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As filed with the Securities and Exchange Commission on October 15, 2019

Registration No. 333-233970


UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549



PRE-EFFECTIVE
AMENDMENT No. 1
TO
FORM S-4
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933



C&F FINANCIAL CORPORATION
(Exact name of registrant as specified in its charter)



Virginia
(State or other jurisdiction of
Incorporation or organization)
  6022
(Primary Standard Industrial
Classification Code Number)
  54-1680165
(I.R.S. Employer
Identification Number)

802 Main Street
West Point, Virginia 23181
Telephone: (804) 843-2360
(Address, including zip code, and telephone number, including
area code, of registrant's principal executive offices)



Thomas F. Cherry
President and Chief Executive Officer
802 Main Street
West Point, Virginia 23181
Telephone: (804) 843-2360
(Name, address, including zip code, and telephone number, including area code, of agent for service)



Copies to:

Scott H. Richter, Esq.
Benjamin A. McCall, Esq.
Williams Mullen
200 South 10th Street, Suite 1600
Richmond, Virginia 23219
(804) 420-6000

 

Jacob A. Lutz, III, Esq.
Seth A. Winter, Esq.
Troutman Sanders LLP
1001 Haxall Point
Richmond, Virginia 23219
(804) 697-1200



         Approximate date of commencement of 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 herein.

         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:    o

         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.    o

         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.    o

         Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or 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.

Large accelerated filer o   Accelerated filer ý   Non-accelerated filer o   Smaller reporting company ý

Emerging growth company o

         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.    o

         If applicable, place an ý 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)    o

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

         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 or until the registration statement shall become effective on such date as the Securities and Exchange Commission acting pursuant to Section 8(a) of the Securities Act, may determine.

   


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The 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 proxy statement/prospectus does not constitute an offer to sell these securities, nor a 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 is not permitted.

PRELIMINARY—SUBJECT TO COMPLETION—DATED OCTOBER 15, 2019

LOGO   LOGO

Dear Fellow Shareholders of Peoples Bankshares, Incorporated:

         You are cordially invited to attend a special meeting of shareholders of Peoples Bankshares, Incorporated ("Peoples") to be held at 11:00 a.m. local time, on December 11, 2019 at The Dining Room at Stratford Hall, located at 483 Great House Road, Stratford, Virginia 22558. At the special meeting, you will be asked to consider and vote upon a proposal to approve an agreement and plan of reorganization and a related plan of merger pursuant to which Peoples will be merged with and into C&F Financial Corporation ("C&F").

         If the merger agreement is approved and the merger is subsequently completed, each outstanding share of Peoples common stock will be converted into the right to receive:

    $27.00 in cash; and

    0.5366 shares of C&F common stock.

         The merger consideration will not be adjusted to reflect any stock price changes prior to completion of the merger. As a result, the market value of the stock consideration that you will receive will fluctuate with the market price of C&F common stock and will not be known at the time you vote on the merger. Based on the closing sale price of C&F common stock on the Nasdaq Global Select Market on August 13, 2019 ($51.79), the last trading day before public announcement of the merger, the merger consideration represented approximately $54.79 in value for each share of Peoples common stock, or $21.45 million on an aggregate basis. Based on the closing sale price of C&F common stock on the Nasdaq Global Select Market on October 14, 2019 ($52.20), the last trading day before the date of this proxy statement/prospectus, the merger consideration represented approximately $55.01 in value for each share of Peoples common stock, or $21.53 million on an aggregate basis. The last sales price of Peoples common stock reported on or prior to August 13, 2019 was $28.30. The last sales price of Peoples common stock reported on or prior to October 14, 2019 was $52.50. We urge you to obtain current market quotations for C&F common stock, which is listed on the Nasdaq Global Select Market (trading symbol "CFFI") and Peoples common stock, which is quoted on the OTC Markets Group's Pink marketplace (trading symbol "PBVA").

         Based on the number of shares of Peoples common stock outstanding as of June 30, 2019, C&F expects to issue 210,052 shares of common stock in the aggregate upon completion of the merger, with current C&F shareholders owning approximately 94.2% of C&F's outstanding common stock, on a fully diluted basis, and former holders of Peoples common stock owning approximately 5.8% of C&F's outstanding common stock, on a fully diluted basis.

         Approval of the merger agreement requires the affirmative vote of more than two-thirds of the outstanding shares of Peoples common stock. Your vote is very important!

         Based on our reasons for the merger described in the accompanying proxy statement/prospectus, our board of directors unanimously determined that the merger is fair to you and in your best interests. Accordingly, our board of directors unanimously recommends that you vote "FOR" approval of the merger agreement and the related plan of merger.

         The accompanying proxy statement/prospectus gives you detailed information about the special meeting, the merger and related matters. We urge you to read this entire document carefully, including the considerations discussed under "Risk Factors," beginning on page 17, and the appendices to the accompanying document, which include the merger agreement and the related plan of merger.

         Whether or not you plan to attend the special meeting, it is important that your shares be represented at the meeting and your vote recorded. Please take the time to vote by completing and mailing the enclosed proxy card or by voting via the Internet or telephone using the instructions given on the proxy card. Even if you return the proxy card, you may attend the special meeting and vote your shares in person.

         We appreciate your continuing loyalty and support.

    Sincerely,

 

 

GRAPHIC
    Robert K. Bailey, III
President and Chief Executive Officer
Peoples Bankshares, Incorporated

         Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of the securities to be issued in connection with the merger or determined if this proxy statement/prospectus is accurate or complete. Any representation to the contrary is a criminal offense.

         The securities to be issued in the merger are not savings or deposit accounts or other obligations of any bank or non-bank subsidiary of either C&F or Peoples, and they are not insured by the Federal Deposit Insurance Corporation or any other governmental agency.

         This proxy statement/prospectus is dated [    ·    ], 2019 and is first being mailed to Peoples shareholders on or about [    ·    ], 2019.


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LOGO



NOTICE OF SPECIAL MEETING OF SHAREHOLDERS



To be held on December 11, 2019

        A special meeting of shareholders of Peoples Bankshares, Incorporated ("Peoples") will be held at 11:00 a.m. local time, on December 11, 2019 at The Dining Room at Stratford Hall, located at 483 Great House Road, Stratford, Virginia 22558, for the following purposes:

    1.
    To consider and vote on a proposal to approve the Agreement and Plan of Reorganization, dated as of August 13, 2019, between C&F Financial Corporation ("C&F") and Peoples, including the related plan of merger (together, the "merger agreement"), pursuant to which Peoples will merge with and into C&F, as more fully described in the accompanying proxy statement/prospectus (the "merger proposal"). A copy of the merger agreement is attached as Appendix A to the accompanying proxy statement/prospectus.

    2.
    To consider and vote on a proposal to adjourn the meeting, if necessary or appropriate, to permit further solicitation of proxies in the event there are not sufficient votes at the time of the meeting to approve the merger proposal (the "adjournment proposal").

    3.
    To transact such other business as may properly come before the meeting or any adjournments or postponements thereof.

        Only holders of record of Peoples common stock at the close of business on October 10, 2019, are entitled to notice of and to vote at the meeting and any adjournments or postponements thereof.

        The Peoples board of directors unanimously recommends that you vote "FOR" the merger proposal and "FOR" the adjournment proposal.

        Please promptly vote by completing, signing, dating and returning the enclosed proxy card, whether or not you plan to attend the special meeting. You may also vote via the Internet or telephone by following the instructions on the proxy card. If you attend the meeting in person, you may revoke your proxy card and vote your shares in person. If your shares are held in the name of a broker, bank or other fiduciary, please follow the instructions on the voting instruction card provided by such person.

        Peoples shareholders may assert appraisal rights with respect to the merger under applicable provisions of Virginia law. A copy of the applicable Virginia statutory provisions is included in the accompanying proxy statement/prospectus as Appendix C.

    By Order of the Board of Directors,

 

 

GRAPHIC
    Zirkle Blakey, III
Corporate Secretary
Peoples Bankshares, Incorporated

[    ·    ], 2019


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ADDITIONAL INFORMATION

        This proxy statement/prospectus is part of a registration statement filed by C&F with the Securities and Exchange Commission (the "SEC") under the Securities Act of 1933, as amended (the "Securities Act") that registers the shares of C&F common stock to be issued to shareholders of Peoples in the merger. The registration statement, including the attached exhibits, contains additional relevant information about C&F and its common stock, Peoples and the combined company. The rules and regulations of the SEC allow C&F to omit some information included in the registration statement from this proxy statement/prospectus. See "Where You Can Find More Information" on page 91.

        The SEC maintains an Internet website that contains information about issuers, like C&F, that file electronically with the SEC. The address of that site is http://www.sec.gov. C&F is subject to the informational and reporting requirements of the Securities Exchange Act of 1934, as amended (the "Exchange Act") and, in accordance with those requirements, files reports and proxy statements with the SEC. You may inspect and obtain copies of these reports and proxy statements and other information on the SEC's website at the address set forth above.

        C&F's website is http://www.cffc.com. C&F will make available on its website its annual reports on Form 10-K, quarterly reports on Form 10-Q, current reports on Form 8-K and any amendments to those reports filed or furnished pursuant to Section 13(a) or 15(d) of the Exchange Act as soon as reasonably practicable after it electronically files such materials with, or furnishes them to, the SEC. The information on C&F's website is not a part of, and is not incorporated into, this proxy statement/prospectus. Peoples's website is http://www.peoplescommunitybank.biz. The information on Peoples's website is not a part of, and is not incorporated into, this proxy statement/prospectus.

        Additional information about C&F may be obtained by directing a request to C&F Financial Corporation, 3600 La Grange Parkway, Toano, Virginia 23168, Attn.: Investor Relations, or by calling (804) 843-2360, and additional information about Peoples may be obtained by directing a request to Peoples Bankshares, Incorporated, 15960 Kings Highway, PO Box 306, Montross, Virginia 22520, Attention: Corporate Secretary, or by calling (804) 493-8031.

        You may obtain more information about the merger and proxy materials by contacting Peoples's proxy solicitor, Regan & Associates, Inc., by calling (800) 737-3426 or by writing to Regan & Associates, Inc., 505 Eighth Avenue, Suite 800, New York, New York 10018, Attention: Artie Regan.

        To receive timely delivery of documents in advance of the special meeting, please make your request no later than December 4, 2019.

        You should rely only on the information contained or incorporated by reference into this proxy statement/prospectus. No one has been authorized to provide you with information that is different from that contained in, or incorporated by reference into, this proxy statement/prospectus. This proxy statement/prospectus is dated [    ·    ], 2019, and you should assume that the information in this proxy statement/prospectus is accurate only as of such date. You should assume that the information incorporated into this proxy statement/prospectus by reference to another document is accurate only as of the date of such other document. Neither the mailing of this proxy statement/prospectus to Peoples shareholders nor the issuance by C&F of shares of C&F common stock in connection with the merger will create any implication to the contrary.

        This proxy statement/prospectus 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. Except where the context otherwise indicates, information contained in this proxy statement/prospectus regarding C&F has been

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provided by C&F and information contained in this proxy statement/prospectus regarding Peoples has been provided by Peoples.



        Unless otherwise specified in this proxy statement/prospectus or the context otherwise requires:

    C&F Financial Corporation is referred to as "C&F"

    Citizens and Farmers Bank, the wholly-owned bank subsidiary of C&F is referred to as "C&F Bank"

    Peoples Bankshares, Incorporated is referred to as "Peoples"

    the merger of Peoples with and into C&F is referred to as the "merger"

    the Agreement and Plan of Reorganization, dated as of August 13, 2019, between C&F and Peoples, including the related Plan of Merger to be filed with the State Corporation Commission of the Commonwealth of Virginia (the "Virginia SCC") (along with the articles of merger), is referred to as the "merger agreement," a copy of which is attached as Appendix A to this proxy statement/prospectus

    the effective date and time of the merger set forth on the certificate of merger issued by the Virginia SCC effecting the merger are referred to collectively as the "effective time" of the merger

    the merger of Peoples Community Bank with and into C&F Bank, which will occur after the merger of Peoples into C&F, is referred to as the "subsidiary bank merger"

    the proposal to approve the merger agreement is referred to as the "merger proposal"

    the proposal to adjourn the special meeting, if necessary or appropriate, to permit further solicitation of proxies in the event there are not sufficient votes at the time of the meeting to approve the merger proposal is referred to as the "adjournment proposal"

    the special meeting of shareholders of Peoples is sometimes referred to as the "special meeting"

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TABLE OF CONTENTS

 
  Page  

QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETING

    1  

SUMMARY

    6  

SELECTED HISTORICAL FINANCIAL DATA OF C&F

    14  

SELECTED HISTORICAL FINANCIAL DATA OF PEOPLES

    16  

RISK FACTORS

    17  

CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

    22  

THE SPECIAL MEETING

    24  

Date, Place and Time

    24  

Purposes of the Special Meeting

    24  

Recommendation of the Peoples Board of Directors

    24  

Record Date and Voting Rights; Quorum

    24  

Votes Required

    24  

Stock Ownership of Peoples Executive Officers and Directors

    25  

Voting at the Special Meeting

    25  

Changes of Votes and Revocation of Proxies

    26  

Solicitation of Proxies

    27  

PROPOSALS TO BE CONSIDERED AT THE SPECIAL MEETING

    28  

Approval of the Merger Proposal (Proposal No. 1)

    28  

Approval of the Adjournment Proposal (Proposal No. 2)

    28  

THE MERGER

    29  

General

    29  

Background of the Merger

    29  

Peoples's Reasons for the Merger; Recommendation of the Peoples Board of Directors

    34  

C&F's Reasons for the Merger

    36  

Opinion of Peoples's Financial Advisor

    38  

Certain Unaudited Prospective Financial Information

    50  

Interests of Certain Peoples Directors and Executive Officers in the Merger

    53  

Regulatory Approvals

    54  

Dissenters' Appraisal Rights

    55  

Certain Differences in the Rights of Shareholders

    57  

Accounting Treatment

    57  

Resales of C&F Common Stock

    58  

THE MERGER AGREEMENT

    59  

Structure of the Merger

    59  

Merger Consideration

    59  

Effective Time; Closing

    60  

Exchange of Shares in the Merger

    60  

Representations and Warranties

    61  

Conditions to Completion of the Merger

    62  

Business Pending the Merger

    63  

Regulatory Matters

    66  

Shareholder Meeting and Recommendation of the Peoples Board of Directors

    66  

No Solicitation

    66  

Termination of the Merger Agreement

    67  

Termination Fee

    68  

Indemnification and Insurance

    69  

Expenses

    69  

Waiver and Amendment

    69  

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  Page  

Support and Non-Competition Agreements

    70  

Assumption of Peoples's Subordinated Term Note

    71  

Possible Alternative Merger Structure

    71  

MATERIAL U.S. FEDERAL INCOME TAX CONSEQUENCES

    72  

MARKET FOR COMMON STOCK AND DIVIDENDS

    76  

INFORMATION ABOUT C&F FINANCIAL CORPORATION

    78  

INFORMATION ABOUT PEOPLES BANKSHARES, INCORPORATED

    79  

DESCRIPTION OF C&F CAPITAL STOCK

    80  

Authorized and Outstanding Capital Stock

    80  

Common Stock

    80  

Preferred Stock

    81  

COMPARATIVE RIGHTS OF SHAREHOLDERS

    82  

Authorized Capital Stock

    82  

Dividend Rights

    82  

Voting Rights

    82  

Directors and Classes of Directors

    82  

Anti-takeover Provisions

    83  

Amendments to Articles of Incorporation and Bylaws

    85  

Dissenters' Appraisal Rights

    85  

Director and Officer Exculpation

    86  

Indemnification

    86  

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT OF C&F

    87  

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT OF PEOPLES

    89  

LEGAL MATTERS

    90  

EXPERTS

    90  

FUTURE SHAREHOLDER PROPOSALS

    90  

OTHER MATTERS

    91  

WHERE YOU CAN FIND MORE INFORMATION

    91  

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QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETING

        The following questions and answers briefly address some commonly asked questions about the special meeting and the merger. They may not include all of the information that is important to Peoples shareholders. We urge shareholders to read carefully this proxy statement/prospectus, including the appendices and the other documents referred to herein.

Q:
What is the merger?

A:
C&F and Peoples have entered into the merger agreement whereby Peoples will merge with and into C&F, with C&F being the surviving company. If the merger is completed, Peoples Community Bank, Peoples's wholly-owned bank subsidiary, will merge with and into C&F Bank, C&F's wholly-owned bank subsidiary, after the merger of Peoples into C&F. A copy of the merger agreement is attached to this proxy statement/prospectus as Appendix A.

Q:
Why do C&F and Peoples want to merge?

A:
The proposed merger will provide C&F access to new markets in the Northern Neck area of Virginia and in Fredericksburg, Virginia. The Peoples shareholders are expected to benefit from the size and strength of the combined company, and the more active trading market for C&F's common stock. To review the reasons for the merger in more detail, see "The Merger—C&F's Reasons for the Merger" beginning on page 36 and "The Merger—Peoples's Reasons for the Merger; Recommendation of the Peoples Board of Directors" beginning on page 34.

Q:
What will I receive in the merger?

A:
Pursuant to the terms of the merger agreement, as a result of the merger, Peoples shareholders will be entitled to receive (i) $27.00 in cash (the "per share cash consideration") and (ii) 0.5366 shares (the "exchange ratio") of C&F common stock, plus cash in lieu of any fractional shares of C&F common stock (together with the per share cash consideration, the "merger consideration"), in exchange for each share of Peoples common stock. The merger consideration will not be adjusted to reflect stock price changes prior to the closing of the merger.

Q:
Why am I receiving these materials?

A:
These materials describe the proposed merger between C&F and Peoples. Because you are a shareholder of Peoples, you are being asked to vote on the merger proposal and approve the merger agreement. We are sending you these materials to solicit your proxy and help you decide how to vote your shares of Peoples common stock at the special meeting.

Q:
In addition to the merger proposal, what else are the Peoples shareholders being asked to vote on?

A:
In addition to the merger proposal, Peoples is soliciting proxies from its shareholders with respect to a proposal to adjourn the special meeting, if necessary or appropriate, to solicit additional proxies in favor of the merger proposal.

Q:
How does the Peoples board of directors recommend that the Peoples shareholders vote?

A:
The Peoples board of directors unanimously recommends that the Peoples shareholders vote "FOR" the merger proposal and "FOR" the adjournment proposal.

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Q:
What do I need to do now to vote my shares?

A:
After carefully reading and considering the information contained in this proxy statement/prospectus, please vote your shares as soon as possible so that your shares will be represented at the special meeting. If you hold your shares in your name as a shareholder of record, please complete, sign, date and mail your proxy card in the enclosed postage-paid return envelope, or follow the telephone or Internet voting procedures described on the proxy card, as soon as possible. If you hold your shares in "street name" through a bank or broker, please direct your bank or broker how to vote in accordance with the instructions you have received from your bank or broker. You may also cast your vote in person at the special meeting. "Street name" shareholders who wish to vote in person at the special meeting will need to obtain a legal proxy form from the institution that holds their shares.

Q:
If my shares are held in "street name" by a broker or other nominee, will my broker or nominee vote my shares for me if I do not provide instructions on how to vote my shares?

A:
No. Your broker or other nominee does not have authority to vote on the merger proposal or the adjournment proposal if you do not provide instructions to it on how to vote. Your broker or other nominee will vote your shares held by it in "street name" with respect to these matters ONLY if you provide instructions to it on how to vote. You should follow the directions your broker or other nominee provides.

Q:
When and where is the special meeting of shareholders?

A:
The special meeting of shareholders of Peoples will be held at 11:00 a.m. local time, on December 11, 2019 at The Dining Room at Stratford Hall, located at 483 Great House Road, Stratford, Virginia 22558. All holders of Peoples common stock as of the record date for the special meeting (October 10, 2019), or their duly appointed proxies, may attend the special meeting.

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

A:
The merger proposal requires the affirmative vote of the holders of more than two-thirds of the outstanding shares of Peoples common stock entitled to vote on the proposal.

    The adjournment proposal requires the affirmative vote of a majority of the shares voted on the proposal, whether or not a quorum is present.

Q:
Why is my vote as a holder of Peoples common stock important?

A:
If you do not vote your shares of Peoples common stock, it will be more difficult for Peoples to obtain the necessary quorum to hold its special meeting. In addition, approval of the merger proposal requires the affirmative vote of more than two-thirds of the outstanding shares of Peoples common stock entitled to vote at the special meeting. If you do not vote your shares by proxy or in person, the effect will be the same as a vote against the merger proposal.

    The Peoples board of directors unanimously recommends that you vote for the merger proposal.  Further, due to the importance of the vote to approve the merger proposal, Peoples is also seeking authority from shareholders through the adjournment proposal to grant authority to the board of directors to adjourn the special meeting to temporarily delay the meeting to provide time for management to solicit additional proxies in the event there are insufficient votes to approve the merger proposal.

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Q:
What if I do not vote on the merger proposal?

A:
If you fail to vote or fail to instruct your broker or other nominee how to vote on the merger proposal, your failure to vote will have the same effect as a vote against the merger proposal. If you respond with an "abstain" vote, your proxy will have the same effect as a vote against the merger proposal. If you are a holder of record of common stock and you sign and return your proxy card but do not indicate how you want to vote on the merger proposal, your proxy will be counted as a vote in favor of the merger proposal.

Q:
May I change my vote after I have delivered my proxy or voting instruction card?

A:
Yes. If you are a holder of record of common stock, you may change your vote at any time before your proxy is voted at the special meeting. You may do this in any of the following ways:

    by sending a notice of revocation to Peoples's corporate secretary;

    by timely sending a completed proxy card bearing a later date than your original proxy card;

    by voting by telephone or the Internet at a later time (but prior to the Internet and telephone voting deadline); or

    by attending the special meeting and voting in person; your attendance alone will not revoke any proxy.

    If you choose one of the first two methods, your notice or new proxy must be actually received before the voting takes place at the special meeting.

    If your shares are held in a stock brokerage account or by a bank or other nominee, you should call your broker or other nominee for information on how to change your vote.

Q:
Who may solicit proxies on Peoples's behalf?

A:
Peoples's directors and employees are soliciting proxies by mail and may also solicit proxies personally and by telephone, facsimile or other means. Peoples has also retained Regan & Associates, Inc., a proxy solicitation firm, to assist in the solicitation of proxies for a fee not to exceed $3,500, including expenses. For more information on solicitation of proxies in connection with the special meeting, see "The Special Meeting—Solicitation of Proxies" beginning on page 27.

Q:
How are the directors of Peoples going to vote in the merger?

A:
Each of Peoples's directors has entered into a support and non-competition agreement with C&F (each, a "support agreement"), pursuant to which each director has agreed to vote all shares of Peoples common stock over which he or she exercises sole rights of voting and disposition in favor of the merger proposal. As of October 10, 2019, the record date for the special meeting, directors of Peoples owned and are entitled to vote 31,101 shares of Peoples common stock, or approximately 7.95% of the total voting power of the shares of Peoples common stock outstanding on that date, of which 30,581 shares or 7.81% of the total voting power of the shares of Peoples common stock outstanding on that date are subject to a support agreement.

Q:
What are the material U.S. federal income tax consequences of the merger to Peoples shareholders?

A:
The merger will be treated as a tax-free "reorganization" within the meaning of Section 368(a) of the Internal Revenue Code of 1986, as amended (the "Code"). Accordingly, a holder of Peoples common stock who receives cash and C&F common stock generally will not recognize any loss but will recognize gain, if any, in an amount equal to the lesser of (1) the excess, if any, of the sum of

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    the cash received and the fair market value of the shares of C&F common stock received pursuant to the merger over that shareholder's adjusted tax basis in the holder's shares of Peoples common stock surrendered, and (2) the amount of cash received by that holder in exchange for shares of Peoples common stock pursuant to the merger. Additionally, a holder will recognize gain or loss on any cash the holder receives in lieu of fractional shares of C&F common stock. For greater detail, see "Material U.S. Federal Income Tax Consequences" beginning on page 72. Tax matters can be complicated and the tax consequences of the merger to you will depend on your particular tax situation. You should consult your tax advisor to determine the specific tax consequences of the merger to you.

Q:
Do I have dissenters' or appraisal rights?

A:
Yes. Under Virginia law, shareholders of Peoples are entitled to exercise appraisal rights in connection with the merger. In order to perfect appraisal rights, a Peoples shareholder must comply with the exact requirements under Virginia law that are described later in this proxy statement/prospectus and the attached sections of the Code of Virginia regarding appraisal rights. However, it is a condition to closing the merger that the aggregate number of shares of Peoples common stock for which appraisal rights have been perfected under the Virginia Stock Corporation Act (the "Virginia SCA") shall not represent 10% or more of the outstanding shares of Peoples common stock, unless waived by C&F.

Q:
If I am a Peoples shareholder with shares represented by stock certificates, should I send in my Peoples stock certificates now?

A:
No. Please do not send your stock certificates with your proxy card. You will receive written instructions from the exchange agent promptly after the merger is completed on how to exchange your Peoples stock certificates for shares of C&F common stock and the cash portion of the merger consideration, along with cash in lieu of any fractional shares of C&F common stock.

Q:
What should I do if I my Peoples stock certificate has been lost, stolen or destroyed?

A:
If your Peoples stock certificate has been lost, stolen or destroyed, you may receive a new stock certificate upon the making of an affidavit of that fact. You will receive written instructions from the exchange agent promptly after the merger is completed on how to receive a new stock certificate and how to exchange the stock certificate for shares of C&F common stock and the cash portion of the merger consideration, along with cash in lieu of any fractional shares of C&F common stock. C&F may require you to post a bond in a reasonable amount as an indemnity against any claim that may be made against C&F with respect to the lost, stolen or destroyed Peoples stock certificate.

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

A:
After completion of the merger, the exchange agent will mail written instructions on how to exchange your shares of Peoples common stock held in book-entry form for shares of C&F common stock and your check for the cash consideration and cash in lieu of any fractional shares of C&F common stock.

Q:
Will the merger affect outstanding shares of C&F common stock?

A:
No. C&F shareholders will continue to own their existing shares of C&F common stock. Each share of C&F common stock will continue to represent one share of C&F common stock following the merger.

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Q:
When do you expect to complete the merger?

A:
C&F and Peoples currently expect to complete the merger in early 2020. However, they cannot assure you when or if the merger will occur. C&F and Peoples must, among other things, obtain the approval of the Peoples shareholders at the special meeting and required regulatory approvals described below in "The Merger Agreement—Conditions to Completion of the Merger" and "The Merger—Regulatory Approvals" beginning on pages 62 and 54, respectively.

Q:
What happens if the merger is not completed?

A:
If the merger is not completed, holders of Peoples common stock will retain their Peoples common stock and will not receive any consideration for their shares in connection with the merger. Instead, Peoples will remain an independent company. In addition, in certain circumstances, a termination fee may be required to be paid by Peoples to C&F. See "The Merger Agreement—Termination Fee" beginning on page 68 for a complete discussion of the circumstances under which a termination fee would be required to be paid.

Q:
What happens if I sell or transfer ownership of shares of Peoples common stock after the record date for the special meeting?

A:
The record date for the special meeting is earlier than the expected date of completion of the merger. Therefore, if you sell or transfer ownership of your shares of Peoples common stock after the record date for the special meeting, but prior to completion of the merger, you will retain the right to vote at the special meeting, but the right to receive the merger consideration will transfer with the shares of Peoples common stock.

Q:
Who should I contact if I have any questions about the proxy materials or voting?

A:
If you have any questions about the merger or if you need assistance in submitting your proxy or voting your shares or need additional copies of the proxy statement/prospectus or the enclosed proxy card, you should contact Peoples's corporate secretary by calling (804) 493-8031 or by writing to Peoples Bankshares, Incorporated, 15960 Kings Highway, PO Box 306, Montross, Virginia 22520, Attention: Corporate Secretary. You may also obtain more information about the merger and the proxy materials by contacting Regan & Associates, Inc., Peoples's proxy solicitor, by calling (800) 737-3426 or by writing to Regan & Associates, Inc., 505 Eighth Avenue, Suite 800, New York, New York 10018, Attention: Artie Regan.

    If your shares are held in a stock brokerage account or by a bank or other nominee, you should call your broker or other nominee for additional information.

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SUMMARY

        This summary highlights selected information from this proxy statement/prospectus. We urge you to read carefully the proxy statement/prospectus and the other documents to which this proxy statement/prospectus refers to understand fully the merger and related matters. See "Where You Can Find More Information" beginning on page 91. Each item in this summary refers to the page of this proxy statement/prospectus on which that subject is discussed in more detail.

The Merger (page 29)

        The merger agreement provides for the merger of Peoples into C&F, with C&F being the surviving corporation in the merger. The merger agreement also calls for Peoples Community Bank, the wholly-owned bank subsidiary of Peoples, to be merged into C&F Bank, the wholly-owned bank subsidiary of C&F, after the merger of Peoples into C&F. The parties currently expect to complete the merger in early 2020.

        The merger agreement is attached to this proxy statement/prospectus as Appendix A. We encourage you to read the merger agreement, as it is the legal document that governs the merger.

Consideration to be Received in the Merger by Peoples Shareholders (page 29)

        Pursuant to the terms of the merger agreement, as a result of the merger, each share of Peoples common stock issued and outstanding before the effective time of merger will be converted into the right to receive:

    $27.00 in cash; and

    0.5366 shares of C&F common stock.

        The exchange ratio of 0.5366 shares of C&F common stock will not be adjusted to reflect stock price changes before the effective time of the merger. No fractional shares will be issued; instead cash will be paid for fractional shares. You will not have the ability to elect to receive all stock or all cash, or any combination of cash and stock other than the merger consideration as described above, as consideration for your shares of Peoples common stock.

        Based on the closing sale price of C&F common stock on the Nasdaq Global Select Market on August 13, 2019 ($51.79), the last trading day before public announcement of the merger, the merger consideration represented approximately $54.79 in value for each share of Peoples common stock, or $21.45 million on an aggregate basis. Based on the closing sale price of C&F common stock on the Nasdaq Global Select Market on October 14, 2019 ($52.20), the last trading day before the date of this proxy statement/prospectus, the merger consideration represented approximately $55.01 in value for each share of Peoples common stock, or $21.53 million on an aggregate basis. The last sales price of Peoples common stock reported on or prior to August 13, 2019 was $28.30. The last sales price of Peoples common stock reported on or prior to October 14, 2019 was $52.50.

        Based on the current number of shares of Peoples common stock outstanding as of June 30, 2019, C&F expects that it will issue approximately 210,052 shares of C&F common stock to the holders of Peoples common stock in the merger. At the completion of the merger, it is expected that there will be issued and outstanding approximately 3,648,807 shares of C&F common stock, with current C&F shareholders owning approximately 94.2% of C&F's outstanding common stock, on a fully diluted basis, and former holders of Peoples common stock owning approximately 5.8% of C&F's outstanding common stock, on a fully diluted basis.

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Dividend Information (page 76)

        C&F is currently paying a quarterly cash dividend on shares of its common stock at a rate of $0.37 per share. C&F does not currently intend to change its dividend strategy of paying a quarterly cash dividend, but has and will continue to evaluate that decision based on a quarterly review of earnings, growth, capital, applicable governmental regulations and policies, and such other factors that the C&F board of directors considers relevant to the dividend decision process. Peoples does not currently pay a regular cash dividend on shares of its common stock.

Material U.S. Federal Income Tax Consequences (page 72)

        The merger will be treated as a tax-free "reorganization" within the meaning of Section 368(a) of the Code. Accordingly, a holder of Peoples common stock who receives cash and C&F common stock generally will not recognize any loss but will recognize gain, if any, in an amount equal to the lesser of (1) the excess, if any, of the sum of the cash received and the fair market value of the shares of C&F common stock received pursuant to the merger over that shareholder's adjusted tax basis in the holder's shares of Peoples common stock surrendered, and (2) the amount of cash received by that holder in exchange for shares of Peoples common stock pursuant to the merger. Additionally, a holder will recognize gain or loss on any cash the holder receives in lieu of fractional shares of C&F common stock.

        The U.S. federal income tax consequences described above may not apply to all Peoples shareholders. Your tax consequences will depend on your individual situation. Accordingly, we strongly urge you to consult your own tax advisor to determine the particular tax consequences of the merger to you.

        For further information, please see "Material U.S. Federal Income Tax Consequences" beginning on page 72.

The Peoples Board of Directors Unanimously Recommends that Peoples Shareholders Vote "FOR" the Merger Proposal and "FOR" the Adjournment Proposal (page 34)

        The Peoples board of directors has determined that the merger, the merger agreement and the transactions contemplated by the merger agreement are in the best interests of Peoples and its shareholders and has unanimously approved the merger agreement. The Peoples board of directors unanimously recommends that Peoples shareholders vote "FOR" the merger proposal and "FOR" the adjournment proposal. For the factors considered by Peoples's board of directors in reaching its decision to approve the merger agreement, see "The Merger—Peoples's Reasons for the Merger; Recommendation of the Peoples Board of Directors."

Opinion of Peoples's Financial Advisor (page 38)

        On August 13, 2019, the Peoples board of directors received an oral opinion, which was confirmed in writing by delivery of the written opinion of the same date, from Sandler O'Neill & Partners, L.P. ("Sandler O'Neill"), Peoples financial advisor, to the effect that, as of such date and subject to the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken by Sandler O'Neill as set forth in its opinion, the merger consideration in the proposed merger was fair, from a financial point of view, to the holders of Peoples common stock. The full text of Sandler O'Neill's written opinion is attached as Appendix B to this proxy statement/prospectus. Peoples shareholders should read the entire opinion carefully for a discussion of, among other things, the assumptions made, matters considered and qualifications and limitations on the review undertaken by Sandler O'Neill in rendering its opinion.

        Sandler O'Neill's opinion speaks only as of the date of the opinion. The opinion was directed to the Peoples board of directors in connection with its consideration of the merger agreement and the

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merger and does not constitute a recommendation to any shareholder of Peoples as to how any such shareholder should vote at any meeting of shareholders called to consider and vote upon the approval of the merger. Sandler O'Neill's opinion was directed only to the fairness, from a financial point of view, of the merger consideration to the holders of Peoples common stock and does not address the underlying business decision of Peoples to engage in the merger, the form or structure of the merger or any other transactions contemplated in the merger agreement, the relative merits of the merger as compared to any other alternative transactions or business strategies that might exist for Peoples or the effect of any other transaction in which Peoples might engage.

The Parties to the Merger (pages 78 and 79)

        C&F Financial Corporation.    C&F Financial Corporation, headquartered in West Point, Virginia, is a bank holding company incorporated under the laws of the Commonwealth of Virginia. C&F owns all of the stock of Citizens and Farmers Bank, a commercial bank chartered under the laws of the Commonwealth of Virginia. C&F Bank originally opened for business under the name Farmers and Mechanics Bank on January 22, 1927. C&F Bank provides retail banking services at its main office in West Point, Virginia, 24 retail branches located throughout the Hampton to Charlottesville corridor of Virginia, and three commercial loan offices. C&F Bank has five wholly owned subsidiaries. C&F Mortgage Corporation, organized in 1995, originates and sells residential mortgages. C&F Finance Company, acquired in 2002, is a finance company purchasing automobile, marine and recreational vehicle loans through indirect lending programs. C&F Wealth Management Corporation, organized in 1995, is a full-service brokerage firm offering a comprehensive range of wealth management services. C&F Insurance Services, Inc. owns an equity interest in an independent insurance agency. CVB Title Services, Inc. owns an equity interest in a full service title and settlement agency. The common stock of C&F is traded on the Nasdaq Global Select Market under the symbol "CFFI."

        As of June 30, 2019, C&F had approximately $1.6 billion in total assets, approximately $1.2 billion in deposits, approximately $1.2 billion in gross loans, and approximately $159.4 million of total equity.

        The principal executive offices of C&F are located at 802 Main Street, West Point, Virginia 23181, and its telephone number is (804) 843-2360. C&F's website can be accessed at https://www.cffc.com. Information contained on C&F's website does not constitute part of, and is not incorporated into, this proxy statement/prospectus. Additional information about C&F is included in documents incorporated by reference in this proxy statement/prospectus. See "Where You Can Find More Information."

        Peoples Bankshares, Incorporated.    Peoples Bankshares, Incorporated, headquartered in Montross, Virginia, is a bank holding company incorporated under the laws of the Commonwealth of Virginia. Peoples owns all of the stock of Peoples Community Bank, a commercial bank chartered under the laws of the Commonwealth of Virginia. Peoples Community Bank originally opened for business on June 17, 1913 under the name "The Peoples Bank of Montross, Virginia." Peoples Community Bank conducts its business through its main office in Montross, Virginia and four branch offices located in Fredericksburg, King George, and Warsaw, Virginia. Peoples's common stock is quoted on the OTC Markets Group's Pink marketplace under the symbol "PBVA."

        As of June 30, 2019, Peoples had approximately $194.0 million in total assets, approximately $172.4 million in deposits, approximately $147.5 million in gross loans, and approximately $15.8 million of total shareholders' equity.

        The principal executive offices of Peoples are located at 15960 Kings Highway, Montross, Virginia 22520, and its telephone number is (804) 493-8031. Peoples's website can be accessed at http://www.peoplescommunitybank.biz. Information contained on Peoples's website does not constitute part of, and is not incorporated into, this proxy statement/prospectus.

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Regulatory Approvals (page 54)

        C&F and Peoples cannot complete the merger without prior approval from the Board of Governors of the Federal Reserve System (the "Federal Reserve") and the Bureau of Financial Institutions of the Virginia SCC. On or about October 8, 2019, C&F filed the required applications with the Federal Reserve and Virginia SCC seeking approval of the merger.

        The subsidiary bank merger cannot be completed without prior approval from the Federal Deposit Insurance Corporation (the "FDIC") and the Bureau of Financial Institutions of the Virginia SCC. On or about October 8, 2019, C&F Bank filed the required applications with the FDIC and the Virginia SCC seeking approval of the subsidiary bank merger.

        As of the date of this proxy statement/prospectus, C&F has not yet received the required regulatory approvals for the merger and C&F Bank has not yet received the required regulatory approvals for the subsidiary bank merger. While C&F and C&F Bank do not know of any reason why they would not be able to obtain the necessary regulatory approvals in a timely manner, they cannot be certain when or if they will receive such approvals.

Conditions to Completion of the Merger (page 62)

        C&F's and Peoples's respective obligations to complete the merger are subject to the satisfaction or waiver of certain conditions, including the following:

    approval of the merger proposal by Peoples shareholders;

    approval of the merger by the necessary federal and state regulatory authorities without the imposition of a burdensome condition (as defined in "The Merger—Regulatory Approvals");

    effectiveness of C&F's registration statement on Form S-4, of which this proxy statement/prospectus is a part;

    the absence of any order, decree or injunction of a court or regulatory agency that enjoins or prohibits the completion of the merger;

    approval from the Nasdaq Stock Market for the listing on the Nasdaq Global Select Market of the shares of common stock of C&F to be issued in the merger;

    the receipt by C&F and Peoples from its respective outside legal counsel of a written legal opinion to the effect that the merger will be treated as a "reorganization" within the meaning of Section 368(a) of the Code;

    the accuracy of the other party's representations and warranties in the merger agreement, subject to the material adverse effect standard in the merger agreement;

    the other party's performance in all material respects of its obligations under the merger agreement; and

    no material adverse effect with respect to the other party shall have occurred.

        In addition, C&F's obligation to complete the merger is subject to the satisfaction or waiver of the conditions set forth below:

    the aggregate number of shares of Peoples common stock for which appraisal rights have been perfected under the Virginia SCA shall not represent 10% or more of the outstanding shares of Peoples common stock; and

    each of the directors of Peoples shall have entered into a support agreement with C&F and such agreements shall be effective.

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        Where the merger agreement and law permits, C&F and Peoples could choose to waive a condition to its obligation to complete the merger even if that condition has not been satisfied. C&F and Peoples cannot be certain when, or if, the conditions to the merger will be satisfied or waived or that the merger will be completed.

Timing of the Merger (page 60)

        C&F and Peoples expect to complete the merger after all conditions to the merger in the merger agreement are satisfied or waived, including after shareholder approval is received at Peoples's special meeting and all required regulatory approvals are received. We currently expect to complete the merger in early 2020. However, it is possible that factors outside of either party's control could require the parties to complete the merger at a later time or not to complete it at all.

Interests of Certain Peoples Directors and Executive Officers in the Merger (page 53)

        Certain directors and executive officers of Peoples have interests in the merger that differ from, or are in addition to, their interests as shareholders of Peoples. These interests include, among other things, payments to certain of Peoples's executive officers after their respective Peoples employment agreements are terminated in connection with the merger, continued employment of certain of Peoples's executive officers with C&F following completion of the merger, and rights to indemnification and directors' and officers' liability insurance following the merger.

        The members of the Peoples board of directors were fully informed about these additional interests and thoroughly considered them when they approved the merger agreement and the merger. These interests are discussed in more detail in "The Merger—Interests of Certain Peoples Directors and Executive Officers in the Merger" beginning on page 53.

No Solicitation (page 66)

        Peoples has agreed that, while the merger agreement is in effect, it will not directly or indirectly:

    initiate, solicit, endorse or encourage any inquiries or proposals with respect to any "acquisition proposal" (as defined in the merger agreement); or

    engage or participate in any negotiations or discussions concerning, or provide any confidential or nonpublic information relating to, an acquisition proposal.

        The merger agreement does not, however, prohibit Peoples from considering an unsolicited bona fide acquisition proposal from a third party if certain specified conditions are met.

Termination of the Merger Agreement (page 67)

        The merger agreement may be terminated, and the merger abandoned, by C&F and Peoples at any time before the merger is completed by mutual consent of C&F and Peoples. In addition, the merger agreement may be terminated, and the merger abandoned, under the following circumstances:

    by C&F or Peoples if the merger has not been completed by August 13, 2020 or such later date as agreed to by the parties in writing, provided that this right to terminate shall not be available to any party whose breach or failure to perform an obligation under the merger agreement has caused the failure of the merger to occur prior to such date;

    by C&F or Peoples if there is a breach by the other party of any representation, warranty, covenant or agreement contained in the merger agreement that would cause the failure of the closing conditions described above, and the breach cannot be or is not cured within 30 days following written notice to the breaching party, provided that the terminating party is not then in

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      breach of any representation, warranty, covenant or agreement (as applicable) contained in the merger agreement;

    by C&F or Peoples if Peoples shareholders do not approve the merger proposal;

    by C&F at any time before special meeting if (i) Peoples breaches its obligations regarding the nonsolicitation of competing offers for certain corporate transactions, (ii) the Peoples board (a) fails to recommend to the Peoples shareholders that they approve the merger proposal, or (b) withdraws, modifies or changes such recommendation in any manner adverse to C&F; or (iii) Peoples fails to comply in all material respects with its obligations in the merger agreement requiring the calling and holding of a meeting of shareholders to consider the merger proposal or its obligations regarding the non-solicitation of competing offers for certain corporate transactions;

    by C&F, if (i) Peoples or Peoples Community Bank enters into an agreement with any person to merge or consolidate with or acquire Peoples or Peoples Community Bank, or purchase, lease or otherwise acquire all or substantially all of the assets of Peoples or Peoples Community Bank, or purchase or otherwise acquire from Peoples securities representing 20% or more of the voting power of Peoples or (ii) a tender or exchange offer is commenced for 20% or more of the outstanding shares of Peoples common stock, and the Peoples board recommends that Peoples's shareholders tender their shares or otherwise fails to recommend that shareholders reject such offer; or

    by Peoples at any time before the special meeting in order for Peoples to enter into an agreement with respect to a "superior proposal" (as defined in the merger agreement), which has been received and considered by Peoples in compliance with the applicable terms of the merger agreement.

        In the event of termination, the merger agreement will become null and void, except that certain provisions thereof relating to fees and expenses (including the obligation to pay the termination fee described below in certain circumstances) and confidentiality of information exchanged between the parties will survive any such termination.

Termination Fee and Expenses (pages 68 and 69)

        Peoples must pay C&F a termination fee of $900,000 if the merger agreement is terminated by either party under certain specified circumstances. The termination and payment circumstances are more fully described elsewhere in this proxy statement/prospectus. See "The Merger Agreement—Termination Fee" on page 68 and Article 7 of the merger agreement.

        In general, whether or not the merger is completed, C&F and Peoples will each pay its respective expenses incident to preparing, entering into and carrying out the terms of the merger agreement, except that the costs and expenses of printing and mailing this proxy statement/prospectus will be incurred by Peoples.

The Special Meeting (page 24)

        The special meeting of shareholders of Peoples will be held at 11:00 a.m. local time, on December 11, 2019 at The Dining Room at Stratford Hall, located at 483 Great House Road, Stratford, Virginia 22558.

        At the special meeting, the shareholders of Peoples common stock will be asked to vote on the merger proposal and the adjournment proposal.

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Record Date

        You can vote at the special meeting of shareholders if you owned Peoples common stock at the close of business on October 10, 2019, the record date. On that date, Peoples had 391,450 shares of common stock outstanding and entitled to vote. For each proposal presented at the special meeting, a shareholder can cast one vote for each share of Peoples common stock owned on the record date.

Votes Required

        The votes required to approve the proposals at the special meeting are as follows:

    The merger proposal requires the affirmative vote of more than two-thirds of the outstanding shares of Peoples common stock entitled to vote on the proposal.

    The adjournment proposal requires the affirmative vote of a majority of the shares voted on the proposal, whether or not a quorum is present.

Support and Non-competition Agreements (page 70)

        C&F has entered into a support and non-competition agreement (each, a "support agreement") with each director of Peoples, in his or her capacity as a shareholder of Peoples, regarding the voting of shares of Peoples common stock in connection with the merger. Each of Peoples's directors has agreed, subject to certain limited exceptions, to vote all shares of Peoples common stock owned beneficially or of record by such director, and over which such director has sole rights of voting and disposition, in favor of the merger proposal. As of October 10, 2019, the record date for the special meeting, directors of Peoples owned and are entitled to vote 31,101 shares of Peoples common stock, or approximately 7.95% of the total voting power of the shares of Peoples common stock outstanding on that date, of which 30,581 shares or 7.81% of the total voting power of the shares of Peoples common stock outstanding on that date are subject to a support agreement.

        In addition, the support agreements contain certain non-solicitation and non-competition provisions that (i) limit the ability of Peoples's directors to act with respect to third party inquiries and proposals and (ii) limit the ability of Peoples's directors to compete with C&F (subject to limited exceptions), in each case for 12 months from the effective time of the merger. The form of support agreement is Exhibit 5.8 to the merger agreement, which is attached to this proxy statement/ prospectus as Appendix A.

Dissenters' Appraisal Rights (page 55)

        Shareholders of Peoples have the right to assert appraisal rights with respect to the merger and demand in writing to be paid the fair value of their shares of Peoples common stock following consummation of the merger. These appraisal rights are governed by Virginia law. A copy of the applicable provisions of the Virginia SCA is included in this proxy statement/prospectus as Appendix C.

Shareholders of C&F and Peoples Have Different Rights (page 82)

        C&F and Peoples are Virginia corporations governed by the Virginia SCA. In addition, the rights of C&F and Peoples shareholders are governed by their respective articles of incorporation and bylaws. Upon completion of the merger, Peoples shareholders will become shareholders of C&F, and as such their shareholder rights will then be governed by the articles of incorporation and bylaws of C&F, each as amended, and by the Virginia SCA. The rights of shareholders of C&F differ in certain respects from the rights of shareholders of Peoples.

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Listing of C&F Common Stock (page 76)

        C&F will list the shares of common stock to be issued in the merger on the Nasdaq Global Select Market.

Market Prices and Share Information (page 76)

        C&F's common stock is listed on the Nasdaq Global Select Market under the symbol "CFFI." Peoples's common stock is quoted on the OTC Markets Group's Pink marketplace under the symbol "PBVA." The following table sets forth the closing sale prices per share of C&F common stock as reported on the Nasdaq Global Select Market on August 13, 2019, the last trading day before the parties announced the signing of the merger agreement, and on October 14, 2019, the last trading day before the date of this proxy statement/prospectus. The table also sets forth the last sales price of Peoples common stock reported on or before August 13, 2019 (which sale occurred on August 9, 2019), and the last sales price of Peoples common stock reported on or before the date of this proxy statement/prospectus (which sale occurred on October 4, 2019). The following table also includes the equivalent market value per share of Peoples common stock on August 13, 2019 and on October 14, 2019, which reflects the sum of (i) the product of the exchange ratio of 0.5366 multiplied by the closing sale price of C&F common stock on the dates indicated, plus (ii) the per share cash consideration of $27.00.

 
  C&F
Common Stock
  Peoples
Common Stock
  Equivalent Market
Value Per Share
of Peoples
 

August 13, 2019

  $ 51.79   $ 28.30   $ 54.79  

October 14, 2019

  $ 52.20   $ 52.50   $ 55.01  

        The value of the stock portion of the merger consideration to be received for each share of Peoples common stock will be based on the most recent closing price of C&F's common stock prior to the completion of the merger. Because the merger consideration will not be adjusted for fluctuations in market value and because the market value of the shares of C&F common stock to be received by Peoples shareholders will change prior to completion of the merger, shareholders of Peoples are not assured of receiving a specific market value of C&F common stock, and thus a specific market value for their shares of Peoples common stock, at the effective time of the merger. C&F cannot assure you that its common stock will continue to trade at or above the prices shown above. You should obtain current stock price quotations for the C&F common stock from a newspaper, via the Internet or by calling your broker.

Risk Factors (page 17)

        You should consider all the information contained in or incorporated by reference into this proxy statement/prospectus in deciding how to vote for the proposals presented in the proxy statement/prospectus. In particular, you should consider the factors under "Risk Factors" beginning on page 17.

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SELECTED HISTORICAL FINANCIAL DATA OF C&F

        The following tables set forth certain of C&F's consolidated financial data as of the end of and for each of the years in the five-year period ended December 31, 2018, and as of and for the six months ended June 30, 2019 and 2018. The historical consolidated financial information as of the end of and for each of the years in the five-year period ended December 31, 2018 is derived from C&F's audited consolidated financial statements. The historical consolidated financial information as of and for the six-month periods ended June 30, 2019 and 2018 is derived from C&F's unaudited consolidated financial statements. In C&F's opinion, such unaudited consolidated financial statements include all adjustments (consisting of normal recurring adjustments) necessary for a fair presentation of its financial position and results of operations for such periods. Interim results for the six months ended June 30, 2019 are not necessarily indicative of, and are not projections for, the results to be expected for the full year ending December 31, 2019.

        The selected historical financial data below is only a summary and should be read in conjunction with C&F's audited and unaudited consolidated financial statements that are incorporated by reference into this proxy statement/prospectus and their accompanying notes.

 
  Six Months Ended
June 30,
(Unaudited)
  Twelve Months Ended December 31,  
 
  2019   2018   2018   2017   2016   2015   2014  
 
  (Amounts in thousands, except per share information)
 

Financial Condition:

                                           

Total assets(1)

  $ 1,567,996   $ 1,535,643   $ 1,521,411   $ 1,509,056   $ 1,451,992   $ 1,405,076   $ 1,338,187  

Securities, available for sale

    200,427     221,869     214,910     218,976     210,026     219,476     221,897  

Loans held for sale

    89,185     55,054     41,895     55,384     52,027     44,000     28,279  

Loan (net of allowance for loan losses)

    1,056,934     996,412     1,028,097     992,062     962,674     865,892     800,198  

Total deposits

    1,210,209     1,193,431     1,181,661     1,171,429     1,119,921     1,073,633     1,026,101  

Total equity

    159,351     146,453     151,958     141,702     139,214     131,059     123,610  

Results of Operations:

   
 
   
 
   
 
   
 
   
 
   
 
   
 
 

Interest income

  $ 47,227   $ 45,395   $ 92,548   $ 89,593   $ 89,439   $ 87,049   $ 86,495  

Interest expense

    6,955     5,240     11,027     9,601     8,968     8,694     8,525  

Net interest income

    40,272     40,155     81,521     79,992     80,471     78,355     77,970  

Provision for loan losses

    4,205     5,300     11,006     16,435     18,040     15,512     16,330  

Net interest income after provision for loan losses

    36,067     34,855     70,515     63,557     62,431     62,843     61,640  

Noninterest income

    15,305     13,687     25,758     27,232     26,047     21,220     19,821  

Noninterest expenses

    39,226     37,300     73,732     72,823     70,560     66,680     63,973  

Income before taxes

    12,146     11,242     22,541     17,966     17,918     17,383     17,488  

Income tax expense(2)

    2,533     2,280     4,521     11,394     4,459     4,853     5,144  

Net income(2)

  $ 9,613   $ 8,962   $ 18,020   $ 6,572   $ 13,459   $ 12,530   $ 12,344  

Share Data:

                                           

Earnings per share, basic(2)

  $ 2.77   $ 2.56   $ 5.15   $ 1.89   $ 3.90   $ 3.68   $ 3.63  

Earnings per share, assuming Dilution(2)

    2.77     2.56     5.15     1.88     3.89     3.68     3.59  

Dividends per share

    0.74     0.68     1.41     1.33     1.29     1.22     1.19  

Weighted average number of shares, basic

    3,473,875     3,502,139     3,501,221     3,486,510     3,454,282     3,401,426     3,404,112  

Weighted average number of shares, assuming dilution

    3,473,875     3,502,139     3,501,221     3,486,589     3,455,883     3,401,834     3,436,278  

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  Six Months Ended
June 30,
(Unaudited)
  Twelve Months Ended December 31,  
 
  2019   2018   2018   2017   2016   2015   2014  
 
  (Amounts in thousands, except per share information)
 

Selected Ratios:

                                           

Net interest margin

    5.71 %   5.77 %   5.80 %   5.99 %   6.30 %   6.35 %   6.55 %

Return on average assets(2)

    1.26     1.19     1.19     0.45     0.96     0.92     0.93  

Return on average equity(2)

    12.54     12.62     12.40     4.58     9.90     9.87     10.32  

Dividend payout ratio

    26.72     26.56     27.38     70.37     33.08     33.20     32.80  

Average equity to average assets

    10.02     9.42     9.63     9.82     9.65     9.29     9.02  

Asset Quality:

   
 
   
 
   
 
   
 
   
 
   
 
   
 
 

Allowance for loan losses (ALL)

                                           

Retail Banking

  $ 10,427   $ 10,792   $ 10,426   $ 10,775   $ 11,115   $ 11,017   $ 10,961  

Mortgage Banking

    598     598     598     598     598     598     553  

Consumer Finance

    22,376     24,003     22,999     24,353     25,353     23,954     24,092  

Ratio of ALL to total loans

                                           

Retail Banking

    1.34 %   1.48 %   1.37 %   1.48 %   1.63 %   1.86 %   2.08 %

Mortgage Banking

    16.94     18.15     17.19     18.22     18.26     17.12     16.82  

Consumer Finance

    7.26     8.11     7.77     8.34     8.33     8.21     8.50  

(1)
On January 1, 2019, C&F adopted Accounting Standards Update 2016-02, "Leases (Topic 842)" on a modified retrospective basis, which resulted in recognition of a lease liability of approximately $3.14 million and a corresponding right-of-use asset. Periods prior to January 1, 2019 have not been restated.

(2)
In connection with the reduction in the federal corporate income tax rate as a result of the enactment of the Tax Cuts and Jobs Act of 2017, C&F recognized a one-time remeasurement of its federal net deferred tax asset in 2017, which resulted in additional income tax expense and a decrease in net income of $6.6 million.

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SELECTED HISTORICAL FINANCIAL DATA OF PEOPLES

        The following tables set forth certain of Peoples's consolidated financial data as of the end of and for each of the years in the five-year period ended December 31, 2018 and as of and for the six months ended June 30, 2019 and 2018. The historical consolidated financial information as of the end of and for each of the years in the five-year period ended December 31, 2018, is derived from Peoples's audited consolidated financial statements. The historical consolidated financial information as of and for the six-month periods ended June 30, 2019 and 2018 is derived from Peoples's unaudited consolidated financial statements. In Peoples's opinion, such unaudited consolidated financial statements include all adjustments (consisting of normal recurring adjustments) necessary for a fair presentation of its financial position and results of operations for such periods. Interim results for the six months ended June 30, 2019 are not necessarily indicative of, and are not projections for, the results to be expected for the full year ending December 31, 2019.

 
  Six Months Ended
June 30,
(Unaudited)
  Twelve Months Ended December 31,  
 
  2019   2018   2018   2017   2016   2015   2014  
 
  (Amounts in thousands, except per share information)
 

Financial Condition:

                                           

Total assets

  $ 194,037   $ 203,635   $ 200,833   $ 184,191   $ 171,324   $ 161,155   $ 157,099  

Securities, available for sale

    20,721     24,654     27,777     26,395     18,944     18,718     22,909  

Loans held for sale

                                           

Loan (net of allowance for loan losses)

    143,552     162,941     155,038     142,542     133,104     127,790     119,682  

Total deposits

    172,410     177,402     181,010     166,481     152,269     141,110     137,755  

Total shareholders' equity

    15,768     16,026     14,748     15,762     15,042     14,257     13,688  

Results of Operations:

   
 
   
 
   
 
   
 
   
 
   
 
   
 
 

Interest income

  $ 4,299   $ 4,102   $ 8,380   $ 7,248   $ 6,831   $ 6,395   $ 6,094  

Interest expense

    1,158     822     1,934     1,124     900     814     810  

Net interest income

    3,141     3,280     6,446     6,124     5,931     5,581     5,284  

Provision for loan losses

    350     25     2,515     25     100     340     100  

Net interest income after provision for loan losses

    2,791     3,255     3,931     6,099     5,831     5,241     5,184  

Noninterest income

    426     385     641     595     1,004     926     871  

Noninterest expenses

    2,679     2,696     5,330     4,974     5,086     5,009     4,977  

Income before taxes

    538     944     (758 )   1,720     1,749     1,158     1,078  

Income tax expense(1)

    95     151     (211 )   872     473     271     260  

Net income(1)

  $ 443   $ 793   $ (547 ) $ 848   $ 1,276   $ 887   $ 818  

Share Data:

                                           

Earnings per share, basic and assuming dilution(1)

  $ 1.13   $ 2.03   $ (1.40 ) $ 2.17   $ 3.26   $ 2.27   $ 2.09  

Dividends per share

        0.28     0.58     0.56     0.55     0.52     0.50  

Weighted average number of shares

    391,450     391,450     391,450     391,450     391,450     391,450     391,450  

Selected Ratios:

   
 
   
 
   
 
   
 
   
 
   
 
   
 
 

Net interest margin

    3.50 %   3.70 %   3.60 %   3.73 %   3.94 %   3.82 %   3.78 %

Return on average assets(1)

    0.22     0.41     (0.28 )   0.47     0.76     0.55     0.52  

Return on average equity(1)

    2.90     4.99     (3.59 )   5.44     8.64     6.37     6.21  

Dividend payout ratio

        13.87     (41.51 )   25.85     16.87     22.95     23.93  

Average equity to average assets

    7.73     8.20     7.92     8.66     8.81     8.78     8.49  

Asset Quality:

   
 
   
 
   
 
   
 
   
 
   
 
   
 
 

Ratio of ALL to total loans

    2.68 %   1.34 %   2.46 %   1.51 %   1.77 %   1.89 %   1.92 %

(1)
In connection with the reduction in the federal corporate income tax rate as a result of the enactment of the Tax Cuts and Jobs Act of 2017, Peoples recognized a one-time remeasurement of its federal net deferred tax asset in 2017, which resulted in additional income tax expense and a decrease in net income of approximately $362 thousand.

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RISK FACTORS

        In addition to general investment risks and the other information contained in or incorporated by reference into this proxy statement/prospectus, including the matters addressed under the heading "Cautionary Statement Regarding Forward-Looking Statements" on page 22, you should consider carefully the following risk factors in deciding how to vote on the proposals presented in this proxy statement/prospectus. Information about certain risks and uncertainties, including risks and uncertainties regarding C&F's business, can also be found in the documents incorporated by reference into this proxy statement/prospectus by C&F. See "Where You Can Find More Information" on page 91.

Because of the fixed exchange ratio of the stock portion of the merger consideration and the fluctuation of the market price of C&F common stock, the Peoples shareholders will not know at the time of the special meeting the market value of the stock portion of the merger consideration to be paid by C&F to the Peoples shareholders.

        In the merger, each share of Peoples common stock will be converted into the right to receive (i) $27.00 in cash and (ii) 0.5366 shares of C&F common stock, plus cash in lieu of any fractional shares of C&F common stock. The value of 0.5366 shares of C&F common stock will depend upon the price of C&F common stock at the effective time of the merger. The price of C&F common stock as of the effective time of the merger may vary from its price at the date the fixed exchange ratio was established, at the date of this proxy statement/prospectus and at the date of the special meeting. Such variations in the price of C&F common stock may result from changes in the business, operations or prospects of C&F, regulatory considerations, general market and economic conditions, and other factors. Many of these factors are beyond C&F's control. At the time of the special meeting, shareholders of Peoples will not know the exact value of the consideration to be paid by C&F when the merger is completed. You should obtain current market quotations for shares of C&F common stock.

The market price of C&F common stock after the merger may be affected by factors different from those affecting the shares of C&F or Peoples currently.

        Upon completion of the merger, holders of Peoples common stock will become holders of C&F common stock. C&F's business differs in important respects from that of Peoples, and, accordingly, the results of operations of the combined company and the market price of C&F common stock after the completion of the merger may be affected by factors different from those currently affecting the independent results of operations of each of C&F and Peoples. For a discussion of the businesses of C&F and Peoples, see the information described elsewhere in this proxy statement/prospectus and the documents incorporated herein by reference.

Combining Peoples into C&F may be more difficult, costly or time-consuming than we expect.

        The success of the merger will depend, in part, on C&F's ability to realize the anticipated benefits and cost savings from combining the business of Peoples into the business of C&F without materially disrupting the existing customer relationships of Peoples or C&F. If C&F is not able to achieve these objectives, the anticipated benefits and cost savings of the merger may not be realized fully, or at all, or may take longer to realize than expected.

        C&F and Peoples have operated, and, until the completion of the merger, will continue to operate, independently. The success of the merger will depend, in part, on C&F's ability to successfully combine the businesses of C&F and Peoples. To realize these anticipated benefits, after the completion of the merger, C&F will integrate Peoples's business into its own. The integration process in the merger could result in the disruption of each party's ongoing business, inconsistencies in standards, controls, procedures, and policies that affect adversely either party's ability to maintain relationships with customers and employees or achieve the anticipated benefits of the merger. If C&F experiences difficulties with the integration process, the anticipated benefits of the merger may not be realized, fully

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or at all, or may take longer to realize than expected. As with any merger of financial institutions, there also may be disruptions that cause C&F and Peoples to lose customers or cause customers to withdraw their deposits from Peoples's or C&F's banking subsidiaries, or other unintended consequences that could have a material adverse effect on C&F's results of operations or financial condition after the merger. These integration matters could have an adverse effect on each of Peoples and C&F during this transition period and for an indeterminate period after consummation of the merger.

C&F may not be able to effectively integrate the operations of Peoples Community Bank into C&F Bank.

        The future operating performance of C&F and C&F Bank will depend, in part, on the success of the merger of Peoples Community Bank with and into C&F Bank, which is expected to occur after the merger of Peoples with and into C&F. The success of the subsidiary bank merger will, in turn, depend on a number of factors, including C&F's ability to (i) integrate the operations and branches of Peoples Community Bank and C&F Bank, (ii) retain the deposits and customers of Peoples Community Bank and C&F Bank, (iii) control the incremental increase in noninterest expense arising from the merger in a manner that enables the combined bank to improve its overall operating efficiencies, and (iv) retain and integrate the appropriate personnel of Peoples Community Bank into the operations of C&F Bank, and reduce overlapping bank personnel. The integration of Peoples Community Bank and C&F Bank following the subsidiary bank merger will require the dedication of the time and resources of the banks' management teams and may temporarily distract managements' attention from the day-to-day business of the banks. If C&F Bank is unable to successfully integrate Peoples Community Bank, C&F Bank may not be able to realize expected operating efficiencies and eliminate redundant costs.

The merger may distract management of C&F and Peoples from their other responsibilities.

        The merger and the subsidiary bank merger could cause the respective management teams of C&F and Peoples to focus their time and energy on matters related to the transaction that otherwise would be directed to their business and operations. Any such distraction on the part of either company's management could affect its ability to service existing business and develop new business and adversely affect the business and earnings of C&F or Peoples before the merger, or the business and earnings of C&F after the merger.

Termination of the merger agreement could negatively impact C&F or Peoples.

        If the merger agreement is terminated, C&F's or Peoples's business may be 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 C&F's or Peoples's common stock could decline to the extent that the current market prices reflect a market assumption that the merger will be completed. Furthermore, costs relating to the merger, such as legal, accounting and financial advisory fees, must be paid even if the merger is not completed. If the merger agreement is terminated under certain circumstances, Peoples may be required to pay to C&F a termination fee of $900,000. See "The Merger Agreement—Termination Fee" on page 68.

The fairness opinion received by Peoples in connection with the merger does not reflect changes in circumstances since the date of such opinion.

        The opinion rendered by Sandler O'Neill, financial advisor to Peoples, on August 13, 2019, was based upon information available as of such date. Such opinion has not been updated to reflect changes that may occur or may have occurred after the date on which it was delivered, including changes to the operations and prospects of C&F or Peoples, changes in general market and economic conditions or other changes. Any such changes may alter the relative value of C&F or Peoples or the prices of shares of C&F common stock or Peoples common stock by the time the merger is completed. The opinion does not speak as of the date the merger will be completed or as of any date other than

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the date of such opinion. For a description of the opinion that Peoples received from its financial advisor, please see "The Merger—Opinion of Peoples's Financial Advisor," beginning on page 38.

Peoples's directors and executive officers have interests in the merger that differ from the interests of Peoples's other shareholders.

        Peoples shareholders, in deciding how to vote on the merger proposal, should be aware that Peoples's directors and executive officers have interests in the merger that are different from, or in addition to, the interests of Peoples shareholders generally. These interests include, among other things, payments to certain of Peoples's executive officers after their respective Peoples employment agreements are terminated in connection with the merger, continued employment of certain of Peoples's executive officers with C&F following completion of the merger, and rights to indemnification and directors' and officers' liability insurance following the merger. These interests may cause directors and executive officers of Peoples to view the merger proposal differently than other Peoples shareholders view the proposal. See "The Merger—Interests of Certain Peoples Directors and Executive Officers in the Merger" beginning on page 53.

The merger agreement limits the ability of Peoples to pursue alternatives to the merger and might discourage competing offers for a higher price or premium.

        The merger agreement contains "no-shop" provisions that, subject to limited exceptions, limit the ability of Peoples to discuss, facilitate or commit to competing third party proposals to acquire all or a significant part of its company. In addition, under certain circumstances, if the merger agreement is terminated and Peoples, subject to certain restrictions, consummates a similar transaction other than the merger, Peoples must pay C&F a termination fee of $900,000. These provisions might discourage a potential competing acquirer that might have an interest in acquiring all or a significant percentage of ownership of Peoples from considering or proposing the acquisition even if it were prepared to pay consideration with a higher per share market value than that proposed in the merger. See "The Merger Agreement—Termination Fee" beginning on page 68.

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 may be completed, C&F and Peoples must obtain approvals from the Federal Reserve and the Bureau of Financial Institutions of the Virginia SCC. C&F Bank and Peoples Community Bank must obtain approval from the FDIC and the Bureau of Financial Institutions of the Virginia SCC for the subsidiary bank merger. Other approvals, waivers or consents from regulators may also be required. These regulators may impose conditions on the completion of the merger or require changes to the terms of the merger. Such conditions or changes and the process of obtaining regulatory approvals could have the effect of delaying completion of the merger and the subsidiary bank merger, imposing addition costs on the combined company or limiting the revenues of the combined company, any of which might have an adverse effect on the combined company following the merger. Furthermore, such conditions or changes may constitute, result in or be reasonably expected to result in a burdensome condition that may allow C&F to refuse to complete the merger. See "The Merger—Regulatory Approvals" beginning on page 54.

A significant delay in the completion of the merger could have a material adverse effect on C&F and Peoples as a combined company.

        The merger agreement is subject to a number of conditions that must be fulfilled in order to complete the merger. Those conditions include, among others: (1) approval of the merger agreement by the Peoples shareholders, (2) receipt of all required approvals from bank regulatory authorities and expiration of all applicable waiting periods, (3) absence of any statute, rule, regulation, judgment,

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decree, injunction or other order prohibiting the completion of the merger, and (4) effectiveness of the registration statement of which this proxy statement/prospectus is a part.

        If these conditions to the completion of the merger are not fulfilled when expected and, as a result, the completion of the merger is delayed, the diversion of management attention from pursuing other opportunities, the constraints in the merger agreement on the ability to make significant changes to each company's ongoing business during the pendency of the merger, the incurrence of additional merger-related expenses, and other market and economic factors could have a material adverse effect on the combined company's business, financial condition and results of operations.

If the number of shares of Peoples common stock for which appraisal rights are perfected equals or exceeds 10% of the outstanding shares of Peoples common stock, C&F and Peoples may not be able to complete the merger and may incur significant additional costs.

        Shareholders of Peoples are entitled to assert dissenters' appraisal rights provided by the Virginia SCA. See "The Merger—Dissenters' Appraisal Rights" beginning on page 55. If the merger is completed, a shareholder of Peoples who has complied with applicable requirements under the Virginia SCA may require C&F to pay, instead of the merger consideration, the fair value of such shareholder's dissenting shares of Peoples common stock in cash. Such fair value would be determined pursuant to the process provided by the Virginia SCA. The merger agreement contains a closing condition that can only be waived by C&F that the aggregate number of shares of Peoples common stock for which appraisal rights have been perfected under the Virginia SCA shall not represent 10% or more of the outstanding shares of Peoples common stock. C&F and Peoples cannot predict the number of shares of Peoples common stock that will constitute dissenting shares in the merger, the additional amount of cash that C&F may be required to pay following the merger with respect to dissenting shares, or the expenses that C&F and Peoples may incur in connection with addressing any assertion of dissenters' appraisal rights. If the number of dissenting shares exceeds the percentage described above, or if C&F or Peoples incurs additional costs in connection with any assertion of dissenters' appraisal rights, it could prevent the merger from being completed or have a material adverse effect on C&F or Peoples.

If outside legal counsel to C&F or Peoples cannot render a tax opinion that the merger will be treated as a "reorganization" within the meaning of Section 368(a) of the Code, the exchange ratio and cash portion of the merger consideration may be adjusted.

        If either Williams Mullen, as outside counsel to C&F, or Troutman Sanders LLP, as outside counsel to Peoples, reasonably determines that it cannot render its respective federal tax opinion that the merger will be treated as a "reorganization" within the meaning of Section 368(a) of the Code because of the continuity of interest requirements therein, then C&F, with the consent of Peoples which shall not be unreasonably withheld, has the right to increase the exchange ratio and proportionately decrease the cash component of the merger consideration by the minimum amount necessary to satisfy the requirements of Section 368(a) of the Code. As a general matter, the continuity of interest requirements in Section 368(a) of the Code require that C&F pay no more than 60% of the aggregate merger consideration in cash. Accordingly, if a sufficient number of shares of Peoples common stock constitute dissenting shares that would cause C&F to pay more than 60% of the aggregate merger consideration in cash, C&F may decide, with Peoples's consent, to increase the exchange ratio and proportionately reduce the per share cash consideration.

C&F and Peoples 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 C&F and Peoples. These uncertainties may impair C&F's and Peoples's ability to attract, retain and motivate key personnel until the merger is completed, and could cause customers and others that deal with C&F and Peoples to seek to change existing business relationships with C&F and

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Peoples. Retention of certain employees by C&F and Peoples may be challenging while the merger is pending, as certain employees may experience uncertainty about their future roles with C&F or Peoples. If key employees depart because of issues relating to the uncertainty and difficulty of integration or a desire not to remain with C&F or Peoples, C&F's or Peoples's business, or the business of the combined company following the merger, could be harmed. In addition, subject to certain exceptions, C&F and Peoples have each agreed to operate its business in the ordinary course prior to closing and refrain from taking certain specified actions until the merger occurs, which may prevent Peoples from pursuing attractive business opportunities that may arise prior to the completion of the merger. See "The Merger Agreement—Business Pending the Merger" on page 63 for a description of the restrictive covenants applicable to C&F and Peoples.

Current holders of Peoples common stock will have less influence as holders of C&F common stock after the merger.

        It is expected that, as a group, the current holders of common stock of Peoples will own approximately 5.8% of the outstanding common stock of C&F after the merger. Each current holder of Peoples common stock will own a significantly smaller percentage of C&F after the merger than they currently own of Peoples. As a result of the merger, holders of Peoples common stock will have less influence on the management and policies of C&F than they currently have on the management and policies of Peoples.

C&F is not obligated to pay cash dividends on its common stock.

        C&F is a bank holding company and, currently, its primary source of funds for paying dividends to its shareholders is dividends it receives from C&F Bank. C&F is currently paying a quarterly cash dividend to holders of its common stock at a rate of $0.37 per share. However, C&F is not obligated to pay dividends in any particular amounts or at any particular times. C&F's decision to pay dividends in the future will depend on a number of factors, including its capital, applicable governmental regulations and policies, and the availability of funds from which dividends may be paid. See "Market for Common Stock and Dividends" on page 76 and "Description of C&F Capital Stock" on page 80.

The shares of C&F common stock to be received by Peoples shareholders as a result of the merger will have different rights than shares of Peoples common stock.

        Upon completion of the merger, Peoples shareholders will become C&F shareholders and their rights as shareholders will be governed by Virginia law and the C&F articles of incorporation and bylaws. The rights associated with Peoples common stock are different from the rights associated with C&F common stock. See "Comparative Rights of Shareholders" beginning on page 82 for a discussion of the different rights associated with C&F common stock.

The trading volume of C&F's common stock has been relatively low, and market conditions and other factors may affect the value of its common stock, which may make it difficult for C&F shareholders to sell their shares at times, volumes or prices they find attractive.

        While C&F's common stock is traded on the Nasdaq Global Select Market, the shares are thinly traded and the common stock has substantially less liquidity than the average trading market for many other publicly traded financial institutions. Thinly traded stocks can be more volatile than stocks trading in a more active public market. As such, C&F's stock price could fluctuate significantly in the future, with such fluctuations being unrelated to its performance. General market declines or market volatility in the future, especially in the financial institutions sector of the economy, could adversely affect the price of C&F common stock, and the current market price may not be indicative of future market prices. Therefore, C&F shareholders may not be able to sell their shares at the volume, prices or times that they desire.

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CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

        The Private Securities Litigation Reform Act of 1995 provides a "safe harbor" for forward-looking statements to encourage companies to provide prospective information, so long as those statements are identified as forward-looking and are accompanied by meaningful cautionary statements identifying important factors that could cause actual results to differ materially from those discussed in the statement. C&F and Peoples desire to take advantage of these "safe harbor" provisions with regard to the forward-looking statements in this proxy statement/prospectus and in the documents that are included with and/or incorporated herein by reference. These forward-looking statements reflect the current views of C&F and Peoples with respect to future events and financial performance. Specifically, forward-looking statements may include:

    statements relating to the ability of C&F and Peoples to timely complete the merger and the benefits thereof, including anticipated efficiencies, opportunities, synergies and cost savings estimated to result from the merger;

    projections of revenues, expenses, income, income per share, net interest margins, asset growth, loan production, asset quality, deposit growth and other performance measures;

    statements regarding expansion of operations, including branch openings, entrance into new markets, development of products and services, and execution of strategic initiatives;

    discussions of the future state of the economy, competition, regulation, taxation, and our business strategies, subsidiaries, investment risk and policies; and

    statements preceded by, followed by or that include the words "estimate," "plan," "project," "forecast," "intend," "expect," "anticipate," "believe," "could," "seek," "target" or similar expressions.

        These forward-looking statements express the best judgment of C&F and Peoples based on currently available information and the companies believe that the expectations reflected in these forward-looking statements are reasonable.

        By their nature, however, forward-looking statements often involve assumptions about the future. Such assumptions are subject to risks and uncertainties that could cause actual results to differ materially from those described in the forward-looking statements. As such, C&F and Peoples cannot guarantee you that the expectations reflected in or implied by our forward-looking statements actually will be achieved. Actual results may differ materially from those reflected in or implied by the forward-looking statements due to, among other things, the following factors:

    the ability to obtain required regulatory and shareholder approvals and meet other closing conditions to the transaction;

    the ability to complete the proposed transaction as expected and within the expected time frame;

    disruptions to customer and employee relationships and business operations caused by the proposed transaction;

    the ability to implement integration plans associated with the transaction, which integration may be more difficult, time-consuming or costly than expected;

    the ability to achieve the cost savings and synergies contemplated by the proposed transaction within the expected time frame, or at all;

    revenues following the merger may be lower than expected;

    changes in interest rates, deposit flow, local and national economies, or market conditions;

    changes in law, regulations, accounting principles, and fiscal and monetary policies;

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    loan demand and asset quality, including values of real estate and other collateral;

    the impact of competition from traditional or new sources;

    volatility in the securities markets generally or in the market price of C&F's stock specifically; and

    the risks outlined in "Risk Factors" beginning on page 17.

        We caution you not to place undue reliance on any forward-looking statements, which speak only as of the date of this proxy statement/prospectus or, in the case of a document included with and/or incorporated herein by reference, as of the date of that document. Except as required by law, neither C&F nor Peoples undertakes any obligation to publicly update or release any revisions to these forward-looking statements to reflect any events or circumstances after the date hereof or to reflect the occurrence of unanticipated events.

        Additional factors that could cause actual results to differ materially from those expressed in the forward-looking statements are discussed in reports filed by C&F with the SEC. See "Where You Can Find More Information" beginning on page 91 for a list of the documents incorporated herein by reference.

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THE SPECIAL MEETING

Date, Place and Time

        This proxy statement/prospectus is first being mailed on or about [    ·    ], 2019 to Peoples shareholders who held shares of Peoples common stock on the record date for the special meeting of shareholders. This proxy statement/prospectus is accompanied by the notice of the special meeting and a form of proxy that is solicited by the board of directors of Peoples for use at the special meeting to be held at 11:00 a.m. local time, on December 11, 2019 at The Dining Room at Stratford Hall, located at 483 Great House Road, Stratford, Virginia 22558, and at any adjournments of that meeting.

Purposes of the Special Meeting

        At the special meeting, the shareholders of Peoples will be asked:

    to approve the merger proposal as more fully described in this proxy statement/prospectus; and

    to approve the adjournment proposal as more fully described in this proxy statement/prospectus.

Recommendation of the Peoples Board of Directors

        The Peoples board of directors believes that the proposed merger with C&F is fair to and is in the best interests of Peoples and its shareholders and unanimously recommends that Peoples shareholders vote "FOR" each of the proposals that will be presented at the special meeting as described in this proxy statement/prospectus.

Record Date and Voting Rights; Quorum

        The Peoples board of directors has fixed the close of business on October 10, 2019 as the record date for determining the shareholders of Peoples entitled to notice of and to vote at the special meeting or any adjournments thereof. Accordingly, you are only entitled to notice of and to vote at the special meeting if you were a record holder of Peoples common stock at the close of business on the record date. At that date, 391,450 shares of Peoples common stock were outstanding and entitled to vote.

        To have a quorum that permits Peoples to conduct business at the special meeting, we require the presence, whether in person or by proxy, of the holders of Peoples's common stock representing a majority of the shares of common stock outstanding on the record date. You are entitled to one vote for each outstanding share of Peoples common stock you held as of the close of business on the record date.

        Holders of shares of Peoples common stock present in person at the special meeting but not voting, and shares of the common stock for which proxy cards are received indicating that their holders have abstained, will be counted as present at the special meeting for purposes of determining whether there is a quorum for transacting business. Shares held in "street name" that have been designated by brokers on proxies as not voted will not be counted as votes cast for or against any proposal. These broker non-votes will, however, be counted for purposes of determining whether a quorum exists.

Votes Required

        Vote Required for Approval of the Merger Proposal.    The approval of the merger proposal requires the affirmative vote of more than two-thirds of the shares of Peoples common stock outstanding on the record date for the special meeting.

        Failures to vote, abstentions and broker non-votes will not count as votes cast. Because, however, approval of the merger proposal requires the affirmative vote of more than two-thirds of the shares of

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Peoples common stock outstanding on the record date, failures to vote, abstentions and broker non-votes will have the same effect as votes against the merger proposal.

        Vote Required for Approval of the Adjournment Proposal.    The approval of the adjournment proposal requires the affirmative vote of a majority of the shares of Peoples common stock voted on the proposal, whether or not a quorum is present.

        Failures to vote, abstentions and broker non-votes will not count as votes cast and will have no effect for purposes of determining whether the adjournment proposal has been approved.

Stock Ownership of Peoples Executive Officers and Directors

        C&F has entered into a support agreement with each director of Peoples, in his or her capacity as a shareholder of Peoples, regarding the voting of shares of Peoples common stock in connection with the merger. Pursuant to the support agreements, each of Peoples's directors has agreed, among other things and subject to several conditions and exceptions, to vote all shares of Peoples common stock owned beneficially or of record by such director, and over which such director has sole rights of voting and disposition, in favor of the merger proposal. As of the record date, directors and executive officers of Peoples were entitled to vote approximately 31,201 shares of Peoples common stock at the special meeting, or approximately 7.97% of the total voting power of shares of Peoples common stock entitled to vote at the special meeting, of which approximately 30,581 or approximately 7.81% of the total voting power of shares of Peoples common stock entitled to vote at the special meeting are subject to a support agreement.

        For more information about the support agreements, see "The Merger Agreement—Support and Non-Competition Agreements" on page 70.

Voting at the Special Meeting

        Record Holders.    If your shares of Peoples common stock are held of record in your name, your shares can be voted at the special meeting in any of the following ways:

    By Mail.  You can vote your shares by completing and signing the enclosed proxy card and returning it in the enclosed postage-paid envelope. If you complete, sign and return the proxy card, you will be appointing the "proxies" named in the proxy card to vote your shares for you at the special meeting. The authority you will be giving the proxies is described in the proxy card. When your proxy card is returned properly executed, the shares of Peoples common stock represented by it will be voted at the special meeting in accordance with the instructions contained in the proxy card. If proxy cards are returned properly executed without an indication as to how the proxies should vote, the Peoples common stock represented by each such proxy card will be voted (i) "FOR" the merger proposal, and (ii) "FOR" the adjournment proposal.

    By Telephone.  You can appoint the proxies to vote your shares by calling 1-800-PROXIES on a touch-tone phone and following the recorded instructions. The authority you will be giving the proxies is described in the proxy card.

    Via the Internet.  You can appoint the proxies to vote your shares by going to the Internet website (www.voteproxy.com)and following the instructions on such site. The authority you will be giving the proxies is described in the proxy card.

    In Person.  You can attend the special meeting and vote in person. A ballot will be provided for your use at the meeting.

        Your vote is very important. Whether or not you plan to attend the special meeting, please take the time to vote by completing, signing and returning the enclosed proxy card or by voting via the Internet or telephone.

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        Shares Held in "Street Name."    Only the record holders of shares of Peoples common stock, or their appointed proxies, may vote those shares. As a result, if your shares of Peoples common stock are held for you in "street name" by a broker or other nominee, such as a bank or custodian, then only your broker or nominee (i.e., the record holder) may vote them for you, or appoint the proxies to vote them for you, unless you previously have made arrangements for your broker or nominee to assign its voting rights to you or for you to be recognized as the person entitled to vote your shares. You will need to follow the directions your broker or nominee provides you and give it instructions as to how it should vote your shares by following the instructions you received from your broker or nominee with your copy of this proxy statement/prospectus. Brokers and other nominees who hold shares in "street name" for their clients typically have the discretionary authority to vote those shares on "routine" proposals when they have not received instructions from beneficial owners of the shares. However, they may not vote those shares on non-routine matters, such as the proposals that will be presented at the special meeting, unless their clients give them voting instructions. To ensure that your shares are represented at the special meeting and voted in the manner you desire, it is important that you instruct your broker or nominee as to how it should vote your shares.

        If your shares are held in "street name" and you wish to vote them in person at the special meeting, you must obtain a proxy, executed in your favor, from the holder of record.

Changes of Votes and Revocation of Proxies

        Record Holders.    If you are the record holder of shares of Peoples common stock and you sign and return a proxy card or vote via the telephone or Internet and you later wish to revoke the authority or change the voting instructions you gave the proxies, you can do so at any time before the voting takes place at the special meeting by taking the appropriate action described below.

        To change the voting instructions you gave the proxies, you can complete, sign and submit a new proxy card, dated after the date of your original proxy card, which contains your new instructions, and submit it so that it is received before the special meeting or, if hand delivered, before the voting takes place at the special meeting. You may also change the voting instructions you gave the proxies by timely submitting a later proxy via telephone or the Internet. The proxies will follow the last voting instructions received from you before the special meeting.

        To revoke your proxy card:

    you can give Peoples's corporate secretary a written notice, before the special meeting or, if hand delivered, before the voting takes place at the special meeting, that you want to revoke your proxy card; or

    you can attend the special meeting and vote in person or notify Peoples's corporate secretary, before the voting takes place, that you want to revoke your proxy card. Simply attending the special meeting alone, without voting in person or notifying Peoples's corporate secretary, will not revoke your proxy card.

        If you submit your new proxy card or notice of revocation by mail, it should be addressed to Peoples's corporate secretary at Peoples Bankshares, Incorporated, 15960 Kings Highway, PO Box 306, Montross, Virginia 22520, Attention: Corporate Secretary, and must be received no later than the beginning of the special meeting or, if the special meeting is adjourned, before the adjourned meeting is actually held. If hand delivered, your new proxy card or notice of revocation must be received by Peoples's corporate secretary before the voting takes place at the special meeting or at any adjourned meeting.

        If you need assistance in changing or revoking your proxy, please contact Peoples's corporate secretary by calling (804) 493-8031 or by writing to Peoples Bankshares, Incorporated, 15960 Kings

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Highway, PO Box 306, Montross, Virginia 22520, Attention: Corporate Secretary. You may also contact Regan & Associates, Inc., Peoples's proxy solicitor, at (800) 737-3426.

        Shares Held in "Street Name."    If your shares are held in "street name" and you want to change or revoke voting instructions you have given to the record holder of your shares, you must follow the directions given by your bank, broker, custodian or nominee.

Solicitation of Proxies

        This solicitation is made on behalf of the Peoples board of directors, and Peoples will pay the costs of soliciting and obtaining proxies, including the cost of reimbursing banks and brokers for forwarding proxy materials to shareholders and gathering voting instructions. Proxies may be solicited, without extra compensation, by Peoples's officers and employees personally and by mail, telephone, facsimile or other means. Peoples has also retained Regan & Associates, Inc., a proxy solicitation firm, to assist in the solicitation of proxies for a fee not to exceed $3,500, including expenses.

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PROPOSALS TO BE CONSIDERED AT THE SPECIAL MEETING

Approval of the Merger Proposal (Proposal No. 1)

        At the special meeting, shareholders of Peoples will be asked to approve the merger proposal providing for the merger of Peoples with and into C&F. Shareholders of Peoples should read this proxy statement/prospectus carefully and in its entirety, including the appendices, for more detailed information concerning the merger agreement and the merger. A copy of the merger agreement is attached to this proxy statement/prospectus as Appendix A.

        After careful consideration, the Peoples board of directors, by a unanimous vote of all directors, approved the merger agreement and the merger, and determined it to be advisable and in the best interests of Peoples and the shareholders of Peoples. See "The Merger—Peoples's Reasons for the Merger; Recommendation of the Peoples Board of Directors" included elsewhere in this proxy statement/prospectus for a more detailed discussion of the Peoples board of directors' recommendation.

        The Peoples board of directors unanimously recommends that Peoples shareholders vote "FOR" the merger proposal.

Approval of the Adjournment Proposal (Proposal No. 2)

        If at the special meeting there are not sufficient votes to approve the merger proposal, the meeting may be adjourned to a later date or dates, if necessary or appropriate, to permit further solicitation of proxies to approve the merger proposal. In that event, Peoples shareholders will be asked to vote on the adjournment proposal and will not be asked to vote on the merger proposal at the special meeting.

        In order to allow proxies that have been received by Peoples at the time of the special meeting to be voted for the adjournment proposal, Peoples is submitting the adjournment proposal to its shareholders as a separate matter for their consideration. This proposal asks Peoples shareholders to authorize the holder of any proxy solicited by the Peoples board of directors on a discretionary basis to vote in favor of adjourning the special meeting to another time and place for the purpose of soliciting additional proxies, including the solicitation of proxies from Peoples shareholders who have previously voted.

        If it is necessary to adjourn the special meeting, then, unless the meeting will have been adjourned for a total of more than 120 days, no notice of such adjourned meeting is required to be given to shareholders, other than an announcement at the special meeting of the place, date and time to which the special meeting is adjourned. Even if a quorum is not present, shareholders who are represented at a meeting may approve an adjournment of the meeting.

        The Peoples board of directors unanimously recommends that Peoples shareholders vote "FOR" the adjournment proposal.

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THE MERGER

        The following is a discussion of the merger. This summary may not contain all of the information about the merger that is important to you. The discussion is subject to and is qualified in its entirety by reference to the merger agreement, which is attached as Appendix A to this proxy statement/prospectus and incorporated herein by reference. We urge you to read carefully this proxy statement/prospectus, including the merger agreement attached as Appendix A, for a more complete understanding of the merger.

General

        The C&F board of directors and the Peoples board of directors have each approved the merger agreement and the merger, which provides for the merger of Peoples with and into C&F, with C&F being the surviving company in the merger.

        Pursuant to the terms of the merger agreement, as a result of the merger, each share of Peoples common stock issued and outstanding before the effective time of merger (except for any shares of Peoples common stock owned by C&F and any dissenting shares) will be converted into the right to receive:

    $27.00 in cash; and

    0.5366 shares of C&F common stock.

        The exchange ratio of 0.5366 shares of C&F common stock will not be adjusted to reflect stock price changes prior to the effective time of the merger. No fractional shares will be issued; instead cash will be paid for fractional shares.

        Based on the number of shares of Peoples common stock outstanding as of June 30, 2019, C&F expects to issue 210,052 shares of common stock in the aggregate upon completion of the merger. At the completion of the merger, it is expected that there will be issued and outstanding approximately 3,648,807 shares of C&F common stock, with current C&F shareholders owning approximately 94.2% of C&F's outstanding common stock, on a fully diluted basis, and former holders of Peoples common stock owning approximately 5.8% of C&F's outstanding common stock, on a fully diluted basis.

        If either Williams Mullen, as outside counsel to C&F, or Troutman Sanders LLP, as outside counsel to Peoples, reasonably determines that it cannot render its respective federal tax opinion that the merger will be treated as a "reorganization" within the meaning of Section 368(a) of the Code because of the continuity of interest requirements therein, then C&F, with the consent of Peoples which shall not be unreasonably withheld, has the right to increase the exchange ratio and proportionately decrease the per share cash consideration by the minimum amount necessary to satisfy the requirements of Section 368(a) of the Code.

        After the merger, it is expected that Peoples Community Bank, the wholly-owned bank subsidiary of Peoples, will merge with and into C&F Bank, the wholly-owned bank subsidiary of C&F. C&F Bank will be the surviving bank in the subsidiary bank merger.

Background of the Merger

        The merger agreement is the result of arms-length negotiations between representatives of C&F and Peoples, during which the parties consulted their respective legal and financial advisors. The following is a brief discussion of the background of these negotiations.

        C&F's board of directors and management have, from time to time, engaged in long-term strategic reviews and considered ways to enhance shareholder value and C&F's performance and prospects in light of industry and market conditions, including through potential strategic transactions such as an acquisition of another financial institution.

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        Similarly, as part of the ongoing evaluation of its business, Peoples periodically has reviewed and assessed various strategic alternatives to enhance shareholder value, including whether it should remain independent, raise capital to support future growth, or combine with a larger financial institution. Beginning in 2017, in light of excess liquidity and capital held on Peoples's balance sheet and recent trends in merger and acquisition activity in the banking market, Peoples began to consider ways to increase earnings as a way to enhance shareholder value. One method involved the purchase of loan portfolios and loan participations in brokered transactions. An attractive loan product for Peoples involved the purchase of medical student loan portfolios with an aggregate principal value of approximately $7 million, the principal and interest of which were backed by surety bonds issued by Reliamax Surety Co. ("Reliamax"). Unexpectedly, Reliamax was declared insolvent in June 2018, leading to a deterioration in the credit quality of the loan portfolios and unanticipated losses. Peoples immediately increased the frequency and depth of credit quality monitoring and management efforts and worked with its federal and state banking regulators to conservatively reserve against credit losses in these portfolios. As of March 31, 2019, Peoples had recorded general and specific allowances for loan losses in these portfolios of $4,095,000 and had recorded related provisions for loan losses of $200,000 from January 1, 2019 through the first quarter of 2019.

        Beginning in late 2018, the Peoples board of directors and executive management began meeting to review strategic alternatives to address the performance of the purchased student loan portfolios. These discussions merged with more general discussions regarding strategic alternatives to enhance shareholder value. In addition, throughout early 2019, Peoples's Chairman of the Board, George R. Sisson, III, its President and Chief Executive Officer, Robert K. Bailey, III, and its Chief Financial Officer, Zirkle Blakey, III, met several times to informally discuss these and other considerations, including the current banking environment in Eastern and Central Virginia, recent transactions in the banking and financial services industry, Peoples's current financial and regulatory health, and possible strategic transactions available to Peoples to enhance shareholder value.

        On February 28, 2019, the Peoples board of directors held a regular meeting at which Mr. Bailey updated the full board regarding the bank's overall performance and financial condition, including the acquired loan portfolios and other factors significant to the bank's performance and profitability, including the goal to enhance shareholder value. Mr. Bailey outlined several strategic options for Peoples, including a sale or merger and a potential capital raise. The Peoples board of directors determined to interview investment banking firms regarding the complete range of strategic options available to the company.

        On April 4, 2019, the Peoples board of directors held a special meeting at which representatives from Sandler O'Neill presented an analysis of several potential merger and acquisition strategic partners as well as certain capital raising alternatives. The Peoples board of directors asked the representatives of Sandler O'Neill to provide more information on potential merger and acquisition transactions, but did not engage Sandler O'Neill at this time. Thereafter, at the direction of the Peoples board of directors, Messrs. Bailey and Blakey continued discussions with representatives of Sandler O'Neill about various alternatives to maintain Peoples's competitiveness and increase shareholder value.

        By a letter dated April 4, 2019, Peoples received an unsolicited indication of interest from a larger peer bank holding company with banking operations adjacent to Peoples (the "Peer Company"). Peoples's management shared the letter with legal counsel at Troutman Sanders LLP ("Troutman") and relayed the key terms to representatives of Sandler O'Neill.

        On April 16, 2019, the Peoples board of directors held a regular meeting at which representatives from Sandler O'Neill and Troutman joined via conference call to discuss the variables, benefits, and costs of the sale of Peoples and a possible capital raise, as well as the Peer Company's indication of interest. Representatives of Troutman discussed applicable fiduciary duties and standards of director conduct under Virginia law with the Peoples board of directors, as well as federal and state securities

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laws. On April 17, 2019 the Peoples board of directors engaged Sandler O'Neill to act as an independent financial advisor to the Peoples Board of directors in connection with a potential business combination and to assist the Peoples board of directors in evaluating the Peer Company's indication of interest from a financial point of view. With the consent of the board, Mr. Bailey began discussions with the Peer Company regarding a potential business combination.

        On April 19, 2019, the Peoples board of directors participated in a telephone conference call during which representatives from Sandler O'Neill and Troutman presented their views on the process for exploring a merger that would create value for Peoples's shareholders. The Peoples board of directors authorized Mr. Blakey to execute a mutual confidentiality agreement with the Peer Company and directed representatives of Troutman and Sandler O'Neill to investigate legal and transactional concerns presented by a potential merger with the Peer Company.

        On April 23, 2019, the Peoples board of directors held a special meeting at which representatives from Sandler O'Neill and Troutman participated by telephone to discuss concerns related to the regulatory approval of a merger with the Peer Company. As a result of this discussion, the Peoples board of directors asked representatives of Sandler O'Neill to identify and analyze other entities that may have the interest and financial ability to acquire Peoples.

        Throughout the remainder of April 2019 and early May 2019, Messrs. Bailey and Blakey conferred with representatives of Sandler O'Neill and Troutman regarding a possible merger of Peoples with the Peer Company. On May 9, 2019, Messrs. Bailey and Blakey met with representatives of the Peer Company to discuss a potential merger and concerns related to the regulatory approval process. As a result of that meeting, Messrs. Bailey and Blakey agreed to allow the Peer Company additional time to consider those issues.

        On May 21, 2019, the Peoples board of directors held a regular meeting at which representatives of Sandler O'Neill and Troutman participated by telephone. In light of the potential for heightened regulatory scrutiny during the regulatory approval process of a merger involving the Peer Company, the Peoples board of directors authorized representatives of Sandler O'Neill to solicit other financial institutions regarding a potential merger with Peoples. The Peoples board of directors also instructed bank management to complete a confidential information memorandum and assemble diligence materials for posting to a virtual data room. Subsequently, from late May 2019 through June 2019, representatives of Sandler O'Neill contacted 37 financial institutions to discuss their interest in a merger with Peoples. Of those contacted, 22 signed a non-disclosure agreement in order to access the data room. C&F signed a non-disclosure agreement on May 22, 2019 and on May 28, 2019 received the confidential information memorandum and was granted access to the electronic data room. On June 11, 2019, Peoples's management had a conference call with representatives of Sandler O'Neill and Troutman to discuss the parties, the diligence review process, and the prospects for a successful merger.

        On June 13, 2019, at a regular meeting of the C&F board of directors, senior management discussed with the board the outreach from Sandler O'Neill regarding C&F's interest in a possible merger with Peoples. Senior management shared information about Peoples that it had gathered during its preliminary due diligence review and, together with representatives of Keefe, Bruyette & Woods, Inc. ("KBW"), C&F's financial advisor, discussed the financial considerations related to the potential transaction. Following a discussion of Peoples's business and various aspects of the transaction, the C&F board authorized management to submit to Sandler O'Neill a preliminary non-binding indication of interest, which was submitted on June 19, 2019.

        On June 18 and 19, 2019, Peoples received letters of intent from five of the 22 financial institutions that signed a non-disclosure agreement. C&F and the Peer Company were among the five interested parties. Each of the five letters of intent presented a range of values per share, subject to further due diligence.

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        On June 20, 2019, the Peoples board of directors held a regular meeting at which representatives of Sandler O'Neill and Troutman participated via telephone to discuss the five letters of intent. Representatives of Sandler O'Neill assisted the Peoples board of directors in analyzing the five letters from a financial point of view and facilitated discussions regarding whether the parties would be a good fit for a strategic transaction with Peoples.

        On June 24, 2019, at a special meeting of the Peoples board of directors attended by representatives from Troutman and Sandler O'Neill, the Peoples board of directors engaged in a meaningful discussion of the financial basis of each of the five letters and the prospect of a merger with each of the interested parties. Based on the presentation by representatives of Sandler O'Neill and the discussion among the directors, the Peoples board of directors authorized representatives of Sandler O'Neill to invite four of the five parties to participate in a second round of discussions, to include further due diligence, loan review, and in-person meetings. C&F was one of the four parties chosen to participate in the second round. Based on the comparative analysis of the various offers and the likelihood of heightened scrutiny during the regulatory approval process, the Peoples board of directors determined not to pursue further discussions with the Peer Company. Shortly thereafter, one of the parties invited to participate in the second round withdrew from the process for reasons unrelated to Peoples.

        From the end of June 2019 through mid-July 2019, representatives of Sandler O'Neill continued discussions with the three remaining interested parties. Executive management of Peoples conducted in-person meetings with executive management from each of the three parties, at which the parties discussed, among other things: (i) each other's respective background and current business operations; (ii) the variables, costs, and benefits of combining their respective banking operations and personnel; and (iii) the likelihood for a successful merger transaction process from a legal, regulatory, and financial outlook.

        On July 19, 2019, at a special meeting of the C&F board of directors, senior management lead a discussion regarding Peoples, the results of the due diligence performed to date, and the advisability of the potential merger. Representatives of KBW assisted the board with its review of the financial aspects of the merger. The board debated certain perceived positive and negative considerations about the transaction and identified the terms of a proposal that it believed would result in a positive outcome for C&F and its shareholders. Following this discussion, the board authorized management to submit a second non-binding indication of interest to Peoples.

        On July 22, 2019, the three parties each submitted a second round indication of interest with revised bids. The indications of interest presented a range of values per share of Peoples common stock, including all cash and mixed stock-and-cash consideration offers, each subject to further due diligence.

        On July 25, 2019, the Peoples board of directors held a regular meeting at which representatives from Sandler O'Neill and Troutman participated to discuss the second round bids. Representatives from Sandler O'Neill reported on the current environment for a merger with each of the three parties, including key modeling assumptions, estimated costs, and financial analyses. Representatives of Sandler O'Neill noted the process resulted in two competitive bids and one non-competitive bid. With respect to the two competitive bids, C&F submitted a bid with an implied value of $54.00 per share of Peoples's common stock, and an out-of-market publicly-traded bank holding company submitted a bid with an implied value of $52.00 per share of Peoples common stock. Representatives of Sandler O'Neill discussed their comparison of the competitive proposals and the two bidders, which focused on distinguishing terms between the respective bids, and responded to questions from the Peoples board of directors regarding its analysis. Representatives from Troutman advised the Peoples board of directors on aspects of the two competitive bids, including the merger consideration, financial performance and dividend history, market areas and branch networks, select legal terms in the bids, and the potential

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impact on Peoples's shareholders, employees, communities, and customers. Representatives of Sandler O'Neill and Troutman also advised the Peoples board of directors on market trends in recent bank merger transactions, the anticipated timeline for negotiating a transaction with each bidder, and a preliminary compensation and benefits analysis for key Peoples executives.

        After detailed discussion of the proposals from C&F and the out-of-market bank holding company, including extensive deliberations regarding Peoples's financial condition, the impact to Peoples's operations during the merger transaction process, and the anticipated benefits for Peoples's shareholders, the Peoples board of directors determined that it was in the best interests of Peoples and its shareholders to pursue the proposal received from C&F. By a unanimous vote, the Peoples board of directors authorized Mr. Bailey to perform additional due diligence related to the merger and to execute a non-binding letter of intent with C&F and directed Peoples's management and advisors to negotiate a definitive agreement for the merger of Peoples with and into C&F. The Peoples board of directors further directed representatives of Sandler O'Neill to communicate Peoples's decision to the other participants in the second round and directed Troutman to contact representatives of Williams Mullen, legal counsel to C&F.

        Thereafter, Peoples and C&F pursued further discussions concerning a potential merger. In connection therewith, and continuing through execution of the definitive agreement, C&F and Peoples conducted extensive business, legal, and financial due diligence investigations. Throughout this period, Peoples and C&F each updated its electronic data room for use by the other party in connection with the ongoing due diligence process. Each party prepared disclosure letters based on such diligence investigations.

        On July 29, 2019, Messrs. Bailey and Blakey met with executive management of C&F at C&F's principal office in Toano, Virginia, to discuss the terms of a potential definitive agreement. This meeting included, among other things, discussion of how the respective organizations' operations, personnel, and properties might be integrated and potential severance compensation for displaced Peoples employees. Also on July 29, 2019, representatives of C&F and a third-party loan review firm engaged by C&F began a detailed, onsite review of Peoples's loan portfolio, which was completed on August 6, 2019.

        On July 31, 2019, representatives of Williams Mullen delivered an initial draft of the merger agreement, including ancillary support agreements for each of Peoples's directors, to representatives of Troutman. Over the next several days, representatives of Troutman reviewed and discussed the merger agreement with Peoples's management and representatives of Sandler O'Neill. On August 5, 2019, Troutman delivered comments on the draft merger agreement and related documents to representatives of Williams Mullen.

        From August 5 through August 12, 2019, C&F and Peoples, with the assistance of their respective financial advisors and legal counsel, negotiated the terms of the merger agreement and related documents, including benefits and compensation matters related to Messrs. Bailey and Blakey, as well as various matters related to the proposed combination of C&F and Peoples, additional due diligence, and preparation of the parties' disclosure letters.

        On August 7, 2019, representatives of Sandler O'Neill and Messrs. Bailey and Blakey participated in a reverse due diligence call with representatives of C&F and KBW to discuss financial and operational aspects of C&F including a further discussion of C&F's business lines.

        On August 13, 2019, the C&F board of directors convened a special meeting to consider the proposed merger and the merger agreement. The board and representatives of KBW discussed financial aspects of the transaction. Representatives of Williams Mullen advised the C&F board of directors regarding their fiduciary duties, the legal structure and terms of the proposed transaction, and the proposed merger agreement, and addressed other matters related to the merger and advised the board

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generally regarding the merger. After detailed discussion and careful deliberation, the C&F board of directors unanimously (i) determined that the merger agreement and the transactions contemplated thereby were advisable and in their shareholders' best interests, and (ii) approved and adopted the merger agreement and approved the merger.

        Also on August 13, 2019, the Peoples board of directors held a special meeting to consider the terms of the proposed merger with C&F. At the meeting, representatives of Sandler O'Neill reviewed and discussed with the Peoples board of directors its financial analyses of Peoples, C&F, and the proposed merger. Sandler O'Neill rendered its oral opinion to the Peoples board of directors, which was subsequently confirmed in writing by delivery of Sandler O'Neill's written opinion dated August 13, 2019, to the effect that, as of August 13, 2019 and subject to the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken by Sandler O'Neill, the merger consideration in the proposed merger was fair, from a financial point of view, to the holders of Peoples common stock. Representatives of Troutman reviewed the final negotiated terms and conditions of the proposed merger agreement, related transaction documents (including the support agreements with directors of Peoples and the parties' disclosure letters), and reviewed with the Peoples board of directors the legal standards applicable to its decisions and actions with respect to the proposed merger. After considering the proposed terms of the merger agreement and other transaction documents and its discussions with Peoples's financial and legal advisors, and taking into consideration the matters discussed during meetings of the Peoples board of directors, including the factors described below under "—Peoples's Reasons for the Merger; Recommendation of the Peoples Board of Directors," the Peoples board of directors unanimously (i) approved and adopted the merger agreement, (ii) determined that the merger, the merger agreement and the transactions contemplated by the merger agreement were in the best interests of Peoples and its shareholders, and (iii) determined to recommend that the Peoples shareholders approve the merger agreement and the transactions contemplated thereby.

        On August 13, 2019, C&F and Peoples executed the definitive merger agreement. After the closing of financial markets on August 13, 2019, C&F and Peoples issued a press release publicly announcing the merger.

Peoples's Reasons for the Merger; Recommendation of the Peoples Board of Directors

        After extensive review and discussion, Peoples's board of directors, at a meeting held on August 13, 2019, unanimously determined that the merger agreement is in the best interests of Peoples and its shareholders. Accordingly, Peoples's board of directors adopted and approved the merger agreement and unanimously recommends that Peoples shareholders vote "FOR" the approval of the merger proposal and "FOR" the approval of the adjournment proposal.

        In reaching its decision to adopt and approve the merger agreement and to recommend that its shareholders approve the merger agreement, the Peoples board of directors consulted with Peoples management, as well as its financial and legal advisors, and considered a number of factors, including, without limitation, the following principal factors:

    a review of the prospects, challenges and risks of Peoples remaining independent, including management by Peoples of certain of its purchased loan portfolios, versus merging with C&F given the current and prospective environment in the financial services industry, including national and local economic conditions, competition and consolidation in the financial services industry, and the regulatory and compliance environment;

    the ability of Peoples's shareholders to benefit from the combined company's potential growth and stock appreciation, and the expectation that the combined company will have superior future earnings and prospects compared to Peoples's earnings and prospects on an independent basis;

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    the value of C&F common stock and information concerning the financial performance and condition, business operations, capital levels, asset quality, loan portfolio breakdown, and prospects of C&F, taking into account the results of Peoples's due diligence investigation of C&F;

    the strength of C&F's management and board of directors;

    the expected cash dividend payments to be received by Peoples's shareholders, as shareholders of C&F following the merger, due to the quarterly cash dividend paid by C&F (currently $0.37 per common share), although C&F has no obligation to pay dividends in any particular amounts or at any particular times;

    the financial and other terms of the merger, including that Peoples shareholders will receive C&F common stock for a portion of their shares of Peoples common stock, enabling them to participate in any growth opportunities of the combined company;

    Peoples's understanding of the current and prospective environment in which Peoples and C&F operate, including local economic conditions and the competitive environment for financial institutions generally;

    the advantages of being part of a larger entity, including the expectation of cost savings and operating efficiencies and the ability of a larger institution to compete in the banking environment and to leverage overhead costs, including the cost of financial technology;

    that C&F common stock is traded on the Nasdaq Global Select Market and has substantially greater liquidity than Peoples common stock;

    the compatibility of Peoples's business, operations and culture with those of C&F;

    the possible effects of the proposed merger on Peoples's employees and customers, including the benefits to Peoples's customers through enhancements in bank products and services, higher lending limits and greater financial resources;

    Peoples's and C&F's similar commitments to their communities;

    the regulatory and other approvals required in connection with the merger and the expectation that the approvals will be received in a timely manner and without imposition of unacceptable conditions; and

    the financial analyses delivered to Peoples's board of directors by representatives of Sandler O'Neill as well as the opinion of Sandler O'Neill rendered to the Peoples board of directors on August 13, 2019 to the effect that, as of such date and subject to the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken by Sandler O'Neill as set forth in the opinion, the merger consideration to be received by the holders of Peoples common stock was fair, from a financial point of view, to such holders.

        The Peoples board of directors also considered the risks and potential negative factors outlined below, but concluded that the anticipated benefits of combining with C&F were likely to outweigh substantially these risks and factors. These risks included:

    that the exchange ratio for the stock component of the merger consideration is fixed, so if the market price of C&F common stock is lower at the time of consummation of the merger than at the date of this proxy statement/prospectus or the date of the Peoples special meeting of shareholders, the economic value of the merger consideration to be received by holders of Peoples common stock would be lower;

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    that certain of Peoples's officers have interests in the merger that are in addition to their interests generally as Peoples shareholders, which have the potential to influence such officers' views and actions in connection with the merger;

    the challenges of integrating Peoples's business, operations and employees with those of C&F;

    the risk that the benefits and cost savings sought in the merger would not be fully realized;

    the costs associated with the merger and the risk that the merger would not be consummated;

    the possibility that regulatory agencies may not approve the merger or may impose terms and conditions on their approvals that adversely affect the business and financial results of the combined company;

    the effect of the public announcement of the merger on Peoples's customer relationships, its ability to retain employees and the potential for disruption of Peoples's ongoing business;

    the potential risk of diverting management attention and resources from the operation of Peoples's business and towards the completion of the merger;

    that while the merger is pending, Peoples will be subject to restrictions on how it conducts business that could delay or prevent Peoples from pursuing business opportunities or preclude it from taking actions that would be advisable if it was to remain independent;

    the termination fee payable, under certain circumstances, by Peoples to C&F, including the risk that the termination fee might discourage third parties from offering to acquire Peoples by increasing the cost of a third party acquisition; and

    the possibility of litigation challenging the merger, and its belief that any such litigation would be without merit.

        The foregoing discussion of the information and factors considered by the Peoples board of directors is not exhaustive, but includes the principal factors that the board of directors considered and discussed in approving and recommending the merger. In view of the wide variety of factors considered and discussed by the Peoples board of directors in connection with its evaluation of the merger and the complexity of these factors, the board of directors did not quantify, rank or assign any relative or specific weight to the foregoing factors. Rather, it considered all of the factors as a whole. The board of directors discussed the foregoing factors, including asking questions of Peoples's management and legal and financial advisors, and reached general consensus that the merger was in the best interests of Peoples and its shareholders. In considering the foregoing factors, individual directors may have assigned different weights to different factors. The board of directors did not undertake to make any specific determination as to whether any factor, or particular aspect of any factor, supported or did not support its ultimate decision to approve the merger agreement.

        The foregoing explanation of Peoples's board of directors' reasoning and all other information presented in this section is forward-looking in nature and, therefore, should be read in light of the factors discussed in the section entitled "Cautionary Statement Regarding Forward-Looking Statements."

C&F's Reasons for the Merger

        After careful consideration, C&F's board of directors, at a meeting held on August 13, 2019, unanimously determined that the merger agreement is in the best interests of C&F and its shareholders. Accordingly, C&F's board of directors adopted and approved the merger agreement.

        In reaching its decision to adopt and approve the merger agreement, C&F's board of directors evaluated the merger and the merger agreement in consultation with C&F management, as well as

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C&F's financial and legal advisors, and considered a number of factors, including, but not limited to, the following principal factors:

    Peoples's financial condition, earnings, business, operations, and prospects, taking into account the results of C&F's due diligence investigation of Peoples;

    the nature of Peoples's business culture, its customer-focused approach, and its commitment to the communities in which it operates;

    the longevity of Peoples's customer base;

    the composition of the branch networks of C&F and Peoples in contiguous market areas and that the merger will provide C&F access to new markets in the Northern Neck area of Virginia and in Fredericksburg, Virginia;

    C&F's expectation that the merger with Peoples will increase the portion of C&F's earnings that is derived from traditional retail banking activities;

    C&F's expectations and analyses of cost synergies, earnings accretion, tangible book value dilution, earn back period for tangible book value dilution and internal rate of return;

    the strong capital position maintained by C&F prior to the merger and the anticipated strong capital position for the combined entity following the merger;

    the market for alternative merger or acquisition transactions in the financial services industry and the likelihood and timing of other material strategic transactions;

    the current and prospective environment in the financial services industry, including national and local economic conditions, competition and consolidation in the industry;

    the regulatory and other approvals required in connection with the merger and the expectation that the approvals will be received in a timely manner and without imposition of unacceptable conditions; and

    the financial and other terms of the transaction, including that the merger consideration is a mix of cash and stock, expected tax treatment, deal protection and termination fee provisions.

        The C&F board of directors also considered the risks and potential negative factors outlined below, but concluded that the anticipated benefits of acquiring Peoples were likely to outweigh substantially these risks and factors. These risks included:

    the potential risks associated with achieving anticipated cost synergies and savings and successfully integrating Peoples's business, operations and workforce with those of C&F , including the execution risk of data system conversion and the possible negative effect on customer relationships;

    the potential risks of diverting management attention and resources from the operation of C&F's business and towards the completion of the merger;

    expenses to be incurred in working toward completion of the merger; and

    the risks of the type and nature described under the "Risk Factors" section of this proxy statement/prospectus and described in the filings of C&F that are incorporated in this proxy statement/prospectus by reference.

        The foregoing discussion of the information and factors considered by the C&F board of directors is not exhaustive, but includes the principal factors that the board of directors considered and discussed in approving and recommending the merger. In view of the wide variety of factors considered and discussed by the C&F board of directors in connection with its evaluation of the merger and the

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complexity of these factors, the board of directors did not quantify, rank or assign any relative or specific weight to the foregoing factors. Rather, it considered all of the factors as a whole. The board of directors discussed the foregoing factors and reached general consensus that the merger was in the best interests of C&F and its shareholders. In considering the foregoing factors, individual directors may have assigned different weights to different factors. The board of directors did not undertake to make any specific determination as to whether any factor, or particular aspect of any factor, supported or did not support its ultimate decision to approve the merger agreement.

        The foregoing explanation of C&F's board of directors' reasoning and all other information presented in this section is forward-looking in nature and, therefore, should be read in light of the factors discussed in the section entitled "Cautionary Statement Regarding Forward-Looking Statements."

Opinion of Peoples's Financial Advisor

        Peoples retained Sandler O'Neill to act as financial advisor to the Peoples board of directors in connection with Peoples's consideration of a possible business combination. Sandler O'Neill is a nationally recognized investment banking firm whose principal business specialty is financial institutions. In the ordinary course of its investment banking business, Sandler O'Neill is regularly engaged in the valuation of financial institutions and their securities in connection with mergers and acquisitions and other corporate transactions.

        Sandler O'Neill acted as financial advisor to the Peoples board of directors in connection with the proposed merger and participated in certain of the negotiations leading to the execution of the merger agreement. At the August 13, 2019 meeting at which the Peoples board of directors considered the merger and the merger agreement, Sandler O'Neill delivered to the Peoples board of directors its oral opinion, which was subsequently confirmed in writing on August 13, 2019, to the effect that, as of such date, the merger consideration was fair to the holders of Peoples common stock from a financial point of view. The full text of Sandler O'Neill's opinion is attached as Appendix B to this proxy statement/prospectus. The opinion outlines the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken by Sandler O'Neill in rendering its opinion. The description of the opinion set forth below is qualified in its entirety by reference to the full text of the opinion. Holders of Peoples common stock are urged to read the entire opinion carefully in connection with their consideration of the proposed merger and the merger proposal.

        Sandler O'Neill's opinion was directed to the Peoples board of directors in connection with its consideration of the merger and the merger agreement and does not constitute a recommendation to any shareholder of Peoples as to how any such shareholder should vote at any meeting of shareholders called to consider and vote upon the approval of the merger proposal. Sandler O'Neill's opinion was directed only to the fairness, from a financial point of view, of the merger consideration to the holders of Peoples common stock and did not address the underlying business decision of Peoples to engage in the merger, the form or structure of the merger or any other transactions contemplated in the merger agreement, the relative merits of the merger as compared to any other alternative transactions or business strategies that might exist for Peoples or the effect of any other transaction in which Peoples might engage. Sandler O'Neill also did not express any opinion as to the fairness of the amount or nature of the compensation to be received in the merger by any officer, director or employee of Peoples or C&F, or any class of such persons, if any, relative to the compensation to be received in the merger by any other shareholder. Sandler O'Neill's opinion was approved by Sandler O'Neill's fairness opinion committee.

        In connection with rendering its opinion, Sandler O'Neill reviewed and considered, among other things:

    an execution copy of the merger agreement;

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    certain publicly available financial statements and other historical financial information of Peoples and its banking subsidiary that Sandler O'Neill deemed relevant;

    certain publicly available financial statements and other historical financial information of C&F and its banking subsidiary that Sandler O'Neill deemed relevant;

    certain internal financial projections for Peoples for the years ending December 31, 2019 through December 31, 2021 as well as an assumed long-term annual net income growth rate for the years ending December 31, 2022 and December 31, 2023, as provided by the senior management of Peoples;

    certain internal financial projections for C&F for the years ending December 31, 2019 through December 31, 2023 and assumed dividends per share for the years ending December 31, 2019 through December 31, 2023, as provided by the senior management of C&F;

    the pro forma financial impact of the merger on C&F based on certain assumptions relating to purchase accounting adjustments, transaction expenses and cost savings, as provided by the senior management of C&F, as well as certain internal financial projections for Peoples for the years ending December 31, 2019 through December 31, 2023, as provided by the senior management of Peoples and adjusted by the senior management of C&F;

    the publicly reported historical price and trading activity for Peoples common stock and C&F common stock, including a comparison of certain stock market information for Peoples common stock and C&F common stock and certain stock indices as well as publicly available information for certain other similar companies, the securities of which are publicly traded;

    a comparison of certain financial information for Peoples and C&F with similar financial institutions for which information is publicly available;

    the financial terms of certain recent business combinations in the bank and thrift industry (on a regional and nationwide basis), to the extent publicly available;

    the current market environment generally and the banking environment in particular; and

    such other information, financial studies, analyses and investigations, and financial, economic and market criteria that Sandler O'Neill considered relevant.

        Sandler O'Neill also discussed with certain members of the senior management of Peoples the business, financial condition, results of operations and prospects of Peoples and held similar discussions with certain members of senior management of C&F and its representatives regarding the business, financial condition, results of operations and prospects of C&F.

        In performing its review, Sandler O'Neill relied upon the accuracy and completeness of all of the financial and other information that was available to and reviewed by Sandler O'Neill from public sources, that was provided to Sandler O'Neill by Peoples or C&F or their respective representatives, or that was otherwise reviewed by Sandler O'Neill, and Sandler O'Neill assumed such accuracy and completeness for purposes of rendering its opinion without any independent verification or investigation. Sandler O'Neill relied on the assurances of the respective managements of Peoples and C&F that they were not aware of any facts or circumstances that would have made any of such information inaccurate or misleading. Sandler O'Neill was not asked to and did not undertake an independent verification of any of such information and Sandler O'Neill did not assume any responsibility or liability for the accuracy or completeness thereof. Sandler O'Neill did not make an independent evaluation or perform an appraisal of the specific assets, the collateral securing assets or the liabilities (contingent or otherwise) of Peoples or C&F or any of their respective subsidiaries, nor was Sandler O'Neill furnished with any such evaluations or appraisals. Sandler O'Neill rendered no opinion or evaluation on the collectability of any assets or the future performance of any loans of

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Peoples or C&F or any of their respective subsidiaries. Sandler O'Neill did not make an independent evaluation of the adequacy of the allowance for loan losses of Peoples or C&F, or of the combined entity after the merger, and Sandler O'Neill did not review any individual credit files relating to Peoples or C&F or any of their respective subsidiaries. Sandler O'Neill assumed, with the consent of Peoples, that the respective allowances for loan losses for both Peoples and C&F were adequate to cover such losses and would be adequate on a pro forma basis for the combined entity.

        In preparing its analyses, Sandler O'Neill used certain internal financial projections for Peoples for the years ending December 31, 2019 through December 31, 2021 as well as an assumed long-term annual net income growth rate for the years ending December 31, 2022 and December 31, 2023, as provided by the senior management of Peoples. In addition, Sandler O'Neill used certain internal financial projections for C&F for the years ending December 31, 2019 through December 31, 2023 and assumed dividends per share for the years ending December 31, 2019 through December 31, 2023, as provided by the senior management of C&F. Sandler O'Neill also received and used in its pro forma analyses certain assumptions relating to the pro forma financial impact of the merger on C&F based on certain assumptions relating to purchase accounting adjustments, transaction expenses and cost savings, as provided by the senior management of C&F, as well as certain internal financial projections for Peoples for the years ending December 31, 2019 through December 31, 2023, as provided by the senior management of Peoples and adjusted by the senior management of C&F. With respect to the foregoing information, the respective senior managements of Peoples and C&F confirmed to Sandler O'Neill that such information reflected the best currently available projections, estimates and judgments of those respective managements as to the future financial performance of Peoples and C&F, respectively, and the other matters covered thereby, and Sandler O'Neill assumed that the future financial performance reflected in such information would be achieved. Sandler O'Neill expressed no opinion as to such information, or the assumptions on which such information was based. Sandler O'Neill also assumed that there had been no material change in the respective assets, financial condition, results of operations, business or prospects of Peoples or C&F since the date of the most recent financial statements made available to Sandler O'Neill. Sandler O'Neill assumed in all respects material to its analysis that Peoples and C&F would remain as going concerns for all periods relevant to its analysis.

        Sandler O'Neill also assumed, with the consent of Peoples, that (i) each of the parties to the merger agreement would comply in all material respects with all material terms and conditions of the merger agreement and all related agreements, that all of the representations and warranties contained in such agreements were true and correct in all material respects, that each of the parties to such agreements would perform in all material respects all of the covenants and other obligations required to be performed by such party under such agreements and that the conditions precedent in such agreements were not and would not be waived, (ii) in the course of obtaining the necessary regulatory or third party approvals, consents and releases with respect to the merger, no delay, limitation, restriction or condition would be imposed that would have an adverse effect on Peoples, C&F, the merger or any related transactions, and (iii) the merger and any related transactions would be consummated in accordance with the terms of the merger agreement without any waiver, modification or amendment of any material term, condition or agreement thereof and in compliance with all applicable laws and other requirements. Finally, with the consent of Peoples, Sandler O'Neill relied upon the advice that Peoples received from its legal, accounting and tax advisors as to all legal, accounting and tax matters relating to the merger and the other transactions contemplated by the merger agreement. Sandler O'Neill expressed no opinion as to any such matters.

        Sandler O'Neill's opinion was necessarily based on financial, economic, regulatory, market and other conditions as in effect on, and the information made available to Sandler O'Neill as of, the date thereof. Events occurring after the date thereof could materially affect Sandler O'Neill's opinion. Sandler O'Neill has not undertaken to update, revise, reaffirm or withdraw its opinion or otherwise comment upon events occurring after the date thereof. Sandler O'Neill expressed no opinion as to the

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trading value of Peoples common stock or C&F common stock at any time or what the value of C&F common stock would be once it is actually received by the holders of Peoples common stock.

        In rendering its opinion, Sandler O'Neill performed a variety of financial analyses. The summary below is not a complete description of all the analyses underlying Sandler O'Neill's opinion or the presentation made by Sandler O'Neill to the Peoples board of directors, but is a summary of the material analyses performed and presented by Sandler O'Neill. The summary includes information presented in tabular format. In order to fully understand the financial analyses, these tables must be read together with the accompanying text. The tables alone do not constitute a complete description of the financial analyses. The preparation of a fairness opinion is a complex process involving subjective judgments as to the most appropriate and relevant methods of financial analysis and the application of those methods to the particular circumstances. The process, therefore, is not readily susceptible to a partial analysis or summary description. Sandler O'Neill believes that its analyses must be considered as a whole and that selecting portions of the factors and analyses to be considered without considering all factors and analyses, or attempting to ascribe relative weights to some or all such factors and analyses, could create an incomplete view of the evaluation process underlying its opinion. Also, no company included in Sandler O'Neill's comparative analyses described below is identical to Peoples or C&F and no transaction is identical to the merger. Accordingly, an analysis of comparable companies or transactions involves complex considerations and judgments concerning differences in financial and operating characteristics of the companies and other factors that could affect the public trading values or transaction values, as the case may be, of Peoples and C&F and the companies to which they were compared. In arriving at its opinion, Sandler O'Neill did not attribute any particular weight to any analysis or factor that it considered. Rather, Sandler O'Neill made qualitative judgments as to the significance and relevance of each analysis and factor. Sandler O'Neill did not form an opinion as to whether any individual analysis or factor (positive or negative) considered in isolation supported or failed to support its opinion, rather, Sandler O'Neill made its determination as to the fairness of the merger consideration to the holders of Peoples common stock on the basis of its experience and professional judgment after considering the results of all its analyses taken as a whole.

        In performing its analyses, Sandler O'Neill also made numerous assumptions with respect to industry performance, business and economic conditions and various other matters, many of which cannot be predicted and are beyond the control of Peoples, C&F and Sandler O'Neill. The analyses performed by Sandler O'Neill are not necessarily indicative of actual values or future results, both of which may be significantly more or less favorable than suggested by such analyses. Sandler O'Neill prepared its analyses solely for purposes of rendering its opinion and provided such analyses to the Peoples board of directors at its August 13, 2019 meeting. Estimates on the values of companies do not purport to be appraisals or necessarily reflect the prices at which companies or their securities may actually be sold. Such estimates are inherently subject to uncertainty and actual values may be materially different. Accordingly, Sandler O'Neill's analyses do not necessarily reflect the value of Peoples common stock or C&F common stock or the prices at which Peoples or C&F common stock may be sold at any time. The analyses of Sandler O'Neill and its opinion were among a number of factors taken into consideration by the Peoples board of directors in making its decision to approve the merger agreement and the merger and the analyses described below should not be viewed as determinative of the decision of the Peoples board of directors with respect to the fairness of the merger consideration.

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    Summary of Proposed Merger Consideration and Implied Transaction Metrics

        Sandler O'Neill reviewed the financial terms of the proposed merger. Pursuant to the terms of the merger agreement, at the effective time of the merger each share of Peoples common stock issued and outstanding immediately prior to the effective time of the merger, except for certain shares as set forth in the merger agreement, shall be converted into the right to receive (i) cash in the amount of $27.00 per share, and (ii) 0.5366 shares of C&F common stock. Sandler O'Neill calculated an aggregate implied transaction value of approximately $21.8 million, and an implied purchase price per share of $55.64 consisting of the implied value of $28.64 stock consideration based on the closing price of C&F common stock on August 9, 2019 of $53.38 and the cash consideration in the amount of $27.00 per share. Based upon financial information for Peoples as of or for the last twelve months ("LTM") ended June 30, 2019 and the closing price of Peoples common stock on August 9, 2019, Sandler O'Neill calculated the following implied transaction metrics:

Transaction Price Per Share / Peoples Book Value Per Share

    138 %

Transaction Price Per Share / Peoples Tangible Book Value Per Share

    138 %

Transaction Price / Peoples Year-to-Date Annualized Earnings Per Share

    24.6x  

Transaction Price Per Share / Peoples 2019E(1) Earnings Per Share

    30.0x  

Transaction Price Per Share / Peoples 2020E(1) Earnings Per Share

    23.7x  

Tangible Book Premium / Core Deposits(2)

    4.6 %

Tangible Book Premium / Core Deposit(3)

    3.7 %

Market Premium as of August 9, 2019

    96.6 %

(1)
As provided by Peoples senior management.

(2)
Core deposits defined as total deposits less time deposits with balances greater than $100,000.

(3)
Core deposits defined as total deposits less time deposits with balances greater than $250,000.

    Stock Trading History

        Sandler O'Neill reviewed the publicly available historical reported trading prices of Peoples common stock and C&F common stock for the one-year and three-year periods ended August 9, 2019. Sandler O'Neill then compared the relationship between the movements in the price of Peoples common stock and C&F common stock, respectively, to movements in their respective peer groups (as described below) as well as certain stock indices.

    Peoples One-Year Stock Performance

 
  Beginning Value
August 9, 2018
  Ending Value
August 9, 2019
 

Peoples

    100 %   63.6 %

Peoples Peer Group

    100 %   96.2 %

S&P 500 Index

    100 %   102.3 %

Nasdaq Bank Index

    100 %   83.8 %

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    Peoples Three-Year Stock Performance

 
  Beginning Value
August 9, 2016
  Ending Value
August 9, 2019
 

Peoples

    100 %   138.0 %

Peoples Peer Group

    100 %   128.8 %

S&P 500 Index

    100 %   133.8 %

Nasdaq Bank Index

    100 %   121.5 %

    C&F's One-Year Stock Performance

 
  Beginning Value
August 9, 2018
  Ending Value
August 9, 2019
 

C&F

    100 %   86.8 %

C&F Peer Group

    100 %   96.2 %

S&P 500 Index

    100 %   102.3 %

Nasdaq Bank Index

    100 %   83.8 %

    C&F's Three-Year Stock Performance

 
  Beginning Value
August 9, 2016
  Ending Value
August 9, 2019
 

C&F

    100 %   124.2 %

C&F Peer Group

    100 %   136.0 %

S&P 500 Index

    100 %   133.8 %

Nasdaq Bank Index

    100 %   121.5 %

    Comparable Company Analyses

        Sandler O'Neill used publicly available information to compare selected financial information for Peoples with a group of financial institutions selected by Sandler O'Neill. The Peoples peer group included publicly-traded banks and thrifts headquartered in Virginia with total assets less than $500 million, but excluded targets of announced merger transactions (the "Peoples Peer Group"). The Peoples Peer Group consisted of the following companies:

Bank of Botetourt   Oak View National Bank
Bank of Fincastle   Pinnacle Bankshares Corporation
Citizens Bancorp of Virginia, Inc.   Pioneer Bankshares, Inc.
Farmers Bank of Appomattox   Touchstone Bank
Freedom Bank of Virginia   Virginia Bank Bankshares, Incorporated

        The analysis compared publicly available financial information for Peoples and financial data provided by Peoples management with corresponding data for the Peoples Peer Group as of or for the period ended June 30, 2019 (unless otherwise noted) with pricing data as of August 9, 2019. The table below sets forth the data for Peoples and the median, mean, low and high data for the Peoples Peer Group.

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    Peoples Comparable Company Analysis

 
  Peoples   Peoples
Peer Group
Median
  Peoples
Peer Group
Mean
  Peoples
Peer Group
Low
  Peoples
Peer Group
High
 

Total assets ($ in millions)

    194     326     342     201     490  

Loans/Deposits (%)

    85.6     89.9     88.6     65.7     103.9  

Non-performing assets(1) /Total assets (%)

    2.96     0.90     1.13     0.14     2.85  

Tangible common equity/Tangible assets (%)

    8.13     11.81     11.48     8.87     13.60  

Tier 1 leverage ratio (%)

    9.80     11.64     11.61     9.37     14.37  

Total RBC ratio (%)

    15.49     16.14     16.53     12.25     24.40  

CRE/Total RBC ratio (%)

    106.1     127.4     136.5     49.6     227.3  

YTD Return on average assets (%)

    0.45     0.89     0.86     0.40     1.44  

YTD Return on average equity (%)

    5.72     8.04     7.50     3.32     12.11  

YTD Net interest margin (%)

    3.49     3.98     3.99     3.40     4.68  

YTD Efficiency ratio (%)

    75.1     70.9     73.6     61.8     88.0  

Price/Tangible book value (%)

    72     101     106     96     123  

Price/Annualized YTD earnings per share (x)

    12.9     12.3     15.2     9.6     29.9  

Current dividend yield (%)

    0.0     2.2     2.2     0.0     6.0  

Market value ($ in millions)

    11     37     40     25     68  

(1)
Nonperforming assets defined as nonaccrual loans, restructured loans, and other real estate owned.

Note:
Financial data for Pinnacle Bankshares Corporation, Farmers Bank of Appomattox, Pioneer Bankshares, Incorporated and Virginia Bank Bankshares, Incorporated as of or for the period ending March 31, 2019.

        Sandler O'Neill used publicly available information to perform a similar analysis for C&F by comparing selected financial information for C&F with a group of financial institutions selected by Sandler O'Neill. The C&F peer group included publicly-traded banks and thrifts headquartered Virginia, Maryland, North Carolina and West Virginia with total assets between $1.0 billion and $3.0 billion, but excluded targets of announced merger transactions (the "C&F Peer Group"). The C&F Peer Group consisted of the following companies:

American National Bankshares Inc.   MVB Financial Corp.
Bay Banks of Virginia, Inc.   National Bankshares, Inc.
Capital Bancorp, Inc.   Old Point Financial Corporation
Community Bankers Trust Corporation   Peoples Bancorp of North Carolina, Inc.
Community Financial Corporation   Premier Financial Bancorp, Inc.
First Bancorp, Inc.   Revere Bank
First Community Bankshares, Inc.   Select Bancorp, Inc.
First United Corporation   Shore Bancshares, Inc.
FVCBankcorp, Inc.   Southern BancShares (N.C.), Inc.
Howard Bancorp, Inc.   Southern National Bancorp of Virginia, Inc.
John Marshall Bancorp, Inc.   Summit Financial Group, Inc.
MainStreet Bancshares, Inc.    

        The analysis compared publicly available financial information for C&F with corresponding data for the C&F Peer Group as of or for the year ended June 30, 2019 (unless otherwise noted) with pricing data as of August 9, 2019. The table below sets forth the data for C&F and the median, mean, low and high data for the C&F Peer Group.

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    C&F Comparable Company Analysis

 
  C&F   C&F
Peer Group
Median
  C&F
Peer Group
Mean
  C&F
Peer Group
Low
  C&F
Peer Group
High
 

Total assets ($ in millions)

    1,568     1,494     1,741     1,029     2,761  

Loans/Deposits (%)

    90.1     96.8     93.7     68.2     107.9  

Non-performing assets(1) /Total assets (%)

    0.40     0.84     0.92     0.14     2.52  

Tangible common equity/Tangible assets (%)

    9.24     10.26     10.53     8.26     14.75  

Tier 1 leverage ratio (%)

    11.30     10.70     10.93     8.91     14.26  

Total RBC ratio (%)

    14.80     13.60     14.38     11.90     22.53  

CRE/Total RBC ratio (%)

    185.6 (2)   261.4     259.6     127.5     413.7  

LTM Return on average assets (%)

    1.23     1.22     1.13     0.47     1.70  

LTM Return on average equity (%)

    12.37     10.45     9.96     3.52     14.18  

LTM Net interest margin (%)

    5.77     3.66     3.82     3.33     5.57  

LTM Efficiency ratio (%)

    68.7     59.0     61.8     49.8     78.8  

Price/Tangible book value (%)

    128     127     137     97     236  

Price/Annualized LTM Earnings per share (x)

    10.0     12.8     14.0     8.1     26.6  

Current Dividend yield (%)

    2.8     1.6     1.4     0.0     3.9  

Market value ($ in millions)

    183     212     239     108     518  

(1)
Nonperforming assets defined as nonaccrual loans and leases, renegotiated loans and leases and real estate owned.

(2)
Bank level financial data shown as consolidated financial data unavailable.

Note:
Financial data for Southern BancShares (N.C.), Inc. and First Bancorp, Inc. as of or for the period ending March 31, 2019.

    Analysis of Precedent Transactions.

        Sandler O'Neill reviewed both a regional group and a national group of merger and acquisition transactions. The regional group consisted of bank and thrift transactions announced from January 1, 2017 through August 9, 2019 with targets headquartered in the District of Columbia, Delaware, Maryland, North Carolina, West Virginia and Virginia with total assets less than $500 million, but excluded deals with undisclosed deal value (the "Regional Precedent Transactions"). The nationwide group consisted of transactions announced from January 1, 2017 through August 9, 2019 with total assets less than $300 million, Nonperforming Assets/Assets greater than 2.0% and LTM Return on Average Assets less than 0.50%, but excluded deals with undisclosed deal value, recapitalizations and banks with less than 5.0% Tangible Common Equity/Tangible Assets (the "Nationwide Precedent Transactions").

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        The Regional Precedent Transactions group was composed of the following transactions:

Acquiror
  Target
ACNB Corp.   Frederick County Bancorp
Blue Ridge Bankshares Inc.   Virginia Community Bankshares
Allegheny Bancshares Inc.   Mount Hope Bankshares Inc.
Delmar Bancorp   Virginia Partners Bank
Summit Financial Group Inc.   Peoples Bankshares Inc.
FVCBankcorp Inc.   Colombo Bank
Premier Financial Bancorp Inc.   First Bank of Charleston Inc.
First US Bancshares Inc.   Peoples Bank
Parkway Acquisition Corp   Great State Bank
Park National Corp.   NewDominion Bank
CB Financial Services Inc.   First WV Bancorp Inc.
Old Point Financial Corp.   Citizens National Bank
PB Financial Corp   CB Financial Corp.
Community Finl Corp.   County First Bank
Select Bancorp Inc.   Premara Financial Inc.
Bank of McKenney   CCB Bankshares Inc.
Emclaire Financial Corp   Northern Hancock B&TC
West Town Bancorp Inc.   Sound Banking Co.
Old Line Bancshares Inc   DCB Bancshares Inc.

        The Nationwide Precedent Transactions group was composed of the following transactions:

Acquiror
  Target
Citizens Holding Co.   Charter Bank
First Bank   Grand Bank NA
NB Holdings LLC   Merit Bancorp Inc.
Hanover Bancorp Inc.   Chinatown FSB
PBD Holdings LLC   First Columbia Bancorp Inc.
BOLC Corp.   North Alabama Bancshares Inc.
NorthWest Indiana Bancorp   First Personal Financial Corp.
Guaranty Federal Bcshs Inc.   Hometown Bancshares Inc.
First Bank   Delanco Bancorp Inc.
Delmar Bancorp   Liberty Bell Bank
BCB Bancorp Inc.   IA Bancorp Inc.
Emclaire Financial Corp   Northern Hancock B&TC
First Bank   Bucks County Bank
First Guaranty Bancshares Inc.   Premier Bancshares Inc.

        Using the latest publicly available information prior to the announcement of the relevant transaction, Sandler O'Neill reviewed the following transaction metrics: transaction price to last-twelve-months earnings per share, transaction price to tangible book value per share, core deposit premium, and 1-day market premium. Sandler O'Neill compared the indicated transaction metrics for the transaction to the median, mean, low and high metrics of the Regional Precedent Transactions group as well as to the median, mean, low and high metrics of the Nationwide Precedent Transactions group.

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  Regional Precedent Transactions  
 
  C&F/
Peoples
 
 
  Median   Mean   Low   High  

Transaction Price/LTM Earnings Per Share (x)

    24.6 (1)   23.6     21.7     9.8     30.0  

Transaction Price/Tangible Book Value Per Share (%)

    138     141     142     60     194  

Tangible Book Value Premium to Core Deposits (%)

    4.6     6.8     8.1     0.2     23.6  

1-Day Market Premium (%)

    96.6     30.5     29.5     (64.2 )   101.8  

 

 
   
  Nationwide Precedent
Transactions
 
 
  C&F/
Peoples
 
 
  Median   Mean   Low   High  

Transaction Price/LTM Earnings Per Share (x)

    24.6 (1)                

Transaction Price/Tangible Book Value Per Share (%)

    138     117     115     60     169  

Tangible Book Value Premium to Core Deposits (%)

    4.6     3.7     3.4     0.2     6.8  

1-Day Market Premium (%)

    96.6     35.7     33.0     8.0     55.3  

(1)
Year-to-date annualized earnings per share.

    Net Present Value Analyses

        Sandler O'Neill performed an analysis that estimated the net present value per share of Peoples common stock assuming Peoples performed in accordance with internal financial projections for Peoples for the years ending December 31, 2019 through December 31, 2021 as well as an assumed long-term annual net income growth rate for the years ending December 31, 2022 and December 31, 2023, as provided by the senior management of Peoples. To approximate the terminal value of a share of Peoples common stock at December 31, 2023, Sandler O'Neill applied price to 2023 earnings multiples ranging from 12.0x to 17.0x and multiples of December 31, 2023 tangible book value ranging from 75% to 125%. The terminal values were then discounted to present values using different discount rates ranging from 9.0% to 15.0%, which were chosen to reflect different assumptions regarding required rates of return of holders or prospective buyers of Peoples common stock. As illustrated in the following tables, the analysis indicated an imputed range of values per share of Peoples common stock of $21.56 to $38.88 when applying multiples of earnings and $21.19 to $44.95 when applying multiples of tangible book value.

    Earnings Per Share Multiples

Discount
Rate
  12.0x   13.0x   14.0x   15.0x   16.0x   17.0x  
9.0%   $ 27.44   $ 29.73   $ 32.02   $ 34.30   $ 36.59   $ 38.88  
10.0%   $ 26.34   $ 28.53   $ 30.73   $ 32.92   $ 35.12   $ 37.31  
11.0%   $ 25.29   $ 27.40   $ 29.50   $ 31.61   $ 33.72   $ 35.82  
12.0%   $ 24.29   $ 26.31   $ 28.34   $ 30.36   $ 32.38   $ 34.41  
13.0%   $ 23.34   $ 25.28   $ 27.22   $ 29.17   $ 31.11   $ 33.06  
14.0%   $ 22.43   $ 24.30   $ 26.17   $ 28.04   $ 29.90   $ 31.77  
15.0%   $ 21.56   $ 23.36   $ 25.16   $ 26.95   $ 28.75   $ 30.55  

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    Tangible Book Value Per Share Multiples

Discount
Rate
  75%   85%   95%   105%   115%   125%  
9.0%   $ 26.97   $ 30.56   $ 34.16   $ 37.75   $ 41.35   $ 44.95  
10.0%   $ 25.88   $ 29.33   $ 32.78   $ 36.23   $ 39.69   $ 43.14  
11.0%   $ 24.85   $ 28.16   $ 31.48   $ 34.79   $ 38.10   $ 41.41  
12.0%   $ 23.87   $ 27.05   $ 30.23   $ 33.41   $ 36.59   $ 39.78  
13.0%   $ 22.93   $ 25.99   $ 29.04   $ 32.10   $ 35.16   $ 38.22  
14.0%   $ 22.04   $ 24.98   $ 27.92   $ 30.85   $ 33.79   $ 36.73  
15.0%   $ 21.19   $ 24.01   $ 26.84   $ 29.67   $ 32.49   $ 35.32  

        Sandler O'Neill also considered and discussed with the Peoples board of directors how this analysis would be affected by changes in the underlying assumptions, including variations with respect to earnings. To illustrate this impact, Sandler O'Neill performed a similar analysis, assuming Peoples's earnings varied from 15% above projections to 15% below projections. This analysis resulted in the following range of per share values for Peoples common stock, applying the price to 2023 earnings multiples range of 12.0x to 17.0x referred to above and a discount rate of 13.16%.

    Earnings Per Share Multiples

Annual Estimate
Variance
  12.0x   13.0x   14.0x   15.0x   16.0x   17.0x  
(15.0)%   $ 19.71   $ 21.35   $ 22.99   $ 24.64   $ 26.28   $ 27.92  
(10.0)%   $ 20.87   $ 22.61   $ 24.35   $ 26.09   $ 27.82   $ 29.56  
(5.0)%   $ 22.03   $ 23.86   $ 25.70   $ 27.53   $ 29.37   $ 31.21  
0.0%   $ 23.19   $ 25.12   $ 27.05   $ 28.98   $ 30.92   $ 32.85  
5.0%   $ 24.35   $ 26.38   $ 28.40   $ 30.43   $ 32.46   $ 34.49  
10.0%   $ 25.51   $ 27.63   $ 29.76   $ 31.88   $ 34.01   $ 36.13  
15.0%   $ 26.67   $ 28.89   $ 31.11   $ 33.33   $ 35.55   $ 37.78  

        Sandler O'Neill also performed an analysis that estimated the net present value per share of C&F common stock, assuming C&F performed in accordance with internal financial projections for C&F for the years ending December 31, 2019 through December 31, 2023 and assumed dividends per share for the years ending December 31, 2019 through December 31, 2023, as provided by the senior management of C&F. To approximate the terminal value of a share of C&F common stock at December 31, 2023, Sandler O'Neill applied price to 2023 earnings multiples ranging from 11.0x to 16.0x and multiples of December 31, 2023 tangible book value ranging from 110% to 160%. The terminal values were then discounted to present values using different discount rates ranging from 9.0% to 15.0%, which were chosen to reflect different assumptions regarding required rates of return of holders or prospective buyers of C&F common stock. As illustrated in the following tables, the analysis indicated an imputed range of values per share of C&F common stock of $37.28 to $65.75 when applying multiples of earnings and $39.36 to $69.60 when applying multiples of tangible book value.

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    Earnings Per Share Multiples

Discount
Rate
  11.0x   12.0x   13.0x   14.0x   15.0x   16.0x  
9.0%   $ 46.86   $ 50.64   $ 54.42   $ 58.19   $ 61.97   $ 65.75  
10.0%   $ 45.06   $ 48.69   $ 52.32   $ 55.94   $ 59.57   $ 63.19  
11.0%   $ 43.35   $ 46.84   $ 50.32   $ 53.80   $ 57.28   $ 60.76  
12.0%   $ 41.73   $ 45.07   $ 48.41   $ 51.76   $ 55.10   $ 58.44  
13.0%   $ 40.17   $ 43.39   $ 46.60   $ 49.81   $ 53.02   $ 56.24  
14.0%   $ 38.69   $ 41.78   $ 44.87   $ 47.96   $ 51.04   $ 54.13  
15.0%   $ 37.28   $ 40.25   $ 43.22   $ 46.19   $ 49.16   $ 52.13  

    Tangible Book Value Per Share Multiples

Discount
Rate
  110%   120%   130%   140%   150%   160%  
9.0%   $ 49.51   $ 53.52   $ 57.54   $ 61.56   $ 65.58   $ 69.60  
10.0%   $ 47.60   $ 51.46   $ 55.32   $ 59.17   $ 63.03   $ 66.89  
11.0%   $ 45.79   $ 49.49   $ 53.20   $ 56.90   $ 60.60   $ 64.31  
12.0%   $ 44.07   $ 47.62   $ 51.18   $ 54.74   $ 58.29   $ 61.85  
13.0%   $ 42.42   $ 45.84   $ 49.26   $ 52.67   $ 56.09   $ 59.51  
14.0%   $ 40.86   $ 44.14   $ 47.43   $ 50.71   $ 53.99   $ 57.28  
15.0%   $ 39.36   $ 42.52   $ 45.68   $ 48.84   $ 51.99   $ 55.15  

        Sandler O'Neill also considered and discussed with the Peoples board of directors how this analysis would be affected by changes in the underlying assumptions, including variations with respect to earnings. To illustrate this impact, Sandler O'Neill performed a similar analysis assuming C&F's earnings varied from 15% above projections to 15% below projections. This analysis resulted in the following range of per share values for C&F common stock, applying the price to 2023 earnings multiples range of 11.0x to 16.0x referred to above and a discount rate of 13.16%.

    Earnings Per Share Multiples

Annual Estimate
Variance
  11.0x   12.0x   13.0x   14.0x   15.0x   16.0x  
(15.0)%   $ 34.67   $ 37.38   $ 40.09   $ 42.81   $ 45.52   $ 48.23  
(10.0)%   $ 36.42   $ 39.29   $ 42.17   $ 45.04   $ 47.91   $ 50.79  
(5.0)%   $ 38.18   $ 41.21   $ 44.24   $ 47.27   $ 50.31   $ 53.34  
0.0%   $ 39.93   $ 43.12   $ 46.32   $ 49.51   $ 52.70   $ 55.89  
5.0%   $ 41.69   $ 45.04   $ 48.39   $ 51.74   $ 55.09   $ 58.45  
10.0%   $ 43.44   $ 46.95   $ 50.47   $ 53.98   $ 57.49   $ 61.00  
15.0%   $ 45.20   $ 48.87   $ 52.54   $ 56.21   $ 59.88   $ 63.55  

        In connection with its analysis, Sandler O'Neill considered and discussed with the Peoples board of directors how the present value analyses would be affected by changes in the underlying assumptions. Sandler O'Neill noted that the net present value analysis is a widely used valuation methodology, but the results of such methodology are highly dependent upon the numerous assumptions that must be made, and the results thereof are not necessarily indicative of actual values or future results.

    Pro Forma Transaction Analysis

        Sandler O'Neill analyzed certain potential pro forma effects of the merger on C&F assuming the merger closes on December 31, 2019. Sandler O'Neill utilized the following information and

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assumptions: purchase accounting adjustments, transaction expenses and cost savings, as provided by the senior management of C&F, as well as certain internal financial projections for Peoples for the years ending December 31, 2019 through December 31, 2023, as provided by the senior management of Peoples and adjusted by the senior management of C&F. The analysis indicated that the merger could be accretive to C&F's estimated earnings per share (excluding one-time transaction costs and expenses) in the years ending December 31, 2020 through December 31, 2023 and dilutive to C&F's estimated tangible book value per share at closing.

        In connection with this analysis, Sandler O'Neill considered and discussed with the Peoples board of directors how the analysis would be affected by changes in the underlying assumptions, including the impact of final purchase accounting adjustments determined at the closing of the merger, and noted that the actual results achieved by the combined company may vary from projected results and the variations may be material.

    Sandler O'Neill's Relationship

        Sandler O'Neill is acting as Peoples's financial advisor in connection with the merger and will receive a fee for such services in an amount equal to $350,000, which fee is contingent upon the closing of the merger. Sandler O'Neill also received a $150,000 fee from Peoples upon rendering its opinion, which opinion fee will be credited in full towards the $350,000 transaction fee which will become payable to Sandler O'Neill upon closing of the merger. Peoples has also agreed to indemnify Sandler O'Neill against certain claims and liabilities arising out of Sandler O'Neill's engagement and to reimburse Sandler O'Neill for certain of its out-of-pocket expenses incurred in connection with Sandler O'Neill's engagement.

        In the two years preceding the date of Sandler O'Neill's opinion, Sandler O'Neill did not provide any other investment banking services to Peoples. Sandler O'Neill did not provide any investment banking services to C&F in the two years preceding the date of its opinion. In the ordinary course of Sandler O'Neill's business as a broker-dealer, Sandler O'Neill may purchase securities from and sell securities to Peoples, C&F and their respective affiliates. Sandler O'Neill may also actively trade the equity and debt securities of Peoples, C&F and their respective affiliates for Sandler O'Neill's account and for the accounts of Sandler O'Neill's customers.

Certain Unaudited Prospective Financial Information

        Peoples and C&F do not as a matter of course make public projections as to future performance, revenues, earnings or other financial results due to, among other reasons, the inherent uncertainty of the underlying assumptions and estimates. However, C&F and Peoples are including in this proxy statement/prospectus certain unaudited prospective financial information that was made available to Sandler O'Neill, Peoples's financial advisor, in connection with the merger. The inclusion of this information should not be regarded as an indication that any of C&F, Peoples, Sandler O'Neill, their respective representatives or any other recipient of this information considered, or now considers, it to be necessarily predictive of actual future results, or that it should be construed as financial guidance, and it should not be relied on as such.

        For purposes of Sandler O'Neill's net present value analysis of Peoples performed in connection with Sandler O'Neill's opinion, Sandler O'Neill used projected net income for the years ending December 31, 2019 through December 31, 2021, as provided by the senior management of Peoples, as well as an estimated long-term annual net income growth rate for the years ending December 31, 2022 and December 31, 2023, as provided by senior management of Peoples. The following table summarizes

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this unaudited prospective financial information with respect to Peoples as used by Sandler O'Neill for its net present value analysis of Peoples:

 
  As of or for the years ended December 31,  
 
  2019   2020   2021   2022   2023  

Net income ($000s)

  $ 725   $ 920   $ 1,197   $ 1,257   $ 1,319  

Earnings per share

  $ 1.85   $ 2.35   $ 3.06   $ 3.21   $ 3.37  

        For purposes of Sandler O'Neill's net present value analysis of C&F performed in connection with Sandler O'Neill's opinion, Sandler O'Neill used estimated net income for the years ending December 31, 2019 through December 31, 2023 and estimated dividends per share for the years ending December 31, 2019 through December 31, 2023, as provided by the senior management of C&F. The following table summarizes this unaudited prospective financial information with respect to C&F as used by Sandler O'Neill for its net present value analysis of C&F:

 
  As of or for the years ended December 31,  
 
  2019   2020   2021   2022   2023  

Net income ($000s)

  $ 17,000   $ 17,500   $ 18,000   $ 18,500   $ 19,000  

Earnings per share

  $ 4.94   $ 5.13   $ 5.27   $ 5.42   $ 5.57  

Dividends per share

  $ 0.74   $ 1.48   $ 1.48   $ 1.48   $ 1.48  

        For purposes of Sandler O'Neill's pro forma merger analysis performed in connection with Sandler O'Neill's opinion, Sandler O'Neill used estimated net income for Peoples for the years ending December 31, 2020, December 31, 2021, December 31, 2022 and December 31, 2023, as provided by the senior management of Peoples and adjusted by the senior management of C&F. The following table summarizes this unaudited prospective financial information for the periods presented with respect to Peoples as used by Sandler O'Neill for its pro forma merger analysis.

 
  As of or for the years ended December 31,  
 
  2020   2021   2022   2023  

Net income

  $ 1.0 million   $ 1.5 million   $ 2.0 million   $ 2.5 million  

        This information was prepared solely for internal use and is subjective in many respects. While presented with numeric specificity, the unaudited prospective financial information reflects numerous estimates and assumptions with respect to business, economic, market, competition, regulatory and financial conditions and matters specific to C&F's and Peoples's respective business, all of which are difficult to predict and many of which are beyond C&F's and Peoples's control. The unaudited prospective financial information reflects both assumptions as to certain business decisions that are subject to change and, in many respects, subjective judgment, and therefore, is susceptible to multiple interpretations and periodic revisions based on actual experience and business developments. No assurance can be given that the unaudited prospective financial information and the underlying estimates and assumptions will be realized. In addition, since the unaudited prospective financial information covers multiple years, such information by its nature becomes subject to greater uncertainty with each successive year. Actual results may differ materially from those set forth above, and important factors that may affect actual results and cause the unaudited prospective financial information to be inaccurate include, but are not limited to, risks and uncertainties relating to C&F's and Peoples's business, industry performance, general business and economic conditions, customer requirements, competition and adverse changes in applicable laws, regulations or rules. For other factors that could cause actual results to differ, please see the sections entitled "Risk Factors" and "Cautionary Statement Regarding Forward-Looking Statements."

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        The unaudited prospective financial information appearing above was not prepared with a view toward public disclosure, nor was it prepared with a view toward compliance with generally accepted accounting principles in the U.S. ("GAAP"), the prevailing practices in the banking industry, published guidelines of the SEC or the guidelines established by the American Institute of Certified Public Accountants for preparation and presentation of prospective financial information. In addition, the unaudited prospective financial information requires significant estimates and assumptions that make it inherently less comparable to the similarly titled GAAP measures in C&F's or Peoples's historical GAAP financial statements. Neither C&F nor Peoples's independent registered public accounting firm, nor any other independent accountants, have compiled, examined or performed any procedures with respect to the unaudited prospective financial information contained in this document, nor have they expressed any opinion or any other form of assurance on such information or its achievability, and assume no responsibility for, and disclaim any association with, the unaudited prospective financial information. The independent registered public accountant reports included in this proxy statement/prospectus relate to historical financial information of C&F. They do not extend to the unaudited prospective financial information and should not be read to do so.

        Furthermore, the unaudited prospective financial information does not take into account any circumstances or events occurring after August 13, 2019. No assurance can be given that, had the unaudited prospective financial information been prepared as of the date of this proxy statement/prospectus, similar estimates and assumptions would be used. Neither C&F nor Peoples intends to, and expressly disclaims any obligation to, make publicly available any update or other revision to the unaudited prospective financial information to reflect circumstances existing since their preparation or to reflect the occurrence of unanticipated events, even if any or all of the underlying assumptions are shown to be in error, or to reflect changes in general economic or industry conditions. The unaudited prospective financial information does not take into account the possible financial and other effects on C&F or Peoples of the merger and does not attempt to predict or suggest future results of the combined company after giving effect to the merger. The unaudited prospective financial information does not give effect to the merger, including the impact of negotiating or executing the merger agreement, the expenses that may be incurred in connection with completing the merger, the potential synergies that may be achieved by the combined company as a result of the merger, the effect on C&F or Peoples of any business or strategic decision or action that has been or will be taken as a result of the merger agreement having been executed, or the effect of any business or strategic decisions or actions that would likely have been taken if the merger agreement had not been executed, but that were instead altered, accelerated, postponed or not taken in anticipation of the merger. Further, the unaudited prospective financial information does not take into account the effect on C&F or Peoples of any possible failure of the mergers to occur. By inclusion of the unaudited prospective financial information in this document, none of C&F, Peoples, Sandler O'Neill, or their respective affiliates, associates, officers, directors, advisors, agents or other representatives makes any representation to any shareholder of C&F or Peoples or any other person regarding C&F's or Peoples's ultimate performance compared to the information contained in the unaudited prospective financial information or that the projected results will be achieved.

        In light of the foregoing, and considering that the special meeting of the Peoples shareholders will be held several months after the unaudited prospective financial information was prepared, as well as the uncertainties inherent in any forecasted information, shareholders are cautioned not to place unwarranted reliance on such information, and all Peoples shareholders are urged to review C&F's and Peoples's financial and other information contained elsewhere in this document for a description of C&F's and Peoples's respective businesses and reported financial results. See the section entitled "Where You Can Find More Information." See also the full text of Sandler O'Neill's opinion, which is attached as Appendix B, for more details about the information that Sandler O'Neill relied on in rendering its opinion.

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Interests of Certain Peoples Directors and Executive Officers in the Merger

        In considering the recommendations of the Peoples board of directors that Peoples shareholders vote in favor of the merger proposal, Peoples shareholders should be aware that Peoples executive officers may have interests in the merger that differ from, or are in addition to, their interests as shareholders of Peoples. The Peoples board of directors was aware of these interests and took them into account in its decision to approve the merger agreement.

        Change of Control Payments and Benefits under Current Peoples Employment Agreements.    The employees of Peoples who have employment agreements are: Robert K. Bailey, III; and Zirkle Blakey, III. For the purposes of the employment agreements, the merger will constitute a "change of control."

        Under the terms of the employment agreements, if the executive's employment is terminated within one year following a "change of control" (i) by Peoples (or C&F as successor to Peoples) without "cause" (as defined in the agreement), or (ii) by the executive with "good reason" (as defined in the agreement), the executive will be entitled to receive a cash amount equal to 2.99 times the sum of (x) the executive's base salary in effect at the time of such termination or, if higher, in effect immediately prior to the change of control, plus (y) the executive's most recent annual bonus paid prior to such termination or, if greater, paid by Peoples before the change of control. Under the employment agreements, "good reason" occurs when any of the following conditions exist: the assignment of duties without the executive's consent which results in him having significantly less authority or responsibility than he has on the date of the employment agreement; requiring the executive to maintain his principal office or offices outside of the Counties of King George or Westmoreland, Virginia, unless Peoples (or C&F as successor to Peoples) moves its principal executive offices to the place which the executive is required to move; the continued failure of Peoples (or C&F as successor to Peoples) to comply with any material term of the employment agreement; or a material diminution in executive's title, without his express written consent.

        Each employment agreement provides that amounts payable and benefits provided thereunder on account of a change of control shall be reduced to one dollar less than the maximum amount which may be paid without causing any such payment or benefit to be nondeductible as an "excess parachute payment" under Section 280G of the Internal Revenue Code. Each employment agreement also contains non-competition, non-solicitation and non-diversion covenants that apply for 12 months following the executive's termination of employment.

        C&F and Peoples have agreed that Peoples will terminate Mr. Bailey's employment agreement, with such termination to be effective immediately preceding the effective time of the merger, and Mr. Bailey will receive a lump sum payment of $641,367 net of applicable tax withholdings and subject to reduction as necessary to ensure that such payment will not constitute an "excess parachute payment" under Section 280G of the Internal Revenue Code. The merger agreement requires Peoples to obtain a general release from Mr. Bailey prior to the effective time of the merger. Such release shall be in a form reasonably acceptable to C&F.

        If Mr. Blakey's employment agreement with Peoples is terminated at the effective time of the merger (assuming for this purpose that the merger is effective on January 1, 2020), Peoples estimates that Mr. Blakey would receive $491,541 in lump-sum severance payments pursuant to such agreement.

        Benefits under Peoples Supplemental Executive Retirement Agreements.    Peoples has entered into a Supplemental Executive Retirement Agreement (each, a "SERP Agreement") with each of Messrs. Bailey and Blakey which will be assumed by C&F as a result of the merger. Subject to the terms and conditions therein, each SERP Agreement provides for monthly installments payable over a 10-year period, commencing on the first day of the month following the date on which the executive attains the age of 65 and following his separation of service. Mr. Bailey's SERP Agreement provides

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for a $40,000 annual benefit, and Mr. Blakey's SERP Agreement provides for a $25,000 annual benefit. Both SERP Agreements provide for vesting in 10% increments over a 10-year period, commencing March 11, 2010. As of the date of this proxy statement/prospectus, Messrs. Bailey and Blakey have each vested in 90% of the SERP benefit and shall become fully vested on March 11, 2020, subject to continued employment with Peoples or C&F (as successor to Peoples) on such date.

        Notwithstanding the foregoing, under each SERP Agreement, if the executive incurs a "separation from service" within two years following a "change in control," the present value of the executive's SERP benefit shall be paid in one lump sum on the first day of the month following such separation from service, subject to a six-month delay in limited circumstances. For the purposes of each SERP Agreement, the merger shall constitute a "change in control," and "separation from service" shall mean executive's separation from service with Peoples (or C&F as successor to Peoples) for any reason.

        Employment Following the Merger.    C&F has entered into an employment agreement with Mr. Bailey that will be effective as of the effective time of the merger and will terminate on the one-year anniversary thereof. Pursuant to this employment agreement, Mr. Bailey will serve as Senior Banking Officer of C&F and will receive base salary payments at the rate of $150,000 annually. Mr. Bailey will be eligible to participate in benefit plans and programs offered to other senior executives of C&F and will continue to vest in benefits under his current SERP Agreement. Mr. Bailey will be subject to non-competition and non-solicitation covenants through the later of (x) one year after Mr. Bailey is no longer employed by C&F or (y) if Mr. Bailey's employment is terminated during the term of the employment agreement (i) by C&F without "good cause" (as defined in the agreement) or (ii) by Mr. Bailey for "good reason" (as defined in the agreement), two years after the effective time of the merger.

        Under Mr. Bailey's employment agreement with C&F, if Mr. Bailey's employment with C&F is terminated (i) by C&F without good cause or (ii) by Mr. Bailey for good reason, Mr. Bailey will be entitled to receive the following payments: (x) accrued but unpaid base salary, reimbursement for unreimbursed expenses, and employee benefits to which Mr. Bailey is entitled under C&F's benefits plans; (y) vesting of the last 10% portion of the SERP benefit, if the termination occurs prior to March 11, 2020; and (z) continuation of his base salary as in effect on the date of termination through the end of the employment agreement's term. The SERP vesting and salary continuation benefits described in (y) and (z) above are subject to Mr. Bailey signing a release and waiver of claims in favor of C&F in a form provided by C&F.

        C&F Bank remains in discussions with Mr. Blakey with respect to potential employment with C&F following the merger. If C&F decides to terminate the employment agreement of Mr. Blakey and he is employed by C&F Bank after the merger, such post-merger employment may be on an at-will basis or pursuant to an offer letter, retention agreement, change in control agreement or other arrangement. Otherwise, C&F will assume Mr. Blakey's current employment agreement.

        Indemnification and Insurance.    C&F has agreed to indemnify the officers and directors of Peoples against certain liabilities arising before the effective date of the merger. C&F has also agreed to purchase a six year "tail" prepaid policy, on the same terms as Peoples's existing directors' and officers' liability insurance, for the current officers and directors of Peoples, subject to a cap on the cost of such policy equal to 200% of Peoples's current annual premium.

Regulatory Approvals

        C&F and Peoples cannot complete the merger without prior approval from the Federal Reserve and the Bureau of Financial Institutions of the Virginia SCC. The subsidiary bank merger cannot be completed without prior approval from the FDIC and Bureau of Financial Institutions of the Virginia SCC. On or about October 8, 2019, C&F filed the required applications with the Federal Reserve and Virginia SCC seeking approval of the merger, and on or about October 8, 2019, C&F Bank filed the

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required applications with the FDIC and the Virginia SCC seeking approval of the subsidiary bank merger.

        Under the merger agreement, in no event is C&F or any of its subsidiaries required, and Peoples and its subsidiaries are not permitted (without C&F's prior written consent), to take any action, or commit to take any action, or to accept any restriction, commitment or condition, involving C&F or its subsidiaries or Peoples or its subsidiaries, which would reasonably be expected to be materially financially burdensome to the business, operations, financial condition or results of operations of C&F or Peoples (which restriction, commitment, or condition could include materially increasing capital, divesting or reducing lines of businesses or asset classes, entering into compliance or remediation programs, and making material lending or investment commitments), which condition, commitment or restriction is referred to in this proxy statement/prospectus as a "burdensome condition."

        As of the date of this proxy statement/prospectus, C&F has not yet received the required approvals from the Federal Reserve and the Virginia SCC for the merger and C&F Bank has not yet received the required approvals from the FDIC and the Virginia SCC for the subsidiary bank merger. While C&F and C&F Bank do not know of any reason why they would not be able to obtain the necessary approvals in a timely manner, or why they would be received with conditions that constitute a burdensome condition, they cannot be certain when or if they will receive them or as to the nature of any conditions imposed.

Dissenters' Appraisal Rights

        Appraisal rights are statutory rights that, if provided under applicable law, provide shareholders a right to dissent from an extraordinary transaction, such as a merger, and to demand that the company pay the fair value of their shares as determined by the company or a court in a judicial proceeding, instead of receiving the consideration offered to shareholders in connection with the extraordinary transaction.

        Shareholders of Peoples have the right to assert appraisal rights with respect to the merger and demand in writing to be paid the fair value of the shares of Peoples common stock following consummation of the merger. These appraisal rights are governed by Virginia law. A copy of the applicable provisions of the Virginia SCA, sections 13.1-729 through 13.1-741.1 of the Code of Virginia, is included in this proxy statement/prospectus as Appendix C. The following summary is not a complete summary of the provisions of the Virginia SCA relating to appraisal rights and is qualified in its entirety by reference to the full text of the provisions of the Virginia SCA pertaining to appraisal rights, which is incorporated herein by reference.

        If you intend to exercise your appraisal rights, you should carefully review the following summary and comply with all requirements of the Virginia SCA. You should also consult with your attorney. Failure by a Peoples shareholder to follow the steps required under Virginia law for asserting and perfecting appraisal rights may result in the loss of such rights. To exercise appraisal rights, before the vote on the merger agreement is taken at the special meeting, you must deliver to Peoples written notice of your intent to demand payment for your shares if the merger is completed; and you must not vote your shares in favor of the merger agreement at the special meeting.

        In other words, you do not have to vote against the merger agreement, or even vote at all, in order to exercise appraisal rights, but you may not vote in favor of the merger agreement, and in all cases you must give the required written notice. If you fail to satisfy these requirements, you will not be entitled to exercise appraisal rights or to receive payment for your shares under the provisions of the Virginia SCA pertaining to appraisal rights. Even if you vote against the merger agreement (either in person or by proxy), you still must send the required notice of intent in order to exercise appraisal rights.

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        You should remember that if you return a signed proxy card, but fail to provide instructions as to the manner in which your shares are to be voted, you will be considered to have voted in favor of the merger agreement and you will not be able to assert appraisal rights. If you do not return a proxy card or do not otherwise vote at all at the People special meeting, you will not be treated as waiving your appraisal rights as long as you have given the required notice of intent as described above.

        Notices of intent to assert appraisal rights with respect to shares of Peoples common stock must be mailed or delivered to Peoples's corporate secretary at Peoples's principal office located at 15960 Kings Highway, PO Box 306, Montross, Virginia 22520, or hand delivered to Peoples's corporate secretary at the special meeting, but before voting on the merger proposal begins. A notice of intent to assert appraisal rights is effective (i) when received by Peoples at its address prior to the special meeting, (ii) five days after its deposit in the U.S. mail (as evidenced by the postmark) if mailed postage prepaid and correctly addressed to Peoples prior to the special meeting, or (iii) on the date shown on the return receipt, if sent by registered or certified mail with return receipt requested, and if the return receipt is signed on behalf of Peoples prior to the special meeting, whichever is earliest.

        If a you deliver a timely notice of intent to assert appraisal rights, do not vote in favor of the merger proposal, and the merger proposal is approved at the special meeting (or any adjournment or postponement thereof), then within 10 days following the effective date of the merger, C&F as the surviving company in the merger will send you an appraisal notice by first-class mail, postage prepaid, to your address as shown in Peoples record of shareholders, as long as you have satisfied the requirements to exercise appraisal rights. The appraisal notice will include another copy of the provisions of the Virginia SCA pertaining to appraisal rights and will:

    include a form you can use for demanding payment that will (i) specify the first date of any announcement to Peoples shareholders of the terms of the merger, (ii) require you to certify that you acquired beneficial ownership of your shares of Peoples common stock before that date, and (iii) require you to certify that you did not vote for or consent to the merger;

    state where your Peoples share certificates must be deposited and the date by which those certificates must be deposited;

    specify where the form described above must be sent and the date by which C&F must receive the form (which may not be fewer than 40 nor more than 60 days after the date of delivery of the appraisal notice), and state that you will have waived the right to demand appraisal with respect to your shares unless the form is received by C&F by such date;

    state C&F's estimate of the fair value of the shares;

    state that, if requested in writing, C&F will provide to you, within 10 days after the date by which C&F must receive the form, the number of shareholders who returned the form by the specified date and the total number of shares owned by them; and

    state the date by which any notice to withdraw from the appraisal process must be received, which date must be within 20 days after the date by which C&F must receive the form.

        If you do not timely deliver to C&F the appraisal form or comply with the terms and conditions of the appraisal notice or the appraisal form, you will not be entitled to demand appraisal for shares of Peoples common stock and instead will receive the merger consideration set forth in the merger agreement. If you timely deliver the appraisal form and comply with all other conditions and requirements set forth in the appraisal notice and the appraisal form, you will lose all rights as a former Peoples shareholder unless you withdraw the appraisal form and payment demand by the date specified in the appraisal notice.

        Within 30 days after the appraisal form is due, C&F will pay you (and any former Peoples shareholder who has asserted and perfected appraisal rights) the amount C&F estimates to be the fair

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value of your shares of Peoples common stock plus accrued interest. C&F's payment will be accompanied by:

    the annual financial statements of Peoples as of a date ending not more than 16 months before the date of payment (or reasonably equivalent information if not available);

    a statement of C&F's estimate of the fair value of the shares of Peoples common stock, which estimate must equal or exceed C&F's estimate given in the appraisal notice;

    an explanation of your rights to demand further payment if you are not satisfied; and

    a statement that failure to demand further payment within a specified time period will be deemed your acceptance of C&F's estimate of fair value as full payment.

        Virginia law sets forth additional procedures that C&F must follow with respect to any former shareholder of Peoples who has taken all required actions, but whose exercise of appraisal rights and demand for payment remains unsettled, including an obligation for C&F to file a lawsuit to petition the appropriate Virginia circuit court to determine the fair value of the shares of Peoples common stock. Virginia law provides that the costs of any such litigation would be assessed against C&F unless the court determines that some or all of the shareholders exercising appraisal rights acted arbitrarily, vexatiously, or not in good faith in demanding payment.

        Shareholders considering seeking appraisal rights for their shares of Peoples common stock should note that the value of their shares determined under Virginia law could be more, the same, or less than the consideration they would receive pursuant to the merger agreement if they did not seek appraisal of their shares.

        If you fail to strictly comply with the procedures set forth under the applicable provisions of the Virginia SCA, you will lose your appraisal rights.

Certain Differences in the Rights of Shareholders

        C&F and Peoples are Virginia corporations governed by the Virginia SCA. In addition, the rights of C&F and Peoples shareholders are governed by their respective articles of incorporation and bylaws. Upon completion of the merger, Peoples shareholders will become shareholders of C&F, and as such their shareholder rights will then be governed by the articles of incorporation and bylaws of C&F, each as amended, and by the Virginia SCA. The rights of shareholders of C&F differ in certain respects from the rights of shareholders of Peoples.

        A summary of the material differences between the rights of a Peoples shareholder under the Virginia SCA and Peoples's articles of incorporation and bylaws, on the one hand, and the rights of a C&F shareholder under the Virginia SCA and the articles of incorporation and bylaws of C&F, on the other hand, is provided in this proxy statement/prospectus in the section "Comparative Rights of Shareholders" on page 82.

Accounting Treatment

        The merger will be accounted for under the acquisition method of accounting pursuant to GAAP. Under the acquisition method of accounting, the assets and liabilities, including identifiable intangible assets arising from the transaction, of Peoples will be recorded, as of completion of the merger, at their respective fair values and added to those of C&F. Any excess of purchase price paid over the fair values of the assets and liabilities acquired is recorded as goodwill. Financial statements and reported results of operations of C&F issued after completion of the merger will reflect these values, but will not be restated retroactively to reflect the historical financial position or results of operations of Peoples.

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Resales of C&F Common Stock

        All shares of C&F common stock to be issued to Peoples shareholders in the merger will be freely transferable under the Securities Act, except shares issued to any shareholder who is an "affiliate" of C&F as defined by Rule 144 under the Securities Act. These affiliates may only sell their shares in transactions permitted by Rule 144 under the Securities Act or as otherwise permitted under the Securities Act. "Affiliates" typically include directors, executive officers and those who control, are controlled by or are under common control with C&F and may include significant shareholders of C&F.

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THE MERGER AGREEMENT

        The following is a summary description of the material provisions of the merger agreement. The following description of the merger agreement is subject to and is qualified in its entirety by reference to the merger agreement, which is attached as Appendix A to this proxy statement/prospectus and incorporated herein by reference. We urge you to read the merger agreement in its entirety as it is the legal document governing the merger.

Structure of the Merger

        The C&F board of directors and the Peoples board of directors have each approved the merger agreement, which provides for the merger of Peoples with and into C&F, with C&F being the surviving company in the merger.

        After the merger, it is expected that Peoples Community Bank, the wholly-owned bank subsidiary of Peoples, will merge with and into C&F Bank, the wholly-owned bank subsidiary of C&F. C&F Bank will be the surviving bank in the subsidiary bank merger.

Merger Consideration

        General.    Pursuant to the terms of the merger agreement, as a result of the merger, each share of Peoples common stock issued and outstanding before the effective time of merger (except for any shares of Peoples common stock owned by C&F and any dissenting shares) will be converted into the right to receive:

    $27.00 in cash; and

    0.5366 shares of C&F common stock.

        The exchange ratio of 0.5366 shares of C&F common stock will not be adjusted to reflect stock price changes prior to the effective time of the merger. You will not have the ability to elect to receive all stock or all cash as merger consideration, or any other combination of cash and stock, for your shares of Peoples common stock except with respect to any dissenting shares.

        If either Williams Mullen, as outside counsel to C&F, or Troutman Sanders LLP, as outside counsel to Peoples, reasonably determines that it cannot render its respective federal tax opinion that the merger will be treated as a "reorganization" within the meaning of Section 368(a) of the Code because of the continuity of interest requirements therein, then C&F, with the consent of Peoples which shall not be unreasonably withheld, has the right to increase the exchange ratio and proportionately decrease the cash component of the merger consideration by the minimum amount necessary to satisfy the requirements of Section 368(a) of the Code.

        If the number of shares of C&F common stock changes before the merger is completed because of a stock split, stock dividend, recapitalization, reclassification, reorganization or similar event, then a proportionate adjustment will be made to the exchange ratio.

        C&F's shareholders will continue to own their existing shares of C&F common stock. Each share of C&F common stock outstanding immediately prior to the effective time of the merger will continue to represent one share of common stock of C&F following the merger.

        Fractional Shares.    C&F will not issue any fractional shares of common stock. Instead, a Peoples shareholder who would otherwise have received a fraction of a share will receive an amount of cash equal to the fraction of a share of C&F common stock to which such holder would otherwise be entitled multiplied by the average closing sale price per share of C&F common stock, as reported on the Nasdaq Global Select Market, for the 10 consecutive trading days ending on and including the last trading day immediately prior to the effective time of the merger.

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Effective Time; Closing

        The merger will become effective on the date and time set forth on the certificate of merger issued by the Virginia SCC effecting the merger. Subject to the satisfaction or waiver of the closing conditions in the merger agreement, the parties will use their reasonable best efforts to cause the effective time to occur on the fifth business day after all required regulatory and shareholder approvals have been received or such other date mutually agreed by the parties. We anticipate that we will complete the merger in early 2020, subject to the receipt of required shareholder and regulatory approvals, and the satisfaction or waiver of the closing conditions set forth in the merger agreement. See "—Conditions to Completion of the Merger" beginning on page 62.

        There can be no assurances as to if or when the shareholder and regulatory approvals will be obtained or that the merger will be completed. If we do not complete the merger by August 13, 2020, either party may terminate the merger agreement, provided that such termination right is not available to a party whose breach or failure to perform an obligation under the merger agreement has caused the failure of the merger to occur on or before such date.

Exchange of Shares in the Merger

        Before the effective time of the merger, C&F will cause to be deposited with its transfer agent, American Stock Transfer & Trust Company, or another transfer agent approved by the parties (the "exchange agent"), shares of C&F common stock and cash equal to the aggregate amount of the per share cash consideration, for the benefit of the Peoples shareholders, and cash instead of any fractional shares that would otherwise be issued to Peoples shareholders in the merger.

        Promptly after the completion of the merger, the exchange agent will send transmittal materials to each holder of Peoples common stock for use in exchanging shares of Peoples common stock for the merger consideration. Once the exchange agent receives the properly completed transmittal materials together with a holder's shares of Peoples common stock, the exchange agent will deliver the merger consideration comprised of shares of C&F common stock and a check representing the cash component of the merger consideration plus cash in lieu of fractional shares of C&F common stock.

        Peoples stock certificates should NOT be returned with the enclosed proxy card. They also should NOT be forwarded to the exchange agent until you receive a transmittal letter following completion of the merger.

        Shares of Peoples common stock may be exchanged for the merger consideration with the exchange agent for up to 12 months after the completion of the merger. At the end of that period, any remaining shares of C&F common stock and cash deposited with the exchange agent will be returned to C&F and any holders of shares of Peoples common stock who have not exchanged their shares will be entitled to look only to C&F, and only as general creditors of C&F, for payment of the merger consideration.

        Until you exchange your shares of Peoples common stock for the merger consideration, you will not receive any dividends or other distributions in respect of shares of C&F common stock. Once you exchange your shares of Peoples common stock for the merger consideration, you will receive, without interest, any dividends or distributions with a record date after the effective time of the merger and payable with respect to your shares of C&F common stock.

        If you own Peoples common stock in book entry form or through a broker, bank or other holder of record, you will not need to obtain Peoples stock certificates with respect to these shares to surrender them to the exchange agent.

        If your Peoples stock certificate has been lost, stolen or destroyed, you may receive a new stock certificate upon the making of an affidavit of that fact. You will receive written instructions from the

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exchange agent promptly after the merger is completed on how to receive a new stock certificate and how to exchange the stock certificate for shares of C&F common stock and the cash portion of the merger consideration, along with cash in lieu of any fractional shares of C&F common stock. C&F may require you to post a bond in a reasonable amount as an indemnity against any claim that may be made against C&F with respect to the lost, stolen or destroyed Peoples stock certificate.

        Neither C&F nor Peoples, nor any other person, including the exchange agent, will be liable to any former holder of Peoples stock for any amount properly delivered to a public official pursuant to applicable abandoned property, escheat or similar laws.

Representations and Warranties

        The merger agreement contains representations and warranties relating to C&F and Peoples's respective businesses, including:

    corporate organization, standing and power, and subsidiaries;

    requisite corporate authority to enter into the merger agreement and to complete the contemplated transactions;

    capital structure;

    financial statements and accounting controls;

    regulatory reports filed with governmental agencies and other regulatory matters;

    absence of certain changes or events and absence of certain undisclosed liabilities;

    legal proceedings and compliance with applicable laws;

    tax matters and tax treatment of merger;

    employee benefit matters;

    brokers and finders;

    engagement of financial advisors;

    insurance;

    information systems and security; and

    Community Reinvestment Act compliance.

        In addition, the merger agreement contains representations and warranties relating to Peoples's business specifically, such as:

    material contracts;

    ownership and leasehold interests in properties;

    labor and employment matters;

    loan portfolio and allowance for loan losses;

    environmental matters;

    books and records;

    intellectual property;

    derivative instruments;

    brokered deposits;

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    investment securities;

    anti-takeover statutes and regulations;

    transaction with affiliates; and

    fairness opinion from its financial advisor.

        With the exception of specified representations and warranties relating to corporate authority, that must be true and correct in all material respects, and representations and warranties relating to capitalization, absence of certain changes reasonably likely to have a material adverse effect, and brokers and finders, which must be true and correct in all respects, no representation or warranty will be deemed untrue or incorrect as a consequence of the existence or absence of any fact, event or circumstance unless that fact, event or circumstance, individually or taken together with all other facts, events or circumstances, has had or is reasonably likely to have a material adverse effect (as such term is defined in the merger agreement) on the party making the representation or warranty.

        The representations and warranties described above and included in the merger agreement were made for purposes of the merger agreement and are subject to qualifications and limitations agreed to by the parties in connection with negotiating the terms of the merger agreement, including being qualified by confidential disclosures, and were made for the purposes of allocating contractual risk between C&F and Peoples instead of establishing these matters as facts. The representations and warranties do not survive the effective time of the merger. In addition, certain representations and warranties were made as of a specific date and may be subject to a contractual standard of materiality different from what might be viewed as material to shareholders. The representations and warranties and other provisions of the merger agreement should not be read alone, but instead should only be read together with the information provided elsewhere in this proxy statement/prospectus, in the documents incorporated by reference into this proxy statement/prospectus, and in the periodic and current reports and statements that C&F files with the SEC. See "Where You Can Find More Information" beginning on page 91.

Conditions to Completion of the Merger

        The respective obligations of C&F and Peoples to complete the merger are subject to the satisfaction or waiver of certain conditions, including the following:

    approval of the merger proposal by Peoples shareholders;

    approval of the merger by the necessary federal and state regulatory authorities without imposition of a burdensome condition;

    effectiveness of C&F's registration statement on Form S-4, of which this proxy statement/prospectus is a part;

    the absence of any order, decree or injunction of a court or regulatory agency that enjoins or prohibits the completion of the merger;

    approval from the Nasdaq Stock Market for the listing on the Nasdaq Global Select Market of the shares of common stock of C&F to be issued in the merger;

    the receipt by C&F and Peoples from its respective outside legal counsel of a written legal opinion to the effect that the merger will be treated as a "reorganization" within the meaning of Section 368(a) of the Code;

    the accuracy of the other party's representations and warranties in the merger agreement, subject to the material adverse effect standard in the merger agreement;

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    the other party's performance in all material respects of its obligations under the merger agreement; and

    no material adverse effect with respect to the other party shall have occurred.

        In addition, C&F's obligation to complete the merger is subject to the satisfaction or waiver of the conditions set forth below:

    the aggregate number of shares of Peoples common stock for which appraisal rights have been perfected under the Virginia SCA shall not represent 10% or more of the outstanding shares of Peoples common stock; and

    each of the directors of Peoples shall have entered into a support agreement with C&F and such agreements shall be effective.

        Where the merger agreement and law permits, C&F and Peoples could choose to waive a condition to its obligation to complete the merger even if that condition has not been satisfied. C&F and Peoples cannot be certain when, or if, the conditions to the merger will be satisfied or waived or that the merger will be completed.

Business Pending the Merger

        C&F and Peoples have agreed to customary restrictions on their respective business activities until the completion of the merger. In general, C&F and Peoples are required to (i) conduct their respective businesses in the ordinary and usual course, (ii) take no action that would affect adversely or delay the ability to obtain the required approvals and consents for the merger, perform the covenants and agreements under the merger agreement or complete the merger on a timely basis, (iii) take no action that would prevent the merger from qualifying as a reorganization within the meaning of Section 368(a) of the Code, (iv) materially follow their existing policies or practices with respect to managing interest rate risk and use commercially reasonable means to avoid any material increase in their exposure to interest rate risk, (v) take no action to adopt or enter into a plan of complete or partial liquidation, dissolution, restructuring, recapitalization or other reorganization, and (vi) take no action that would make any of its representation or warranties untrue, taking into account the material adverse effect standard set forth in the merger agreement.

        Peoples also agreed that, until the effective time of the merger and with certain exceptions, it will not, and will not permit any of its subsidiaries to, without the prior written consent of C&F:

    amend, modify or repeal its articles of incorporation, bylaws or other similar governing instruments;

    issue or sell any additional shares of capital stock or grant any stock options, restricted shares or other stock-based awards;

    enter into or amend or renew any employment or severance agreement or similar arrangement with any of its directors, officers or employees, or grant any salary or wage increase or increase any employee benefit, except for normal individual merit increases in the ordinary course of business consistent with past practice (excluding executive officers), provided that no such salary or wage increase will result in an annual adjustment in any individual officer's or employee's salary or wages of more than 2.5%;

    enter into, establish, adopt, amend, terminate or make any contributions to (except to satisfy contractual obligations as previously disclosed to C&F or to comply with the requirements of the merger agreement), any pension, retirement, stock option, stock purchase, savings, profit sharing, deferred compensation, consulting, bonus, group insurance or other material employee benefit, incentive or welfare contract, plan or arrangement, or any trust agreement related thereto, in

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      respect of any director, officer or employee, or take any action to accelerate the vesting or exercise of any benefits payable thereunder;

    exchange, cancel, borrow from, surrender, or increase or decrease the death benefit provided under, or otherwise amend or terminate, any existing bank or corporate owned life insurance covering any current or former employee, other than any such change that is required by law;

    incur any indebtedness for borrowed money, other than overnight borrowings and draws under Peoples's lines of credit as existing on the date of the merger agreement (or subsequently renewed), in each case in the ordinary course of business consistent with past practice, or assume, guarantee, endorse or otherwise as an accommodation become responsible for the obligations of any other person, other than with respect to the collection of checks and other negotiable instruments in the ordinary course of business consistent with past practices;

    hire any person as an employee or promote any employee, except (i) to satisfy contractual obligations as previously disclosed to C&F and (ii) persons hired to fill any employee or non-officer vacancies arising after the date of the merger agreement and whose employment is terminable at will and who are not subject to or eligible for any additional severance or similar benefits or payments that would become payable as a result of the merger, the subsidiary bank merger or the completion thereof, other than as disclosed to C&F;

    make, declare, pay any dividend on, or redeem, purchase or otherwise acquire any shares of capital stock, or adjust, split, combine or reclassify any shares of capital stock;

    sell, transfer, mortgage, encumber or otherwise dispose of or discontinue any of its assets, deposits in bulk, business or properties except for (i) other real estate owned ("OREO") that is sold in the ordinary course of business consistent with past practice, (ii) certain transactions previously disclosed by Peoples to C&F, (iii) "QwikRate" and other reciprocal funding products offered by Promontory Interfinancial Network LLC and transactions through the Certificate of Deposit Account Registry Service ("CDARS") in the ordinary course of business consistent with past practice, or (iv) transactions in the ordinary course of business consistent with past practice in amounts that do not exceed $25,000 individually or $100,000 in the aggregate;

    acquire all or any portion of the assets, business, securities, deposits or properties of any other person, except for (i) acquisitions of securities permitted by the merger agreement, (ii) by way of foreclosures or of control in a bona fide fiduciary capacity or in satisfaction of debts previously contracted in good faith, (iii) "QwikRate" and other reciprocal funding products offered by Promontory Interfinancial Network LLC and transactions through the CDARS in the ordinary course of business consistent with past practice, and (iv) in the ordinary course of business consistent with past practice in amounts that do not exceed $25,000 individually or $100,000 in the aggregate;

    implement or adopt any change in its tax or financial accounting principles, practices or methods, including reserving methodologies, other than as may be required by GAAP, regulatory accounting guidelines or applicable law, or as recommended by Peoples's outside auditor;

    make, change or revoke any material tax election, change an annual tax accounting period, adopt or change any tax accounting method, file any amended tax return, enter into any closing agreement with respect to taxes, or settle any tax claim, audit, assessment or dispute or surrender any right to claim a refund of a material amount of taxes;

    enter into any new material line of business, introduce any material new products or services, make any material change to deposit products or deposit gathering or retention policies or strategies, change its material lending, investment, underwriting, pricing, originating, servicing, risk and asset liability management and other material banking, operating or board policies or

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      practices or otherwise fail to follow such policies or practices, except as required by applicable law, regulation or policies imposed by any regulatory agency, or the manner in which its investment securities or loan portfolio is classified or reported, or file any application or enter into any contract with respect to the opening, relocation or closing of, or open, relocate or close, any branch, office, service center or other facility;

    (i) make, renew, restructure or otherwise modify any loan other than loans made or acquired in the ordinary course of business consistent with past practice and that have (A) in the case of unsecured loans made to any one borrower that are originated in compliance with Peoples's internal loan policies, a principal balance not in excess of $40,000 in total, or (B) in the case of secured loans made to any one borrower that are originated in compliance with Peoples's internal loan policies, a principal balance not in excess of $800,000 in total, (ii) except in the ordinary course of business, take any action that would result in any discretionary release of collateral or guarantees or otherwise restructure the respective amounts set forth in clause (i) above, or (iii) enter into any loan securitization or create any special purpose funding entity;

    enter into, modify, amend, terminate, cancel, fail to renew or extend any material contract or expressly waive any material benefits under any material contract, or enter into, amend or modify in any material respect any contract related to the offering of investment services, correspondent mortgage banking or other financial services in its branches by a third party service provider;

    (i) acquire (other than by way of foreclosures or acquisitions in a bona fide fiduciary capacity or in satisfaction of debts previously contracted in good faith, in each case in the ordinary course of business consistent with past practice) any debt security or equity investment other than federal funds or U.S. Government securities or U.S. Government agency securities, in each case with a term of one year or less, (ii) dispose of any debt security or equity investment, or (iii) restructure or materially change its investment securities or derivatives portfolio or its interest rate exposure, through purchases, sales or otherwise, or the manner in which the portfolio is classified or reported;

    enter into or settle any derivative contract;

    except as previously disclosed to C&F, make any capital expenditures, other than capital expenditures in the ordinary course of business consistent with past practice, in amounts not exceeding $25,000 individually or $100,000 in the aggregate;

    settle any claim, action, suit, proceeding, order or investigation, except (i) in the ordinary course of business consistent with past practice involving a settlement in an amount and for consideration not in excess of $25,000 and that would not impose any material restriction on the business of it or its subsidiaries or C&F after the merger; and (ii) as previously disclosed to C&F;

    make any investment or commitment to invest in real estate or in any real estate development project (other than by way of foreclosure or acquisitions in a bona fide fiduciary capacity or in satisfaction of a debt previously contracted in good faith, in each case in the ordinary course of business consistent with past practice);

    introduce any material new sales compensation or incentive programs or arrangements (except those the material terms of which have been fully disclosed in writing to, and approved by, C&F prior to the date of the merger agreement); or

    agree to take any of the actions prohibited by the preceding bullet points.

        C&F also agreed that, until the effective time of the merger, it will not, and will not permit any of its subsidiaries to, without the prior written consent of Peoples, amend, repeal or modify any articles of

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incorporation, bylaws or other similar governing instruments in a manner which would adversely affect Peoples, shareholders of Peoples relative to other shareholders of C&F, or the transactions contemplated by the merger agreement.

Regulatory Matters

        C&F and Peoples have each agreed to cooperate and use their reasonable best efforts to prepare as promptly as possible all documentation, to effect all filings and to obtain all regulatory approvals necessary to consummate the merger. Please see "The Merger—Regulatory Approvals" beginning on page 54.

Shareholder Meeting and Recommendation of the Peoples Board of Directors

        Peoples has agreed to call a special meeting of shareholders as soon as reasonably practicable for the purpose of obtaining the required shareholder approval of the merger proposal.

        In connection with the special meeting, Peoples agreed that its board of directors would support and recommend approval of the merger agreement and the transactions contemplated thereby and use its reasonable best efforts to obtain the required shareholder votes in favor of the merger proposal unless the Peoples board has received and recommended (or submitted to shareholders) an acquisition proposal from a third party that qualifies as a "superior proposal" under the merger agreement as described and under the circumstances set forth in the next section ("—No Solicitation").

No Solicitation

        Peoples has agreed that, while the merger agreement is in effect, it will not directly or indirectly:

    initiate, solicit, endorse or encourage any inquiries or proposals with respect to any "acquisition proposal" (as defined in the merger agreement); or

    engage or participate in any negotiations or discussions concerning, or provide any confidential or nonpublic information relating to, an acquisition proposal.

        For purposes of the merger agreement, an "acquisition proposal" means, other than the transactions contemplated by the merger agreement, any offer, proposal or inquiry relating to, or any third party indication of interest in, any of the following transactions involving Peoples or Peoples Community Bank:

    a merger, consolidation, share exchange, business combination, reorganization, recapitalization, liquidation, dissolution or other similar transaction;

    any acquisition or purchase, direct or indirect, of 20% or more of the consolidated assets of Peoples or 20% or more of any class of equity or voting securities of Peoples or its subsidiaries whose assets, individually or in the aggregate, constitute more than 20% of the consolidated assets of Peoples; or

    any tender offer (including a self-tender offer) or exchange offer that, if consummated, would result in a third party beneficially owning 20% or more of any class of equity or voting securities of Peoples or its subsidiaries whose assets, individually or in the aggregate, constitute more than 20% of the consolidated assets of Peoples.

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        Under the merger agreement, however, if Peoples receives an unsolicited bona fide written acquisition proposal, it may engage in negotiations or discussions with or provide nonpublic information to the person or entity making the acquisition proposal only if:

    the Peoples board of directors receives the acquisition proposal prior to approval of the merger proposal by Peoples shareholders;

    the Peoples board concludes in good faith, after consultation with outside legal counsel and its financial advisors, that the failure to take such actions would be more likely than not to result in a violation of its fiduciary duties to shareholders under Virginia law;

    the Peoples board also concludes in good faith, after consultation with outside legal counsel and financial advisors, that the acquisition proposal constitutes or is reasonably likely to result in a superior proposal (as defined below); and

    Peoples receives from the person or entity making the proposal an executed confidentiality agreement, which confidentiality agreement does not provide such person or entity with any exclusive right to negotiate with Peoples.

        Peoples has agreed to advise C&F, within 24 hours of the receipt of any such acquisition proposal, including a description of the material terms and conditions of the proposal (including the identity of the proposing party), and to keep C&F apprised of any related developments, discussions and negotiations on a current basis.

        For purposes of the merger agreement, a "superior proposal" means an unsolicited, bona fide written acquisition proposal made by a person or entity that the board of directors of Peoples concludes in good faith, after consultation with its financial and outside legal advisors, taking into account all legal, financial, regulatory and other aspects of the acquisition proposal and including the terms and conditions of the merger agreement:

    is more favorable to the shareholders of Peoples from a financial point of view, than the transactions contemplated by the merger agreement; and

    is fully financed or reasonably capable of being fully financed and reasonably likely to receive all required approvals of governmental authorities on a timely basis and otherwise reasonably capable of being completed on the terms proposed on a timely basis.

        With respect to the definition of "superior proposal," the term "acquisition proposal" has the same meaning as described above, except the reference to "20% or more" is deemed to be a reference to "a majority" and an "acquisition proposal" can only refer to a transaction involving Peoples or Peoples Community Bank.

        Except as otherwise provided in the merger agreement, nothing contained in the non-solicitation provisions of the merger agreement will permit Peoples to terminate the merger agreement or affect any of its other obligations under the merger agreement.

Termination of the Merger Agreement

        The merger agreement may be terminated, and the merger abandoned, by C&F and Peoples at any time before the merger is completed by mutual consent of C&F and Peoples. In addition, the merger agreement may be terminated, and the merger abandoned, under the following circumstances:

    by C&F or Peoples if the merger has not been completed by August 13, 2020 or such later date as agreed to by the parties in writing, provided that this right to terminate shall not be available to any party whose breach or failure to perform an obligation under the merger agreement has caused the failure of the merger to occur prior to such date;

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    by C&F or Peoples if there is a breach by the other party of any representation, warranty, covenant or agreement contained in the merger agreement that would cause the failure of the closing conditions described above, and the breach cannot be or is not cured within 30 days following written notice to the breaching party, provided that the terminating party is not then in breach of any representation, warranty, covenant or agreement (as applicable) contained in the merger agreement;

    by C&F or Peoples if Peoples shareholders do not approve the merger proposal;

    by C&F at any time before the special meeting if (i) Peoples breaches its obligations regarding the non-solicitation of competing offers for certain corporate transactions; (ii) the Peoples board (a) fails to recommend to the Peoples shareholders that they approve the merger proposal, or (b) withdraws, modifies or changes such recommendation in any manner adverse to C&F; or (iii) Peoples materially breaches its obligations in the merger agreement requiring the calling and holding of a meeting of shareholders to consider the merger proposal;

    by C&F, if (i) Peoples or Peoples Community Bank enters into an agreement with any person to merge or consolidate with or acquire Peoples or Peoples Community Bank, or purchase, lease or otherwise acquire all or substantially all of the assets of Peoples or Peoples Community Bank, or purchase or otherwise acquire from Peoples securities representing 20% or more of the voting power of Peoples or (ii) a tender or exchange offer is commenced for 20% or more of the outstanding shares of Peoples common stock, and the Peoples board recommends that the Peoples shareholders tender their shares or otherwise fails to recommend that shareholders reject such offer; or

    by Peoples at any time before the special meeting in order for Peoples to enter into an agreement with respect to a "superior proposal" (as defined in the merger agreement), which has been received and considered by Peoples in compliance with the applicable terms of the merger agreement.

        In the event of termination, the merger agreement will become null and void, except that certain provisions thereof relating to fees and expenses (including the obligation to pay the termination fee described below in certain circumstances) and confidentiality of information exchanged between the parties will survive any such termination.

Termination Fee

        The merger agreement provides that Peoples must pay C&F a $900,000 termination fee under the circumstances and in the manner described below:

    if, before the special meeting, C&F terminates the merger agreement because (i) Peoples breaches its obligations regarding the non-solicitation of competing offers for certain corporate transactions; (ii) the Peoples board (a) fails to recommend to the Peoples shareholders that they approve the merger proposal, or (b) withdraws, modifies or changes such recommendation in any manner adverse to C&F; or (iii) Peoples materially breaches its obligations in the merger agreement requiring the calling and holding of a meeting of shareholders to consider the merger proposal;

    if C&F terminates the merger agreement because (i) Peoples or Peoples Community Bank enters into an agreement with any person to merge or consolidate with or acquire Peoples or Peoples Community Bank, or purchase, lease or otherwise acquire all or substantially all of the assets of Peoples or Peoples Community Bank, or purchase or otherwise acquire from Peoples securities representing 20% or more of the voting power of Peoples or (ii) a tender or exchange offer is commenced for 20% or more of the outstanding shares of Peoples common stock, and

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      the Peoples board recommends that the Peoples shareholders tender their shares or otherwise fails to recommend that shareholders reject such offer;

    if, before the special meeting, Peoples terminates the merger agreement in order for Peoples to enter into an agreement with respect to a "superior proposal" (as defined in the merger agreement), which has been received and considered by Peoples in compliance with the applicable terms of the merger agreement; or

    if (i) the merger agreement is terminated (A) by C&F as a result of a breach by Peoples of any representation, warranty, covenant or agreement contained in the merger agreement that would cause the failure of the closing conditions described above, and the breach cannot be or is not cured within 30 days following written notice to Peoples, (B) by C&F or Peoples if the merger has not been completed by August 13, 2020 or such later date as agreed to by the parties in writing, or (C) by either C&F or Peoples because the merger has not been approved by the shareholders of Peoples at the special meeting, and in the case of termination pursuant to clauses (A), (B) or (C) an acquisition proposal has been publicly announced or otherwise communicated or made known to the shareholders, senior management or board of directors of Peoples (or any person has publicly announced, communicated or made known an intention, whether or not conditional, to make an acquisition proposal) prior to the taking of the vote of the shareholders of Peoples contemplated by the merger agreement, in the case of clause (C) above, or prior to the date of termination, in the case of clauses (A) or (B) above, and (ii) within 12 months after such termination Peoples enters into an agreement or consummates a transaction with respect to an acquisition proposal (whether or not the same acquisition proposal as that referred to above).

        Any termination fee that becomes payable to C&F pursuant to the merger agreement will be paid by wire transfer of immediately available funds to an account designated by C&F. If Peoples fails to timely pay the termination fee to C&F, Peoples also will be obligated to pay the costs and expenses incurred by C&F to collect such payment, together with interest.

Indemnification and Insurance

        C&F has agreed to indemnify the directors and officers of Peoples against certain liabilities arising before the effective time of the merger. C&F has also agreed to purchase a six year "tail" prepaid policy, on the same terms as Peoples's existing directors' and officers' liability insurance, for the current directors and officers of Peoples, subject to a cap on the cost of such policy equal to 200% of Peoples's current annual premium.

Expenses

        In general, whether or not the merger is completed, C&F and Peoples will each pay its respective expenses incident to preparing, entering into and carrying out the terms of the merger agreement, except that the costs and expenses of printing and mailing this proxy statement/prospectus will be incurred by Peoples.

Waiver and Amendment

        At any time on or before the effective time of the merger, any term or provision of the merger agreement, other than the merger consideration, may be waived by the party which is entitled to the benefits thereof, without shareholder approval, to the extent permitted under applicable law. The terms of the merger agreement may be amended at any time before the merger by agreement of the parties, whether before or after the special meeting, except with respect to statutory requirements and requisite shareholder and regulatory authority approvals.

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Support and Non-Competition Agreements

        Among other conditions described above, C&F's obligation to complete the merger is subject to all of the directors of Peoples having, concurrent with the execution of the merger agreement, entered into a support and non-competition agreement, and all such support agreements remaining in full force and effect. On August 13, 2019, each of the directors of Peoples entered into a support agreement with C&F. The following summary describes certain material provisions of the form of support agreement and is qualified in its entirety by reference to the form of support agreement, which is Exhibit 5.8 to the merger agreement, which is attached to this proxy statement/prospectus as Appendix A. This summary does not purport to be complete and may not contain all of the information about the support agreements that may be important to you. You are encouraged to read the form of support agreement carefully and in its entirety.

        Agreement to Vote Covered Shares.    Under the support agreements, each Peoples director agreed to cause all of the shares of Peoples common stock over which he or she exercises sole rights of voting and disposition to be voted in favor of approving the merger agreement, unless C&F is in material default with respect to a material covenant, representation, warranty or agreement made by it in the merger agreement. As of the record date of the Peoples special meeting, there were 30,581 covered shares subject to support agreements, which represented 7.81% of the Peoples common stock outstanding.

        Transfer Restrictions.    Each Peoples director also agreed, subject to certain exceptions, not to tender into any tender or exchange offer or to sell, transfer, hypothecate, grant a security interest in, or otherwise dispose of or encumber any covered shares without the prior written consent of C&F, provided that such restriction does not apply to shares of Peoples common stock that are hypothecated or as to which a security interest already has been granted as of the date of the support agreement.

        Non-Solicitation.    Each Peoples director also agreed to not solicit, and to not authorize, direct or encourage any other person to solicit, from any third party any inquiries or proposals relating to the disposition of Peoples's business or assets, the acquisition of voting securities of Peoples or the merger of Peoples with any person other than C&F or a subsidiary of C&F. The support agreements also restrict Peoples directors from providing a third party with information or assistance relating to, or conducting discussions in furtherance of, such inquiries or proposals, except as permitted in limited circumstances under the merger agreement.

        Non-Competition.    For a period of twelve months from the effective time of the merger, each Peoples director (other than the President and Chief Executive Officer and Executive Vice President and Chief Financial Officer of Peoples, who are subject to separate non-competition obligations under their respective employment agreements with Peoples) has agreed not to, directly or indirectly:

    serve as a member of the board of directors (including any advisory board) of any financial institution, or the direct or indirect holding company or subsidiary of a financial institution or holding company, with an office or branch located within a 35-mile radius of any office or branch of C&F, C&F Bank, Peoples, Peoples Community Bank, or any subsidiary or affiliate thereof, as of the date of the merger agreement or at the effective time of the merger (the "covered area");

    serve on the board of directors of any company with an office or branch in the covered area that provides any of the products or services provided by C&F, C&F Bank, Peoples, Peoples Community Bank, or any subsidiary or affiliate thereof, as of the date of the merger agreement or the effective time of the merger, subject to certain limited exceptions;

    solicit to employ or engage the services of any of the officers or employees of C&F or C&F Bank, including former employees of Peoples (other than such employees or officers who have

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      been terminated by C&F, C&F Bank, Peoples, or Peoples Community Bank prior to such solicitation or engagement);

    initiate or maintain contact with any officer, director or employee of C&F or C&F Bank, including former employees of Peoples, regarding the business, operations, prospects or finances of C&F or C&F Bank, except for conversations with employees that are necessary to conduct routine banking business or transactions; or

    solicit customers of C&F or C&F Bank, or any subsidiary or affiliate thereof on behalf of any bank or provider of any of the products or services offered by C&F or C&F Bank or any subsidiary or affiliate thereof.

        Termination.    The provisions of the support agreements related to the voting of the Covered Shares and the transfer restrictions on the Covered Shares expires upon the earlier of (i) the termination of the merger agreement and (ii) the effective time of the merger. The provisions of the support agreements relating to the non-competition periods and non-solicitation periods expire on the date that is 12 months after the effective time of the merger.

Assumption of Peoples's Subordinated Term Note

        At the effective time of the merger, C&F will assume the due and punctual payment of the principal of and any premium and interest on Peoples's subordinated term note due April 1, 2028 in accordance with its terms, and the due and punctual performance of all covenants and conditions thereof on the part of Peoples to be performed or observed. As of June 30, 2019, the principal balance of the note was $4.0 million.

Possible Alternative Merger Structure

        The merger agreement provides that C&F and Peoples may mutually agree to change the method or structure of the merger. However, no change may be made that:

    alters or changes the merger consideration;

    adversely affects the tax treatment of C&F or Peoples pursuant to the merger agreement;

    materially impedes or delays completion of the merger in a timely manner; or

    requires the approval of the shareholders of C&F or Peoples unless such change is conditioned upon obtaining such approval.

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MATERIAL U.S. FEDERAL INCOME TAX CONSEQUENCES

        Subject to the limitations, assumptions and qualifications described herein, in the opinion of each of Williams Mullen and Troutman Sanders LLP, the following discussion summarizes the material U.S. federal income tax consequences of the merger generally applicable to "U.S. holders" (as defined below) of Peoples common stock. The opinions of Williams Mullen and Troutman Sanders LLP, tax counsel for each of C&F and Peoples, respectively, are filed as Exhibit 8.1 and Exhibit 8.2, respectively, to the registration statement on Form S-4 of which this document is a part.

        For purposes of this discussion, a "U.S. holder" is a beneficial owner of Peoples common stock and is, for U.S. federal income tax purposes, (1) an individual citizen or resident of the United States, (2) a corporation (or entity treated as a corporation for U.S. federal income tax purposes) organized in or under the laws of the United States or any state thereof or the District of Columbia, (3) a trust if (a) a court within the United States is able to exercise primary supervision over the administration of the trust and one or more U.S. persons have the authority to control all substantial decisions of such trust, or (b) such trust has made a valid election to be treated as a U.S. person for U.S. federal income tax purposes, or (4) an estate, the income of which is subject to U.S. federal income tax regardless of its source.

        This discussion applies only to U.S. holders who hold their shares of Peoples common stock as a capital asset within the meaning of Section 1221 of the Code (generally, property held for investment) and exchange those shares for the merger consideration in the merger. Further, this discussion does not purport to consider all aspects of U.S. federal income taxation that might be relevant to U.S. holders in light of their particular circumstances and does not apply to U.S. holders subject to special treatment under the U.S. federal income tax laws (such as, for example, dealers or brokers in securities, commodities or foreign currencies; traders in securities that elect to apply a mark-to-market method of accounting; banks and certain other financial institutions; insurance companies; regulated investment companies and real estate investment trusts; tax-exempt organizations; holders of Peoples common stock subject to the alternative minimum tax provisions of the Code; S corporations; partnerships or other pass-through entities (or investors in S corporations, partnerships or other pass-through entities); holders of Peoples common stock whose functional currency is not the U.S. dollar; holders who hold shares of Peoples common stock as part of a "hedge," "straddle," "constructive sale" or "conversion transaction" (as such terms are used in the Code) or other integrated investment; holders of Peoples common stock who exercise appraisal rights; persons who purchased their shares of Peoples common stock as part of a wash sale; or holders required to accelerate the recognition of any item of gross income for U.S. federal income tax purposes with respect to C&F common stock as a result of such item being taken into account in an applicable financial statement).

        This discussion does not address any tax consequences arising under any U.S. state or local, or foreign laws, the Medicare contribution tax, the alternative minimum tax or under any U.S. federal laws other than U.S. federal income tax laws (such as estate or gift tax laws).

        If an entity or an arrangement treated as a partnership for U.S. federal income tax purposes holds Peoples common stock, the tax treatment of a partner in such partnership generally will depend on the status of the partner and the activities of the partnership. Any entity treated as a partnership for U.S. federal income tax purposes that holds Peoples common stock, and any partners in such partnership, are strongly urged to consult their own tax advisors about the tax consequences of the merger to them.

        This discussion, and the tax opinions referred to herein, is based upon the Code, the U.S. Treasury regulations promulgated thereunder and judicial and administrative authorities, rulings, and decisions, all as in effect on the date of this joint proxy statement/prospectus. These authorities may change, possibly with retroactive effect, and any such change could affect the accuracy of the statements and conclusions set forth in this discussion. The opinions described herein will not be binding on the IRS, or any court. C&F and Peoples have not sought and will not seek any ruling from the IRS regarding

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any matters relating to the mergers, and as a result, there can be no assurance that the IRS will not assert, or that a court would not sustain, a position contrary to any of the conclusions set forth below. In addition, if any of the representations or assumptions upon which the opinion is based are inconsistent with the actual facts, the U.S. federal income tax consequences of the merger could be adversely affected.

        Determining the actual tax consequences of the merger to you may be complex and will depend on your specific situation and on factors that are not within our control. You are strongly urged to consult with your own tax advisor as to the specific tax consequences of the merger in your particular circumstances, including the applicability and effect of the alternative minimum tax and any U.S. federal, state and local, foreign and other tax laws and of changes in those laws.

U.S. Federal Income Tax Consequences of the Merger Generally

        Subject to the limitations, assumptions and qualifications described herein, the merger will qualify as a "reorganization" within the meaning of Section 368(a) of the Code. It is a condition to each of Peoples's and C&F's obligation to complete the merger that each receive an opinion from its tax counsel, Troutman Sanders LLP and Williams Mullen, respectively, dated the closing date of the merger, to the effect that, on the basis of facts, representations and assumptions set forth or referred to in such opinion, the merger will constitute a reorganization within the meaning of Section 368(a) of the Code. These tax opinions will be based on representations by C&F and Peoples, as well as certain covenants and undertakings by C&F and Peoples and customary assumptions. Each of C&F and Peoples has the ability to waive receipt of the legal opinion of its counsel as a condition to consummating the merger; however, neither C&F nor Peoples currently intends to waive these conditions to the consummation of the merger. In the event that C&F or Peoples waives the condition to receive such tax opinion and the tax consequences of the merger materially change, then C&F and Peoples will recirculate appropriate soliciting materials and seek new approval of the merger from Peoples and C&F shareholders. The remainder of this discussion is based on the merger qualifying as a "reorganization" within the meaning of Section 368(a) of the Code.

Tax Consequences to Holders of Peoples Common Stock Who Receive C&F Common Stock and Cash

        If you are a holder of Peoples common stock that exchanges shares of Peoples common stock for shares of C&F common stock and cash pursuant to the merger, you generally will recognize gain (but not loss) with respect to such cash in an amount equal to the lesser of (1) the excess, if any, of the sum of the cash received and the fair market value of the shares of C&F common stock received pursuant to the merger over your adjusted tax basis in your shares of Peoples common stock surrendered, or (2) the amount of cash you received in exchange for your shares of Peoples common stock pursuant to the merger. If you acquired different blocks of Peoples common stock at different times or at different prices, gain or loss must be calculated separately for each identifiable block of shares of Peoples common stock surrendered in the merger. You should consult your tax advisor regarding the manner in which cash and shares of C&F common stock should be allocated among different blocks of your Peoples common stock surrendered in the merger and the manner in which gain or loss should be determined. Any gain recognized generally will be treated as capital gain and will be long-term capital gain if, as of the effective time of the merger, your holding period with respect to the shares of Peoples common stock surrendered exceeds one year.

        The aggregate tax basis of your shares of C&F common stock received (including any fractional shares deemed received and exchanged for cash) in exchange for your shares of Peoples common stock pursuant to the merger will be equal to the aggregate tax basis of your shares of Peoples common stock surrendered, reduced by the amount of cash you received pursuant to the merger (other than cash received in lieu of a fractional share of C&F common stock) and increased by the amount of gain, if any, recognized by you on the exchange (other than any gain or dividend income recognized on the

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receipt of cash for a fractional share of C&F common stock). The holding period of the shares of C&F common stock you receive in the merger (including any fractional shares deemed received and exchanged for cash) will include your holding period of the shares of Peoples common stock surrendered in the merger. If you acquired different blocks of Peoples common stock at different times or at different prices, the basis and holding period of each block of C&F common stock you receive will be determined on a block-for-block basis depending on the basis and holding period of the blocks of Peoples common stock exchanged for such block of C&F common stock. You should consult your tax advisor regarding the manner in which cash and the shares of C&F common stock should be allocated among your shares of Peoples common stock and the manner in which the above rules would apply to your particular circumstances.

Tax Consequences to Holders of Peoples Common Stock Who Receive Cash in Lieu of Fractional Shares

        If you are a holder of Peoples common stock and, as a result of the merger, you receive cash in lieu of a fractional share of C&F common stock, your receipt of such cash will be treated as if the fractional share of C&F common stock had been distributed to you as part of the merger, and then as having sold such fractional share. Consequently, you generally will recognize gain or loss with respect to the cash received in lieu of such fractional share equal to the difference between the amount of cash received and the tax basis allocated to such fractional share (as described above). Such gain or loss generally will be a capital gain or loss and will be a long-term capital gain or loss if you have held your shares of Peoples common stock for more than one year as of the effective time of the merger. In general, long-term capital gains for non-corporate taxpayers may be eligible for a reduced rate of taxation. The deductibility of capital losses is subject to limitations.

Tax Consequences to Peoples and C&F

        Each of C&F and Peoples will be a party to the merger within the meaning of Section 368(b) of the Code. Neither Peoples nor C&F will recognize gain or loss for U.S. federal income tax purposes as a result of the merger.

Backup Withholding and Information Reporting

        If you are a non-corporate U.S. holder of Peoples common stock you may be subject, under certain circumstances, to backup withholding (currently at a rate of 24%) with respect to any cash payment you received in the merger. However, backup withholding will not apply to you if you either (a) furnish a correct taxpayer identification number and certify that you are not subject to backup withholding or (b) otherwise prove to C&F and its exchange agent that you are exempt from backup withholding. Any amounts withheld under the backup withholding rules generally will be allowed as a refund or credit against the your U.S. federal income tax liability, provided you timely furnish the required information to the IRS.

Certain Reporting Requirements

        If you are a U.S. holder that receives C&F common stock in the merger and are considered a "significant holder," you will be required (1) to file a statement with your U.S. federal income tax return providing certain facts pertinent to the merger, including your tax basis in, and the fair market value of, the Peoples common stock that you surrendered, and (2) to retain permanent records of these facts relating to the merger. You are a "significant holder" if, immediately before the merger, you (a) owned at least 5% (by vote or value) of the outstanding stock of Peoples, or (b) owned Peoples securities with a tax basis of $1.0 million or more.

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        The foregoing discussion of material U.S. federal income tax consequences is for general information purposes only and is not intended to be, and may not be construed as, tax advice. Holders of Peoples common stock are urged to consult their tax advisors with respect to the application of U.S. federal income tax laws to their particular situations 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 tax treaty.

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MARKET FOR COMMON STOCK AND DIVIDENDS

        C&F common stock is traded on the Nasdaq Global Select Market under the symbol "CFFI." Peoples common stock is quoted on the OTC Markets Group's Pink marketplace under the symbol "PBVA."

        As of October 10, 2019, the last day prior to the date of this proxy statement/prospectus for which it was practicable to obtain this information, there were 3,423,539 shares of C&F common stock outstanding, which were held by approximately 1,600 holders of record, and 391,450 shares of Peoples common stock outstanding, which were held by approximately 394 holders of record. Such numbers of record holders do not reflect the number of individuals or institutional investors holding stock in nominee name through banks, brokerage firms and others.

        The following table sets forth during the periods indicated the high and low sales prices of C&F common stock as reported on the Nasdaq Global Select Market and Peoples common stock as reported on the OTC Markets Group's Pink marketplace, and the dividends declared per share of C&F common stock and Peoples common stock. The prices for Peoples common stock shown in the table below reflect inter-dealer prices, without retail mark-up, mark-down or commission and may not necessarily represent actual transactions.

 
  C&F Common Stock   Peoples Common Stock  
 
  Sales Price    
  Sales Price    
 
 
  Dividends
Declared
Per Share
  Dividends
Declared
Per Share
 
 
  High   Low   High   Low  

2019

                                     

First Quarter

  $ 55.69   $ 47.76   $ 0.37   $ 38.00   $ 31.00   $  

Second Quarter

    54.61     46.28     0.37     31.50     29.59      

Third Quarter

    56.00     45.66     0.37     54.00     27.20      

Fourth Quarter (through October 14, 2019)

    53.59     49.20         52.50     51.50      

2018

   
 
   
 
   
 
   
 
   
 
   
 
 

First Quarter

  $ 59.60   $ 45.28   $ 0.34   $ 37.03   $ 34.25   $ 0.14  

Second Quarter

    66.08     51.65     0.34     39.00     34.25     0.14  

Third Quarter

    67.40     54.76     0.36     44.50     37.50     0.14  

Fourth Quarter

    59.81     45.77     0.37     43.00     36.75     0.16  

2017

   
 
   
 
   
 
   
 
   
 
   
 
 

First Quarter

  $ 50.10   $ 42.25   $ 0.33   $ 29.00   $ 23.75   $ 0.14  

Second Quarter

    52.00     45.50     0.33     33.90     28.00     0.14  

Third Quarter

    55.80     46.45     0.33     33.90     32.50     0.14  

Fourth Quarter

    65.05     53.66     0.34     37.01     32.10     0.14  

        The following table sets forth the closing sale prices per share of C&F common stock as reported on the Nasdaq Global Select Market on August 13, 2019, the last trading day before the parties announced the signing of the merger agreement, and on October 14, 2019, the last trading day before the date of this proxy statement/prospectus. The table also sets forth the last sales price of Peoples common stock reported on or before August 13, 2019 (which sale occurred on August 9, 2019), and the last sales price of Peoples common stock reported on or before the date of this proxy statement/prospectus (which sale occurred on October 4, 2019). The following table also includes the equivalent market value per share of Peoples common stock on August 13, 2019 and on October 14, 2019, which

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reflects the sum of (i) the product of the exchange ratio of 0.5366 multiplied by the closing sale price of C&F common stock on the dates indicated, plus (ii) the per share cash consideration of $27.00.

 
  C&F
Common Stock
  Peoples
Common Stock
  Equivalent Market
Value Per Share
of Peoples
 

August 13, 2019

  $ 51.79   $ 28.30   $ 54.79  

October 14, 2019

  $ 52.20   $ 52.50   $ 55.01  

        The value of the stock portion of the merger consideration to be received for each share of Peoples common stock will be based on the most recent closing price of C&F's common stock prior to the completion of the merger. Because the merger consideration will not be adjusted for fluctuations in market value and because the market value of the shares of C&F common stock to be received by Peoples shareholders will change prior to completion of the merger, shareholders of Peoples are not assured of receiving a specific market value of C&F common stock, and thus a specific market value for their shares of Peoples common stock, at the effective time of the merger. C&F cannot assure you that its common stock will continue to trade at or above the prices shown above. You should obtain current stock price quotations for the C&F common stock from a newspaper, via the Internet or by calling your broker.

        C&F and Peoples are legal entities separate and distinct from their subsidiaries, and their revenues depend primarily on the payment of dividends from their subsidiary banks. Therefore, C&F's and Peoples's principal sources of funds with which to pay dividends on their stock and their other separate expenses are dividends they receive, respectively, from C&F Bank and Peoples Community Bank. C&F Bank and Peoples Community Bank are subject to certain regulatory and other legal restrictions on the amount of dividends they are permitted to pay to C&F and Peoples. See "Description of C&F Capital Stock—Common Stock—Dividends and Liquidation Rights" on page 80.

        C&F currently pays dividends on its common stock on a quarterly basis, and it anticipates declaring and paying quarterly dividends after completion of the merger. C&F does not intend to change its dividend strategy, but has and will continue to evaluate that decision on a quarterly basis. After the merger, the final determination of the timing, amount and payment of dividends on C&F common stock will be at the discretion of its board of directors and will depend upon the earnings of C&F and its subsidiaries, the financial condition of C&F and other factors, including general economic conditions and applicable governmental regulations and policies.

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INFORMATION ABOUT C&F FINANCIAL CORPORATION

        C&F Financial Corporation, headquartered in West Point, Virginia, is a bank holding company incorporated under the laws of the Commonwealth of Virginia. C&F owns all of the stock of Citizens and Farmers Bank, a commercial bank chartered under the laws of the Commonwealth of Virginia. C&F Bank originally opened for business under the name Farmers and Mechanics Bank on January 22, 1927. C&F Bank provides retail banking services at its main office in West Point, Virginia, 24 retail branches located throughout the Hampton to Charlottesville corridor of Virginia, and three commercial loan offices. C&F Bank has five wholly owned subsidiaries. C&F Mortgage Corporation, organized in 1995, originates and sells residential mortgages. C&F Finance Company, acquired in 2002, is a finance company purchasing automobile, marine and recreational vehicle loans through indirect lending programs. C&F Wealth Management Corporation, organized in 1995, is a full-service brokerage firm offering a comprehensive range of wealth management services. C&F Insurance Services, Inc. owns an equity interest in an independent insurance agency. CVB Title Services, Inc. owns an equity interest in a full service title and settlement agency. The common stock of C&F is traded on the Nasdaq Global Select Market under the symbol "CFFI."

        As of June 30, 2019, C&F had approximately $1.6 billion in total assets, approximately $1.2 billion in deposits, approximately $1.2 billion in gross loans, and approximately $159.4 million of total shareholders' equity.

        The principal executive offices of C&F are located at 802 Main Street, West Point, Virginia 23181, and its telephone number is (804) 843-2360. C&F's website can be accessed at https://www.cffc.com. Information contained on C&F's website does not constitute part of, and is not incorporated into, this proxy statement/prospectus. Additional information about C&F is included in documents incorporated by reference in this proxy statement/prospectus. See "Where You Can Find More Information."

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INFORMATION ABOUT PEOPLES BANKSHARES, INCORPORATED

        Peoples Bankshares, Incorporated, headquartered in Montross, Virginia, is a bank holding company incorporated under the laws of the Commonwealth of Virginia. Peoples conducts substantially all of its operations through its wholly-owned bank subsidiary, Peoples Community Bank, a commercial bank chartered under the laws of the Commonwealth of Virginia and a Federal Reserve member (for the purposes of this section only, the "bank.").

        The bank currently conducts its business through its main office in Montross, Virginia and four branch offices located in Fredericksburg, King George, and Warsaw, Virginia. The bank was initially established on June 17, 1913 under the name "The Peoples Bank of Montross, Virginia." The bank changed its name to "Peoples Community Bank" on January 1, 1996, effective approximately four months following the establishment of Peoples as the bank's holding company.

        The bank serves businesses, professionals and consumers with a wide variety of financial services. Products include checking accounts, savings accounts, money market accounts, cash management accounts, certificates of deposit, individual retirement accounts, commercial and industrial loans, residential mortgages, commercial mortgages, home equity loans, consumer installment loans, investment accounts, insurance, credit cards, debit cards, online banking, telephone banking and mobile banking. A substantial amount of the bank's deposits are interest bearing, and the majority of the bank's loan portfolio is secured by real estate. Deposits of the bank are insured by the Deposit Insurance Fund of the FDIC.

        As a Virginia-chartered corporation and bank holding company, Peoples is subject to regulation by the Federal Reserve and the Bureau of Financial Institutions of the Virginia SCC. The bank's primary regulators are also the Federal Reserve and the Bureau of Financial Institutions of the Virginia SCC, as it is a state-chartered bank that is a Federal Reserve member.

        As of June 30, 2019, Peoples had approximately $194.0 million in total assets, approximately $172.4 million in deposits, approximately $147.5 million in gross loans, and approximately $15.8 million of total shareholders' equity. The principal executive offices of Peoples are located at 15960 Kings Highway, Montross, Virginia 22520, and its telephone number is (804) 493-8031. Peoples's website can be accessed at www.peoplescommunitybank.biz. Information contained on Peoples's website does not constitute part of, and is not incorporated into, this proxy statement/prospectus.

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DESCRIPTION OF C&F CAPITAL STOCK

        The following summary description of the material features of the capital stock of C&F is qualified in its entirety by reference to the applicable provisions of Virginia law and by C&F's articles of incorporation and bylaws, each as amended.

        As a result of the merger, Peoples shareholders who receive shares of C&F common stock in the merger will become shareholders of C&F. Your rights as shareholders of C&F will be governed by Virginia law and the articles of incorporation and the bylaws of C&F, each as amended. We urge you to read the applicable provisions of the Virginia SCA, C&F's articles of incorporation and bylaws and federal laws governing bank holding companies carefully and in their entirety.

Authorized and Outstanding Capital Stock

        The authorized capital stock of C&F consists of (i) 8,000,000 shares of common stock, par value $1.00 per share, of which 3,423,539 shares were issued and outstanding and held by approximately 1,600 holders of record as of October 10, 2019, and (ii) 3,000,000 shares of undesignated serial preferred stock, par value $1.00 per share, of which no shares were issued and outstanding as of October 10, 2019.

        As of October 10, 2019, there were no options outstanding to purchase shares of C&F common stock and 136,455 shares of C&F common stock that were subject to unvested restricted stock awards granted under the C&F Financial Corporation 2013 Stock and Incentive Compensation Plan.

Common Stock

        General.    Each share of C&F common stock has the same relative rights as, and is identical in all respects to, each other share of C&F common stock. C&F common stock is traded on the Nasdaq Global Select Market under the symbol "CFFI." The transfer agent and registrar for C&F common stock is American Stock Transfer & Trust Company, LLC, of P.O. Box 391, 59 Maiden Lane, Plaza Level, New York, New York 10038.

        Dividends and Liquidation Rights.    Holders of C&F common stock are entitled to receive dividends as may be declared by C&F's board of directors out of funds legally available therefor. The payment of distributions by C&F is subject to the restrictions of Virginia law applicable to the declaration of distributions by a corporation. A Virginia corporation generally may not authorize and make distributions if, after giving effect to the distribution, it would be unable to meet its debts as they become due in the usual course of business or if the corporation's total assets would be less than the sum of its total liabilities plus the amount that would be needed, if it were dissolved at that time, to satisfy the preferential rights of shareholders whose rights are superior to the rights of those receiving the distribution. In addition, the payment of distributions to common shareholders is subject to any prior rights of outstanding preferred stock.

        Consequently, upon liquidation, dissolution or winding up of C&F, holders of shares of C&F common stock may receive pro rata assets, in cash or kind, if any, available for distribution after the payment of creditors and satisfaction of the preferences of any class or series of preferred stock outstanding at the time of liquidation.

        In addition, as a bank holding company, C&F's ability to pay dividends is affected by the ability of C&F Bank, its Virginia-chartered banking subsidiary, to pay dividends to the holding company. The ability of C&F Bank, as well as C&F, to pay dividends in the future is, and could be further, influenced by bank regulatory requirements and capital guidelines.

        Voting Rights.    The holders of C&F common stock are entitled to one vote per share. A quorum at any meeting of C&F shareholders is a majority of the votes entitled to be cast, represented in person

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or by proxy. If a quorum exists, action on a matter is approved by a majority of the votes cast within the voting group, unless a greater vote is required by law or the articles of incorporation, except that in elections of directors those receiving the greatest number of votes shall be elected even though less than a majority. C&F shareholders are not entitled to cumulative voting rights in the election of C&F directors.

        Directors and Classes of Directors.    C&F's board of directors is divided into three classes, apportioned as evenly as possible, with directors serving staggered three-year terms. Currently, the C&F board consists of 11 directors. Under C&F's articles of incorporation, the C&F board of directors must consist of a minimum of five and a maximum of 15 directors, and the C&F board of directors may increase the number of directors without shareholder approval. Any director of C&F may be removed only for cause and with the affirmative vote of at least two-thirds of the outstanding shares of C&F common stock entitled to vote.

        No Preemptive Rights; Redemption and Assessment.    Holders of C&F common stock have no preemptive rights to subscribe for any additional securities of any class that C&F may issue, nor any conversion, redemption or sinking fund rights. The outstanding shares of C&F common stock are fully paid and nonassessable. The rights and privileges of holders of C&F common stock are subject to any preferences that the C&F board of directors may set for any series of C&F preferred stock that may be issued by C&F in the future.

        For more information regarding the rights of holders of C&F common stock, see the section entitled "Comparative Rights of Shareholders" beginning on page 82.

Preferred Stock

        The board of directors of C&F is empowered to authorize the issuance, in one or more series, of shares of preferred stock at such times, for such purposes and for such consideration as it may deem advisable without shareholder approval. The C&F board is also authorized to fix the designations, voting, conversion, preference and other relative rights, qualifications and limitations of any such series of preferred stock. The C&F board of directors, without shareholder approval, may authorize the issuance of one or more series of preferred stock with voting and conversion rights which could adversely affect the voting power of the holders of C&F common stock and, under certain circumstances, discourage an attempt by others to gain control of C&F.

        The creation and issuance of any series of preferred stock, and the relative rights, designations and preferences of such series, if and when established, will depend on, among other things, the future capital needs of C&F, then existing market conditions and other factors that, in the judgment of the C&F board of directors, might warrant the issuance of preferred stock.

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COMPARATIVE RIGHTS OF SHAREHOLDERS

        C&F and Peoples are Virginia corporations subject to the provisions of the Virginia SCA. The rights of shareholders of C&F and Peoples are governed by their respective articles of incorporation and bylaws. Upon completion of the proposed merger, Peoples shareholders will become shareholders of C&F and, as such, their shareholder rights will be governed by the articles of incorporation and bylaws of C&F and will continue to be governed by the Virginia SCA.

        The following is a summary of the material differences in the rights of shareholders of C&F and Peoples, but is not a complete statement of all those differences. Shareholders should read carefully the relevant provisions of the Virginia SCA and the respective articles of incorporation and bylaws of C&F and Peoples. This summary is qualified in its entirety by reference to the articles of incorporation and bylaws of C&F and Peoples and to the provisions of the Virginia SCA.

Authorized Capital Stock

        C&F.    C&F is authorized to issue 8,000,000 shares of common stock, par value $1.00 per share, of which 3,423,539 shares were issued and outstanding as of October 10, 2019, and 3,000,000 shares of preferred stock, par value $1.00 per share, of which no shares were issued and outstanding as of October 10, 2019.

        C&F's articles of incorporation permit its board of directors, without shareholder approval, to fix the preferences, limitations, and relative rights of its preferred stock and to establish series of such preferred stock and determine the variations between each series. Holders of C&F stock of any class do not have any preemptive right to subscribe to or purchase (i) any shares of capital stock of C&F, (ii) any securities convertible into such shares, or (iii) any options, warrants or rights to purchase such shares or securities convertible into such shares.

        Peoples.    Peoples is authorized to issue 1,000,000 shares of common stock, par value $2.00 per share, of which 391,450 shares were issued and outstanding as of the record date for the Peoples special meeting.

        Holders of Peoples stock of any class do not have any preemptive right to subscribe to or purchase (i) any shares of capital stock of Peoples, (ii) any securities convertible into such shares, or (iii) any options, warrants or rights to purchase such shares or securities convertible into such shares.

Dividend Rights

        The holders of C&F and Peoples common stock are entitled to share ratably in dividends when and as declared by their respective board of directors out of funds legally available therefor. C&F's articles of incorporation permit its board to issue preferred stock with terms set by the board, which terms may include the right to receive dividends ahead of the holders of C&F common stock. C&F does not currently have any issued and outstanding shares of preferred stock.

Voting Rights

        The holders of both C&F and Peoples common stock have one vote for each share held on any matter presented for consideration by the holders of common stock at a shareholder meeting. Neither the holders of C&F nor Peoples common stock are entitled to cumulative voting in the election of directors.

Directors and Classes of Directors

        C&F.    The C&F board is divided into three classes, apportioned as evenly as possible, with directors serving staggered three-year terms. Currently, the C&F board consists of 11 directors. Under C&F's articles of incorporation, the C&F board of directors must consist of a minimum of five and a

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maximum of 15 directors, and the C&F board of directors may increase the number of directors in its discretion without shareholder approval. Directors of C&F may be removed by shareholders of C&F only for cause and with the affirmative vote of at least two-thirds of the outstanding shares of C&F common stock entitled to vote.

        Peoples.    The Peoples board is not divided into classes and all directors are elected at each annual meeting of shareholders to serve one-year terms. The Peoples bylaws require the board to have not less than five nor more than 15 directors, and the board is authorized to set and change the actual number of directors from time to time within those limits. Currently, the Peoples board consists of eight directors. Directors of Peoples may be removed with or without cause upon the affirmative vote of at least two-thirds of the outstanding shares entitled to vote.

Anti-takeover Provisions

        Certain provisions of the Virginia SCA and the articles of incorporation and bylaws of C&F and Peoples may discourage attempts to acquire control of C&F or Peoples, respectively, that the majority of either company's shareholders may determine was in their best interests. These provisions also may render the removal of one or all directors more difficult or deter or delay corporate changes of control that the C&F or Peoples boards did not approve.

        Classified Board of Directors.    The provisions of C&F's articles of incorporation providing for classification of the board of directors into three separate classes may have certain anti-takeover effects.

        Peoples's articles of incorporation do not classify the board of directors.

        Authorized Preferred Stock.    C&F's articles of incorporation authorize the issuance of preferred stock. The C&F board may, subject to application of Virginia law and federal banking regulations, authorize the issuance of preferred stock at such times, for such purposes, and for such consideration as it may deem advisable without further shareholder approval. The issuance of preferred stock under certain circumstances may have the effect of discouraging an attempt by a third party to acquire control of C&F by, for example, authorizing the issuance of a series of preferred stock with rights and preferences designed to impede the proposed transaction.

        Peoples's articles of incorporation do not authorize the issuance of preferred stock.

        Supermajority Voting Provisions.    The Virginia SCA provides that, unless a corporation's articles of incorporation provide for a greater or lesser vote, certain significant corporate actions must be approved by the affirmative vote of more than two-thirds of all the votes entitled to be cast on the matter. Certain corporate actions requiring a more than two-thirds vote include:

    adoption of plans of merger or share exchange;

    sales of all or substantially all of a corporation's assets other than in the ordinary course of business; and

    adoption of plans of dissolution.

        The Virginia SCA provides that a corporation's articles may either increase the vote required to approve those actions or may decrease the vote required to not less than a majority of all the votes cast by each voting group entitled to vote at a meeting at which a quorum of the voting group exists.

        The articles of incorporation of C&F state that the actions outlined above must be approved by the vote of a majority of all the votes entitled to be cast on such transactions by each voting group entitled to vote on the transaction at a meeting at which a quorum of the voting group is present, provided that the transaction has been approved and recommended by at least two-thirds of the directors in office at the time of such approval and recommendation. If the transaction is not so approved and recommended by two-thirds of the directors in office, then the transaction must be

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approved by the affirmative vote of 80% or more of all of the votes entitled to be cast on such transaction by each voting group entitled to vote.

        Peoples's articles of incorporation do not contain any supermajority voting provisions corresponding to the provisions in C&F's articles of incorporation. Accordingly, the provisions of the Virginia SCA outlined above control with respect to approval of certain significant corporate actions.

        Anti-takeover Statutes.    Virginia has two anti-takeover statutes in force, the Affiliated Transactions Statute and the Control Share Acquisitions Statute.

        The Affiliated Transaction Statute of the Virginia SCA (Va. Code § 13.1-725 et seq.) contains provisions governing "affiliated transactions." These include various transactions such as mergers, share exchanges, sales, leases, or other dispositions of material assets, issuances of securities, dissolutions, and similar transactions with an "interested shareholder." An interested shareholder is generally the beneficial owner of more than 10% of any class of a corporation's outstanding voting shares. During the three years following the date a shareholder becomes an interested shareholder, any affiliated transaction with the interested shareholder must be approved by both a majority (but not less than two) of the "disinterested directors" (those directors who were directors before the interested shareholder became an interested shareholder or who were recommended for election by a majority of the disinterested directors) and by the affirmative vote of the holders of two-thirds of the corporation's voting shares other than shares beneficially owned by the interested shareholder. These requirements do not apply to affiliated transactions if, among other things, a majority of the disinterested directors approve the interested shareholder's acquisition of voting shares making such a person an interested shareholder before such acquisition. Beginning three years after the shareholder becomes an interested shareholder, the corporation may engage in an affiliated transaction with the interested shareholder if:

    the transaction is approved by the holders of two-thirds of the corporation's voting shares, other than shares beneficially owned by the interested shareholder;

    the affiliated transaction has been approved by a majority of the disinterested directors; or

    subject to certain additional requirements, in the affiliated transaction the holders of each class or series of voting shares will receive consideration meeting specified fair price and other requirements designed to ensure that all shareholders receive fair and equivalent consideration, regardless of when they tendered their shares.

        Under the Virginia SCA's Control Share Acquisitions Statute (Va. Code § 13.1-728.1 et seq.), voting rights of shares of stock of a Virginia corporation acquired by an acquiring person or other entity at ownership levels of 20%, 331/3%, and 50% of the outstanding shares may, under certain circumstances, be denied. The voting rights may be denied:

    unless conferred by a special shareholder vote of a majority of the outstanding shares entitled to vote for directors, other than shares held by the acquiring person and officers and directors of the corporation; or

    among other exceptions, such acquisition of shares is made pursuant to a merger agreement with the corporation or the corporation's articles of incorporation or bylaws permit the acquisition of such shares before the acquiring person's acquisition thereof.

        If authorized in the corporation's articles of incorporation or bylaws, the statute also permits the corporation to redeem the acquired shares at the average per share price paid for such shares if the voting rights are not approved or if the acquiring person does not file a "control share acquisition statement" with the corporation within 60 days of the last acquisition of such shares. If voting rights are approved for control shares comprising more than 50% of the corporation's outstanding stock, objecting shareholders may have the right to have their shares repurchased by the corporation for "fair value."

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        A corporation may elect to opt out of the application of both the Affiliated Transactions Statute and the Control Share Acquisitions Statute by adopting a provision in its articles of incorporation or bylaws. Further, the Affiliated Transactions Statute does not apply to any corporation that has fewer than 300 shareholders of record (unless the reduction in the number of shareholders is the result of action by an interested shareholder).

        Neither C&F nor Peoples has elected to opt out of the Affiliated Transactions Statute. C&F has not elected to opt out of the Control Share Acquisitions Statute. Peoples has elected to opt out of the Control Share Acquisitions Statute.

Amendments to Articles of Incorporation and Bylaws

        The Virginia SCA generally requires that in order for an amendment to the articles of incorporation to be adopted it must be approved by each voting group entitled to vote on the proposed amendment by more than two-thirds of all the votes entitled to be cast by that voting group, unless the Virginia SCA otherwise requires a greater vote, or the articles of incorporation provide for a greater or lesser vote, or a vote by separate voting groups. However, under the Virginia SCA, no amendment to the articles of incorporation may be approved by a vote that is less than a majority of all the votes cast on the amendment by each voting group entitled to vote at a meeting at which a quorum of the voting group exists.

        Under the Virginia SCA, unless another process is set forth in the articles of incorporation or bylaws, a majority of the directors or, if a quorum exists, a majority of the shareholders present and entitled to vote may adopt, amend or repeal the bylaws.

        C&F.    C&F's articles of incorporation state that an amendment to the articles of incorporation must be approved by the vote of a majority of all the votes entitled to be cast on the amendment by each voting group entitled to vote on the amendment at a meeting at which a quorum of the voting group is present, provided that the amendment has been approved and recommended by at least two-thirds of the directors in office at the time of such approval and recommendation. If the amendment is not so approved and recommended, then the amendment must be approved by the vote of 80% or more of all votes entitled to be cast on the amendment by each voting group entitled to vote thereon.

        C&F's bylaws may be amended or repealed by the C&F board of directors except to the extent that (i) such power is reserved exclusively to the shareholders by law or C&F's articles of incorporation or (ii) the shareholders in adopting or amending particular bylaws provide expressly that the C&F board of directors may not amend or repeal the same. C&F's bylaws may be amended or repealed by the shareholders even though the same also may be amended or repealed by its board of directors.

        Peoples.    Peoples's articles of incorporation do not contain any provisions regarding amendments thereto. Accordingly, the provisions of the Virginia SCA outlined above control with respect to any amendment of the Peoples articles of incorporation.

        Peoples's bylaws may be amended or repealed by the Peoples board of directors except to the extent that (i) such power is reserved exclusively to the shareholders by law or Peoples's articles of incorporation or (ii) the shareholders in adopting or amending particular bylaws provide expressly that the Peoples board of directors may not amend or repeal the same. Peoples's bylaws may be amended or repealed by the shareholders even though the same also may be amended or repealed by its board of directors.

Dissenters' Appraisal Rights

        The Virginia SCA provides appraisal rights to shareholders of a Virginia corporation in certain circumstances, including upon consummation of a merger to which the corporation is a party if

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shareholder approval is required for the merger under the Virginia SCA. The Virginia SCA further provides that appraisal rights are not available to holders of shares of any class or series of shares of a Virginia corporation in a merger when the stock is either listed on a national securities exchange, such as the Nasdaq Global Select Market, or is held by at least 2,000 shareholders of record and has a public float of at least $20 million. Despite this exception, appraisal rights will be available to holders of common stock of a Virginia corporation in a merger if:

    the articles of incorporation provide for appraisal rights regardless of an available exception;

    in the case of a merger or share exchange, shareholders are required by the terms of the merger to accept anything for their shares other than cash, shares of the surviving or acquiring corporation, or shares of another corporation that are either listed on a national securities exchange or held by more than 2,000 shareholders of record having a public float of at least $20 million, or a combination of cash or such shares; or

    the merger is an "affiliated transaction," as described in the section above entitled "—Anti-takeover Provisions," and it has not been approved by a majority of the disinterested directors.

        Peoples does not qualify for any of the above-outlined exceptions under the Virginia SCA. Consequently, shareholders of Peoples are entitled to appraisal rights in connection with the merger. For more detailed information regarding the appraisal rights available to Peoples's shareholders, please see the section above entitled "—Dissenters' Appraisal Rights."

Director and Officer Exculpation

        The Virginia SCA provides that in any proceeding brought by or in the right of a corporation or brought by or on behalf of shareholders of the corporation, the damages assessed against an officer or director arising out of a single transaction, occurrence or course of conduct may not exceed the lesser of (a) the monetary amount, including the elimination of liability, specified in the articles of incorporation or, if approved by the shareholders, in the bylaws as a limitation on or elimination of the liability of the officer or director, or (b) the greater of (i) $100,000 or (ii) the amount of cash compensation received by the officer or director from the corporation during the twelve months immediately preceding the act or omission for which liability was imposed. The liability of an officer or director is not limited under the Virginia SCA or a corporation's articles of incorporation and bylaws if the officer or director engaged in willful misconduct or a knowing violation of the criminal law or of any federal or state securities law.

        The articles of incorporation of C&F provide that, to the full extent that the Virginia SCA permits the limitation or elimination of liability of directors or officers, a director or officer of C&F is not liable to C&F or its shareholders for monetary damages. The articles of incorporation of Peoples provide that, to the full extend that the Virginia SCA permits the limitation or elimination of liability of directors or officers, a director or officer of Peoples is not liable to Peoples or its shareholders for any monetary damages in excess of $1.

Indemnification

        The articles of incorporation of C&F and Peoples provide that, to the full extent permitted by the Virginia SCA, each of C&F and Peoples is required to indemnify a director or officer against liabilities, fines, penalties and claims imposed upon or asserted against him or her by reason of having been a director or officer and against all expenses reasonably incurred by him or her in connection therewith, except in relation to matters as to which he or she is liable by reason of his or her willful misconduct or knowing violation of criminal law. Each of C&F's and Peoples's board of directors is empowered, by a majority vote of a quorum of disinterested directors, to contract in advance to indemnify any director or officer, as set forth above.

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SECURITY OWNERSHIP OF CERTAIN BENEFICIAL
OWNERS AND MANAGEMENT OF C&F

        The following table sets forth certain information as of October 10, 2019, concerning the number and percentage of shares of C&F common stock beneficially owned by each of C&F's directors and named executive officers, and by C&F's directors and executive officers as a group. Except as otherwise indicated, all shares are owned directly and the named person possesses sole voting and sole investment power with respect to all such shares, and none of such shares is pledged as security. Percentage ownership is calculated based on 3,423,539 outstanding shares of C&F common stock as of October 10, 2019.

Name of Beneficial Owner
  Number of
Shares
Beneficially
Owned(1)
  Percentage
of Class
Beneficially
Owned
 

Julie R. Agnew

    1,617 (2)   *  

J.P. Causey Jr. 

    27,116 (2)   *  

Barry R. Chernack

    13,001 (2)   *  

Thomas F. Cherry

    35,322 (3)   1.0 %

S. Dustin Crone

    10,670 (3)   *  

Larry G. Dillon

    44,379 (3)   1.3 %

Audrey D. Holmes

    10,693 (2)   *  

James H. Hudson, III

    12,393 (2)   *  

Elizabeth R. Kelley

    1,617 (2)   *  

Jason E. Long

    4,288 (3)   *  

Bryan E. McKernon

    14,100 (3)   *  

James T. Napier

    3,080 (2)   *  

C. Elis Olsson

    11,040 (2)   *  

Paul C. Robinson

    13,422 (2)   *  

All C&F directors and executive officers as a group (15 persons)

    207,725     6.1 %

*
Represents less than 1% of C&F's outstanding common stock.

(1)
For purposes of this table, beneficial ownership has been determined in accordance with the provisions of Rule 13d-3 of the Exchange Act under which, in general, a person is deemed to be the beneficial owner of a security if he or she has or shares the power to vote or direct the voting of the security, the power to dispose of or direct the disposition of the security, or the right to acquire beneficial ownership of the security within 60 days. The mailing address of the individuals included in the table is 3600 La Grange Parkway, Toano, Virginia 23168.

(2)
Includes 1,235 shares each of stock restricted as to sale or other transfer for each non-employee director. Subject to accelerated vesting in certain circumstances, these shares of restricted stock, granted between 2017 and 2019, will vest at the completion of three years of continuous service as a director of C&F from the date of grant. Also includes 1,860 shares held by Mr. Olsson's child, with respect to which shares Mr. Olsson has authority to make investment decisions, 1,860 shares held by Mr. Olsson's child, with respect to which shares Mr. Olsson shares voting and investment power, and 500 shares held in a family trust, of which Mr. Olsson is co-trustee, with respect to which shares Mr. Olsson shares voting and investment power. Also includes 1,200 shares held by the Mary Hedrick Causey Family Trust, with respect to which shares Mr. Causey has voting and investment power in his capacity as trustee for the trust. Excludes 389 and 762 shares

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    held solely by Mr. Hudson's and Mr. Olsson's spouses, respectively, as to which Mr. Hudson and Mr. Olsson disclaim beneficial ownership; and excludes 3,488 shares held solely by Ms. Holmes' mother as to which Ms. Holmes disclaims beneficial ownership.

(3)
Includes 16,640, 7,320, 16,640, 3,695 and 4,400 shares of stock restricted as to sale or other transfer for Messrs. Cherry, Crone, Dillon, Long and McKernon, respectively. Subject to accelerated vesting in certain circumstances, these shares of restricted stock, granted between 2014 and 2019, will vest at the completion of five years of continuous service as an employee of C&F or its subsidiaries.

        As of October 10, 2019, there is no shareholder known to C&F to be the beneficial owner of more than 5% of C&F's common stock, which is C&F's only class of voting capital stock outstanding.

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SECURITY OWNERSHIP OF CERTAIN BENEFICIAL
OWNERS AND MANAGEMENT OF PEOPLES

        The following table sets forth certain information as of October 10, 2019, concerning the number and percentage of shares of Peoples common stock beneficially owned by each of Peoples's directors and executive officers, and by Peoples's directors and executive officers as a group. In addition, the table includes information with respect to persons known to Peoples who own or may be deemed to own more than 5% of Peoples common stock as of October 10, 2019. Except as otherwise indicated, all shares are owned directly and the named person possesses sole voting and sole investment power with respect to all such shares, and none of such shares is pledged as security. Percentage ownership is calculated based on 391,450 outstanding shares of Peoples common stock as of October 10, 2019.

Name of Beneficial Owner
  Number of
Shares
Beneficially
Owned(1)
  Percentage
of Class
Beneficially
Owned
 

Directors:

             

Robert K. Bailey, III

    540 (2)   *  

Zirkle Blakey, III

    380     *  

William C. Herbert, II

    1,300     *  

Michael A. O'Malley

    380     *  

Margaret Ransone

    211     *  

George R. Sisson, III

    3,877     *  

Linwood E. Wadsworth

    4,100     *  

James W. Wilkerson

    20,313     5.19 %

Executive Officers:

   
 
   
 
 

Randy L. Phelps

    0     *  

William Ware, III

    100     *  

All Peoples directors and executive officers as a group (10 persons)

    31,201     7.97 %

5% shareholders who are not directors or named executive officers:

   
 
   
 
 

Edwards Family Trust

    30,244 (3)   7.73 %

1656 Eighth Avenue

             

Sacramento, California 95818

             

*
Represents less than 1% of Peoples's outstanding common stock.

(1)
For purposes of this table, beneficial ownership has been determined in accordance with the provisions of Rule 13d-3 of the Exchange Act under which, in general, a person is deemed to be the beneficial owner of a security if he or she has or shares the power to vote or direct the voting of the security, the power to dispose of or direct the disposition of the security, or the right to acquire beneficial ownership of the security within 60 days. The mailing address of the individuals included in the table is 15960 Kings Highway, PO Box 306, Montross, Virginia 22520.

(2)
Includes shares held jointly with spouses or as custodians or trustees, as follows: Mr. Bailey, 20 shares; Mr. Herbert, 500 shares.

(3)
According to information provided to Peoples by the Edwards Family Trust, voting power and dispositive power with respect to these shares are shared by Benjamin Edwards and Regina Gandour-Edwards.

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LEGAL MATTERS

        The validity of the C&F common stock to be issued upon completion of the merger will be passed upon for C&F by Williams Mullen. Certain U.S. federal income tax consequences relating to the merger will be passed upon for C&F by Williams Mullen, and for Peoples by Troutman Sanders LLP.


EXPERTS

        The consolidated financial statements of C&F and C&F management's assessment of the effectiveness of internal control over financial reporting incorporated into this proxy statement/prospectus by reference to C&F's Annual Report on Form 10-K for the year ended December 31, 2018 have been so incorporated in reliance on the reports of Yount, Hyde & Barbour, P.C., an independent registered public accounting firm, given on the authority of such firm as experts in auditing and accounting.


FUTURE SHAREHOLDER PROPOSALS

    C&F

        If any C&F shareholder intends to present a proposal to be considered for inclusion in C&F's proxy materials in connection with C&F's 2020 annual meeting of shareholders, the proposal must meet the requirements of Rule 14a-8 under the Exchange Act and must be received by C&F's corporate secretary, at C&F's principal office located at 802 Main Street, West Point, Virginia 23181, on or before November 9, 2019.

        If any C&F shareholder intends to propose a matter for consideration at C&F's 2020 annual meeting of shareholders (other than director nominations), notice of the proposal must be received in writing by C&F's corporate secretary by January 23, 2020. If any C&F shareholder intends to nominate a person for election as director at C&F's 2020 annual meeting of shareholders, written notice of such nomination must be received by C&F's corporate secretary, at C&F's principal office located at 802 Main Street, West Point, Virginia 23181, no later than February 7, 2020 and must comply with requirements for shareholder nominations set forth in C&F's bylaws.

    Peoples

        Peoples held its 2019 annual meeting of shareholders on June 24, 2019. If the merger is completed, Peoples will merge into C&F and there will not be any future meetings of Peoples shareholders. In addition, if the merger is completed, Peoples shareholders will become C&F shareholders.

        If the merger is not completed and Peoples holds a 2020 annual meeting of shareholders, if any shareholder intends to propose a matter for consideration (other than a director nomination) at Peoples's 2020 annual meeting of shareholders, based on an anticipated date of June 24, 2020 for Peoples's 2020 annual meeting if held, notice of the proposal must be in proper form in compliance with the requirements set forth in Peoples's bylaws and received in writing at Peoples's principal executive office at 15960 Kings Highway, PO Box 306, Montross, Virginia 22520 no later than April 25, 2020 and not earlier than March 26, 2020.

        Peoples's bylaws prescribe the procedure, including notice requirements, that a shareholder must follow to nominate a person for election to the Peoples board of directors. Based on an anticipated date of June 24, 2020 for Peoples's 2020 annual meeting of shareholders, which will only be held if the merger is not completed, such notice must be received at Peoples's principal executive office located at 15960 Kings Highway, PO Box 306, Montross, Virginia 22520 no later than April 25, 2020 and not earlier than March 26, 2020.

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OTHER MATTERS

        In accordance with Virginia law, no business may be brought before the special meeting unless it is described in the applicable notice of meeting that accompanies this proxy statement/prospectus. As of the date of this proxy statement/prospectus, the Peoples board knows of no matters that will be presented for consideration at the special meeting other than those specifically set forth in the notice for the special meeting. If, however, any other matters properly come before the special meeting, or any adjournments thereof, and are voted upon, it is the intention of the proxy holders to vote such proxies in accordance with the recommendation of the management of Peoples.


WHERE YOU CAN FIND MORE INFORMATION

        C&F files reports, proxy statements and other information with the Securities and Exchange Commission. You may read and copy any reports, statements or other information that C&F files with the SEC at the SEC's Internet website at http://www.sec.gov. The information contained on the SEC's website is expressly not incorporated by reference into this proxy statement/prospectus.

        C&F has filed a registration statement on Form S-4 under the Securities Act to register with the SEC the shares of C&F common stock to be issued in the merger. This document is a part of the registration statement and constitutes a prospectus of C&F and a proxy statement of Peoples for its special meeting of shareholders. As allowed by SEC rules, this document does not contain all the information that you can find in the registration statement or the exhibits to the registration statement.

        The SEC allows C&F to "incorporate by reference" information into this proxy statement/prospectus, which means the companies can disclose important information to you by referring you to another document filed separately with the SEC. The information incorporated by reference is deemed to be a part of this proxy statement/prospectus, except for any information superseded by information contained directly in this proxy statement/prospectus or incorporated by reference subsequent to the date of this proxy statement/prospectus as described below.

        This proxy statement/prospectus incorporates by reference the documents set forth below that C&F has previously filed with the SEC (except Items 2.02 and 7.01 of any Current Report on Form 8-K, unless otherwise indicated in the Form 8-K). These documents contain important business information about C&F and its financial condition.

C&F SEC Filings (File No. 000-23423)

        In addition, C&F incorporates by reference any future filings it makes with the SEC under Sections 13(a), 13(c), 14 or 15(d) of the Exchange Act after the date of this proxy statement/prospectus and before the date of the special meeting (excluding any current reports on Form 8-K to the extent

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disclosure is furnished and not filed). Those documents are considered to be a part of this proxy statement/prospectus, effective as of the date they are filed. In the event of conflicting information in these documents, the information in the latest filed document should be considered correct.

        Documents contained in or incorporated by reference in this document by C&F are available through the SEC as set forth above or from C&F. You may obtain such documents by directing a request to C&F Financial Corporation, 3600 La Grange Parkway, Toano, Virginia 23168, Attn.: Investor Relations, or by calling (804) 843-2360. These documents are available from C&F without charge, excluding any exhibits to them unless the exhibit is specifically listed as an exhibit to the registration statement of which this proxy statement/prospectus forms a part. You can also find information about C&F at its Internet website at https://www.cffc.com and Peoples at its Internet website at https://www.peoplescommunitybank.biz. Information contained on the websites of C&F or Peoples does not constitute part of, and is not incorporated into, this proxy statement/prospectus.

        To receive timely delivery of documents in advance of the special meeting, please make your request no later than December 4, 2019.

        You should rely only on the information contained or incorporated by reference in this proxy statement/prospectus. C&F and Peoples have not authorized anyone to provide you with information that is different than what is contained in this proxy statement/prospectus.

        This proxy statement/prospectus does not constitute an offer to sell, or a solicitation of an offer to buy, any securities, or the solicitation of a proxy,