400 Rella Blvd.
Montebello, New York 10901
(845) 369-8040

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

Approximate date of commencement of the proposed sale of the securities to the public:
As soon as practicable after this Registration Statement becomes effective and upon completion of the merger described in the enclosed document.

If the securities being registered on this Form are being 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 of 1933, as amended, 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 or a smaller reporting company. See the definitions of  “large accelerated filer,” “accelerated filer” and “smaller reporting company” in Rule 12b-2 of the Exchange Act. (Check one):

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)    ☐

Information contained herein is subject to completion or amendment. A registration statement relating to these securities 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 document shall not constitute an offer to sell or the solicitation of any offer to buy nor shall there be any sale of these securities in any jurisdiction in which such offer, solicitation, or sale would be unlawful prior to registration or qualification under the securities laws of any such jurisdiction.

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS

To the Stockholders of Sterling Bancorp:

Sterling Bancorp (which we refer to as “Sterling”) will hold a special meeting of holders of common stock of Sterling (which we refer to as “Sterling stockholders”) at [      ] local time, on [                 ], at Sterling’s business address at 21 Scarsdale Road, Yonkers, New York 10707 (which we refer to as the “Sterling special meeting”) to consider and vote upon the following matters:

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a proposal to adopt the Agreement and Plan of Merger, dated as of March 6, 2017, by and between Astoria Financial Corporation (which we refer to as “Astoria”) and Sterling, as such agreement may be amended from time to time, pursuant to which Astoria will merge with and into Sterling, with Sterling as the surviving corporation, as more fully described in the attached joint proxy statement/prospectus (which we refer to as the “Sterling merger proposal”), a copy of which is attached as Annex A;

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a proposal to approve an amendment to Sterling’s Amended and Restated Certificate of Incorporation (which we refer to as the “Sterling charter”) to increase Sterling’s authorized shares of common stock by 120 million to 310 million (which we refer to as the “Sterling charter amendment proposal”); and

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a proposal to adjourn the Sterling special meeting, if necessary or appropriate, to solicit additional proxies in favor of the Sterling merger proposal and the Sterling charter amendment proposal (which we refer to as the “Sterling adjournment proposal”).

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We have fixed the close of business on [                 ] as the record date for the special meeting. Only Sterling stockholders of record at that time are entitled to notice of, and to vote at, the Sterling special meeting, or any adjournment or postponement of the Sterling special meeting. Approval of each of the Sterling merger proposal and the Sterling charter amendment proposal requires the affirmative vote of holders of a majority of the outstanding shares of common stock of Sterling (which we refer to as “Sterling common stock”). The Sterling adjournment proposal will be approved if a majority of the votes cast at the Sterling special meeting are voted in favor of the adjournment proposal.

Sterling’s board of directors has unanimously approved the merger agreement, has determined that the merger agreement and the transactions contemplated thereby, including the merger, are advisable and in the best interests of Sterling and its stockholders, and unanimously recommends that Sterling stockholders vote “FOR” the Sterling merger proposal, “FOR” the Sterling charter amendment proposal, and “FOR” the Sterling adjournment proposal.

Your vote is very important. We cannot complete the merger unless Sterling’s stockholders adopt the merger agreement.

Regardless of whether you plan to attend the Sterling special meeting, please vote as soon as possible. If you hold stock in your name as a stockholder of record of Sterling, please complete, sign, date, and return the accompanying proxy card in the enclosed postage-paid return envelope. If you hold your stock in “street name” through a bank or broker, please follow the instructions on the voting instruction card furnished by the record holder.

The enclosed joint proxy statement/prospectus provides a detailed description of the Sterling special meeting, the merger, the documents related to the merger, and other related matters. We urge you to read the joint proxy statement/prospectus, including any documents incorporated in the joint proxy statement/prospectus by reference, and its annexes carefully and in their entirety.

BY ORDER OF THE BOARD OF DIRECTORS,

Jack Kopnisky
President and Chief Executive Officer
Sterling Bancorp

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS

To the Stockholders of Astoria Financial Corporation:

NOTICE IS HEREBY GIVEN that Astoria Financial Corporation (which we refer to as “Astoria”) will hold a special meeting of holders of common stock of Astoria (which we refer to as “Astoria common stockholders”) at [      ] local time, on [                 ], at The Inn at New Hyde Park, 214 Jericho Turnpike, New Hyde Park, New York 11040 (which we refer to as the “Astoria special meeting”) to consider and vote upon the following matters:

•

a proposal to adopt the Agreement and Plan of Merger, dated as of March 6, 2017, by and between Astoria and Sterling Bancorp (which we refer to as “Sterling”), as such agreement may be amended from time to time, pursuant to which Astoria will merge with and into Sterling, with Sterling as the surviving corporation, as more fully described in the attached joint proxy statement/prospectus (which we refer to as the “Astoria merger proposal”), a copy of which is attached as Annex A;

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•

a proposal to approve, on an advisory (non-binding) basis, the compensation that certain executive officers of Astoria may receive in connection with the Astoria merger proposal pursuant to existing agreements or arrangements with Astoria (which we refer to as the “Astoria compensation proposal”); and

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•

a proposal to approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the Astoria merger proposal (which we refer to as the “Astoria adjournment proposal”).

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We have fixed the close of business on [                 ] as the record date for the special meeting. Only Astoria common stockholders of record at that time are entitled to notice of, and to vote at, the Astoria special meeting, or any adjournment or postponement of the Astoria special meeting. Approval of the Astoria merger proposal requires the affirmative vote of holders of a majority of the outstanding shares of common stock of Astoria (which we refer to as “Astoria common stock”). Approval of each of the Astoria compensation proposal and the Astoria adjournment proposal requires a majority of the votes cast at the Astoria special meeting to be voted in favor of such proposal.

Astoria’s board of directors has unanimously approved the merger agreement, has determined that the merger, on the terms and conditions set forth in the merger agreement, is advisable and in the best interests of Astoria and its stockholders, and unanimously recommends that Astoria common stockholders vote “FOR” the Astoria merger proposal, “FOR” the Astoria compensation proposal and “FOR” the Astoria adjournment proposal.

Your vote is very important. We cannot complete the merger unless Astoria’s common stockholders adopt the merger agreement.

Regardless of whether you plan to attend the Astoria special meeting, please vote as soon as possible. If you hold stock in your name as a stockholder of record of Astoria, please complete, sign, date, and return the accompanying proxy card in the enclosed postage-paid return envelope. If you hold your stock in “street name” through a bank or broker, please follow the instructions on the voting instruction card furnished by the record holder.

The enclosed joint proxy statement/prospectus provides a detailed description of the special meeting, the merger, the documents related to the merger, and other related matters. We urge you to read the joint proxy statement/prospectus, including any documents incorporated in the joint proxy statement/prospectus by reference, and its annexes carefully and in their entirety .

BY ORDER OF THE BOARD OF DIRECTORS,

Monte N. Redman
President and Chief Executive Officer
Astoria Financial Corporation

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QUESTIONS AND ANSWERS

The following are some questions that you may have about the merger and the Sterling special meeting or the Astoria special meeting, and brief answers to those questions. We urge you to read carefully the remainder of this joint proxy statement/prospectus because the information in this section does not provide all of the information that might be important to you with respect to the merger, the Sterling special meeting or the Astoria special meeting. Additional important information is also contained in the documents incorporated by reference into this joint proxy statement/prospectus. Please see “Where You Can Find More Information.”

Q:

What is the merger?

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A:

Sterling and Astoria have entered into an Agreement and Plan of Merger, dated as of March 6, 2017 (which we refer to as the “merger agreement”). Under the merger agreement, Astoria will be merged with and into Sterling, with Sterling continuing as the surviving corporation (which we refer to as the “merger”). Immediately following the completion of the merger, Astoria Bank, a wholly-owned bank subsidiary of Astoria, will merge with and into Sterling National Bank, a wholly-owned bank subsidiary of Sterling, with Sterling National Bank continuing as the surviving bank (which we refer to as the “bank merger”). A copy of the merger agreement is included in this joint proxy statement/​prospectus as Annex A.

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If the merger is completed, Astoria common stockholders will receive 0.875 shares of Sterling common stock for each share of Astoria common stock they hold immediately prior to the merger, plus cash in lieu of fractional shares. As a result of the foregoing, based on the number of shares of Sterling and Astoria common stock outstanding as of March 6, 2017, on a fully diluted basis, approximately 60% and 40% of Sterling common stock will be held by Sterling stockholders and former holders of Astoria common stock, respectively, immediately following the effectiveness of the merger.

The merger cannot be completed unless, among other things, both Sterling stockholders and Astoria common stockholders approve their respective proposals to adopt the merger agreement.

Q:

Why am I receiving this joint proxy statement/prospectus?

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A:

We are delivering this document to you because it is a joint proxy statement being used by both the Sterling and Astoria boards of directors to solicit proxies of their respective common stockholders in connection with approval of the merger and related matters.

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In order to approve the merger and related matters, Sterling has called a special meeting of its stockholders. This document serves as the proxy statement for the Sterling special meeting and describes the proposals to be presented at the Sterling special meeting.

Astoria has also called a special meeting of its common stockholders to approve the merger and related matters. This document serves as the proxy statement for the Astoria special meeting and describes the proposals to be presented at the Astoria special meeting. Holders of Astoria preferred stock, as defined below, and holders of depositary shares representing shares of Astoria preferred stock (which we refer to as the “Astoria depositary shares”) are not entitled to, and are not requested to, vote at the Astoria meeting.

Finally, this document is also a prospectus that is being delivered to Astoria common stockholders because, in connection with the merger, Sterling is offering shares of its common stock to Astoria common stockholders in a 0.875:1 exchange ratio. Sterling also is issuing shares of Sterling 6.50% Non-Cumulative Perpetual Preferred Stock, Series A, par value $0.01 and liquidation preference of $1,000 per share (which we refer to as the “Sterling preferred stock”), to holders of 6.50% Non-Cumulative Perpetual Preferred Stock, Series C, par value $1.00 and liquidation preference of $1,000 per share (which we refer to as the “Astoria preferred stock”). Each share of Astoria preferred stock will be automatically converted into one share of Sterling preferred stock in the merger. Following the completion of the merger, each outstanding Astoria depositary share will be automatically converted into a depositary share representing a 1/40th interest in a share of Sterling preferred stock (which we refer to as a “Sterling depositary share”).

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This joint proxy statement/prospectus contains important information about the merger and the other proposals being voted on at the Sterling and Astoria special meetings and important information to consider in connection with an investment in Sterling common stock. You should read it carefully and in its entirety. The enclosed materials allow you to have your shares of common stock voted by proxy without attending your meeting. Your vote is important and we encourage you to submit your proxy as soon as possible.

Q:

What are Sterling stockholders being asked to vote on at the Sterling special meeting?

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A:

Sterling is soliciting proxies from its stockholders with respect to the following proposals:

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•

a proposal to adopt the merger agreement, as such agreement may be amended from time to time (which we refer to as the “Sterling merger proposal”);

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•

a proposal to approve an amendment to Sterling’s Amended and Restated Certificate of Incorporation (which we refer to as the “Sterling charter”) to increase Sterling’s authorized shares of common stock by 120 million to 310 million (which we refer to as the “Sterling charter amendment proposal”); and

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•

a proposal to adjourn the Sterling special meeting, if necessary or appropriate, to solicit additional proxies in favor of the Sterling merger proposal (which we refer to as the “Sterling adjournment proposal”).

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Q:

What are Astoria common stockholders being asked to vote on at the Astoria special meeting?

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A:

Astoria is soliciting proxies from its stockholders with respect to the following proposals:

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a proposal to adopt the merger agreement, as such agreement may be amended from time to time (which we refer to as the “Astoria merger proposal”);

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•

a proposal to approve, on an advisory (non-binding) basis, the compensation that certain executive officers of Astoria may receive in connection with the Astoria merger proposal pursuant to existing agreements or arrangements with Astoria (which we refer to as the “Astoria compensation proposal”); and

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•

a proposal to adjourn the Astoria special meeting, if necessary or appropriate, to solicit additional proxies in favor of the Astoria merger proposal (which we refer to as the “Astoria adjournment proposal”).

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Q:

What will Astoria common stockholders receive in the merger?

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A:

If the merger is completed, Astoria common stockholders will receive 0.875 shares of Sterling common stock (which we refer to as the “merger consideration”) for each share of Astoria common stock held immediately prior to the merger. Sterling will not issue any fractional shares of Sterling common stock in the merger. Sterling will pay to each former Astoria common stockholder who holds fractional shares an amount in cash determined by multiplying the average of the closing sale prices of Sterling common stock for the five full trading days ending on the day preceding the closing date of the merger (which we refer to as the “Sterling share closing price”) by the fraction of a share (rounded to the nearest thousandth when expressed in decimal) of Sterling common stock that such stockholder would otherwise be entitled to receive.

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Q:

What will holders of Astoria depositary shares receive in the merger?

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A:

If the merger is completed, holders of Astoria depositary shares will hold depositary shares of the combined company. After the merger is completed, each outstanding Sterling depositary share will represent a 1/40th interest in a share of newly issued Sterling preferred stock, which will have terms that are substantively identical to the terms of Astoria’s outstanding preferred stock (except for the par value). For more information, see “Designation of New Sterling Preferred Stock.”

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Q:

What will Sterling stockholders receive in the merger?

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A:

If the merger is completed, Sterling stockholders will not receive any merger consideration and will continue to hold the shares of Sterling common stock that they currently hold. Following the merger, shares of Sterling common stock will continue to be traded on the New York Stock Exchange (which we refer to as the “NYSE”) under the symbol “STL.”

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Q:

How will the merger affect Astoria equity awards?

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A:

The Astoria equity awards will be affected as follows:

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Restricted Stock:    At the effective time of the merger, each outstanding restricted share of Astoria common stock will fully vest (with any performance-based vesting condition deemed to have been fully achieved (or achieved at the target level if more than one level of achievement has been contemplated)) and be converted automatically into the right to receive the merger consideration (together with any accrued but unpaid dividends corresponding to the restricted stock award).

Restricted Stock Units:    At the effective time of the merger, each outstanding restricted stock unit award in respect of Astoria common stock will fully vest (with any performance-based vesting condition deemed to have been fully achieved (or achieved at the target level if more than one level of achievement has been contemplated)) and be converted automatically into the right to receive the merger consideration in respect of each share of Astoria common stock underlying the restricted stock unit award (together with any accrued but unpaid dividend equivalents corresponding to the restricted stock unit award).

Q:

Will the value of the merger consideration change between the date of this joint proxy statement/​prospectus and the time the merger is completed?

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A:

Yes. Although the merger consideration is fixed, the value of the merger consideration will fluctuate between the date of this joint proxy statement/prospectus and the completion of the merger based upon the market value for Sterling common stock. Any fluctuation in the market price of Sterling common stock after the date of this joint proxy statement/prospectus will change the value of the shares of Sterling common stock that Astoria common stockholders will receive.

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Q:

How does the Sterling board of directors recommend that I vote at the Sterling special meeting?

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A:

Sterling’s board of directors unanimously recommends that you vote “FOR” the Sterling merger proposal, “FOR” the Sterling charter amendment proposal, and “FOR” the Sterling adjournment proposal.

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Q:

How does the Astoria board of directors recommend that I vote at the Astoria special meeting?

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A:

Astoria’s board of directors unanimously recommends that you vote “FOR” the Astoria merger proposal, “FOR” the Astoria compensation proposal, and “FOR” the Astoria adjournment proposal.

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Q:

When and where are the meetings?

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A:

The Sterling special meeting will be held at Sterling’s business address at 21 Scarsdale Road, Yonkers, New York 10707 on [               ], at [      ] local time.

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The Astoria special meeting will be held at The Inn at New Hyde Park, 214 Jericho Turnpike, New Hyde Park, New York 11040 on [               ], at [      ] local time.

Q:

What do I need to do now?

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A:

After you have carefully read this joint proxy statement/prospectus and have decided how you wish to vote your shares, please vote your shares promptly so that your shares are represented and voted at the Sterling special meeting and/or Astoria special meeting, as applicable. If you are a stockholder of both Sterling and Astoria, you will need to vote your Sterling and Astoria shares separately and to submit a separate proxy card to each company. If you hold your shares in your name as a stockholder of record, you must complete, sign, date, and mail your proxy card in the enclosed postage-paid return envelope

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as soon as possible. Alternatively, you may vote through the Internet or by telephone. Information and applicable deadlines for voting through the Internet or by telephone are set forth in the enclosed proxy card instructions. If you hold your shares in “street name” through a bank or broker, you must direct your bank or broker how to vote in accordance with the instructions you have received from your bank or broker. “Street name” stockholders who wish to vote in person at the Sterling special meeting or Astoria special meeting will need to obtain a legal proxy from the institution that holds their shares.

Q:

What constitutes a quorum for the Sterling special meeting?

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A:

The presence at the Sterling special meeting, in person or by proxy, of holders of a majority of the outstanding shares of Sterling common stock entitled to vote at the special meeting (after subtracting any shares in excess of the “Sterling Limit” (as defined below) pursuant to the Sterling charter) will constitute a quorum for the transaction of business. Abstentions will be included in determining the number of shares present at the meeting for the purpose of determining the presence of a quorum.

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Q:

What constitutes a quorum for the Astoria special meeting?

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A:

The presence at the Astoria special meeting, in person or by proxy, of holders of a majority of the outstanding shares of Astoria common stock entitled to vote at the special meeting (after subtracting any shares in excess of the “Astoria Limit” (as defined below) pursuant to the Astoria Certificate of Incorporation, as amended (which we refer to as the “Astoria charter”)) will constitute a quorum for the transaction of business. Abstentions will be included in determining the number of shares present at the meeting for the purpose of determining the presence of a quorum.

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Q:

Is there a limit on voting shares of Sterling common stock or Astoria common stock?

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A:

As provided in the Sterling charter and the Astoria charter, holders of Sterling and Astoria common stock who beneficially own in excess of 10% of the outstanding shares of Sterling or Astoria common stock (which we refer to, respectively, as the “Sterling Limit” and the “Astoria Limit”) are not entitled to any vote with respect to shares held in excess of the Sterling Limit or the Astoria Limit, respectively. A person or entity is deemed to beneficially own shares owned by an affiliate of, as well as by, persons acting in concert with such person or entity. The Sterling charter and the Astoria charter authorize each company’s board of directors (i) to make all determinations necessary to implement and apply the Sterling Limit or the Astoria Limit, respectively, including determining whether persons or entities are acting in concert, and (ii) to demand that any person who is reasonably believed to beneficially own stock in excess of the Sterling Limit or the Astoria Limit supply information to the respective company to enable its board of directors to implement and apply the Sterling Limit or the Astoria Limit. As of the date of this joint proxy statement/prospectus, no person is known to Sterling or Astoria to own in excess of the Sterling Limit or the Astoria Limit.

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Q:

What is the vote required to approve each proposal?

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A:

Sterling merger proposal:

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Standard :   Approval of the Sterling merger proposal requires the affirmative vote of the holders of at least a majority of the outstanding shares of Sterling common stock entitled to vote on the proposal.

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Effect of abstentions and broker non-votes :   If you fail to vote, mark “ABSTAIN” on your proxy, or fail to instruct your bank or broker with respect to the Sterling merger proposal, it will have the same effect as a vote “AGAINST” the proposal.

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Sterling charter amendment proposal:

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Standard :   Approval of the Sterling charter amendment proposal requires the affirmative vote of the holders of at least a majority of the outstanding shares of Sterling common stock entitled to vote on the proposal.

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•

Effect of abstentions and broker non-votes :   If you fail to vote, mark “ABSTAIN” on your proxy, or fail to instruct your bank or broker with respect to the Sterling charter amendment proposal, it will have the same effect as a vote “AGAINST” the proposal.

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Sterling adjournment proposal:

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Standard :   Approval of the Sterling adjournment proposal requires the affirmative vote of the holders of at least a majority of the votes cast at the Sterling special meeting.

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Effect of abstentions and broker non-votes :   If you mark “ABSTAIN” on your proxy card, fail to submit a proxy card or vote in person at the Sterling special meeting, or fail to instruct your bank or broker how to vote with respect to the Sterling adjournment proposal, you will not be deemed to have cast a vote with respect to the proposal and it will have no effect on the proposal.

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Q:

What is the vote required to approve each proposal at the Astoria special meeting?

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A:

Astoria merger proposal:

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•

Standard :   Approval of the Astoria merger proposal requires the affirmative vote of the holders of at least a majority of the outstanding shares of Astoria common stock entitled to vote on the proposal.

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•

Effect of abstentions and broker non-votes :   If you fail to vote, mark “ABSTAIN” on your proxy, or fail to instruct your bank or broker with respect to the Astoria merger proposal, it will have the same effect as a vote “AGAINST” the proposal.

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Astoria compensation proposal:

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Standard :   Approval of the Astoria compensation proposal requires the affirmative vote of the holders of at least a majority of the votes cast at the Astoria special meeting.

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•

Effect of abstentions and broker non-votes :   If you mark “ABSTAIN” on your proxy card, fail to submit a proxy card or vote in person at the Astoria special meeting, or fail to instruct your bank or broker how to vote with respect to the Astoria compensation proposal, you will not be deemed to have cast a vote with respect to the proposal and it will have no effect on the proposal.

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Astoria adjournment proposal:

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Standard :   Approval of the Astoria adjournment proposal requires the affirmative vote of the holders of at least a majority of the votes cast at the Astoria special meeting.

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•

Effect of abstentions and broker non-votes :   If you mark “ABSTAIN” on your proxy card, fail to submit a proxy card or vote in person at the Astoria special meeting, or fail to instruct your bank or broker how to vote with respect to the Astoria adjournment proposal, you will not be deemed to have cast a vote with respect to the proposal and it will have no effect on the proposal.

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Q:

Will holders of Astoria depositary shares be entitled to vote at the Astoria special meeting?

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A:

No. Because the underlying Astoria preferred stock does not have voting rights with respect to any of the proposals that will be considered at the Astoria special meeting, holders of Astoria depositary shares will not be entitled to vote at the Astoria special meeting, and should not submit a proxy card with respect to the Astoria special meeting or otherwise attempt to vote with respect to their Astoria depositary shares.

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Q:

Why is my vote important?

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A:

If you do not vote, it will be more difficult for Sterling or Astoria to obtain the necessary quorum to hold their special meetings. In addition, your failure to submit a proxy or vote in person, or failure to instruct your bank or broker how to vote, or abstention will have the same effect as a vote “AGAINST” adoption of the merger agreement and, if you are a holder of Sterling common stock, a vote “AGAINST” the Sterling charter amendment proposal.

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Q:

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

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A:

No. Your bank or broker cannot vote your shares without instructions from you. If your shares are held in “street name” through a bank, broker, or other holder of record, you must provide the record holder of your shares with instructions on how to vote the shares. Please follow the voting instructions provided by the bank or broker. You may not vote shares held in street name by returning a proxy card directly to Sterling or Astoria, or by voting in person at the Sterling special meeting or the Astoria special meeting, unless you provide a “legal proxy,” which you must obtain from your broker, bank, or other nominee. Further, brokers, banks, or other nominees who hold shares of Sterling common stock or Astoria common stock on behalf of their customers may not give a proxy to Sterling or Astoria to vote those shares with respect to any of the proposals without specific instructions from their customers, as brokers, banks, and other nominees do not have discretionary voting power on these matters. Failure to instruct your bank or broker how to vote will have the same effect as a vote “AGAINST” adoption of the merger agreement and, if you are a holder of Sterling common stock, a vote “AGAINST” the Sterling charter amendment proposal.

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Q:

How do I vote if I own shares through the Sterling 401(k) Plan?

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A:

Participants in the Sterling Bank 401(k) and Profit Sharing Plan, referred to as the Sterling 401(k) Plan, will receive information about how to vote your shares confidentially. Such shares will be voted in accordance with the provisions of the Sterling 401(k) Plan. All shares held under the Sterling 401(k) Plan will be voted by the trustee, but each participant will be given the opportunity to direct the trustee on how to vote the shares of Sterling common stock allocated to his or her account. Unallocated shares and allocated shares for which no timely voting instructions are received will be voted by the trustee on each proposal in the same proportion as shares for which it has received timely voting instructions.

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Q:

How do I vote if I own shares through the Astoria 401(k) Plan?

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A:

Participants in the Astoria Bank 401(k) Plan, referred to as the Astoria 401(k) Plan, as of the record date of the Astoria special meeting, have the right to participate in directing the voting of Astoria common stock held in their plan accounts as of that date, but do not have the right to vote those shares personally at the Astoria special meeting. Such participants should refer to the voting instructions provided by the plan fiduciaries for information on how to direct the voting of such shares.

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Q:

Can I attend the Sterling and Astoria special meetings and vote my shares in person?

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A:

Yes. All holders of the common stock of Sterling and Astoria, including stockholders of record and stockholders who hold their shares through banks, brokers, nominees, or any other holder of record, are invited to attend their respective special meetings. Holders of record of Sterling and Astoria common stock can vote in person at the Sterling special meeting and Astoria special meeting, respectively. If you are not a stockholder of record (i.e., if your shares are held for you in “street name”), you must obtain a legal proxy, executed in your favor, from the record holder of your shares, such as a broker, bank, or other nominee, to be able to vote in person at the meetings. If you plan to attend your meeting, you must hold your shares in your own name or have a letter from the record holder of your shares confirming your ownership. In addition, you must bring a form of personal photo identification with you in order to be admitted to the meeting. Sterling and Astoria reserve the right to refuse admittance to anyone without proper proof of share ownership or without proper photo identification. Whether or not you intend to be present at the Sterling special meeting or the Astoria special meeting, you are urged to sign, date, and return your proxy card, or to vote via the Internet or by telephone, promptly. If you are then present and wish to vote your shares in person, your original proxy may be revoked by voting at the special meeting.

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Q:

Can I change my vote?

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A:

Sterling stockholders:    Yes. If you are a holder of record of Sterling common stock, you may change your vote or revoke any proxy at any time before it is voted by: (1) signing and returning a proxy card

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with a later date, (2) delivering a written revocation letter to Sterling’s corporate secretary, (3) attending the special meeting in person, notifying the corporate secretary and voting by ballot at the special meeting or (4) voting by telephone or the internet at a later time. Attendance at the special meeting will not automatically revoke your proxy. A revocation or later-dated proxy received by Sterling after the vote will not affect the vote. Sterling’s corporate secretary’s mailing address is: Corporate Secretary, Sterling Bancorp, 21 Scarsdale Road, Yonkers, New York 10707. If you hold your shares in “street name” through a bank, broker, or other holder of record, you should contact your record holder to change your vote.

Astoria common stockholders:    Yes. If you are a holder of record of Astoria common stock, you may change your vote at any time before your shares of Astoria common stock are voted at the Astoria special meeting by: (1) signing and returning a proxy card with a later date; (2) attending the special meeting in person, notifying the corporate secretary, and voting by ballot at the special meeting; (3) voting by telephone or the Internet at a later time; or (4) delivering a written revocation letter to Astoria’s Corporate Secretary at One Astoria Bank Plaza, Lake Success, New York 11042. If you hold your shares in “street name” through a bank, broker, or other holder of record, you should contact your record holder to change your vote.

Q:

Will Sterling be required to submit the proposal to adopt the merger agreement to its stockholders even if Sterling’s board of directors has withdrawn, modified, or qualified its recommendation?

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A:

Yes. Unless the merger agreement is terminated before the Sterling special meeting, Sterling is required to submit the proposal to adopt the merger agreement to its stockholders even if Sterling’s board of directors has withdrawn or modified its recommendation.

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Q:

Will Astoria be required to submit the proposal to adopt the merger agreement to its stockholders even if Astoria’s board of directors has withdrawn, modified, or qualified its recommendation?

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A:

Yes. Unless the merger agreement is terminated before the Astoria special meeting, Astoria is required to submit the proposal to adopt the merger agreement to its stockholders even if Astoria’s board of directors has withdrawn or modified its recommendation.

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Q:

What are the U.S. federal income tax consequences of the merger to Astoria common stockholders?

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A:

It is a condition to the completion of the merger that Sterling and Astoria receive written opinions from their respective counsel to the effect that the merger will be treated as a “reorganization” within the meaning of Section 368(a) of the Internal Revenue Code of 1986, as amended (which we refer to as the “Code”). Subject to the limitations and qualifications described in the section entitled “Material U.S. Federal Income Tax Consequences of the Merger,” if you are a U.S. holder of Astoria common stock, you will not recognize gain or loss pursuant to the merger, except in the case of cash received instead of fractional shares of Sterling common stock.

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For a definition of  “U.S. holder” and a more detailed discussion of the material United States federal income tax consequences of the merger, see the section entitled “Material U.S. Federal Income Tax Consequences of the Merger” beginning on page 107 of this joint proxy statement/prospectus.

The U.S. federal income tax consequences described above may not apply to all holders of Astoria common stock. We strongly urge you to consult your independent tax advisor for a full understanding of the application of U.S. federal income tax laws to your particular situation as well as any tax consequences arising under the U.S. federal estate or gift tax rules, or under the laws of any state, local, foreign or other taxing jurisdiction or under any applicable treaty.

Q:

Are Astoria common stockholders entitled to dissenters’ rights?

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A:

No, Astoria stockholders are not expected to be entitled to dissenters’ rights. For further information, see “The Merger—Dissenters’ Rights in the Merger.”

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Q:

If I am an Astoria common stockholder, should I send in my Astoria stock certificate(s) now?

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A:

No. Please do not send in your Astoria stock certificates with your proxy. After the merger, an exchange agent will send you instructions for exchanging Astoria stock certificates for the merger consideration. See “The Merger Agreement—Conversion of Shares; Exchange of Certificates.”

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Q:

What should I do if I hold my shares of Astoria common stock in book-entry form?

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A:

You are not required to take any special additional actions if your shares of Astoria common stock are held in book-entry form. After the completion of the merger, shares of Astoria common stock held in book-entry form automatically will be exchanged for book-entry shares of Sterling common stock.

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Q:

What should I do if I receive more than one set of voting materials?

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A:

Sterling and Astoria common stockholders may receive more than one set of voting materials, including multiple copies of this joint proxy statement/prospectus and multiple proxy cards or voting instruction cards. For example, if you hold shares of Sterling and/or Astoria common stock in more than one brokerage account, you will receive a separate voting instruction card for each brokerage account in which you hold such shares. If you are a holder of record of Sterling common stock or Astoria common stock and your shares are registered in more than one name, you will receive more than one proxy card. In addition, if you are a holder of both Sterling common stock and Astoria common stock, you will receive one or more separate proxy cards or voting instruction cards for each company. Please complete, sign, date and return each proxy card and voting instruction card that you receive or otherwise follow the voting instructions set forth in this joint proxy statement/prospectus to ensure that you vote every share of Sterling common stock and/or Astoria common stock that you own.

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Q:

When do you expect to complete the merger?

​

A:

Sterling and Astoria expect to complete the merger in the fourth quarter of 2017. However, neither Sterling nor Astoria can assure you of when or if the merger will be completed. Sterling and Astoria must obtain the approval of Sterling stockholders and Astoria common stockholders to adopt the merger agreement at their respective special meetings, and also must obtain necessary regulatory approvals in addition to satisfying certain other closing conditions.

​

Q:

What happens if the merger is not completed?

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A:

If the merger is not completed, Astoria common stockholders will not receive any consideration for their shares of Astoria common stock in connection with the merger. Instead, Astoria will remain an independent, public company and Astoria common stock and depositary shares will continue to be listed and traded on the NYSE. In addition, if the merger agreement is terminated in certain circumstances, a termination fee may be required to be paid by either Sterling or Astoria. See “The Merger Agreement—Termination Fee” for a complete discussion of the circumstances under which termination fees will be required to be paid.

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Q:

Whom should I call with questions?

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A:

Sterling stockholders:    If you have any questions concerning the merger or this joint proxy statement/​prospectus, would like additional copies of this joint proxy statement/prospectus, or need help voting your shares of Sterling common stock, please contact Sterling’s proxy solicitor, Okapi Partners LLC, at 1212 Avenue of the Americas, 24th Floor, New York, New York 10036, or toll-free at (877) 274-8654.

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Astoria common stockholders:    If you have any questions concerning the merger or this joint proxy statement/prospectus, would like additional copies of this joint proxy statement/prospectus, or need help voting your shares of Astoria common stock, please contact Astoria’s proxy solicitor, Innisfree M&A Incorporated, at 501 Madison Avenue, 20th Floor, New York, New York 10022, or toll-free at (877) 717-3930.

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10

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12

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operations as a percent of average interest-earning assets for the period. Net interest margin – tax equivalent basis is net interest income adjusted for a portion of Sterling’s net interest income will be exempt from taxation (e.g., was received as a result of holdings of state or municipal obligations), an amount equal to the tax benefit derived from that component is added back to the net interest income total. This adjustment is considered helpful in comparing one financial institution’s net interest income (pre-tax) to that of another institution, as each will have a different proportion of tax-exempt items in their portfolios.

(3)

Prior to the Provident Merger, Sterling was a unitary savings and loan holding company and as a result was not required to maintain or report regulatory capital ratios. Sterling became a bank holding company in connection with the Provident Merger and has maintained and reported regulatory capital ratios since December 31, 2013.

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(4)

Total loans exclude loans held for sale.

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(1)

Returns on average assets are calculated using net income.

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(2)

Returns on average common stockholders’ equity and average tangible common stockholders’ equity are calculated using net income available to common stockholders.

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(3)

Tangible common stockholders’ equity represents common stockholders’ equity less goodwill.

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(4)

Net interest rate spread represents the difference between the average yield on average interest-earning assets and the average cost of average interest-bearing liabilities.

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(5)

Net interest margin represents net interest income divided by average interest-earning assets.

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(6)

Non-performing loans, substantially all of which are non-accrual loans, included loans modified in a TDR totaling $58.6 million at December 31, 2016, $61.0 million at December 31, 2015, $68.4 million at December 31, 2014, $109.8 million at December 31, 2013 and $32.8 million at December 31, 2012. Non-performing loans exclude loans held-for-sale and loans which have been modified in a TDR that have been returned to accrual status.

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(7)

Non-performing assets consist of all non-performing loans and real estate owned.

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COMPARATIVE HISTORICAL AND UNAUDITED PRO FORMA PER SHARE DATA

Presented below are Sterling’s historical per share data for the year ended December 31, 2016, as derived from audited financial statements of Sterling, and Astoria’s historical per share data for the year ended December 31, 2016, as derived from audited financial statements of Astoria. The pro forma combined per share data for the year ended December 31, 2016 and the per equivalent Astoria share information provided in the table below is unaudited. The unaudited pro forma data and equivalent per share information give effect to the merger as if the transaction had been effective on the dates presented, in the case of the book value data, and as if the transactions had become effective on January 1, 2016, in the case of the earnings per share and dividends declared data. This information should be read together with the historical consolidated financial statements and related notes of Sterling and Astoria filed by each with the SEC, and incorporated by reference in this document, and with the unaudited pro forma condensed combined financial statements included under “Unaudited Pro Forma Condensed Combined Financial Statements.”

The unaudited pro forma financial information is presented for illustrative purposes only and does not necessarily indicate the financial results of the combined companies had the companies actually been combined at the beginning of the period presented. The unaudited pro forma financial information also does not consider any potential impacts of current market conditions on revenues, potential revenue enhancements, anticipated cost savings and expense efficiencies, or asset dispositions, among other factors.

(1)

Pro forma combined earnings per share data excludes the impact of anticipated cost savings (refer to Note 4 below in “Notes to Unaudited Pro Forma Condensed Combined Financial Information”) and potential revenue enhancements that may be realized through the merger.

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(2)

Pro forma combined cash dividends declared are based upon Sterling’s historical amounts.

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(3)

Pro forma per equivalent Astoria share information is calculated based on pro forma combined multiplied by the 0.875 exchange ratio.

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Reform and Consumer Protection Act, which we refer to as the “Dodd-Frank Act,” and other changes pertaining to banking, securities, taxation, rent regulation and housing, financial accounting and reporting, environmental protection, and insurance, and the ability to comply with such changes in a timely manner;

•

changes in the monetary and fiscal policies of the U.S. Government, including policies of the U.S. Department of the Treasury and the Federal Reserve Board;

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•

changes in interest rates, which may affect Sterling’s or Astoria’s net income, prepayment penalty income, mortgage banking income, and other future cash flows, or the market value of Sterling’s or Astoria’s assets, including its investment securities;

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•

changes in accounting principles, policies, practices, or guidelines;

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•

changes in Sterling’s credit ratings or in Sterling’s ability to access the capital markets;

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•

natural disasters, war, or terrorist activities; and

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•

other economic, competitive, governmental, regulatory, technological, and geopolitical factors affecting Sterling’s or Astoria’s operations, pricing, and services.

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Additionally, the timing and occurrence or non-occurrence of events may be subject to circumstances beyond Sterling’s or Astoria’s control.

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, Sterling and Astoria claim the protection of the safe harbor for forward-looking statements contained in the Private Securities Litigation Reform Act of 1995. You are cautioned not to place undue reliance on these statements, which speak only as of the date of this joint proxy statement/prospectus or the date of the applicable document incorporated by reference in this joint proxy statement/prospectus. Except to the extent required by applicable law, Sterling and Astoria do not undertake to update forward-looking statements to reflect facts, circumstances, assumptions, or events that occur after the date the forward-looking statements are made. All written and oral forward-looking statements concerning the merger or other matters addressed in this joint proxy statement/prospectus and attributable to Sterling, Astoria, or any person acting on their behalf are expressly qualified in their entirety by the cautionary statements contained or referred to in this joint proxy statement/prospectus.

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independent results of operations of each of Sterling and Astoria. For a discussion of the businesses of Sterling and Astoria and of some important factors to consider in connection with those businesses, see the documents incorporated by reference in this joint proxy statement/prospectus and referred to under “Where You Can Find More Information.”

Regulatory approvals may not be received, may take longer than expected, or may impose conditions that are not presently anticipated or that could have an adverse effect on the combined company following the merger.

Before the merger and the bank merger may be completed, Sterling and Astoria must obtain approvals from the Federal Reserve Board and the OCC. Other approvals, waivers or consents from regulators may also be required. In determining whether to grant these approvals the regulators consider a variety of factors, including the regulatory standing of each party and the factors described under “The Merger—Regulatory Approvals Required for the Merger.” An adverse development in either party’s regulatory standing or these factors could result in an inability to obtain approval or delay their receipt. These regulators may impose conditions on the completion of the merger or the bank merger or require changes to the terms of the merger or the bank merger. Such conditions or changes could have the effect of delaying or preventing completion of the merger or the bank merger or imposing additional costs on or limiting the revenues of the combined company following the merger and the bank merger, any of which might have an adverse effect on the combined company following the merger. See “The Merger—Regulatory Approvals Required for the Merger.”

In a recent approval order, the Federal Reserve Board has stated that if material weaknesses are identified by examiners before a banking organization applies to engage in expansionary activity, the Federal Reserve Board will not in the future allow the application to remain pending while the banking organization addresses its weaknesses. The Federal Reserve Board explained that, in the future, if issues arise during the processing of an application, it will require the applicant banking organization to withdraw its application pending resolution of any supervisory concerns. Accordingly, if there is an adverse development in either party’s regulatory standing, Sterling may be required to withdraw some or all of the applications for approval of the proposed mergers and, if possible, resubmit it after the applicable supervisory concerns have been resolved. See “The Merger—Regulatory Approvals Required for the Merger.”

The success of the merger and integration of Sterling and Astoria will depend on a number of uncertain factors.

The success of the merger will depend on a number of factors, including, without limitation:

•

Sterling’s ability to integrate the branches acquired from Astoria Bank in the merger (which we refer to as the “acquired branches”) into Sterling National Bank’s current operations;

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•

Sterling’s ability to limit the outflow of deposits held by its new customers in the acquired branches and to successfully retain and manage interest-earning assets (i.e., loans) acquired in the merger;

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•

Sterling’s ability to control the incremental non-interest expense from the acquired branches in a manner that enables it to maintain a favorable overall efficiency ratio;

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•

Sterling’s ability to retain and attract the appropriate personnel to staff the acquired branches; and

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•

Sterling’s ability to earn acceptable levels of interest and non-interest income, including fee income, from the acquired branches.

​

Integrating the acquired branches will be an operation of substantial size and expense, and may be affected by general market and economic conditions or government actions affecting the financial industry generally. Integration efforts will also likely divert Sterling’s management’s attention and resources. No assurance can be given that Sterling will be able to integrate the acquired branches successfully, and the integration process could result in the loss of key employees, the disruption of ongoing business, or inconsistencies in standards, controls, procedures and policies that adversely affect Sterling’s ability to maintain relationships with clients, customers, depositors and employees or to achieve the anticipated benefits of the merger. Sterling may also encounter unexpected difficulties or costs during the integration that could adversely

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affect its earnings and financial condition, perhaps materially. Additionally, no assurance can be given that the operation of the acquired branches will not adversely affect Sterling’s existing profitability, that Sterling will be able to achieve results in the future similar to those achieved by its existing banking business, or that Sterling will be able to manage any growth resulting from the merger effectively.

Combining Sterling and Astoria may be more difficult, costly or time consuming than expected and the anticipated benefits and cost savings of the merger may not be realized.

Sterling and Astoria have operated and, until the completion of the merger, will continue to operate, independently. The success of the merger, including anticipated benefits and cost savings, will depend, in part, on Sterling’s ability to successfully combine and integrate the businesses of Sterling and Astoria in a manner that permits growth opportunities and does not materially disrupt the existing customer relations nor result in decreased revenues due to loss of customers. It is possible that the integration process could result in the loss of key employees, the disruption of either company’s ongoing businesses or inconsistencies in standards, controls, procedures and policies that adversely affect the combined company’s ability to maintain relationships with clients, customers, depositors and employees or to achieve the anticipated benefits and cost savings of the merger. The loss of key employees could adversely affect Sterling’s ability to successfully conduct its business, which could have an adverse effect on Sterling’s financial results and the value of its common stock. If Sterling experiences difficulties with the integration process, the anticipated benefits of the merger may not be realized fully or at all, or may take longer to realize than expected. As with any merger of financial institutions, there also may be business disruptions that cause Sterling and/or Astoria to lose customers or cause customers to remove their accounts from Sterling and/or Astoria and move their business to competing financial institutions. Integration efforts between the two companies will also divert management attention and resources. These integration matters could have an adverse effect on each of Astoria and Sterling during this transition period and for an undetermined period after completion of the merger on the combined company. In addition, the actual cost savings of the merger could be less than anticipated.

The combined company may be unable to retain Sterling and/or Astoria personnel successfully after the merger is completed.

The success of the merger will depend in part on the combined company’s ability to retain the talents and dedication of key employees currently employed by Sterling and Astoria. It is possible that these employees may decide not to remain with Sterling or Astoria, as applicable, while the merger is pending or with the combined company after the merger is consummated. If key employees terminate their employment, or if an insufficient number of employees is retained to maintain effective operations, the combined company’s business activities may be adversely affected and management’s attention may be diverted from successfully integrating Astoria to hiring suitable replacements, all of which may cause the combined company’s business to suffer. In addition, Sterling and Astoria may not be able to locate suitable replacements for any key employees who leave either company, or to offer employment to potential replacements on reasonable terms.

The unaudited pro forma condensed combined financial statements included in this document are preliminary and the actual financial condition and results of operations of Sterling after the merger may differ materially.

The unaudited pro forma condensed combined financial statements in this document are presented for illustrative purposes only and are not necessarily indicative of what Sterling’s actual financial condition or results of operations would have been had the merger been completed on the dates indicated. The unaudited pro forma condensed combined financial statements reflect adjustments, which are based upon preliminary estimates, to record the Astoria identifiable assets acquired and liabilities assumed at fair value and the resulting goodwill recognized. The purchase price allocation reflected in this document is preliminary, and final allocation of the purchase price will be based upon the actual purchase price and the fair value of the assets and liabilities of Astoria as of the date of the completion of the merger. Accordingly, the final acquisition accounting adjustments may differ materially from the pro forma adjustments reflected in this document. For more information, please see “Unaudited Pro Forma Condensed Combined Financial Statements” beginning on page 110 .

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In connection with the merger, Sterling will assume Astoria’s outstanding debt obligations and preferred stock, and Sterling’s level of indebtedness following the completion of the merger could adversely affect Sterling’s ability to raise additional capital and to meet its obligations under its existing indebtedness.

In connection with the merger, Sterling will assume approximately $3.9 billion of Astoria’s outstanding indebtedness and Astoria’s obligations related to its outstanding preferred stock. Sterling’s existing debt, together with any future incurrence of additional indebtedness, and assumption of Astoria’s outstanding preferred stock, could have important consequences for Sterling’s creditors and Sterling’s stockholders. For example, it could:

•

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

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•

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

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•

restrict Sterling from paying dividends to its stockholders;

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•

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

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•

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 Sterling’s ability to use cash flows to fund its operations, capital expenditures, and future business opportunities.

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Following completion of the merger, holders of Sterling common stock will be subject to the prior dividend and liquidation rights of the holders of the Sterling preferred stock that Sterling will issue upon completion of the merger. The holders of shares of Astoria preferred stock, which Sterling will assume from Astoria, as well as the holders of any shares of Sterling preferred stock that Sterling may issue in the future, would receive, upon Sterling’s voluntary or involuntary liquidation, dissolution, or winding up, before any payment is made to holders of Sterling common stock, their liquidation preferences as well as any accrued and unpaid distributions. These payments would reduce the remaining amount of Sterling’s assets, if any, available for distribution to holders of its common stock.

General market conditions and unpredictable factors, including conditions and factors different from those affecting Astoria preferred stock and depositary shares currently, could adversely affect market prices for Sterling preferred stock and Sterling depositary shares once the Sterling preferred stock is issued.

There can be no assurance about the market prices for the Sterling preferred stock that will be issued upon completion of the merger or the Sterling depositary shares representing shares of Sterling preferred stock. Several factors, many of which are beyond the control of Sterling, could influence the market prices of the Sterling preferred stock and Sterling depositary shares, including:

•

whether Sterling declares or fails to declare dividends on the Sterling preferred stock from time to time;

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•

real or anticipated changes in the credit ratings assigned to the Sterling depositary shares, Sterling preferred stock, or other Sterling securities;

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•

Sterling creditworthiness;

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•

interest rates;

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•

developments in the securities, credit, and housing markets, and developments with respect to financial institutions generally;

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•

the market for similar securities; and

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•

economic, corporate, securities market, geopolitical, regulatory or judicial events that affect Sterling, the banking industry, or the financial markets generally.

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Shares of Sterling preferred stock will be equity interests and will not constitute indebtedness. As such, Sterling preferred stock and Sterling depositary shares will rank junior to all indebtedness of, and other non-equity claims on, Sterling with respect to assets available to satisfy claims. The market prices for the Sterling preferred stock and Sterling depositary shares may be affected by factors different from those currently affecting the Astoria preferred stock and Astoria depositary shares.

Certain of Astoria’s directors and executive officers have interests in the merger that may differ from the interests of Astoria’s stockholders.

Astoria’s common stockholders should be aware that some of Astoria’s directors and executive officers have interests in the merger and have arrangements that are different from, or in addition to, those of Astoria’s common stockholders generally. Astoria’s board of directors was aware of these interests and considered these interests, among other matters, when making its decision to approve the merger agreement, and in recommending that Astoria’s common stockholders vote in favor of adopting the merger agreement.

For a more complete description of these interests, please see “The Merger—Interests of Astoria’s Directors and Executive Officers in the Merger.”

Termination of the merger agreement could negatively impact Astoria or Sterling.

If the merger agreement is terminated, there may be various consequences. For example, Astoria’s or Sterling’s businesses may have been impacted adversely by the failure to pursue other beneficial opportunities due to the focus of management on the merger, without realizing any of the anticipated benefits of completing the merger. Additionally, if the merger agreement is terminated, the market price of Astoria’s or Sterling’s common stock could decline to the extent that the current market prices reflect a market assumption that the merger will be completed. If the merger agreement is terminated under certain circumstances, Astoria or Sterling may be required to pay to the other party a termination fee of  $75.7 million.

Astoria and Sterling will be subject to business uncertainties and contractual restrictions while the merger is pending.

Uncertainty about the effect of the merger on employees and customers may have an adverse effect on Astoria or Sterling. These uncertainties may impair Astoria’s or Sterling’s ability to attract, retain, and motivate key personnel until the merger is completed, and could cause customers and others that deal with Astoria or Sterling to seek to change existing business relationships with Astoria or Sterling. Retention of certain employees by Astoria or Sterling may be challenging while the merger is pending, as certain employees may experience uncertainty about their future roles with the combined company. If key employees depart because of issues relating to the uncertainty and difficulty of integration, or a desire not to remain with Astoria or Sterling, Astoria’s business or Sterling’s business could be harmed. In addition, subject to certain exceptions, Astoria has agreed to operate its business in the ordinary course prior to closing. See “The Merger Agreement—Covenants and Agreements” for a description of the restrictive covenants applicable to Astoria and Sterling.

If the merger is not completed, Sterling and Astoria will have incurred substantial expenses without realizing the expected benefits of the merger.

Each of Sterling and Astoria has incurred and will incur substantial expenses in connection with the negotiation and completion of the transactions contemplated by the merger agreement, as well as the costs and expenses of filing, printing, and mailing this joint proxy statement/prospectus, and all filing and other fees paid to the SEC in connection with the merger. If the merger is not completed, Sterling and Astoria would have to recognize these expenses without realizing the expected benefits of the merger.

The merger agreement limits Astoria’s ability to pursue acquisition proposals and requires Sterling or Astoria to pay a termination fee of  $75.7 million under limited circumstances, including circumstances relating to acquisition proposals. Additionally, certain provisions of the Sterling and Astoria charter and bylaws may deter potential acquirers.

The merger agreement prohibits Astoria from initiating, soliciting, knowingly encouraging, or knowingly facilitating certain third-party acquisition proposals. See “The Merger Agreement—Agreement Not to

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Solicit Other Offers.” The merger agreement also provides that either Sterling or Astoria will be required to pay a termination fee in the amount of  $75.7 million in the event that the merger agreement is terminated under certain circumstances, including a change of recommendation by such party’s board of directors. See “The Merger Agreement—Termination Fee.” These provisions might discourage a potential competing acquirer that might have an interest in acquiring all or a significant part of Astoria from considering or proposing such an acquisition. Under the Astoria and Sterling charters, certain business combinations involving affiliates or interested stockholders require the approval of a supermajority of stockholders unless they are approved by two-thirds, in the case of Sterling, or a majority, in the case of Astoria, of the disinterested directors on their respective board or certain other requirements are met, and the Astoria and Sterling charters generally prohibit holders of shares that are beneficially owned by a person who beneficially owns more than 10% of the outstanding shares of Sterling common stock or Astoria common stock, as applicable, from voting shares in excess of such 10% limit. See “Comparison of Stockholders’ Rights—Anti-Takeover Provisions and Other Stockholder Protections.” These provisions and other provisions of the Astoria or Sterling charters or bylaws, including provisions regarding Astoria’s classified board of directors, described below, or of the DGCL could make it more difficult for a third-party to acquire control of Astoria or Sterling and may discourage a potential competing acquirer.

The shares of Sterling common stock to be received by Astoria common stockholders as a result of the merger will have different rights from the shares of Astoria common stock.

Upon completion of the merger, Astoria common stockholders will become Sterling stockholders and their rights as stockholders will be governed by the DGCL and the Sterling charter and bylaws. The rights associated with Astoria common stock are different from the rights associated with Sterling common stock. Please see “Comparison of Stockholders’ Rights” beginning on page 132 for a discussion of the different rights associated with Sterling common stock.

Holders of Astoria and Sterling common stock will have a reduced ownership and voting interest in the combined company after the merger and will exercise less influence over management.

Holders of Astoria and Sterling common stock currently have the right to vote in the election of the board of directors and on other matters affecting Astoria and Sterling, respectively. Upon completion of the merger, each Astoria common stockholder who receives shares of Sterling common stock will become a stockholder of Sterling, with a percentage ownership of Sterling that is smaller than the stockholder’s percentage ownership of Astoria. Based on the number of shares outstanding on March 30, 2017 and the shares expected to be issued in the merger, the former stockholders of Astoria as a group will receive shares in the merger constituting approximately 40% of the outstanding shares of Sterling common stock immediately after the merger. As a result, current stockholders of Sterling as a group will own approximately 60% of the outstanding shares of Sterling common stock immediately after the merger. Because of this, Astoria common stockholders may have less influence on the management and policies of Sterling than they now have on the management and policies of Astoria, and current Sterling stockholders may have less influence than they now have on the management and policies of Sterling.

Astoria common stockholders will not have appraisal rights in the merger.

Dissenters’ rights are statutory rights that, if applicable under law, enable stockholders to dissent from an extraordinary transaction, such as a merger, and to demand that the corporation pay the fair value for their shares as determined by a court in a judicial proceeding instead of receiving the consideration offered to stockholders in connection with the extraordinary transaction. Under the DGCL, a stockholder may not dissent from a merger as to shares that are listed on a national securities exchange at the record date fixed to determine the stockholders entitled to receive notice of the meeting of stockholders to vote upon the agreement of merger or consolidation.

Because Astoria common stock is listed on the New York Stock Exchange, a national securities exchange, and is expected to continue to be so listed on the record date, and because the merger otherwise satisfies the foregoing requirements of the DGCL, holders of Astoria common stock will not be entitled to dissenters’ or appraisal rights in the merger with respect to their shares of Astoria common stock.

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Pending Litigation Against Sterling and Astoria Could Result in an Injunction Preventing the Completion of the Merger.

Following the announcement of the execution of the merger agreement, a lawsuit challenging the proposed merger was filed in the Supreme Court of the State of New York, County of Nassau, captioned MSS 1209 Trust v. Astoria Financial Corporation, et al, Index No. 602161/2017 (filed March 13, 2017). The complaint is a putative class action filed on behalf of the stockholders of Astoria and names as defendants Astoria, its directors and Sterling, or collectively, the defendants. The action seeks, among other things, an order enjoining completion of the proposed merger and an award of costs and attorneys’ fees and compensatory damages. One of the conditions to the closing of the merger is that no order, injunction, or decree issued by any court or agency of competent jurisdiction or other legal restraint or prohibition preventing the consummation of the merger shall be in effect. As such, if plaintiffs are successful in obtaining an injunction prohibiting the completion of the merger on the agreed-upon terms, then such injunction may prevent the merger from being completed, or from being completed within the expected timeframe. The defense or settlement of any lawsuit or claim that remains unresolved at the time the merger is completed may adversely affect Sterling’s business, financial condition, results of operations, and cash flows. For more information, see “The Merger—Litigation Related to the Merger.”

Risks Relating to Sterling’s Business

You should read and consider risk factors specific to Sterling’s business that will also affect the combined company after the merger. These risks are described in the sections entitled “Risk Factors” in Sterling’s Annual Report on Form 10-K for the fiscal year ended December 31, 2016 and in other documents incorporated by reference into this proxy statement/prospectus. Please see the section entitled “Where You Can Find More Information” beginning on page 143 of this joint proxy statement/prospectus for the location of information incorporated by reference into this joint proxy statement/prospectus.

Risks Relating to Astoria’s Business

You should read and consider risk factors specific to Astoria’s business that will also affect the combined company after the merger. These risks are described in the sections entitled “Risk Factors” in Astoria’s Annual Report on Form 10-K for the fiscal year ended December 31, 2016 and in other documents incorporated by reference into this proxy statement/prospectus. Please see the section entitled “Where You Can Find More Information” beginning on page 143 of this joint proxy statement/prospectus for the location of information incorporated by reference into this joint proxy statement/prospectus.

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THE STERLING SPECIAL MEETING

This section contains information for Sterling stockholders about the special meeting that Sterling has called to allow its stockholders to consider and vote on the merger agreement and other matters. Sterling is mailing this joint proxy statement/prospectus to you, as a Sterling stockholder, on or about [            ]. This joint proxy statement/prospectus is accompanied by a notice of the special meeting of Sterling stockholders and a form of proxy card that Sterling’s board of directors is soliciting for use at the special meeting and at any adjournments or postponements of the special meeting.

Date, Time, and Place of Meeting

The special meeting of Sterling stockholders will be held at Sterling’s business address at 21 Scarsdale Road, Yonkers, New York 10707 at [            ], Eastern time, on [            ]. On or about [            ], Sterling commenced mailing this document and the enclosed form of proxy card to its stockholders entitled to vote at the Sterling special meeting.

Matters to Be Considered

At the Sterling special meeting, Sterling stockholders will be asked to consider and vote upon the following matters:

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the Sterling merger proposal;

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the Sterling charter amendment proposal; and

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the Sterling adjournment proposal.

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Recommendation of Sterling’s Board of Directors

The Sterling board of directors recommends that you vote “ FOR ” the Sterling merger proposal, “ FOR ” the Sterling charter amendment proposal, and “ FOR ” the Sterling adjournment proposal.

Sterling Record Date and Quorum

The Sterling board of directors has fixed the close of business on [            ], as the record date for determining the holders of Sterling common stock entitled to receive notice of and to vote at the Sterling special meeting.

As of the Sterling record date, there were [            ] shares of Sterling common stock outstanding and entitled to vote at the Sterling special meeting held by [            ] holders of record. Subject to the Sterling Limit, each share of Sterling common stock entitles the holder of record as of the Sterling record date to one vote at the Sterling special meeting on each proposal to be considered at the Sterling special meeting.

The representation (in person or by proxy) of holders of at least a majority of the votes entitled to be cast on the matters to be voted on at the Sterling special meeting constitutes a quorum for transacting business at the Sterling special meeting. All shares of Sterling common stock, whether present in person or represented by proxy, including abstentions, will be treated as present for purposes of determining the presence or absence of a quorum for all matters voted on at the Sterling special meeting.

Vote Required; Treatment of Abstentions and Failure to Vote

Sterling merger proposal:

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Standard :   Approval of the Sterling merger proposal requires the affirmative vote of the holders of at least a majority of the outstanding shares of Sterling common stock entitled to vote on the proposal.

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Effect of abstentions and broker non-votes :   If you fail to vote, mark “ABSTAIN” on your proxy, or fail to instruct your bank or broker with respect to the Sterling merger proposal, it will have the same effect as a vote “AGAINST” the proposal.

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Sterling charter amendment proposal:

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Standard :   Approval of the Sterling charter amendment proposal requires the affirmative vote of the holders of at least a majority of the outstanding shares of Sterling common stock entitled to vote on the proposal.

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Effect of abstentions and broker non-votes :   If you fail to vote, mark “ABSTAIN” on your proxy, or fail to instruct your bank or broker with respect to the Sterling charter amendment proposal, it will have the same effect as a vote “AGAINST” the proposal.

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Sterling adjournment proposal:

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Standard :   Approval of the Sterling adjournment proposal requires the affirmative vote of the holders of at least a majority of the votes cast at the Sterling special meeting.

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Effect of abstentions and broker non-votes :   If you mark “ABSTAIN” on your proxy card, fail to submit a proxy card or vote in person at the Sterling special meeting, or fail to instruct your bank or broker how to vote with respect to the Sterling adjournment proposal, you will not be deemed to have cast a vote with respect to the proposal and it will have no effect on the proposal.

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Shares Held by Officers and Directors

As of the Sterling record date, the directors and executive officers of Sterling and their affiliates owned, and were entitled to vote, [            ] shares of Sterling common stock, representing approximately [            ]% of the shares of Sterling common stock outstanding on that date. Sterling currently expects that Sterling’s directors and executive officers will vote their shares in favor of the Sterling merger proposal, the Sterling charter amendment proposal, and the Sterling adjournment proposal, although none of them has entered into any agreements obligating them to do so. As of the Sterling record date, Astoria, the directors and executive officers of Astoria and their affiliates owned, and were entitled to vote, [            ] shares of Sterling common stock, representing approximately [            ]% of the shares of Sterling common stock outstanding on that date.

Voting of Proxies; Incomplete Proxies

A Sterling stockholder may vote by proxy or in person at the Sterling special meeting. If you hold your shares of Sterling common stock in your name as a stockholder of record, to submit a proxy, you, as a Sterling stockholder, may use one of the following methods:

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By telephone: by calling the toll-free number indicated on your proxy card and following the recorded instructions.

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Through the Internet: by visiting the website indicated on your proxy card and following the instructions.

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Complete and return the proxy card in the enclosed envelope. The envelope requires no additional postage if mailed in the United States.

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Sterling requests that Sterling stockholders vote by telephone, over the Internet, or by completing and signing the accompanying proxy card and returning it to Sterling as soon as possible in the enclosed postage-paid envelope. When the accompanying proxy card is returned properly executed, the shares of Sterling stock represented by it will be voted at the Sterling special meeting in accordance with the instructions contained on the proxy card. If any proxy card is returned without indication as to how to vote, the shares of Sterling common stock represented by the proxy card will be voted as recommended by the Sterling board of directors.

Every Sterling stockholder’s vote is important. Accordingly, each Sterling stockholder should sign, date, and return the enclosed proxy card, or vote via the Internet or by telephone, whether or not the Sterling stockholder plans to attend the Sterling special meeting in person. Sending in your proxy card or voting by telephone or on the Internet will not prevent you from voting your shares personally at the meeting, since you may revoke your proxy at any time before it is voted.

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Shares Held in Street Name; Broker Non-Votes

If you are a Sterling stockholder and your shares are held in “street name” through a bank, broker, or other holder of record, you must provide the record holder of your shares with instructions on how to vote the shares. Please follow the voting instructions provided by the bank or broker. You may not vote shares held in street name by returning a proxy card directly to Sterling or by voting in person at the Sterling special meeting unless you provide a “legal proxy,” which you must obtain from your broker, bank, or other nominee. Further, brokers, banks, or other nominees who hold shares of Sterling common stock on behalf of their customers may not give a proxy to Sterling to vote those shares with respect to any of the proposals without specific instructions from their customers, as brokers, banks, and other nominees do not have discretionary voting power on the proposals that will be voted upon at the Sterling special meeting.

Revocability of Proxies and Changes to a Sterling Stockholder’s Vote

You have the power to change your vote at any time before your shares of Sterling common stock are voted at the Sterling special meeting by:

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signing and returning a proxy card with a later date;

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voting by telephone or the Internet at a later time;

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delivering a written revocation letter to Sterling’s corporate secretary; or

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