Notice of Annual Meeting of Stockholders to be held            , 2025

To the Stockholders of Berkshire Hills Bancorp, Inc.:

Berkshire Hills Bancorp, Inc. (“Berkshire”) will hold a virtual annual meeting of stockholders (the “Berkshire Annual Meeting”) at            , Eastern time, on            , 2025, to be held exclusively via webcast at            , to consider and vote upon the following matters:

(1)

a proposal to approve the issuance of Berkshire common stock to holders of Brookline Bancorp, Inc. (“Brookline”) common stock pursuant to the Agreement and Plan of Merger, dated as of December 16, 2024, by and among Berkshire Hills Bancorp, Inc., Commerce Acquisition Sub, Inc., and Brookline Bancorp, Inc. (the “Merger Agreement”) pursuant to which Commerce Acquisition Sub, Inc. will merge with and into Brookline (the “Merger”), with Brookline surviving the Merger, immediately followed by the merger of Brookline with and into Berkshire (the “Holdco Merger”), with Berkshire surviving the Holdco Merger (together with the Merger, the “Mergers”) (the “Berkshire Share Issuance Proposal”);

​

(2)

a proposal to approve an amendment to Berkshire’s Certificate of Incorporation to increase the number of authorized shares of common stock of the surviving corporation (the “Berkshire Certificate of Incorporation Amendment Proposal”);

​

(3)

a proposal to approve the Berkshire Hills Bancorp, Inc. 2025 Stock Option and Incentive Plan (the “Berkshire Equity Plan Proposal”);

​

(4)

to elect as directors the nominees named in the accompanying Joint Proxy Statement/Prospectus, each to serve a one-year term or until their successors are duly elected and qualified; provided that if the Mergers are consummated, the approval of this proposal will only have an effect until the completion of the Mergers because the composition of Berkshire’s board will be reconstituted upon completion of the Mergers, in accordance with the Merger Agreement (the “Berkshire Director Election Proposal”);

​

(5)

a proposal to approve, on a non-binding advisory basis, the compensation of Berkshire’s named executive officers (the “Berkshire Say-on-Pay Proposal”);

​

(6)

a proposal to ratify, on a non-binding advisory basis, the appointment of Crowe LLP as Berkshire’s independent registered public accounting firm for fiscal year 2025 (the “Berkshire Auditor Ratification Proposal”); and

​

(7)

a proposal to adjourn the Berkshire Annual Meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the annual meeting to approve the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal or the Berkshire Equity Plan Proposal (the “Berkshire Adjournment Proposal”).

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All of these items are described in more detail in the accompanying Joint Proxy Statement/Prospectus and its annexes. We urge you to read these materials carefully and in their entirety. The enclosed document forms a part of this notice.

The Berkshire board of directors unanimously recommends that Berkshire stockholders vote “FOR” the Berkshire Share Issuance Proposal, “FOR” the Berkshire Certificate of Incorporation Amendment Proposal, “FOR” the Berkshire Equity Plan Proposal, “FOR” the Berkshire Director Election Proposal, “FOR” the Berkshire Say-on-Pay Proposal, “FOR” the Berkshire Auditor Ratification Proposal, and “FOR” the Berkshire Adjournment Proposal.

Berkshire stockholders of record as of the close of business on            , 2025 are entitled to notice of, and to vote at, the Berkshire Annual Meeting and any adjournments or postponements of the Berkshire Annual Meeting.

 

 

Your vote is very important.   Your proxy is being solicited by Berkshire’s board of directors. For the Mergers to be completed, the Berkshire Share Issuance Proposal must be approved by the affirmative vote of the majority of the votes cast at the Berkshire Annual Meeting, the Berkshire Certificate of Incorporation Amendment Proposal must be approved by the affirmative vote of the majority of the votes cast at the Berkshire Annual Meeting, and the Berkshire Equity Plan Proposal must be approved by the affirmative vote of the majority of the votes cast at the Berkshire Annual Meeting. The amendments to the Berkshire Certificate of Incorporation and the adoption of the Berkshire Hills Bancorp, Inc. 2025 Stock Option and Incentive Plan each will become effective only if the Merger Agreement is approved by the Berkshire stockholders and the Mergers are completed. Directors are elected by a plurality of votes cast at the Berkshire Annual Meeting. The Berkshire Say-on-Pay Proposal and the Berkshire Auditor Ratification Proposal must be approved by the affirmative vote of the votes cast at the Berkshire Annual Meeting.

Whether or not you plan to attend the Berkshire Annual Meeting virtually, we urge you to vote. Stockholders of record may vote:

•

By internet — access           and follow the on-screen instructions;

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•

By telephone — call           in the United States or           in foreign countries and follow the instructions;

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•

By mail — complete, sign, date and mail your proxy card in the envelope provided as soon as possible; or

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•

By voting at the virtual annual meeting — access           and follow the on-screen instructions;

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If you plan to attend the Berkshire Annual Meeting virtually, you will be required to take certain actions ahead of the meeting so that you can participate. Please carefully read the sections in this document regarding attending and voting at the annual meeting to ensure that you comply with these requirements.

If you hold your stock in “street name” through a banker or broker, please follow the instructions on the voting instruction card furnished by the record holder.

If you have any questions or need assistance voting your shares, please contact our proxy solicitor, Innisfree M&A Incorporated, toll free at            .

By Order of the Board of Directors,

Wm. Gordon Prescott
Senior Executive Vice President, General Counsel and Corporate Secretary

Boston, Massachusetts
           , 2025

 

 

131 Clarendon Street, Boston, Massachusetts 02116
NOTICE OF THE SPECIAL MEETING OF STOCKHOLDERS
TO BE HELD ON            , 2025

To the Stockholders of Brookline Bancorp, Inc.:

Brookline Bancorp, Inc. (“Brookline”) will hold a special meeting of stockholders (the “Brookline Special Meeting”), to be held by means of remote communication on            , 2025 at            , Eastern time, to consider and vote upon the following matters:

1.

a proposal to adopt the Agreement and Plan of Merger, dated as of December 16, 2024, by and among Berkshire Hills Bancorp, Inc. (“Berkshire”), Commerce Acquisition Sub, Inc. and Brookline (the “Merger Agreement”), pursuant to which Commerce Acquisition Sub, Inc. will merge with and into Brookline (the “Merger”), with Brookline surviving the Merger, and, immediately following the Merger, Brookline will merge with and into Berkshire (the “Holdco Merger”), with Berkshire surviving the Holdco Merger (together with the Merger, the “Mergers”) (the “Brookline Merger Proposal”);

​

2.

a proposal to approve, on a non-binding advisory basis, the compensation that may become payable to the named executive officers of Brookline in connection with the Mergers (the “Brookline Merger-Related Compensation Proposal”); and

​

3.

a proposal to adjourn the special meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the special meeting to approve the Brookline Merger Proposal (the “Brookline Adjournment Proposal”).

​

All of these items are described in more detail in the accompanying Joint Proxy Statement/Prospectus and its annexes. We urge you to read these materials carefully and in their entirety. The enclosed document forms a part of this notice.

The Brookline board of directors unanimously recommends that the Brookline stockholders vote “FOR” the Brookline Merger Proposal, “FOR” the Brookline Merger-Related Compensation Proposal, and “FOR” the Brookline Adjournment Proposal.

Brookline stockholders of record as of the close of business on            , 2025, are entitled to notice of, and to vote at, the Brookline Special Meeting and any adjournments or postponements of the Brookline Special Meeting. Stockholders as of the record date may attend the Brookline Special Meeting by visiting                 and entering the 16-digit control number included on their proxy card.

Your vote is very important. Your proxy is being solicited by Brookline’s board of directors. For the proposed merger to be completed, the Brookline Merger Proposal must be approved by the affirmative vote of a majority of the issued and outstanding shares of Brookline common stock. The Brookline Merger-Related Compensation Proposal will be approved if a majority of the votes cast on such proposal at the Brookline Special Meeting are voted in favor of such proposal. The Brookline Adjournment Proposal will be approved if a majority of the votes cast on such proposal at the Brookline Special Meeting are voted in favor of such proposal.

 

 

Whether or not you plan to attend the Brookline Special Meeting, please vote at your earliest convenience by following the instructions included in the accompanying proxy card. You may revoke your proxy at any time before the Brookline Special Meeting by following the instructions provided in the proxy statement/​prospectus.

Sincerely,

Marissa Martin
General Counsel and Corporate Secretary
Boston, Massachusetts
           , 2025

 

 

ADDITIONAL INFORMATION

Both Berkshire and Brookline file annual, quarterly and special reports, proxy statements and other business and financial information electronically with the SEC. In addition, this document incorporates important business and financial information about Berkshire and Brookline from documents filed with the SEC that have not been included in or delivered with this document. You can obtain any of the documents filed with or furnished to the SEC by Berkshire or Brookline at no cost from the SEC’s website at www.sec.gov. You will also be able to obtain these documents free of charge from Berkshire at Berkshire’s website at www.berkshirebank.com under the “About — Investor Relations” tab, and then under “Filings & Financials,” or from Brookline by accessing Brookline’s website at www.brooklinebancorp.com under the “SEC Filings” tab. See “Where You Can Find More Information” on page 154.

You also may request orally or in writing copies of these documents at no cost by contacting the appropriate company at the following addresses:

If you are a Berkshire stockholder or Brookline stockholder and would like to request documents from Berkshire or Brookline, please do so by            , 2025 to receive them before the Berkshire Annual Meeting or the Brookline Special Meeting.

The information on Berkshire’s and Brookline’s websites is not part of this document. References to Berkshire’s and Brookline’s websites in this document are intended to serve as textual references only.

 

 

TABLE OF CONTENTS

 

 

QUESTIONS AND ANSWERS ABOUT THE MERGER,
THE BERKSHIRE ANNUAL MEETING AND THE BROOKLINE SPECIAL MEETING

The following questions and answers are intended to address briefly some commonly asked questions regarding the Berkshire Hills Bancorp, Inc. (“Berkshire”) annual meeting (the “Berkshire Annual Meeting”) and the Brookline Bancorp, Inc. (“Brookline”) special meeting (the “Brookline Special Meeting”). These questions and answers may not address all questions that may be important to you as a Berkshire or Brookline stockholder. To more fully understand the Merger, the Berkshire Annual Meeting and the Brookline Special Meeting, you should read this entire Joint Proxy Statement/Prospectus, including the materials attached as annexes, as well as the documents that have been incorporated by reference into this Joint Proxy Statement/Prospectus.

Q:

Why am I receiving this Joint Proxy Statement/Prospectus?

​

A:

You are receiving this Joint Proxy Statement/Prospectus because Berkshire, Commerce Acquisition Sub, Inc., a wholly-owned subsidiary of Berkshire (“Merger Sub”), and Brookline have entered into an Agreement and Plan of Merger, dated as of December 16, 2024 (as may be amended, supplemented or modified from time to time in accordance with its terms, the “Merger Agreement”), pursuant to which Merger Sub will merge with and into Brookline, with Brookline as the surviving corporation (the “Merger”), immediately followed by the Merger of Brookline with and into Berkshire, with Berkshire as the surviving corporation (the “Holdco Merger”, and together with the Merger, the “Mergers”). The parties then intend to cause Berkshire’s wholly-owned bank subsidiary, Berkshire Bank, and two of Brookline’s wholly-owned bank subsidiaries, Bank Rhode Island and PCSB Bank, to merge with and into Brookline Bank, with Brookline Bank as the surviving bank (the “Bank Merger”).

​

In order to complete the Merger, among other things:

•

Holders of Berkshire common stock (“Berkshire stockholders”) must approve the issuance of shares of Berkshire common stock, $0.01 par value (“Berkshire common stock”), to the stockholders of Brookline (“Brookline stockholders”), pursuant to the Merger Agreement (the “Berkshire Share Issuance Proposal”);

​

•

Berkshire stockholders must approve the amendment of Berkshire’s Certificate of Incorporation to increase the number of authorized shares of common stock of the surviving corporation (the “Berkshire Certificate of Incorporation Amendment Proposal”);

​

•

Berkshire stockholders must approve the Berkshire Hills Bancorp, Inc. 2025 Stock Option and Incentive Plan (the “Berkshire Equity Plan Proposal”); and

​

•

Brookline stockholders must adopt the Merger Agreement (the “Brookline Merger Proposal”).

​

Berkshire is holding the virtual Berkshire Annual Meeting to obtain approval of the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, and the Berkshire Equity Plan Proposal. In addition, Berkshire stockholders will be asked to approve a proposal to adjourn the Berkshire Annual Meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the Berkshire Annual Meeting to approve the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, and the Berkshire Equity Plan Proposal (the “Berkshire Adjournment Proposal”). The amendments to the Berkshire Certificate of Incorporation and the adoption of the Berkshire Hills Bancorp, Inc. 2025 Stock Option and Incentive Plan each will become effective only if the Merger Agreement is approved by the Berkshire stockholders and the Mergers are completed.

Berkshire stockholders will also be asked to vote on the election of directors named in this Joint Proxy Statement/Prospectus, provided that if the Mergers are consummated, the approval of this proposal will only have an effect until the completion of the Mergers because the composition of Berkshire’s board will be reconstituted upon completion of the Mergers, in accordance with the Merger Agreement (the “Berkshire Director Election Proposal”). In addition, Berkshire stockholders will be asked to approve, on a non-binding advisory basis, the compensation paid to the named executive officers of Berkshire (the “Berkshire Say-on-Pay Proposal”), and the ratification of Crowe LLP as Berkshire’s independent registered public accounting firm for fiscal year 2025 (the “Berkshire Auditor Ratification Proposal”).

 

1

 

Brookline is holding a virtual Brookline Special Meeting to obtain approval of the Brookline Merger Proposal.

In addition, Brookline stockholders will be asked to approve, on a non-binding, advisory basis, the compensation payable to the named executive officers of Brookline in connection with the Merger (the “Brookline Merger-Related Compensation Proposal”) and to approve a proposal to adjourn the Brookline Special Meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the Brookline Special Meeting to approve the Brookline Merger Proposal (the “Brookline Adjournment Proposal”).

This document is also a prospectus that is being delivered to Brookline stockholders because, pursuant to the Merger Agreement, Berkshire is offering shares of Berkshire common stock to Brookline stockholders.

We have included in this Joint Proxy Statement/Prospectus important information about the Merger, the Merger Agreement, a copy of which is included as Annex A to this Joint Proxy Statement/Prospectus, the Berkshire proxy solicitation and the Brookline proxy solicitation. You should read this information carefully and in its entirety. Your vote is important, and we encourage you to submit your proxy as soon as possible.

Q:

What will happen in the Mergers?

​

A:

In the Mergers, Merger Sub will merge with and into Brookline, and Brookline will merge with and into Berkshire, with Berkshire as the surviving corporation. In the Bank Merger, which will occur promptly after the Mergers, Berkshire Bank, Bank Rhode Island, and PCSB Bank will merge with and into Brookline Bank, with Brookline Bank as the surviving bank.

​

Each share of Brookline common stock, par value $0.01 per share (“Brookline common stock”), issued and outstanding immediately prior to the effective time of the Merger (the “effective time”) will be canceled and converted into the right to receive 0.42 shares (the “exchange ratio”) of Berkshire common stock (the “Merger Consideration”), as further described in the section entitled “Description of the Mergers — Consideration to be Received in the Mergers” beginning on page [  ].

After completion of the Mergers, (i) Brookline will no longer be a public company and will cease to exist, (ii) Brookline common stock will be delisted from the Nasdaq Stock Market (“Nasdaq”) and will cease to be publicly traded, and (iii) Brookline common stock will be deregistered under the Securities Exchange Act of 1934, as amended (the “Exchange Act”). After the completion of the Mergers, Berkshire stockholders will continue to own their existing shares of Berkshire common stock. See the Merger Agreement for more information about the Merger.

Q:

When and where will the Berkshire Annual Meeting and the Brookline Special Meeting take place?

​

A:

The Berkshire Annual meeting will be held virtually via live webcast, on            , 2025 at            , Eastern time. Berkshire stockholders will not be able to attend the meeting in person.

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The Brookline Special Meeting will be held virtually via live webcast, on            , 2025 at            , Eastern time. Brookline stockholders will not be able to attend the meeting in person.

Q:

What matters will be considered at the Berkshire Annual Meeting and the Brookline Special Meeting?

​

A:

At the Berkshire Annual Meeting, Berkshire stockholders will be asked to consider and vote on the following proposals:

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•

Berkshire Proposal 1: The Berkshire Share Issuance Proposal;

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•

Berkshire Proposal 2: The Berkshire Certificate of Incorporation Amendment Proposal;

​

•

Berkshire Proposal 3: The Berkshire Equity Plan Proposal;

​

•

Berkshire Proposal 4: The Berkshire Director Election Proposal;

​

•

Berkshire Proposal 5: The Berkshire Say-on-Pay Proposal;

​

 

2

 

•

Berkshire Proposal 6: The Berkshire Auditor Ratification Proposal; and

​

•

Berkshire Proposal 7: The Berkshire Adjournment Proposal.

​

At the Brookline Special Meeting, Brookline stockholders will be asked to consider and vote on the following proposals:

•

Brookline Proposal 1: The Brookline Merger Proposal;

​

•

Brookline Proposal 2: The Brookline Merger-Related Compensation Proposal; and

​

•

Brookline Proposal 3: The Brookline Adjournment Proposal.

​

In order to complete the Mergers, among other things, Berkshire stockholders must approve the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, and the Berkshire Equity Plan Proposal, and Brookline stockholders must approve the Brookline Merger Proposal.

None of the approvals of the Berkshire Director Election Proposal, the Berkshire Say-on-Pay Proposal, the Berkshire Auditor Ratification Proposal, the Berkshire Adjournment Proposal, the Brookline Merger-Related Compensation Proposal, or the Brookline Adjournment Proposal is a condition to the obligations of Berkshire or Brookline to complete the Mergers.

Q:

Why must Berkshire stockholders approve the issuance of shares of Berkshire common stock in connection with the Mergers (i.e., the Berkshire Share Issuance Proposal)?

​

The Berkshire stockholders are required to approve the issuance of shares of Berkshire common stock in connection with the Mergers, which will require the affirmative vote of a majority of votes cast at the Berkshire Annual Meeting. Because Berkshire is listed on the New York Stock Exchange (the “NYSE”) and is subject to the NYSE’s listing rules, and Berkshire will issue in excess of 20% of its outstanding shares of Berkshire common stock to Brookline stockholders in connection with the Mergers, under the NYSE’s listing rules, Berkshire stockholders are required to approve the issuance of shares of Berkshire common stock in connection with the Merger. The Mergers cannot be completed unless Berkshire stockholders approve the Berkshire Share Issuance Proposal.

Q:

What will Brookline stockholders receive in the Mergers?

​

A:

In the Mergers, Brookline stockholders will receive 0.42 shares of Berkshire common stock for each share of Brookline common stock held immediately prior to the completion of the Merger. Berkshire will not issue any fractional shares of Berkshire common stock in the Mergers. Brookline stockholders who would otherwise be entitled to a fractional share of Berkshire common stock in the Mergers will instead receive an amount in cash without interest) determined by multiplying such fractional interest by the average closing price per share of Berkshire common stock, as reported on Nasdaq (as reported in The Wall Street Journal or, if not reported therein, in another authoritative source), for the ten consecutive trading days ending on the day immediately prior to the closing date of the Mergers (the “Berkshire average share price”), rounded to the nearest whole cent.

​

Q:

What will Berkshire stockholders receive in the Mergers?

​

A:

In the Mergers, Berkshire stockholders will not receive any consideration, and their shares of Berkshire common stock will remain outstanding and will constitute shares of Berkshire common stock following the Mergers. Following the Mergers, shares of Berkshire common stock will continue to be traded on the NYSE.

​

Q:

Will the value of the Merger Consideration change between the date of the Joint Proxy Statement/​Prospectus and the time the Mergers are completed?

​

A:

Yes. Upon consummation of the Mergers, each issued and outstanding share of Brookline common stock will be canceled and converted into the right to receive a number of shares of Berkshire common stock based upon the exchange ratio. As such, the value of the Merger Consideration will largely

​

 

3

 

depend on the market price for a share of Berkshire common stock at the time the Mergers are completed. The market price for a share of Berkshire common stock when Brookline stockholders receive such shares of Berkshire common stock after the Mergers are completed could be greater than, less than, or the same as the market price of shares of Berkshire common stock on the date of this Joint Proxy Statement/Prospectus. Neither Berkshire nor Brookline is permitted to terminate the Merger Agreement as a result of any increase or decrease in the market price of Berkshire common stock or Brookline common stock.

Q:

What equity stake will Berkshire and Brookline stockholders hold in the surviving corporation immediately following the Mergers?

​

A:

Immediately following completion of the Mergers, current Berkshire stockholders will own in the aggregate approximately 55% of the outstanding shares of the surviving corporation’s common stock, and Brookline stockholders will own in the aggregate approximately 45% of the outstanding shares of the surviving corporation’s common stock.

​

Q:

How will the Mergers affect Brookline equity awards?

​

A:

At the effective time of the Merger, except as otherwise agreed between Berkshire and Brookline, all outstanding time or performance-based restricted stock awards in respect of a share of Brookline common stock under the Brookline Bancorp, Inc. 2021 Stock Option and Incentive Plan (the “Brookline Stock Plan”) will accelerate in full and fully vest, and be converted into the right for the holder to receive shares of Berkshire common stock in accordance with the exchange ratio. Any applicable performance-based vesting conditions will be deemed achieved at the greater of the target level of performance or actual annualized performance measured as of the most recently completed fiscal quarter prior to the closing of the Merger.

​

Q:

How will the Mergers affect Berkshire equity awards?

​

A:

At the effective time of the Merger, except as otherwise agreed between Berkshire and Brookline, all outstanding time or performance-based restricted stock awards in respect of a share of Berkshire common stock under the Berkshire Hills Bancorp, Inc. 2018 Equity Incentive Plan and the Berkshire Hills Bancorp, Inc. 2022 Equity Incentive Plan (the “Berkshire Stock Plans”), will accelerate in full and fully vest. Any applicable performance-based vesting conditions will be deemed achieved at the greater of the target level of performance or actual annualized performance measured as of the most recently completed fiscal quarter prior to the closing of the Mergers.

​

Except as otherwise agreed between Berkshire and Brookline, all outstanding and unexercised stock options in respect of a share of Berkshire common stock under the Berkshire Stock Plans, shall, automatically and without any required action on the part of the holder thereof, accelerate in full and fully vest, and shall remain outstanding with the same exercise price to which they were subject prior to the effective time of the Mergers, and except as noted above, shall not otherwise be affected by the Mergers.

Q:

How will the Merger affect Berkshire’s or Brookline’s existing 401(k) plan?

​

A:

The Merger Agreement provides that, unless otherwise agreed between Berkshire and Brookline no later than ten days prior to the effective time of the Mergers, Brookline will terminate its 401(k) plan effective as of the day immediately prior to the effective time (but contingent upon the occurrence thereof) and adopt all required compliance amendments pursuant to written resolutions, the form and substance of which will be subject to reasonable review and comment by Berkshire. If the Brookline 401(k) plan is terminated, Berkshire agrees to permit participants in the Brookline 401(k) plan who are Brookline employees to roll over their account balances from such plan to Berkshire’s 401(k) plan, and such Brookline employees who satisfy the eligibility requirements of Berkshire’s 401(k) plan (taking into account credit for prior years of service with Brookline pursuant to the Merger Agreement, other than for purposes of profit-sharing contribution) will be eligible to immediately participate in Berkshire’s 401(k) plan.

​

 

4

 

Q:

How does the Berkshire board of directors recommend that I vote at the Berkshire Annual Meeting?

​

A:

The Berkshire board of directors (the “Berkshire board”) has unanimously (i) determined that the issuance of Berkshire common stock is in the best interests of Berkshire and its stockholders, and (ii) approved the Merger Agreement and the consummation of the transactions contemplated thereby, including the issuance of Berkshire common stock. The Berkshire board unanimously recommends that Berkshire stockholders vote “FOR” the Berkshire Share Issuance Proposal, “FOR” the Berkshire Certificate of Incorporation Amendment Proposal, “FOR” the Berkshire Equity Plan Proposal, “FOR” the Berkshire Director Election Proposal; “FOR” the Berkshire Say-on-Pay Proposal, “FOR” the Berkshire Auditor Ratification Proposal, and “FOR” the Berkshire Adjournment Proposal.

​

See the sections entitled “Description of the Mergers — Berkshire’s Reasons for the Merger; Recommendation of the Berkshire Board of Directors” beginning on page [  ] for a more detailed discussion of the Berkshire board’s recommendations and reasons therefor. In addition, certain of Berkshire’s officers and directors have financial interests in the transactions contemplated by the Merger Agreement that are different from, or in addition to, the interests of Berkshire stockholders. These interests are described in more detail in the section titled “Description of the Mergers — Interests of Berkshire Directors and Executive Officers in the Mergers” beginning on page [  ].

Q:

How does the Brookline board of directors recommend that I vote at the Brookline Special Meeting?

​

A:

The Brookline board of directors (the “Brookline board”) has unanimously (i) determined that the Merger Agreement and the Merger are in the best interests of Brookline, and (ii) approved the Merger Agreement, the Merger, and the other actions contemplated by the Merger Agreement. The Brookline board unanimously recommends that Brookline stockholders vote “FOR” the Brookline Merger Proposal, “FOR” the Brookline Merger-Related Compensation Proposal, and “FOR” the Brookline Adjournment Proposal.

​

See the sections entitled “Description of the Mergers — Brookline’s Reasons for the Mergers; Recommendation of the Brookline Board of Directors” beginning on page [  ] for a more detailed discussion of the Brookline board’s recommendations and reasons therefor. In addition, certain of Brookline’s officers and directors have financial interests in the transactions contemplated by the Merger Agreement that are different from, or in addition to, the interests of Brookline stockholders. These interests are described in more detail in the section entitled “Description of the Mergers — Interests of Brookline Directors and Executive Officers in the Mergers” beginning on page [  ].

Q:

Who is entitled to vote at the Berkshire Annual Meeting?

​

A:

The holders of record of Berkshire common stock at the close of business on           , 2025, which is the date the Berkshire board has fixed as the record date for the Berkshire Annual Meeting (the “Berkshire record date”) are entitled to vote at the Berkshire Annual Meeting.

​

Berkshire stockholders are entitled to one vote for each share of Berkshire common stock held as of the Berkshire record date. As of the close of business on the Berkshire record date, there were             outstanding shares of Berkshire common stock.

Attendance at the Berkshire Annual Meeting is not required to vote. See below and the section entitled “Annual Meeting of Berkshire Stockholders — How to Vote” beginning on page [  ] for instructions on how to vote your shares of Berkshire common stock.

Q:

Who is entitled to vote at the Brookline Special Meeting?

​

A:

The holders of record of Brookline common stock at the close of business on           , 2025, which is the date the Brookline board has fixed as the record date for the Brookline Special Meeting (the “Brookline record date”), are entitled to vote at the Brookline Special Meeting.

​

Brookline stockholders are entitled to one vote for each share of Brookline common stock held as of the Brookline record date. As of the close of business on the Brookline record date, there were             outstanding shares of Brookline common stock.

 

5

 

Attendance at the Brookline Special Meeting is not required to vote. See below and the section entitled “Special Meeting of Brookline Stockholders — How to Vote” beginning on page [  ] for instructions on how to vote your shares of Brookline common stock.

Q:

What constitutes a quorum for the Berkshire Annual Meeting?

​

A:

A quorum, consisting of the holders of a majority of all the shares of Berkshire common stock entitled to vote at the Berkshire Annual Meeting, must be present in person or by proxy before any action may be taken at the Berkshire Annual Meeting. Once a share of Berkshire common stock is represented at the Berkshire Annual Meeting, it will be counted for the purpose of determining a quorum not only at the Berkshire Annual Meeting but also at any adjournment or postponement of the Berkshire Annual Meeting. In the event that a quorum is not present at the Berkshire Annual Meeting, it is expected that the Berkshire Annual Meeting will be adjourned or postponed. Abstentions and broker non-votes will not be counted for purposes of determining the number of votes cast on a proposal, but abstentions and broker non-votes will be treated as present for quorum purposes.

​

Q:

What constitutes a quorum for the Brookline Special Meeting?

​

A:

A quorum, consisting of the holders of a majority of all the shares of Brookline common stock entitled to vote at the Brookline Special Meeting, must be present in person or by proxy before any action may be taken at the Brookline Special Meeting. Once a share of Brookline common stock is represented at the Brookline Special Meeting, it will be counted for the purpose of determining a quorum not only at the Brookline Special Meeting but also at any adjournment or postponement of the Brookline Special Meeting. In the event that a quorum is not present at the Brookline Special Meeting, it is expected that the Brookline Special Meeting will be adjourned or postponed. Abstentions and broker non-votes (if any) will not be counted for purposes of determining the number of votes cast on a proposal, but abstentions will be treated as present for quorum purposes.

​

Q:

What vote is required for the approval of each proposal at the Berkshire Annual Meeting?

​

A:

Berkshire Proposal 1 — The Berkshire Share Issuance Proposal.   Approval of the Berkshire Share Issuance Proposal requires the affirmative vote of a majority of votes cast at the Berkshire Annual Meeting. If you fail to submit a proxy or vote in person at the Berkshire Annual Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee (which we refer to as a broker non-vote) with respect to the Berkshire Share Issuance Proposal, it will have no effect on such proposal.

​

Berkshire Proposal 2 — The Berkshire Certificate of Incorporation Amendment Proposal.   Approval of the Berkshire Certificate of Incorporation Amendment Proposal requires the affirmative vote of a majority of the votes cast at the Berkshire Annual Meeting. If you fail to submit a proxy or to vote in person at the Berkshire Annual Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee with respect to the Berkshire Certificate of Incorporation Amendment Proposal, it will have no effect on such proposal.

Berkshire Proposal 3 — The Berkshire Equity Plan Proposal.   Approval of the Berkshire Equity Plan Proposal requires the affirmative vote of a majority of votes cast at the Berkshire Annual Meeting. If you fail to submit a proxy or vote in person at the Berkshire Annual Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee with respect to the Berkshire Equity Plan Proposal, it will have no effect on such proposal.

Berkshire Proposal 4 — The Berkshire Director Election Proposal.   Directors will be elected by a plurality of the votes cast at the Berkshire Annual Meeting. If you fail to submit a proxy or vote in person at the Berkshire Annual Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee with respect to the Berkshire Director Election Proposal, it will have no effect on such proposal.

Berkshire Proposal 5 — The Berkshire Say-on-Pay Proposal.   Approval of the Berkshire Say-on-Pay Proposal requires the affirmative vote of a majority of the votes cast at the Berkshire Annual Meeting.

 

6

 

If you fail to submit a proxy or vote in person at the Berkshire Annual Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee with respect to the Berkshire Say-on-Pay Proposal, it will have no effect on such proposal.

Berkshire Proposal 6 — The Berkshire Auditor Ratification Proposal.   Approval of the Berkshire Auditor Ratification Proposal requires the affirmative vote of a majority of the votes cast at the Berkshire Annual Meeting. If you fail to submit a proxy or vote in person at the Berkshire Annual Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee with respect to the Berkshire Auditor Ratification Proposal, it will have no effect on such proposal.

Berkshire Proposal 7 — The Berkshire Adjournment Proposal.   Approval of the Berkshire Adjournment Proposal requires the affirmative vote of a majority of the votes cast at the Berkshire Annual Meeting. If you fail to submit a proxy or vote in person at the Berkshire Annual Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee with respect to the Berkshire Adjournment Proposal, it will have no effect on such proposal.

Q:

What vote is required for the approval of each proposal at the Brookline Special Meeting?

​

A:

Brookline Proposal 1 — The Brookline Merger Proposal.   Approval of the Brookline Merger Proposal requires the affirmative vote of a majority of the outstanding shares of Brookline capital stock entitled to vote on the proposal. If you fail to submit a proxy or to vote in person at the Brookline Special Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or other nominee (which we refer to as a broker non-vote) with respect to the Brookline Merger Proposal, it will have the same effect as a vote “AGAINST” such proposal.

​

Brookline Proposal 2 — The Brookline Merger-Related Compensation Proposal.   Approval of the non-binding, advisory Brookline Merger-Related Compensation Proposal requires the affirmative vote of a majority of the votes cast at the Brookline Special Meeting. If you fail to submit a proxy or to vote in person at the Brookline Special Meeting, mark “ABSTAIN” on your proxy or submit as a broker non-vote with respect to the Brookline Merger-Related Compensation Proposal, it will have no effect on such proposal.

Brookline Proposal 3 — The Brookline Adjournment Proposal.   Approval of the Brookline Adjournment Proposal requires the affirmative vote of a majority of the votes cast at the Brookline Special Meeting. If a quorum is present at the Brookline Special Meeting, if you fail to submit a proxy or to vote in person at the Brookline Special Meeting, mark “ABSTAIN” on your proxy or fail to instruct your bank, broker or submit as a broker non-vote with respect to the Brookline Adjournment Proposal, it will have no effect on such proposal.

Q:

Why am I being asked to consider and vote on the Brookline Merger-Related Compensation Proposal?

​

A:

Under Securities and Exchange Commission (“SEC”) rules, Brookline is required to seek a non-binding, advisory vote with respect to the compensation that may be paid or become payable to Brookline’s named executive officers that is based on or otherwise relates to the Mergers, or “golden parachute” compensation.

​

Q:

What will happen if Brookline stockholders do not approve the Brookline Merger-Related Compensation Proposal?

​

A:

The vote with respect to the Brookline compensation proposal is an advisory vote and will not be binding on Brookline or the Brookline board. Therefore, if the Brookline Merger Proposal is not approved by Brookline stockholders, the compensation described in the Brookline Merger-Related Compensation Proposal could still be paid to the Brookline named executive officers, if and to the extent required or allowed under applicable law, even if Brookline stockholders do not approve the Brookline compensation proposal.

​

 

7

 

Q:

What if I hold shares in both Berkshire and Brookline?

​

A:

If you hold shares of both Berkshire common stock and Brookline common stock, you will receive separate packages of proxy materials. A vote cast as a Berkshire stockholder will not count as a vote cast as a Brookline stockholder, and a vote cast as a Brookline stockholder will not count as a vote cast as a Berkshire stockholder. Therefore, please submit separate proxies for your shares of Berkshire common stock and your shares of Brookline common stock.

​

Q:

How can I attend, vote and ask questions at the Berkshire Annual Meeting or the Brookline Special Meeting?

​

A:

Record Holders.   If you hold shares directly in your name as the holder of record of Berkshire common stock or Brookline common stock, you are a “record holder” and your shares may be voted at the Berkshire Annual Meeting or the Brookline Special Meeting by you. If you choose to vote your shares virtually at the respective special meeting via the applicable special meeting website, you will need the control number, as described below.

​

Beneficial Owners.   If you hold shares in a brokerage or other account in “street name,” you are a “beneficial owner” and your shares may be voted at the Berkshire Annual Meeting or the Brookline Special Meeting, as applicable, by you as described below. If you choose to vote your shares virtually at the respective special meeting via the applicable special meeting website, you will need the control number, as described below.

Berkshire Annual Meeting.   To participate in the Berkshire Annual Meeting, visit            . Berkshire stockholders may log into the meeting platform beginning at            , Eastern time, on            , 2025. The live webcast will begin promptly at            , Eastern time. Berkshire stockholders are encouraged to access the Berkshire Annual Meeting website prior to the start of the meeting and to allow sufficient time to complete the online registration process. You should plan to have your proxy card available when you vote, as you will need the number that is printed in the box on the proxy card marked by the arrow. This is your control number.

Brookline Special Meeting.   To participate in the Brookline Special Meeting, visit            . Brookline stockholders may log into the meeting platform beginning at            , Eastern time, on            , 2025. The live webcast will begin promptly at            , Eastern time. Brookline stockholders are encouraged to access the Brookline Special Meeting website prior to the start of the meeting and to allow sufficient time to complete the online registration process. You should plan to have your proxy card available when you vote, as you will need the number that is printed in the box on the proxy card marked by the arrow. This is your control number.

Berkshire and Brookline recommend that you vote your shares in advance so that your vote will be counted if you later decide not to or become unable to attend the respective stockholder meeting.

Q:

How can I vote my shares without attending my respective special meeting?

​

A:

Whether you hold your shares directly as the record holder of Berkshire common stock or Brookline common stock or beneficially in “street name,” you may direct your vote by proxy without attending the Berkshire Annual Meeting or the Brookline Special Meeting, as applicable. If you are a record holder of Berkshire common stock or Brookline common stock, you can vote your shares by proxy via the Internet, by mobile device or by mail by following the instructions provided in the enclosed proxy card. If you hold shares beneficially in “street name” as a beneficial owner of Berkshire common stock or Brookline common stock, you should follow the voting instructions provided by your bank, broker, trustee or other nominee.

​

Additional information on voting procedures can be found under the section entitled “Annual Meeting of Berkshire Stockholders — How to Vote” on page [  ] and under the section entitled “Special Meeting of Brookline Stockholders — How to Vote” on page [  ].

 

8

 

Q:

What do I need to do now?

​

A:

Read and consider the information contained in this Joint Proxy Statement/Prospectus, including the Annexes carefully and then please submit as soon as possible either your Berkshire proxy, in the case of Berkshire stockholders, or your Brookline proxy, in the case of Brookline stockholders.

​

Q:

If my shares of Berkshire common stock or Brookline common stock are held in street name by my broker, will my broker automatically vote my shares for me?

​

A:

No. Your bank, broker or other nominee will not be able to vote shares held by it in street name on your behalf without instructions from you. You should instruct your bank, broker or other nominee to vote your shares by following the directions your bank, broker or other nominee provides to you. Please check the voting instructions form used by your bank, broker or other nominee.

​

Q:

What is a “broker non-vote”?

​

A:

A “broker non-vote” occurs when a broker, bank or other nominee holding shares on your behalf does not receive voting instructions from you. If that happens, the broker, bank or other nominee may vote those shares only on matters deemed “routine” under the rules of the NYSE. On non-routine matters, the broker, bank or other nominee cannot vote those shares unless they receive voting instructions from the beneficial owner. A “broker non-vote” occurs when a broker has not received voting instructions and either declines to exercise its discretionary authority to vote on routine matters or is barred from doing so because the matter is non-routine. The Brookline Merger Proposal, the Brookline Merger-Related Compensation Proposal, and the Brookline Adjournment Proposal are considered to be “non-routine” under NYSE rules such that your broker, bank or other agent may not vote your shares on those proposals in the absence of your voting instructions. The Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, the Berkshire Equity Plan Proposal, the Berkshire Director Election Proposal, the Berkshire Say-on-Pay Proposal, and the Berkshire Adjournment Proposal are considered to be “non-routine” under NYSE rules such that your broker, bank or other agent may not vote your shares on those proposals in the absence of your voting instructions. The Berkshire Auditor Ratification Proposal is considered to be a “routine” matter. Your broker, bank or other agent, therefore, may vote your shares in its discretion in the absence of your voting instructions.

​

Q:

What if I abstain from voting or fail to instruct my bank, broker or other nominee?

​

A:

For the purposes of the Berkshire Annual Meeting, an abstention occurs when a Berkshire stockholder attends the Berkshire Annual Meeting and does not vote or returns a proxy with an “ABSTAIN” instruction. Abstentions and broker non-votes of shares of Berkshire common stock will not have any effect on the approval of the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, the Berkshire Equity Plan Proposal, the Berkshire Director Election Proposal, the Berkshire Say-on-Pay Proposal, the Berkshire Auditor Ratification Proposal, or the Berkshire Adjournment Proposal.

​

For purposes of the Brookline Special Meeting, an abstention occurs when a Brookline stockholder attends the Brookline Special Meeting and does not vote or returns a proxy with an “ABSTAIN” instruction. In the event that a quorum is present, abstentions and broker non-votes of shares of Brookline common stock will have the same effect as a vote “AGAINST” the Brookline Merger Proposal. Abstentions and broker non-votes of shares of Berkshire common stock will not have any effect on the approval of the Brookline Merger-Related Compensation Proposal, and the Brookline Adjournment Proposal at the Brookline Special Meeting.

Q:

Why is my vote important?

​

A:

The Merger cannot be completed unless Berkshire stockholders approve the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, and the Berkshire Equity Plan Proposal, and Brookline stockholders approve the Brookline Merger Proposal, which are the only applicable Berkshire or Brookline stockholder proposals necessary to complete the Mergers.

​

 

9

 

Information about the Berkshire Annual Meeting and the Brookline Special Meeting, the Mergers, and other matters to be considered by stockholders of each of Berkshire and Brookline is contained in this document.

Q:

What if I am a record holder and I do not indicate a decision with respect to the matters required to be voted on?

​

A:

If you are a record holder of Berkshire common stock or Brookline common stock and you returned a signed proxy card without indicating how to vote on any particular proposal, the shares of Berkshire common stock represented by your proxy will be voted as recommended by the Berkshire board with respect to such proposals, or the shares of Brookline common stock represented by your proxy will be voted as recommended by the Brookline board with respect to such proposals, as the case may be.

​

Q:

Can I change my vote?

​

A:

You may revoke your proxy at any time before it is exercised.

​

Berkshire stockholders that are stockholders of record must give written notice of revocation to the Corporate Secretary of Berkshire, submit another properly signed proxy with a more recent date, vote again via the Internet or by telephone, or vote at the Berkshire Annual Meeting. Please note that simply participating in the Berkshire Annual Meeting in person without voting will not revoke your proxy.

You may revoke a proxy for shares held by a bank, broker, or other nominee by submitting new voting instructions to the bank, broker, or other nominee or, if you have obtained a legal proxy from the bank, broker, or other nominee giving you the right to vote the shares at the Berkshire Annual Meeting, by following the voting instructions provided in the legal proxy.

Brookline stockholders that are stockholders of record must file a written revocation with the Corporate Secretary of Brookline, submit a new proxy by telephone or the Internet, or submit a new proxy card after the time and date of the previously submitted proxy card, or attend the Brookline Special Meeting and vote at the Brookline Special Meeting. Simply attending the Brookline Special Meeting without voting will not revoke a Brookline proxy.

If you have instructed a bank, broker or other nominee to vote your shares of Brookline common stock, you must follow directions received from the bank, broker or other nominee to change his or her vote. Revocation of a proxy or a later-dated proxy received by Brookline after the vote will not affect the vote. Attendance at the Brookline Special Meeting will not, in and of itself, constitute revocation of a proxy.

Q:

Will Berkshire be required to submit the Berkshire Share Issuance Proposal to its stockholders even if the Berkshire board has withdrawn, modified or qualified its recommendation?

​

A:

Yes. Unless the Merger Agreement is terminated before the Berkshire Annual Meeting, Berkshire is required to submit the Berkshire Share Issuance Proposal to Berkshire stockholders even if the Berkshire board has withdrawn, modified or qualified its recommendation.

​

Q:

Will Brookline be required to submit the Brookline Merger Proposal to its stockholders even if the Brookline board has withdrawn, modified or qualified its recommendation?

​

A:

Yes. Unless the Merger Agreement is terminated before the Brookline Special Meeting, Brookline is required to submit the Brookline Merger Proposal to Brookline stockholders even if the Brookline board has withdrawn, modified or qualified its recommendation.

​

Q:

Will Berkshire stockholders have appraisal or dissenters’ rights in connection with the Mergers?

​

A:

No. Under the provisions of the Delaware General Corporation Law (the “DGCL”), Berkshire stockholders are not entitled to appraisal or dissenters’ rights in the Merger.

​

Q:

Will Brookline stockholders have appraisal or dissenters’ rights in connection with the Mergers?

​

A:

No. Under the provisions of the DGCL, Brookline stockholders are not entitled to appraisal or dissenters’ rights in the Merger.

​

 

10

 

Q:

Are there any risks that should be considered in deciding whether to vote for the matters required to be voted on by the respective stockholders of Berkshire and Brookline?

​

A:

Yes. Set forth under the section entitled “Risk Factors” beginning on page [  ], are a number of risk factors that Berkshire stockholders and Brookline stockholders should consider carefully.

​

Q:

What are the U.S. federal income tax consequences of the Mergers to Brookline stockholders?

​

A:

The Mergers are intended to qualify as a “reorganization” within the meaning of Section 368(a) of the Internal Revenue Code of 1986, as amended (the “Code”) for U.S. federal income tax purposes, and each of Berkshire’s and Brookline’s obligations to complete the Mergers is conditioned on the receipt of a legal opinion to the effect that the Mergers will so qualify. Assuming the Mergers qualify as a reorganization, subject to the limitations and more detailed discussion set forth in the section entitled “Description of the Mergers — Material United States Federal Income Tax Consequences of the Mergers” beginning on page [  ], Brookline stockholders generally will not recognize any gain or loss for U.S. federal income tax purposes on the exchange of their Brookline common stock for Berkshire common stock in the Mergers, except for any gain or loss that may result from the receipt of cash in lieu of a fractional share of Berkshire common stock.

​

Brookline stockholders who receive cash in lieu of fractional shares will be treated as having received the fractional share and then having the fractional share redeemed by Berkshire for cash. Accordingly, a portion of their adjusted basis in shares of Brookline common stock surrendered pursuant to the Mergers will be allocated to the fractional share which is deemed to have been received and the Brookline stockholder will recognize gain or loss in an amount equal to the difference between the cash received for the fractional share and his or her adjusted basis allocable to that fractional share.

The tax consequences of the Mergers to a particular Brookline stockholder will depend in part on such stockholder’s individual circumstances. Accordingly, each Brookline stockholder is urged to consult his or her own tax advisor for a full understanding of the tax consequences of the Merger to such stockholder, including the applicability and effect of U.S. federal, state, local and foreign income and other tax laws.

For further information concerning the U.S. federal income tax consequences of the Mergers, see the section entitled “Description of the Mergers — Material United States Federal Income Tax Consequences of the Mergers” beginning on page [  ].

Q:

When do Berkshire and Brookline expect to complete the Mergers?

​

A:

The parties expect to complete the Mergers by the end of the second half of 2025; however, there is no assurance when or if the Mergers will occur. Prior to the consummation of the Mergers, Berkshire stockholders must approve the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, and the Berkshire Equity Plan Proposal at the Berkshire Annual Meeting, Brookline stockholders must approve the Brookline Merger Proposal at the Brookline Special Meeting, and other conditions to the consummation of the Merger must be satisfied.

​

Q:

What are the conditions to complete the Mergers?

​

A:

The obligations of Berkshire and Brookline to complete the Mergers are subject to the satisfaction or waiver of certain closing conditions contained in the Merger Agreement, including the receipt of requisite regulatory approvals and the expiration of all statutory waiting periods without the imposition of any materially burdensome regulatory condition, the receipt of certain tax opinions, the approval by Berkshire stockholders of the Berkshire Share Issuance Proposal, the Berkshire Certificate of Incorporation Amendment Proposal, and the Berkshire Equity Plan Proposal, the approval by Brookline stockholders of the Brookline Merger Proposal, the authorization for listing on the NYSE of the shares of Berkshire common stock to be issued in the Merger, the effectiveness of the registration statement of which this Joint Proxy Statement/Prospectus forms a part, the absence of legal restraint prohibiting the Merger, the parties’ performance of their respective obligations under the Merger Agreement subject to certain materiality qualifications, and the accuracy of the representations and warranties made in the

​

 

11

 

Merger Agreement subject to certain materiality qualifications. For more information, see the section entitled “Description of the Mergers — Conditions to Completing the Mergers” beginning on page [  ]

Q:

What happens if the Mergers are not completed?

​

A:

If the Mergers are not completed, Brookline stockholders will not receive any consideration for their shares of Brookline common stock in connection with the Mergers. Instead Brookline will remain an independent public company and Brookline common stock will continue to be listed and traded on Nasdaq. In addition, if the Merger Agreement is terminated in certain circumstances, a termination fee of $45.0 million will be payable by either Berkshire or Brookline, as applicable. See the section entitled “Description of the Mergers — Termination Fee” beginning on page [  ] for a more detailed discussion of the circumstances under which a termination fee will be required to be paid.

​

Q:

What happens if I sell my shares after the applicable record date but before the Berkshire Annual Meeting or Brookline Special Meeting, as applicable?

​

A:

Each of the Berkshire record date and Brookline record date is earlier than the date of the Berkshire Annual Meeting and the Brookline Special Meeting, as applicable, and earlier than the date that the Mergers are expected to be completed. If you sell or otherwise transfer your shares of Berkshire common stock or Brookline common stock, as applicable, after the applicable record date but before the date of the applicable special meeting, you will retain your right to vote at such special meeting (provided that such shares remain outstanding on the date of such special meeting), but, with respect to Brookline common stock, you will not have the right to receive the Merger Consideration to be received by Brookline stockholders in connection with the Mergers. In order to receive the Merger Consideration, you must hold your shares of Brookline common stock through the completion of the Mergers.

​

Q:

If the Mergers are completed, when can Brookline stockholders expect to receive the Merger Consideration?

​

A:

Promptly following the completion of the Mergers, the exchange agent will send each former Brookline stockholder of record instructions detailing how such stockholders can exchange their shares of Brookline common stock for the Merger Consideration.

​

Q:

What should I do if I receive more than one set of voting materials for the same special meeting?

​

A:

If you are a beneficial owner and hold shares of Berkshire common stock or Brookline common stock in “street name” and also are a record holder and hold shares directly in your name or otherwise or if you hold shares of Berkshire common stock or Brookline common stock in more than one brokerage account, you may receive more than one set of voting materials relating to the same special meeting.

​

Record Holders.   For shares held directly, please complete, sign, date and return each proxy card (or cast your vote by telephone or the Internet as provided on each proxy card) or otherwise follow the voting instructions provided in this Joint Proxy Statement/Prospectus in order to ensure that all of your shares of Berkshire common stock or Brookline common stock are voted.

Beneficial Owners.   For shares held in “street name” through a bank, broker, trustee or other nominee, you should follow the procedures provided by your bank, broker, trustee or other nominee in order to vote your shares.

Q:

Whom should I call if I have questions?

​

A:

If you are a Berkshire stockholder and have any questions concerning the Mergers or Joint Proxy Statement/Prospectus, would like additional copies of the Joint Proxy Statement/Prospectus or need help voting your shares of Berkshire common stock, please contact Berkshire’s proxy solicitor, Innisfree M&A Incorporated, by calling toll-free at           , or via e-mail to           .

​

If you are a Brookline stockholder and have any questions concerning the Mergers or Joint Proxy Statement/Prospectus, would like additional copies of the Joint Proxy Statement/Prospectus or need help voting your shares of Brookline common stock, please contact Brookline’s proxy solicitor, Alliance Advisors, LLC, by calling toll-free at            , or via e-mail to            .

 

12

 

Q:

Where can I find more information about Berkshire and Brookline?

​

A:

You can find more information about Berkshire and Brookline from the various sources described under the section entitled “Where You Can Find More Information” beginning on page [  ].

​

Q:

What is householding and how does it affect me?

​

A:

The SEC permits companies to send a single set of proxy materials to any household at which two or more stockholders reside, unless contrary instructions have been received, but only if the applicable stockholders provide advance notice and follow certain procedures. In such cases, each stockholder continues to receive a separate notice of the meeting and proxy card. Certain brokerage firms may have instituted householding for beneficial owners of Berkshire common stock and Brookline common stock, as applicable, held through brokerage firms. If your household has multiple accounts holding Berkshire common stock or Brookline common stock, as applicable, you may have already received a householding notification from your broker. Please contact your broker directly if you have any questions or require additional copies of this Joint Proxy Statement/Prospectus. The broker will arrange for delivery of a separate copy of this Joint Proxy Statement/Prospectus promptly upon your written or oral request. You may decide at any time to revoke your decision to household, and thereby receive multiple copies.

​

 

13

 

14

 

15

 

​

​

​

Berkshire Common Stock

​

​

Brookline Common Stock

​

​

Implied Value of One Share of Brookline Common Stock

​

December 13, 2024

​

​

​

$

30.20

​

​

​

​

$

12.56

​

​

​

​

$

12.68

​

​

, 2025

​

​

​

$

​

​

​

​

$

​

​

​

​

$

​

​

​

16

 

17

 

18

 

19

 

20

 

​

21

 

22

 

23

 

RISK FACTORS

In deciding how to vote, you should consider carefully all of the information included in this document and its Annexes and all of the information incorporated by reference and the risk factors identified by Berkshire and Brookline with respect to their operations included in their filings with the SEC, including Berkshire’s Annual Report on Form 10-K for the year ended December 31, 2024, as amended, and Brookline’s Annual Report on Form 10-K for the year ended December 31, 2024, as amended, and other documents incorporated by reference into this document, and see “Where You Can Find More Information.” In addition, you should consider the following risk factors.

Risks Related to the Mergers and Berkshire’s Business Upon Completion of the Mergers

Berkshire and Brookline will be subject to business uncertainties and contractual restrictions while the Mergers are pending.

Uncertainty about the effect of the Mergers on employees and customers may have an adverse effect on Berkshire and Brookline. These uncertainties may impair Berkshire’s or Brookline’s ability to attract, retain and motivate key personnel until the Mergers are completed, and could cause customers and others who deal with Berkshire or Brookline to seek to change existing business relationships with Berkshire or Brookline. In addition, the Merger Agreement requires that Berkshire and Brookline conduct their business in the ordinary course of business consistent with past practice and restricts Berkshire and Brookline from taking certain actions prior to the effective time or termination of the Merger Agreement without Berkshire’s or Brookline’s consent in writing. These restrictions may prevent Berkshire or Brookline from pursuing attractive business opportunities that may arise prior to the completion of the Mergers.

The announcement of the proposed Mergers could disrupt Berkshire’s and Brookline’s relationships with their customers, suppliers, business partners and others, as well as their operating results and businesses generally.

Whether or not the Mergers are ultimately consummated, as a result of uncertainty related to the Mergers, risks relating to the impact of the announcement of the Mergers on Berkshire’s and Brookline’s businesses include the following:

•

their employees may experience uncertainty about their future roles, which might adversely affect Berkshire’s and Brookline’s ability to retain and hire key personnel and other employees;

​

•

customers, suppliers, business partners and other parties with which Berkshire and Brookline maintain business relationships may experience uncertainty about their respective futures and seek alternative relationships with third parties, seek to alter their business relationships with Berkshire and Brookline or fail to extend an existing relationship with Berkshire and Brookline; and

​

•

Berkshire and Brookline have each expended and will continue to expend significant costs, fees and expenses for professional services and transaction costs in connection with the proposed Mergers.

​

If any of the aforementioned risks were to materialize, they could lead to significant costs which may impact each party’s results of operations and financial condition.

The Merger Agreement limits Berkshire’s and Brookline’s abilities to pursue alternatives to the Mergers and may discourage other companies from trying to acquire Berkshire or Brookline.

The Merger Agreement contains “no shop” covenants that restrict each of Berkshire’s and Brookline’s ability to, directly or indirectly, among other things initiate, solicit, knowingly encourage or knowingly facilitate, inquiries or proposals with respect to, or, subject to certain exceptions generally related to the exercise of fiduciary duties by Berkshire’s and Brookline’s respective boards, engage in any negotiations concerning, or provide any confidential or non-public information or data relating to, any alternative acquisition proposals. These provisions, which include a $45.0 million termination fee payable under certain circumstances, may discourage a potential third-party acquirer that might have an interest in acquiring all or a significant part of Berkshire or Brookline from considering or making that acquisition proposal.

 

24

 

In connection with the Mergers, Berkshire will assume Brookline’s outstanding debt obligations, and the combined company’s level of indebtedness following the completion of the Mergers could adversely affect the combined company’s ability to raise additional capital and meet its obligations under existing indebtedness.

In connection with the Mergers, Berkshire has agreed to assume, or to cause its subsidiary to assume, Brookline’s outstanding indebtedness. Berkshire’s existing debt, together with any future incurrence of additional indebtedness, and the assumption of Brookline’s outstanding indebtedness, could have important consequences for the combined company’s creditors and the combined company’s stockholders. For example, it could:

•

limit the combined company’s ability to obtain additional financing for working capital, capital expenditures, debt service requirements, acquisitions and general corporate or other purposes;

​

•

restrict the combined company from making strategic acquisitions or cause the combined company to make non-strategic divestitures;

​

•

restrict the combined company from paying dividends to its stockholders;

​

•

increase the combined company’s vulnerability to general economic and industry conditions; and

​

•

require a substantial portion of cash flow from operations to be dedicated to the payment of principal and interest on the combined company’s indebtedness, thereby reducing the combined company’s ability to use cash flows to fund its operations, capital expenditures and future business opportunities.

​

The combined company will incur significant transaction and merger-related costs in connection with the Mergers.

Berkshire and Brookline will incur costs to combine the operations of the two companies. Berkshire and Brookline are collecting information to formulate detailed integration plans to deliver planned synergies. Additional unanticipated costs may be incurred in the integration of the businesses of Berkshire and Brookline. Whether or not the Mergers are consummated, Berkshire and Brookline will incur substantial expenses, such as legal, accounting, printing and financial advisory fees, in pursuing the Mergers. Although Berkshire and Brookline expect that the elimination of duplicative costs, as well as the realization of other efficiencies related to the integration of the businesses, may offset incremental transactions and merger-related costs over time, this net benefit may not be achieved in the near term, or at all.

If the Mergers are not completed, both parties will have incurred substantial expenses without their respective stockholders realizing the expected benefits of the Mergers.

Both parties have incurred and will incur further substantial expenses in connection with the Mergers, which are charged to earnings as incurred. These costs include legal, financial advisory, accounting, consulting and other advisory fees, severance/employee benefit-related costs, public company filing fees and other regulatory fees, financial printing and other printing costs and other related costs. If the Mergers are not completed, these expenses will still be charged to earnings even though neither party would have realized the expected benefits of the Mergers. There can be no assurance that the Mergers will be completed.

Berkshire and Brookline may not be able to successfully integrate the two companies or to realize the anticipated benefits of the Mergers.

The Mergers involve the combination of two companies that previously have operated independently. A successful combination of the operations of the two entities will depend substantially on both parties’ ability to consolidate cultures, personnel, operations, systems and procedures and to eliminate redundancies and reduce costs of the combined operations. Berkshire may not be able to combine the operations of Brookline with Berkshire’s operations without encountering difficulties, such as:

•

the loss of key employees and customers;

​

•

the disruption of operations and business;

​

•

the inability to maintain and increase competitive presence;

​

 

25

 

•

those associated with entering a new geographic market;

​

•

deposit attrition, customer loss and revenue loss;

​

•

possible inconsistencies in standards, control procedures and policies;

​

•

unexpected problems with costs, operations, personnel, technology and credit; and/or

​

•

problems with the assimilation of new operations, sites or personnel, which could divert resources from regular banking operations.

​

Additionally, general market and economic conditions or governmental actions affecting the financial industry generally may inhibit the successful integration of Brookline.

Berkshire entered into the Merger Agreement with the expectation that the Mergers will result in various benefits including, among other things, enhanced revenues, a strengthened market position for the combined company, cross selling opportunities, improved technology, cost savings and operating efficiencies. Achieving the anticipated benefits of the Mergers are subject to a number of uncertainties, including whether Berkshire and Brookline integrate in an efficient and effective manner, and general competitive factors in the marketplace. Failure to achieve these anticipated benefits could result in increased costs, decreases in the amount of expected revenues and diversion of management’s time and energy and could materially adversely impact Berkshire’s business, financial condition and operating results. Finally, any cost savings that are realized may be offset by losses in revenues or other charges to earnings.

The Merger Agreement may be terminated in accordance with its terms, and the Mergers may not be completed.

The Merger Agreement is subject to a number of conditions that must be fulfilled to complete the Mergers. Those conditions include, among others, certain regulatory and stockholder approvals, the absence of orders prohibiting the completion of the Mergers, the effectiveness of a registration statement to be filed by Berkshire, which will include a Joint Proxy Statement/Prospectus, the continued accuracy of the representations and warranties by both parties, the performance by both parties of their covenants and agreements, and the receipt by both parties of legal opinions from their respective tax counsels. Any of these conditions to closing of the Mergers may not be fulfilled, and as a result the Mergers may not be completed.

The need for regulatory approvals may delay the date of completion of the Mergers or may diminish the benefits of the Mergers.

Berkshire and Brookline are required to obtain the approvals of certain regulatory agencies before completing the Mergers. Satisfying any requirements of these regulatory agencies may delay the date of completion of the Mergers. The requisite regulatory approvals may not be received at all (in which case the Mergers could not be completed), may not be received in a timely fashion, or may contain conditions or restrictions on completion of the Mergers that cannot be satisfied. In addition, any conditions or restrictions imposed could have the effect of imposing additional costs on or limiting the revenues of the combined company following the Mergers, which might have an adverse effect on the combined company following the Mergers. Further, it is possible that, among other things, restrictions on the combined operations of the two companies, including divestitures, may be sought by governmental agencies as a condition to obtaining the required regulatory approvals. This may diminish the benefits of the Mergers to the combined company or otherwise have an adverse effect on the combined company following the Mergers.

Litigation against Berkshire or Brookline, or the members of Berkshire’s or Brookline’s board of directors, could prevent or delay the completion of the Mergers.

Berkshire stockholders or Brookline’s stockholders may file lawsuits against Brookline, Berkshire, and/or the boards of directors of either company in connection with the Mergers. Such legal proceedings could delay or prevent the Mergers from being completed in a timely manner. The existence of litigation related to the Mergers could affect the likelihood of obtaining the required regulatory and stockholders’ approvals. Moreover, any litigation could be time-consuming and expensive and could divert Berkshire’s and Brookline’s management’s attention away from their regular business and their focus on a successful integration of the two companies. Any lawsuit adversely resolved against Brookline, Berkshire or members

 

26

 

of their respective boards of directors could have a material adverse effect on each company’s business, financial condition and results of operations.

Moreover, one of the conditions to the completion of the Mergers is the absence of any restraining order, injunction or decree issued by a court of competent jurisdiction or other legal restraint or prohibition preventing the consummation of the Mergers, and that no governmental authority or regulatory authority of competent jurisdiction shall have enacted, promulgated or enforced any statute, rule, regulation, judgment, decree, injunction or other order prohibiting consummation of the transactions contemplated by the Merger Agreement or making the Mergers illegal. Consequently, if a settlement or other resolution is not reached in any lawsuit that is filed or any regulatory proceeding and a claimant secures injunctive or other relief or a governmental authority issues an order or other directive restricting, prohibiting or making illegal the consummation of the transactions contemplated by the Merger Agreement (including the Mergers), then such injunctive or other relief may prevent the Mergers from becoming effective in a timely manner or at all.

The future results of the combined company following the Mergers may suffer if the combined company does not effectively manage its expanded operations.

Following the Mergers, the size of the business of the combined company will increase beyond the current size of either Berkshire’s or Brookline’s business. The combined company’s future success will depend, in part, upon its ability to manage this expanded business, which may pose challenges for management, including challenges related to the management and monitoring of new operations and associated increased costs and complexity. The combined company may also face increased scrutiny from governmental authorities as a result of the increased size of its business. There can be no assurances that the combined company will be successful or that it will realize the expected operating efficiencies, revenue enhancement or other benefits currently anticipated from the Mergers.

The market price of Berkshire common stock after the Mergers may be affected by factors different from those currently affecting Berkshire common stock.

The results of operations of the combined company and the market price of Berkshire’s common stock after the completion of the Mergers may be affected by factors different from those currently affecting the independent results of operations of each of Berkshire and Brookline. In addition, the issuance of shares of Berkshire’s common stock in the Mergers could depress the market price for Berkshire’s common stock. For example, some Brookline stockholders may decide not to hold the shares of Berkshire’s common stock they receive as a result of the Mergers. Other Brookline stockholders, such as funds with limitations on their permitted holdings of stock in individual issuers, may be required to sell the shares of Berkshire’s common stock they receive as a result of the Mergers. Any such sales of Berkshire’s common stock could depress the market price for Berkshire’s common stock.

Current holders of Berkshire common stock and Brookline common stock will have a significantly reduced ownership and voting interest in the combined company after the Mergers and will therefore have less voting influence over the combined company.

In the Mergers, each Brookline stockholder will become a holder of common stock of the combined company. Upon completion of the Mergers, Berkshire estimates that Brookline stockholders will collectively own approximately 45% and Berkshire stockholders as of immediately before the Mergers will own approximately 55% of the outstanding shares of common stock of the combined company. As a result, each of Berkshire’s and Brookline’s current stockholders will have less voting influence on the combined company and may have less influence on its management and policies than they now have.

The market price of Berkshire common stock may decline in the future as a result of the Mergers.

The market price of Berkshire common stock may decline in the future as a result of the Mergers for a number of reasons, including:

•

the unsuccessful integration of Brookline and Berkshire; and

​

 

27

 

•

the failure of the combined company to achieve the perceived benefits of the Mergers, including financial results, as rapidly as or to the extent anticipated by financial or industry analysts.

​

Many of these factors are beyond the control of Berkshire. As a consequence, current Berkshire stockholders and Brookline stockholders who will become holders of Berkshire common stock after completion of the Mergers could lose the value of their investment in Berkshire common stock.

Risks Related to Berkshire’s Business

You should read and consider risk factors specific to Berkshire’s business that will also affect the combined company after the Mergers. These risks are described in the section entitled “Risk Factors” in Berkshire’s Annual Report on Form 10-K for the fiscal year ended December 31, 2024, as amended, and in other documents incorporated by reference into this Joint Proxy Statement/Prospectus. Please see the section entitled “Where You Can Find More Information” for the location of information incorporated by reference into this Joint Proxy Statement/Prospectus.

Risks Related to Brookline’s Business

You should read and consider risk factors specific to Brookline’s business that will also affect the combined company after the Mergers. These risks are described in the sections entitled “Risk Factors” in Brookline’s Annual Report on Form 10-K for the fiscal year ended December 31, 2024, as amended.

 

28

 

CAUTIONARY STATEMENT ABOUT FORWARD-LOOKING STATEMENTS

This joint proxy statement/prospectus, including the information incorporated by reference, contains statements that may be considered forward-looking statements within the meaning of Section 27A of the Securities Act, and Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). These statements, which are based on certain current assumptions, can generally be identified by the use of the words “may,” “will,” “should,” “could,” “would,” “plan,” “potential,” “estimate,” “project,” “believe,” “intend,” “anticipate,” “expect,” “target” and similar expressions. Berkshire and Brookline intend these forward-looking statements to be covered by the safe harbor provisions for forward-looking statements contained in the Private Securities Litigation Reform Act of 1995 and are including this statement for purposes of complying with these safe harbor provisions. You should read statements that contain these words carefully because they discuss the relevant company’s future expectations, contain projections of the relevant company’s future results of operations or financial condition, or state other “forward-looking” information.

The following factors, among others, could cause actual results to differ materially from the anticipated results or other expectations expressed in the forward-looking statements:

•

the occurrence of any event, change or other circumstances that could give rise to the right of one or both of the parties to terminate the Merger Agreement among Berkshire, Merger Sub and Brookline;

​

•

the outcome of any legal proceedings that may be instituted against Berkshire or Brookline;

​

•

the possibility that the proposed transaction will not close when expected or at all because required regulatory, stockholder or other approvals are not received or other conditions to the closing are not satisfied on a timely basis or at all, or are obtained subject to conditions that are not anticipated (and the risk that required regulatory approvals may result in the imposition of conditions that could adversely affect the combined company or the expected benefits of the proposed transaction);

​

•

the ability of Berkshire and Brookline to meet expectations regarding the timing, completion and accounting and tax treatments of the proposed transaction;

​

•

the risk that any announcements relating to the proposed transaction could have adverse effects on the market price of the common stock of either or both parties to the proposed transaction;

​

•

the possibility that the anticipated benefits of the proposed transaction will not be realized when expected or at all, including as a result of the impact of, or problems arising from, the integration of the two companies or as a result of the strength of the economy and competitive factors in the areas where Berkshire and Brookline do business;

​

•

certain restrictions during the pendency of the proposed transaction that may impact the parties’ ability to pursue certain business opportunities or strategic transactions;

​

•

the possibility that the transaction may be more expensive to complete than anticipated, including as a result of unexpected factors or events;

​

•

diversion of management’s attention from ongoing business operations and opportunities;

​

•

the possibility that the parties may be unable to achieve expected synergies and operating efficiencies in the Merger within the expected timeframes or at all and to successfully integrate Brookline’s operations and those of Berkshire;

​

•

such integration may be more difficult, time consuming or costly than expected;

​

•

the potential impact of general economic, political or market factors on the companies or the Merger and other factors that may affect future results of Berkshire or Brookline;

​

•

volatility in the securities markets generally or in the market price of Berkshire shares specifically;

​

•

changes in loan default and charge-off rates;

​

•

changes in the financial performance and/or condition of borrowers;

​

•

changes in customer borrowing and savings habits; and

​

 

29

 

•

changes in regulations applicable to the financial services industry.

​

Because these forward-looking statements are subject to assumptions and uncertainties, Berkshire’s and Brookline’s actual results may differ materially from those expressed or implied by these forward-looking statements. These forward-looking statements are predicated on the beliefs and assumptions of the management of each of Berkshire and Brookline based on information known to them as of the date of this joint proxy statement/prospectus. Berkshire and Brookline stockholders are cautioned not to place undue reliance on these statements, which speak only as of the date of this joint proxy statement/prospectus.

For any forward-looking statements made in this joint proxy statement/prospectus or in any documents incorporated by reference into this joint proxy statement/prospectus, Berkshire and Brookline claim the protection of the safe harbor for forward-looking statements contained in the Private Securities Litigation Reform Act of 1995, Section 27A of the Securities Act, and Section 21E of the Exchange Act. You are cautioned not to place undue reliance on the forward-looking statements, which speak only as of the date of this joint proxy statement/prospectus or the dates of the documents incorporated by reference in this joint proxy statement/prospectus. Annualized, pro forma, projected and estimated numbers are used for illustrative purposes only, are not forecasts and may not reflect actual results. Except as required by applicable law, neither Brookline nor Berkshire undertakes to update these forward-looking statements to reflect facts, circumstances, assumptions or events that occur after the date the forward-looking statements are made.

For additional information about factors that could cause actual results to differ materially from those described in the forward-looking statements, please see the reports that Berkshire and Brookline have filed with the SEC as described under “Where You Can Find More Information” beginning on page [  ].

All subsequent written and oral forward-looking statements concerning the Merger or other matters addressed in this joint proxy statement/prospectus and attributable to Berkshire or Brookline or any person acting on their behalf are expressly qualified in their entirety by the cautionary statements contained or referred to in this section.

 

30

 

PURCHASE PRICE DETERMINATION

The unaudited pro forma combined condensed balance sheet has been adjusted to reflect the preliminary calculation of the estimated purchase price to net assets acquired. In accordance with FASB ASC 805-40-30-2, the acquisition-date fair value of the consideration transferred by the accounting acquirer for its interest in the accounting acquiree is based on the number of equity interests the legal subsidiary would have had to issue to give the owners of the legal parent the same percentage equity interest in the combined entity that results from the reverse acquisition.

The table below summarizes the pro forma ownership of Berkshire common stock following the Mergers, for each stockholder group, as well as the pro forma market capitalization of the surviving corporation using shares of Berkshire and Brookline common stock outstanding at December 31, 2024 and Berkshire’s closing price on [•], 2025, the latest practicable trading day before the date of this Joint Proxy Statement/Prospectus.

The table below summarizes the hypothetical number of shares as of December 31, 2024 that Brookline would have to issue to give Berkshire owners the same percentage ownership in the surviving corporation.

The purchase price is calculated based on the number of hypothetical shares of Brookline common stock issued to Berkshire stockholders multiplied by the share price as demonstrated in the table below (amounts in thousands except per share data).

 

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UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED FINANCIAL DATA

The unaudited pro forma combined condensed consolidated balance sheet combines the historical information of Berkshire and Brookline as of December 31, 2024 and assumes that the Mergers were completed on that date. The unaudited pro forma combined condensed consolidated income statements combine the historical financial information of Berkshire and Brookline and give effect to the Mergers as if completed as of the beginning of the fiscal year ended December 31, 2024.

The unaudited pro forma combined condensed consolidated financial information assumes that the Mergers are accounted for as a reverse acquisition using the acquisition method of accounting, pursuant to FASB Topic 805-10, Business Combinations, with Berkshire treated as the legal acquirer and Brookline treated as the accounting acquirer. In identifying Brookline as the acquiring entity for accounting purposes, Berkshire and Brookline took into account a number of factors as of the date of this Joint Proxy Statement/​Prospectus, including the relative voting rights of all equity instruments in the surviving corporation and the intended corporate governance structure of the surviving corporation. Following the Mergers, existing stockholders of Brookline will control approximately 45% of the pro forma voting interests in the surviving corporation (based on common shares outstanding as of December 31, 2024). However, no single factor was the sole determinant in the overall conclusion that Brookline is the acquirer for accounting purposes; rather all factors were considered in arriving at such conclusion. See the section entitled “Description of the Mergers — Accounting Treatment of the Mergers” beginning on page [  ]. Under the acquisition method of accounting, the assets and liabilities of Berkshire, as the accounting acquiree, will be recorded at their respective fair values as of the date the Mergers are completed.

The unaudited pro forma combined condensed consolidated financial information is presented for illustrative purposes only and is not necessarily indicative of the results of operations or financial condition had the Mergers been completed on the dates described above, nor is it necessarily indicative of the results of operations in future periods or the future financial position of the combined entities. The financial information should be read in conjunction with the accompanying Notes to the Unaudited Pro Forma Combined Condensed Consolidated Financial Information. Certain reclassifications have been made to Berkshire’s historical financial information to conform to Brookline’s presentation of financial information. In addition, as explained in more detail in the accompanying notes, the preliminary allocation of the pro forma purchase price reflected in the unaudited pro forma combined condensed consolidated financial information is subject to adjustment after the Mergers are completed and may vary significantly from the actual purchase price allocation that will be recorded upon completion of the Mergers.

The pro forma financial information includes estimated adjustments, including adjustments to record assets and liabilities of Berkshire at their respective fair values and represents the pro forma estimates by Berkshire and Brookline based on available fair value information as of the date of the Merger Agreement.

The unaudited pro forma combined condensed consolidated financial data, while helpful in illustrating the financial characteristics of the surviving corporation under one set of assumptions, does not reflect the benefits of expected cost savings or opportunities to earn additional revenue and, accordingly, does not attempt to predict or suggest future results. It also does not necessarily reflect what the historical results of the surviving corporation would have been had the companies been combined during these periods.

The unaudited pro forma combined condensed consolidated financial information has been derived from and should be read in conjunction with the historical consolidated financial statements and the related notes of Berkshire and Brookline, which are incorporated in this document by reference.

 

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Pro Forma Balance Sheet — December 31, 2024 Consolidated

 

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Pro Forma Income Statement — December 31, 2024 Consolidated