S-4 1 e21468_sfnc-s4.htm

As filed with the Securities and Exchange Commission on July 21, 2021.

Registration No. 333-

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

FORM S-4
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933

SIMMONS FIRST NATIONAL CORPORATION

(Exact name of registrant as specified in its charter)

Arkansas	6022	71-0407808

(State or other jurisdiction of incorporation or organization)	(Primary Standard Industrial Classification Code Number)	(I.R.S. Employer Identification Number)

501 Main Street
Pine Bluff, Arkansas 71601
(870) 541-1000
(Address, including zip code, and telephone number, including area code, of registrant’s principal executive offices)

George A. Makris, Jr.
Chairman and Chief Executive Officer
Simmons First National Corporation
501 Main Street
Pine Bluff, Arkansas 71601
(870) 541-1000
(Name, address, including zip code, and telephone number, including area code, of agent for service)

With copies to:

George Makris III
Executive Vice President,
General Counsel and Secretary
Simmons First National Corporation
601 E. 3rd Street, 12th Floor
Little Rock, Arkansas 72201
(501) 558-3162

Frank M. Conner III

Christopher DeCresce

Charlotte May
Covington & Burling LLP
One CityCenter
850 Tenth Street N.W.
Washington, D.C. 20001
(202) 662-6000

James P. Farrell

Chairman, President and CEO

Landmark Community Bank

5880 Ridge Bend Road

Memphis, Tennessee 38120

(901) 457-3111

Jackie G. Prester

Baker, Donelson, Bearman,
Caldwell & Berkowitz, PC

165 Madison Avenue, Suite 2000

Memphis, Tennessee 38103

(901) 577-8114

Hilliard Crews

Chairman

Triumph Bancshares, Inc.

5699 Poplar Avenue

Memphis, Tennessee 38119

(901) 333-8800

John A. Bobango

Farris Bobango PLC

999 South Shady Grove Road

Suite 500

Memphis, Tennessee 38120

(901) 259-7100

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

If the securities being registered on this Form are being offered in connection with the formation of a holding company and there is compliance with General Instruction G, check the following box. 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 x		Accelerated filer o

Non-accelerated filer o (Do not check if a smaller reporting company)		Smaller accelerated filer o

		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 X in the box to designate the appropriate rule provision relied upon in conducting this transaction:

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

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

CALCULATION OF REGISTRATION FEE
Title of Each Class of Securities to be Registered	Amount to be Registered⁽¹⁾	Proposed Maximum Offering Price per Share	Proposed Maximum Aggregate Offering Price⁽²⁾	Amount of Registration Fee⁽³⁾
Class A Common Stock, $0.01 par value per share	8,664,839	N/A	$189,731,184.20	$20,699.67

(1)

Represents the maximum number of shares of common stock of Simmons First National Corporation, or Simmons, the parent company of Simmons Bank, that may be issued as consideration in the mergers described herein between (1) Simmons Bank and Landmark Community Bank, or Landmark, and (2) Simmons and Triumph Bancshares, Inc., or Triumph. This number is based on (i) 4,500,000 shares of Simmons common stock, which is the maximum number of shares to be issued pursuant to the Agreement and Plan of Merger, dated as of June 4, 2021, by and among Simmons, Simmons Bank and Landmark, or the Landmark merger agreement, and (ii) 4,164,839 shares of Simmons common stock, which is the maximum number of shares to be issued pursuant to the Agreement and Plan of Merger, dated as of June 4, 2021, by and between Simmons and Triumph, or the Triumph merger agreement.

(2)

Estimated solely for the purpose of calculating the registration fee required by Section 6(b) of the Securities Act of 1933, as amended, or the Securities Act, and computed pursuant to Rule 457(c), Rule 457(f)(2) and Rule 457(f)(3) under the Securities Act. The maximum aggregate offering price is the sum of (1) the product of $4.6809 (the book value per share of Landmark common stock on June 30, 2021) and 22,434,381 (the maximum number of shares of Landmark common stock that may be exchanged for the merger consideration, including shares underlying outstanding equity awards, without requiring adjustment to the exchange ratio and cash consideration per share), reduced by the cash consideration of $7,000,000 to be paid by Simmons to Landmark shareholders and holders of Landmark options pursuant to the Landmark merger agreement, and (2) the product of $19.920 (the book value per share of Triumph common stock on June 30, 2021) and 4,737,150 (the maximum number of shares of Triumph common stock that may be exchanged for the merger consideration, including shares underlying outstanding equity awards, without requiring adjustment to the exchange ratio and cash consideration per share), reduced by the cash consideration of $2,645,937.83 to be paid by Simmons to Triumph shareholders and holders of Triumph options pursuant to the Triumph merger agreement.

(3)

Determined in accordance with Section 6(b) of the Securities Act, at a rate equal to $109.10 per $1 million of the proposed maximum aggregate offering price, or .0001091 multiplied by the proposed maximum aggregate offering price.

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

Information contained herein is subject to completion or amendment. A registration statement relating to these securities has been filed with the Securities and Exchange Commission. These securities may not be sold nor may offers to buy be accepted prior to the time the registration statement becomes effective. This document shall not constitute an offer to sell or the solicitation of any offer to buy, nor shall there be any sale of these securities in any jurisdiction in which such offer, solicitation or sale would be unlawful prior to registration or qualification under the securities laws of any such jurisdiction.

PRELIMINARY - SUBJECT TO COMPLETION - DATED JULY 21, 2021

PROXY STATEMENT/PROSPECTUS

MERGER PROPOSED-YOUR VOTE IS VERY IMPORTANT

Dear Shareholders of Landmark Community Bank:

On [ ], 2021 we will hold a special meeting of the shareholders of Landmark Community Bank, or Landmark, to vote on a proposal to merge with Simmons Bank, an Arkansas state-chartered bank and wholly owned subsidiary of Simmons First National Corporation, or Simmons, an Arkansas corporation and the parent holding company of Simmons Bank. On June 4, 2021, Simmons, Simmons Bank and Landmark entered into an Agreement and Plan of Merger, which we refer to as the Landmark merger agreement, that provides for the merger of Landmark with and into Simmons Bank, with Simmons Bank as the surviving bank in the merger, which we refer to as the Landmark merger.

Based on the assumptions set forth below, under the terms of the Landmark merger agreement, each share of common stock, no par value per share, of Landmark, which we refer to as Landmark common stock, that is issued and outstanding immediately prior to the effective time of the Landmark merger, which we refer to as the Landmark effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (1) [ ] shares of common stock, $0.01 par value per share, of Simmons, which we refer to as the Landmark stock consideration, with cash paid in lieu of fractional shares, and (2) $[ ] in cash, which we refer to as the Landmark cash consideration, and together with the Landmark stock consideration, the Landmark merger consideration. In the aggregate, Simmons expects to issue approximately [ ] shares of common stock, $0.01 par value per share, of Simmons, which we refer to as Simmons common stock, and pay approximately $[ ] million (minus the cash payment for outstanding stock options of Landmark) to Landmark shareholders upon completion of the Landmark merger, subject to certain conditions and potential adjustments under the Landmark merger agreement. The Landmark merger consideration is based on the assumption that (i) [ ] shares of Landmark common stock are issued and outstanding and (ii) [ ] shares of Landmark common stock are subject to outstanding stock options of Landmark with a weighted average exercise price of $[ ], in each case, immediately prior to the Landmark effective time. In addition, we have assumed that the Landmark/Simmons average closing price (as described herein) is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

In addition to the Landmark merger, Simmons and Triumph Bancshares, Inc., or Triumph, a Tennessee corporation and the parent company of Triumph Bank, a Tennessee state-chartered bank and a wholly owned subsidiary of Triumph, have also entered into an Agreement and Plan of Merger, which we refer to as the Triumph merger agreement, that provides for (i) the merger of Triumph with and into Simmons, with Simmons as the

surviving corporation in the merger, which we refer to as the Triumph merger, and (ii) immediately following the Triumph merger, the merger of Triumph Bank with and into Simmons Bank, with Simmons Bank as the surviving bank. Triumph is headquartered in Memphis, Tennessee, operates out of six branches located in the Memphis and Nashville Metropolitan statistical areas, and had total assets of approximately $0.9 billion as of March 31, 2021. Based on the assumptions set forth below, under the terms of the Triumph merger agreement, each share of common stock, $1.00 par value per share, of Triumph, which we refer to as Triumph common stock, that is issued and outstanding immediately prior to the effective time of the Triumph merger, which we refer to as the Triumph effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (1) [ ] shares of Simmons common stock, which we refer to as the Triumph stock consideration, with cash paid in lieu of fractional shares, and (2) $[ ] in cash, which we refer to as the Triumph cash consideration, and together with the Triumph stock consideration, the Triumph merger consideration. In the aggregate, Simmons expects to issue approximately [ ] shares of common stock and pay approximately $[ ] million (minus the cash payment for outstanding stock options of Triumph) to Triumph shareholders upon completion of the Triumph merger, subject to certain conditions and potential adjustments under the Triumph merger agreement. The Triumph merger consideration is based on the assumption that (i) [ ] shares of Triumph common stock are issued and outstanding and (ii) [ ] shares of Triumph common stock are subject to outstanding stock options of Triumph with a weighted average exercise price of $[ ], in each case, immediately prior to the Triumph effective time. In addition, we have assumed that the Triumph/Simmons average closing price (as described herein) is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

The market value of the Landmark merger consideration and the Triumph merger consideration will fluctuate with the price of Simmons common stock. At the time of the special meetings of Landmark shareholders and Triumph shareholders, the Landmark shareholders and Triumph shareholders will not know or be able to calculate the value of the merger consideration to be received upon completion of the Landmark merger or the Triumph merger, respectively. Based on the closing sale price per share of Simmons common stock on June 4, 2021, the last trading day before the public announcement of the signing of the Landmark merger agreement and the Triumph merger agreement, and on [ ], 2021, the last practicable trading day prior to printing this proxy statement/prospectus, and on certain assumptions as described elsewhere in this proxy statement/prospectus, the implied value of the merger consideration payable for each share of Landmark common stock is approximately $[ ], or $[ ] per share of Landmark common stock, and approximately $[ ], or $[ ] per share of Landmark common stock, respectively. We urge you to obtain current market quotations for Simmons common stock, which is traded on the Nasdaq Global Select Market under the symbol “SFNC.”

While the Triumph shareholders will need to approve the Triumph merger for it to be consummated, the Landmark shareholders will not be required to approve the Triumph merger. Information included in this proxy statement/prospectus with respect to Triumph and the Triumph merger is provided as information for Landmark shareholders to consider when voting upon the Landmark merger.

If the Landmark merger and the Triumph merger, which we refer to collectively as the mergers, are both completed, existing Simmons shareholders would own approximately [ ]% of Simmons common stock immediately following completion of the mergers, while former Landmark shareholders would own approximately [ ]% and former Triumph shareholders would own approximately [ ]%. If the Landmark merger is completed but the Triumph merger is not completed, existing Simmons shareholders and Landmark shareholders would own approximately [ ]% and [ ]%, respectively, of Simmons common stock upon completion of the Landmark merger.

Neither the closing of the Landmark merger nor the closing of the Triumph merger is conditioned upon closing of the other merger.

Landmark will hold a special meeting of its shareholders in connection with the Landmark merger. Simmons and Landmark cannot complete the Landmark merger unless the holders of Landmark common stock approve the Landmark merger agreement and the transactions contemplated thereby, including the Landmark merger. Landmark’s board of directors, or the Landmark board of directors, is providing this document to solicit Landmark shareholders’ proxy to vote in connection with the Landmark merger agreement and related matters. This document is also being delivered to Landmark shareholders and Triumph shareholders as Simmons’ prospectus for its offering of Simmons common stock in connection with the mergers.

The Landmark special meeting will be held on [ ], 2021, at [ ] Central Time, at [ ].

Landmark shareholders, your vote is very important.

To ensure your representation at the Landmark special meeting, please complete, sign, date and return the enclosed proxy. Sending in your proxy will not prevent you from voting your shares personally at the Landmark special meeting, since you may revoke your proxy at any time before it is voted.

The Landmark board of directors approved the Landmark merger agreement and the transactions contemplated thereby and recommends that Landmark shareholders vote “FOR” approval of the Landmark merger agreement, and, if necessary or appropriate, “FOR” the proposal to adjourn the Landmark special meeting to solicit additional proxies in favor of the Landmark merger agreement.

This proxy statement/prospectus describes the special meeting of Landmark, the special meeting of Triumph, the Landmark merger, the Triumph merger, the documents related to the mergers and other related matters. Please carefully read this entire proxy statement/prospectus, including “Risk Factors,” beginning on page 32 for a discussion of the risks relating to the proposed mergers. You also can obtain information about Simmons from documents that it has filed with the Securities and Exchange Commission.

Sincerely,


George A. Makris, Jr.	James P. Farrell
Chairman and Chief Executive Officer	Chairman, President and Chief Executive Officer
Simmons First National Corporation	Landmark Community Bank

Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved the Landmark merger, the Triumph merger, the issuance of the Simmons common stock to be issued in the Landmark merger or the Triumph merger, or the other transactions described in this proxy statement/prospectus or passed upon the adequacy or accuracy of this proxy statement/prospectus. Any representation to the contrary is a criminal offense.

The securities to be issued in the mergers are not savings or deposit accounts or other obligations of any bank or non-bank subsidiary of Simmons, Landmark or Triumph, and they are not insured by the Federal Deposit Insurance Corporation, the Deposit Insurance Fund, or any other governmental agency.

The date of this proxy statement/prospectus is [ ], and it is first being mailed or otherwise delivered to the shareholders of Landmark and Triumph on or about [ ].

iii

PROXY STATEMENT/PROSPECTUS

MERGER PROPOSED-YOUR VOTE IS VERY IMPORTANT

Dear Shareholders of Triumph Bancshares, Inc.:

On [ ], 2021 we will hold a special meeting of the shareholders of Triumph Bancshares, Inc., or Triumph, to vote on a proposal to merge with Simmons First National Corporation, or Simmons, an Arkansas corporation and the parent holding company of Simmons Bank, an Arkansas state-chartered bank and wholly owned subsidiary of Simmons. On June 4, 2021, Simmons and Triumph entered into an Agreement and Plan of Merger, which we refer to as the Triumph merger agreement, that provides for (i) the merger of Triumph with and into Simmons, with Simmons as the surviving corporation in the merger, which we refer to as the Triumph merger, and (ii) immediately following the Triumph merger, the merger of Triumph Bank with and into Simmons Bank, with Simmons Bank as the surviving bank.

Based on the assumptions set forth below, under the terms of the Triumph merger agreement, each share of common stock, $1.00 par value per share, of Triumph, which we refer to as Triumph common stock, that is issued and outstanding immediately prior to the effective time of the Triumph merger, which we refer to as the Triumph effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (1) [ ] shares of common stock, $0.01 par value per share, of Simmons, which we refer to as the Triumph stock consideration, with cash paid in lieu of fractional shares, and (2) $[ ] in cash, which we refer to as the Triumph cash consideration, and together with the Triumph stock consideration, the Triumph merger consideration. In the aggregate, Simmons expects to issue approximately [ ] shares of common stock, $0.01 par value per share, of Simmons, which we refer to as Simmons common stock, and pay approximately $[ ] million (minus the cash payment for outstanding stock options of Triumph) to Triumph shareholders upon completion of the Triumph merger, subject to certain conditions and potential adjustments under the Triumph merger agreement. The Triumph merger consideration is based on the assumption that (i) [ ] shares of Triumph common stock are issued and outstanding and (ii) [ ] shares of Triumph common stock are subject to outstanding stock options of Triumph with a weighted average exercise price of $[ ], in each case, immediately prior to the Triumph effective time. In addition, we have assumed that the Triumph/Simmons average closing price (as described herein) is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

In addition to the Triumph merger, Simmons, Simmons Bank and Landmark Community Bank, or Landmark, a Tennessee state-chartered bank, have also entered into an Agreement and Plan of Merger, which we refer to as the Landmark merger agreement, that provides for the merger of Landmark with and into Simmons Bank, with Simmons Bank as the surviving bank in the merger, which we refer to as the Landmark merger. Landmark is headquartered in Collierville, Tennessee, operates out of eight branches located in the Memphis and Nashville Metropolitan statistical areas, and had total assets of approximately $1.0 billion as of March 31, 2021. Based on the assumptions set forth below, under the terms of the Landmark merger agreement, each share of common stock, no par value per share, of Landmark, which we refer to as Landmark common stock, that is issued and outstanding immediately prior to the effective time of the Landmark merger, which we refer to as the Landmark effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (1) [ ] shares of Simmons common stock, which we refer to as the Landmark stock consideration, with cash paid in lieu of fractional shares, and (2) $[ ] in cash, which we refer to as the Landmark cash consideration, and together with the Landmark stock consideration, the Landmark merger consideration. In the aggregate, Simmons expects to issue approximately [ ] shares of common stock and pay approximately

$[ ] million (minus the cash payment for outstanding stock options of Landmark) to Landmark shareholders upon completion of the Landmark merger, subject to certain conditions and potential adjustments under the Landmark merger agreement. The Landmark merger consideration is based on the assumption that (i) [ ] shares of Landmark common stock are issued and outstanding and (ii) [ ] shares of Landmark common stock are subject to outstanding stock options of Landmark with a weighted average exercise price of $[ ], in each case, immediately prior to the Landmark effective time. In addition, we have assumed that the Landmark/Simmons average closing price (as described herein) is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

The market value of the Triumph merger consideration and the Landmark merger consideration will fluctuate with the price of Simmons common stock. At the time of the special meetings of Triumph shareholders and Landmark shareholders, the Triumph shareholders and Landmark shareholders will not know or be able to calculate the value of the merger consideration to be received upon completion of the Triumph merger or the Landmark merger, respectively. Based on the closing sale price per share of Simmons common stock on June 4, 2021, the last trading day before the public announcement of the signing of the Triumph merger agreement and the Landmark merger agreement, and on [ ], 2021, the last practicable trading day prior to printing this proxy statement/prospectus, and on certain assumptions as described elsewhere in this proxy statement/prospectus, the implied value of the merger consideration payable for each share of Triumph common stock is approximately $[ ], or $[ ] per share of Triumph common stock, and approximately $[ ], or $[ ] per share of Triumph common stock, respectively. We urge you to obtain current market quotations for Simmons common stock, which is traded on the Nasdaq Global Select Market under the symbol “SFNC.”

Triumph’s board of directors, or the Triumph board of directors, may terminate the Triumph merger agreement if the Triumph/Simmons average closing price is below a threshold specified in the Triumph merger agreement and below a threshold relative to the Nasdaq Bank Index, as further described in the accompanying proxy statement/prospectus. If the Triumph board of directors terminates the Triumph merger agreement, Simmons may prevent the Triumph merger agreement from being terminated by increasing the Triumph cash consideration. See the section entitled “The Merger Agreements—Termination of the Merger Agreements.”

While Landmark shareholders will need to approve the Landmark merger for it to be consummated, the Triumph shareholders will not be required to approve the Landmark merger. Information included in this proxy statement/prospectus with respect to Landmark and the Landmark merger is provided as information for Triumph shareholders to consider when voting upon the Triumph merger.

If the Triumph merger and Landmark merger, which we refer to collectively as the mergers, are both completed, existing Simmons shareholders would own approximately [ ]% of Simmons common stock immediately following completion of the mergers, while former Triumph shareholders would own approximately [ ]% and former Landmark shareholders would own approximately [ ]%. If the Triumph merger is completed but the Landmark merger is not completed, existing Simmons shareholders and Triumph shareholders would own approximately [ ]% and [ ]%, respectively, of Simmons common stock upon completion of the Triumph merger.

Neither the closing of the Triumph merger nor the closing of the Landmark merger is conditioned upon closing of the other merger.

Triumph will hold a special meeting of its shareholders in connection with the Triumph merger. Simmons and Triumph cannot complete the Triumph merger unless the holders of Triumph common stock approve the Triumph merger agreement and the transactions contemplated thereby, including the Triumph merger. The Triumph board of directors is providing this document to solicit Triumph shareholders’ proxy to vote in connection with the Triumph merger agreement and related matters. This document is also being delivered to Triumph shareholders and Landmark shareholders as Simmons’ prospectus for its offering of Simmons common stock in connection with the mergers.

The Triumph special meeting will be held on [ ], 2021, at [ ] Central Time, at [ ].

Triumph shareholders, your vote is very important.

To ensure your representation at the Triumph special meeting, please complete, sign, date and return the enclosed proxy. Sending in your proxy will not prevent you from voting your shares personally at the Triumph special meeting, since you may revoke your proxy at any time before it is voted.

The Triumph board of directors approved the Triumph merger agreement and the transactions contemplated thereby and recommends that Triumph shareholders vote “FOR” approval of the Triumph merger agreement, and, if necessary or appropriate, “FOR” the proposal to adjourn the Triumph special meeting to solicit additional proxies in favor of the Triumph merger agreement.

This proxy statement/prospectus describes the special meeting of Triumph, the special meeting of Landmark, the Triumph merger, the Landmark merger, the documents related to the mergers and other related matters. Please carefully read this entire proxy statement/prospectus, including “Risk Factors,” beginning on page 32 for a discussion of the risks relating to the proposed mergers. You also can obtain information about Simmons from documents that it has filed with the Securities and Exchange Commission.

Sincerely,


George A. Makris, Jr.	Hilliard Crews
Chairman and Chief Executive Officer	Chairman
Simmons First National Corporation	Triumph Bancshares, Inc.

Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved the Triumph merger, the Landmark merger, the issuance of the Simmons common stock to be issued in the Triumph merger or the Landmark merger, or the other transactions described in this proxy statement/prospectus or passed upon the adequacy or accuracy of this proxy statement/prospectus. Any representation to the contrary is a criminal offense.

The securities to be issued in the mergers are not savings or deposit accounts or other obligations of any bank or non-bank subsidiary of Simmons, Triumph or Landmark, and they are not insured by the Federal Deposit Insurance Corporation, the Deposit Insurance Fund, or any other governmental agency.

The date of this proxy statement/prospectus is [ ], and it is first being mailed or otherwise delivered to the shareholders of Triumph and Landmark on or about [ ].

ADDITIONAL INFORMATION

This proxy statement/prospectus incorporates important business and financial information about Simmons from documents filed with the U.S. Securities and Exchange Commission, or the SEC, that are not included in or delivered with this proxy statement/prospectus. You can obtain any of the documents filed with or furnished to the SEC by Simmons at no cost from the SEC’s website at www.sec.gov. You will also be able to obtain these documents, free of charge, from Simmons at www.simmonsbank.com. The website addresses of the SEC and Simmons are included as inactive textual references only. Except as specifically incorporated by reference into this proxy statement/prospectus, the information on those websites is not a part of this proxy statement/prospectus and therefore is not incorporated by reference into this proxy statement/prospectus. You may also request copies of these documents concerning Simmons, including documents incorporated by reference into this proxy statement/prospectus, at no cost by contacting Simmons at the following address:

Simmons First National Corporation

P.O. Box 7009
Pine Bluff, Arkansas 71611
Attention: George Makris III
Telephone: (870) 541-1000

For a more detailed description of the information incorporated by reference into the accompanying proxy statement/prospectus and how you may obtain it, see the section entitled “Where You Can Find More Information.”

Neither Landmark nor Triumph has a class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended, or the Exchange Act, and therefore neither Landmark nor Triumph is subject to the reporting requirements of Section 13(a) or 15(d) of the Exchange Act and, accordingly, neither Landmark nor Triumph files documents or reports with the SEC.

If you are a Landmark or Triumph shareholder and (a) have any questions concerning (i) the Landmark special meeting, the Landmark merger or the Landmark merger agreement, (ii) the Triumph special meeting, the Triumph merger or the Triumph merger agreement or (iii) the proxy statement/prospectus, (b) would like additional copies of the proxy statement/prospectus without charge or (c) need help voting your shares of Landmark common stock or Triumph common stock, please contact Landmark or Triumph, as applicable, at the following address:

Landmark Community Bank

5880 Ridge Bend Road

Memphis, Tennessee 38120

Attention: James P. “Jake” Farrell

Telephone: (901) 457-3111

Email: jakefarrell@landmarkbanktn.com

Attention: Charles E. “Buddy” Dickey

Telephone: (901) 457-3123

Email: cdickey@landmarkbanktn.com

Triumph Bancshares, Inc.

5699 Poplar Avenue

Memphis, Tennessee 38119

Attention: Hilliard Crews and William J. Chase Jr.

Telephone: (901) 333-8801

vii

These documents are available without charge upon written or oral request. To obtain timely delivery of these documents, Landmark shareholders must request them no later than [ ], 2021 in order to receive them before the Landmark special meeting and Triumph shareholders must request them no later than [ ], 2021 in order to receive them before the Triumph special meeting.

No one has been authorized to provide you with information that is different from that contained in, or incorporated by reference into, this document. This document is dated [ ], 2021 and you should assume that the information in this document is accurate only as of such date. You should assume that the information incorporated by reference into this document is accurate as of the date of such document. Neither the mailing of this document to the shareholders of Landmark or Triumph nor the issuance by Simmons of shares of Simmons common stock in connection with the Landmark merger or the Triumph merger will create any implication to the contrary. See the section entitled “Where You Can Find More Information” for more details.

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 or from whom it is unlawful to make any such offer or solicitation in that jurisdiction. Except where the context otherwise indicates, information contained in this document regarding Simmons has been provided by Simmons, information contained in this document regarding Landmark has been provided by Landmark and information contained in this document regarding Triumph has been provided by Triumph.

viii

NOTICE OF SPECIAL MEETING OF
LANDMARK COMMUNITY BANK SHAREHOLDERS
TO BE HELD ON [ ], 2021

To the Shareholders of Landmark Community Bank:

Notice is hereby given that Landmark Community Bank, which we refer to as Landmark, will hold a special meeting of holders of common stock, no par value per share, of Landmark, or Landmark common stock, which we refer to as the Landmark special meeting, on [ ], 2021, at [ ] Central Time, at [ ]. The Landmark special meeting will be held for the purposes of allowing holders of Landmark common stock, or Landmark shareholders, to consider and vote upon the following matters:

	·	a proposal to approve the Agreement and Plan of Merger, dated as of June 4, 2021, which we refer to as the Landmark merger agreement, by and among Simmons First National Corporation, which we refer to as Simmons, Simmons Bank, an Arkansas state-chartered bank and wholly owned subsidiary of Simmons, and Landmark, pursuant to which, among other things, Landmark will merge with and into Simmons Bank, with Simmons Bank as the surviving bank, which we refer to as the Landmark merger, as more fully described in the attached proxy statement/prospectus, which we refer to as the Landmark merger proposal; and

	·	a proposal to approve one or more adjournments of the Landmark special meeting, if necessary or appropriate, to solicit additional proxies in favor of approval of the Landmark merger proposal, which we refer to as the Landmark adjournment proposal.

These proposals are described in greater detail in the enclosed proxy statement/prospectus. Landmark will transact no other business at the Landmark special meeting, except for the business properly brought before the Landmark special meeting or any adjournment or postponement thereof.

Landmark has fixed the close of business on [ ] as the record date for the Landmark special meeting. Only Landmark shareholders of record at that time are entitled to notice of, and to vote at, the Landmark special meeting, or any adjournment or postponement thereof. Approval of the Landmark merger proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock entitled to vote on the Landmark merger proposal. Approval of the adjournment proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock present or represented by proxy at the Landmark special meeting and entitled to vote on the Landmark adjournment proposal. At the close of business on the record date, [ ] shares of Landmark common stock were outstanding and entitled to vote.

Your vote is very important. Simmons, Simmons Bank and Landmark cannot complete the Landmark merger unless Landmark shareholders approve the Landmark merger agreement.

To ensure your representation at the Landmark special meeting, please complete, sign, date and return the enclosed proxy by following the instructions on your proxy. If your shares of Landmark common stock are held in “street name” by a bank, broker or other nominee, please follow the instructions on the voting instruction form provided by the record holder. Sending in your proxy will not prevent you from voting your shares personally at the Landmark special meeting, since you may revoke your proxy at any time before it is voted.

Under Tennessee law, Landmark shareholders who do not vote in favor of the Landmark merger proposal and follow certain procedural steps will be entitled to dissenters’ rights. See the section entitled “Questions and Answers—Are Landmark shareholders or Triumph shareholders entitled to dissenters’ rights?” and Annex G, which contains Section 48-23-101 through Section 48-23-302 of the Tennessee Business Corporation Act, or the dissenters’ rights statutes.

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

The Landmark board of directors has approved the Landmark merger agreement and the transactions contemplated thereby and recommends that Landmark shareholders vote “FOR” the Landmark merger proposal and, if necessary or appropriate, “FOR” the Landmark adjournment proposal.

	BY ORDER OF THE BOARD OF DIRECTORS


	James P. Farrell
	Chairman, President and Chief Executive Officer

Collierville, TN
[ ], 2021

NOTICE OF SPECIAL MEETING OF
TRIUMPH BANCSHARES, INC. SHAREHOLDERS
TO BE HELD ON [ ], 2021

To the Shareholders of Triumph Bancshares, Inc.:

Notice is hereby given that Triumph Bancshares, Inc., which we refer to as Triumph, will hold a special meeting of holders of common stock, $1.00 par value per share, of Triumph, or Triumph common stock, which we refer to as the Triumph special meeting, on [ ], 2021, at [ ] Central Time, at [ ]. The Triumph special meeting will be held for the purposes of allowing holders of Triumph common stock, or Triumph shareholders, to consider and vote upon the following matters:

	·	a proposal to approve the Agreement and Plan of Merger, dated as of June 4, 2021, which we refer to as the Triumph merger agreement, by and between Simmons First National Corporation, which we refer to as Simmons, and Triumph, pursuant to which, among other things, Triumph will merge with and into Simmons, with Simmons as the surviving corporation, which we refer to as the merger, as more fully described in the attached proxy statement/prospectus, which we refer to as the Triumph merger proposal; and

	·	a proposal to approve one or more adjournments of the Triumph special meeting, if necessary or appropriate, to solicit additional proxies in favor of approval of the Triumph merger proposal, which we refer to as the Triumph adjournment proposal.

These proposals are described in greater detail in the enclosed proxy statement/prospectus. Triumph will transact no other business at the Triumph special meeting, except for the business properly brought before the Triumph special meeting or any adjournment or postponement thereof.

Triumph has fixed the close of business on [ ] as the record date for the Triumph special meeting. Only Triumph shareholders of record at that time are entitled to notice of, and to vote at, the Triumph special meeting, or any adjournment or postponement thereof. Approval of the Triumph merger proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Triumph common stock entitled to vote on the Triumph merger proposal. Approval of the Triumph adjournment proposal requires the votes cast by the outstanding shares of Triumph common stock present or represented by proxy at the Triumph special meeting and entitled to vote on the proposal favoring the approval to exceed the votes cast opposing the approval. At the close of business on the record date, [ ] shares of Triumph common stock were outstanding and entitled to vote.

Your vote is very important. Simmons and Triumph cannot complete the Triumph merger unless Triumph shareholders approve the Triumph merger agreement.

To ensure your representation at the Triumph special meeting, please complete, sign, date and return the enclosed proxy by following the instructions on your proxy. If your shares of Triumph common stock are held in “street name” by a bank, broker or other nominee, please follow the instructions on the voting instruction form provided by the record holder. Sending in your proxy will not prevent you from voting your shares personally at the Triumph special meeting, since you may revoke your proxy at any time before it is voted.

Under Tennessee law, Triumph shareholders who do not vote in favor of the Triumph merger proposal and follow certain procedural steps will be entitled to dissenters’ rights. See the section entitled “Questions and Answers—Are Landmark shareholders or Triumph shareholders entitled to dissenters’ rights?” and Annex G, which contains Section 48-23-101 through Section 48-23-302 of the Tennessee Business Corporation Act, or the dissenters’ rights statutes.

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

The Triumph board of directors has approved the Triumph merger agreement and the transactions contemplated thereby and recommends that Triumph shareholders vote “FOR” the Triumph merger proposal and, if necessary or appropriate, “FOR” the Triumph adjournment proposal.

	BY ORDER OF THE BOARD OF DIRECTORS


	Hilliard Crews
	Chairman

Memphis, TN
[ ], 2021

xii

TABLE OF CONTENTS

QUESTIONS AND ANSWERS	1
SUMMARY	14
MARKET PRICE AND DIVIDENDS	28
CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS	30
RISK FACTORS	32
Risks Relating to the Mergers	32
Risks Relating to the Combined Company’s Business Following the Mergers	37
Risks Relating to an Investment in Simmons Common Stock	39
THE LANDMARK SPECIAL MEETING	41
THE LANDMARK PROPOSALS	45
THE TRIUMPH SPECIAL MEETING	47
THE TRIUMPH PROPOSALS	51
INFORMATION ABOUT THE COMPANIES	53
THE LANDMARK MERGER	56
Terms of the Landmark Merger	56
Background of the Landmark Merger	56
Landmark’s Reasons for the Landmark Merger and Recommendation of the Landmark Board of Directors	59
Opinion of Landmark’s Financial Advisor	61
Certain Prospective Financial Information	68
Simmons’ Reasons for the Landmark Merger	70
Interests of Landmark’s Directors and Executive Officers in the Landmark Merger	72
THE TRIUMPH MERGER	74
Terms of the Triumph Merger	74
Background of the Triumph Merger	74
Triumph’s Reasons for the Triumph Merger and Recommendation of the Triumph Board of Directors	78
Opinion of Triumph’s Financial Advisor	82
Certain Prospective Financial Information	89
Simmons’ Reasons for the Triumph Merger	91
Interests of Triumph’s Directors and Executive Officers in the Triumph Merger	93
THE MERGERS	95
Board of Directors and Management of Simmons and Simmons Bank After the Mergers	95
Public Trading Markets	95
Accounting Treatment	95
Appraisal and Dissenters’ Rights	95
Regulatory Approvals Required for the Mergers and the Triumph Bank Merger	99
THE MERGER AGREEMENTS	102
MATERIAL UNITED STATES FEDERAL INCOME TAX CONSEQUENCES OF THE MERGERS	126
COMPARISON OF SHAREHOLDERS’ RIGHTS OF SIMMONS AND LANDMARK	129
COMPARISON OF SHAREHOLDERS’ RIGHTS OF SIMMONS AND TRIUMPH	143
SECURITY OWNERSHIP OF LANDMARK DIRECTORS, EXECUTIVE OFFICERS AND CERTAIN BENEFICIAL OWNERS OF LANDMARK	155
SECURITY OWNERSHIP OF TRIUMPH DIRECTORS, EXECUTIVE OFFICERS AND CERTAIN BENEFICIAL OWNERS OF TRIUMPH	158
LEGAL MATTERS	158
EXPERTS	158
OTHER MATTERS	158

xiii

SIMMONS ANNUAL MEETING SHAREHOLDER PROPOSALS	158
LANDMARK ANNUAL MEETING SHAREHOLDER PROPOSALS	159
TRIUMPH ANNUAL MEETING SHAREHOLDER PROPOSALS	159
WHERE YOU CAN FIND MORE INFORMATION	160

Annex Index

Annex A:	Agreement and Plan of Merger, dated as of June 4, 2021, by and among Simmons First National Corporation, Simmons Bank and Landmark Community Bank
Annex B:	Agreement and Plan of Merger, dated as of June 4, 2021, by and between Simmons First National Corporation and Triumph Bancshares, Inc.
Annex C:	Form of Support and Non-Competition Agreement, by and among Simmons First National Corporation, Simmons Bank, Landmark Community Bank and each of the directors and certain executive officers of Landmark Community Bank
Annex D:	Form of Support and Non-Competition Agreement, by and among Simmons First National Corporation, Triumph Bancshares, Inc. and each of the directors and certain executive officers of Triumph Bancshares, Inc.
Annex E:	Opinion of Olsen Palmer LLC
Annex F:	Opinion of Southard Financial, LLC
Annex G:	Section 48-23-101 through Section 48-23-302 of the Tennessee Business Corporation Act: Dissenters’ Rights for Shareholders of Landmark Community Bank and Triumph Bancshares, Inc.

xiv

QUESTIONS AND ANSWERS

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

Unless the context otherwise requires, references in this proxy statement/prospectus to “Simmons” refer to Simmons First National Corporation, an Arkansas corporation; references to “Landmark” refer to Landmark Community Bank, a Tennessee state-chartered bank; references to “Triumph” refer to Triumph Bancshares, Inc., a Tennessee corporation; references to “Triumph Bank” refer to Triumph Bank, a Tennessee state-chartered bank and a wholly owned subsidiary of Triumph; and references to “we,” “our” and “us” refer to Simmons, Landmark and Triumph together.

As described below, it is important to note that the amount of merger consideration for each of the mergers may increase or decrease due to changes in the price of Simmons common stock or the fully diluted number of shares of Landmark common stock or Triumph common stock, as applicable, outstanding after the date hereof. As a result, merger consideration for each of the mergers shown throughout this proxy statement/prospectus is for illustrative purposes only based on the assumptions described herein.

What are the mergers?

Simmons, Simmons Bank and Landmark have entered into an Agreement and Plan of Merger, dated as of June 4, 2021, which we refer to as the Landmark merger agreement, and Simmons and Triumph have entered into an Agreement and Plan of Merger, dated as of June 4, 2021, which we refer to as the Triumph merger agreement, and collectively we refer to the Landmark merger agreement and the Triumph merger agreement as the merger agreements. Under the Landmark merger agreement, Landmark will merge with and into Simmons Bank, with Simmons Bank as the surviving bank, which we refer to as the Landmark merger. Under the Triumph merger agreement, (i) Triumph will merge with and into Simmons, with Simmons as the surviving corporation, which we refer to as the Triumph merger, and collectively with the Landmark merger, the mergers, and (ii) immediately following the Triumph merger, Triumph Bank will merge with and into Simmons Bank, with Simmons Bank as the surviving bank, which we refer to as the Triumph Bank merger. Copies of the Landmark merger agreement and the Triumph merger agreement are attached to this proxy statement/prospectus as Annex A and Annex B, respectively.

The Landmark merger cannot be completed unless, among other things, the holders of Landmark common stock, no par value per share, which we refer to as the Landmark common stock, approve the proposal to approve the Landmark merger agreement. Separately, the Triumph merger cannot be completed unless, among other things, the holders of Triumph common stock, par value $1.00 per share, which we refer to as the Triumph common stock, approve the proposal to approve the Triumph merger agreement.

Is the consummation of one merger conditioned on the consummation of the other merger?

No. The Landmark merger may be consummated regardless of whether the Triumph merger is consummated and the Triumph merger may be consummated regardless of whether the Landmark merger is consummated.

Why am I receiving this proxy statement/prospectus?

We are delivering this document to the holders of Landmark common stock, which we refer to as Landmark shareholders, and the holders of Triumph common stock, which we refer to as Triumph shareholders, because it is a proxy statement being used by the each of the boards of directors of Landmark and Triumph, which we refer to as the Landmark board of directors and the Triumph board of directors, respectively, to solicit proxies of its respective shareholders in connection with approval of the respective mergers and related matters.

In order to approve the mergers and related matters, Landmark and Triumph have each called a special meeting of their shareholders, which we refer to as the Landmark special meeting and the Triumph special meeting, respectively. This document serves as a proxy statement for the Landmark special meeting and the Triumph special meeting, which we refer to collectively as the special meetings, and describes the proposals to be presented at the special meetings.

This document is also a prospectus that is being delivered to Landmark shareholders and Triumph shareholders because Simmons is offering shares of its common stock, par value $0.01 per share, which we refer to as Simmons common stock, to Landmark shareholders and Triumph shareholders as partial consideration for the Landmark merger and the Triumph merger, respectively.

This proxy statement/prospectus contains important information about the mergers and the other proposals being voted on at the special meetings. You should read it carefully and in its entirety. The enclosed materials allow you to have your shares voted by proxy without attending your meeting. Your vote is important. We encourage you to submit your proxy as soon as possible.

What am I being asked to vote on?

Landmark Special Meeting: Landmark is soliciting proxies from its shareholders with respect to (i) a proposal to approve the Landmark merger agreement, a copy of which is attached as Annex A to this proxy statement/prospectus, and the transactions contemplated thereby, including the Landmark merger, which we refer to as the Landmark merger proposal, and (ii) a proposal to adjourn the Landmark special meeting, if necessary or appropriate, to solicit additional proxies in favor of the Landmark merger proposal, which we refer to as the Landmark adjournment proposal.

Shareholder approval of the Landmark merger proposal is required to complete the Landmark merger. Completion of the Landmark merger is not conditioned upon approval of the Landmark adjournment proposal. Landmark expects that the Landmark adjournment proposal will not be brought before the Landmark special meeting if there are sufficient votes to approve the Landmark merger proposal. Landmark will transact no other business at the Landmark special meeting, except for the business properly brought before the Landmark special meeting or any adjournment or postponement thereof.

Triumph Special Meeting: Triumph is soliciting proxies from its shareholders with respect to (i) a proposal to approve the Triumph merger agreement, a copy of which is attached as Annex B to this proxy statement/prospectus, and the transactions contemplated thereby, including the Triumph merger, which we refer to as the Triumph merger proposal, and (ii) a proposal to adjourn the Triumph special meeting, if necessary or appropriate, to solicit additional proxies in favor of the Triumph merger proposal, which we refer to as the Triumph adjournment proposal.

Shareholder approval of the Triumph merger proposal is required to complete the Triumph merger. Completion of the Triumph merger is not conditioned upon approval of the Triumph adjournment proposal. Triumph expects that the Triumph adjournment proposal will not be brought before the Triumph

special meeting if there are sufficient votes to approve the Triumph merger proposal. Triumph will transact no other business at the Triumph special meeting, except for the business properly brought before the Triumph special meeting or any adjournment or postponement thereof.

What will Landmark shareholders receive in the merger?

Based on the assumptions set forth below, at the time the Landmark merger is completed, which we refer to as the Landmark effective time, each share of Landmark common stock that is issued and outstanding immediately prior to the Landmark effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (i) [ ] shares of Simmons common stock, which we refer to as the Landmark stock consideration, with cash paid in lieu of fractional shares, and (ii) $[ ] in cash, which we refer to as the Landmark cash consideration, and together with the Landmark stock consideration, the Landmark merger consideration. In the aggregate, Simmons expects to issue approximately [ ] shares of Simmons common stock and pay approximately $[ ] million (minus the cash payment for outstanding options to purchase shares of Landmark common stock, which we refer to as Landmark stock options) to Landmark shareholders upon completion of the Landmark merger, subject to certain conditions and potential adjustments under the Landmark merger agreement. The Landmark merger consideration is based on the assumption that (A) [ ] shares of Landmark common stock are issued and outstanding and (B) [ ] shares of Landmark common stock are subject to outstanding Landmark stock options with a weighted average exercise price of $[ ], in each case, immediately prior to the Landmark effective time. In addition, we have assumed that the Landmark/Simmons average closing price (as described below) is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

Simmons will not issue any fractional shares of Simmons common stock in the Landmark merger. Instead, a Landmark shareholder who would otherwise be entitled to a fractional share of Simmons common stock will receive, in lieu thereof, an amount in cash, rounded up to the nearest whole cent (without interest), determined by multiplying (i) the fraction of a share (rounded to the nearest thousandth when expressed in decimal form) of Simmons common stock that such Landmark shareholder would otherwise be entitled to receive by (ii) the average of the daily closing prices of shares of Simmons common stock for the 20 consecutive full trading days on which shares are actually traded on the Nasdaq Global Select Market, or Nasdaq, ending at the close of trading on the tenth business day prior to the Landmark effective time (or the immediately preceding day to the tenth business day prior to the Landmark effective time if shares of Simmons common stock are not actually traded on Nasdaq on such day), which average we refer to as the Landmark/Simmons average closing price.

If the mergers are both completed, existing Simmons shareholders would own approximately [ ]% of Simmons common stock immediately following completion of the mergers, while former Landmark shareholders would own approximately [ ]% and former Triumph shareholders would own approximately [ ]%. If the Landmark merger is completed, but the Triumph merger is not completed, existing Simmons shareholders and Landmark shareholders would own approximately [ ]% and [ ]%, respectively, of Simmons common stock upon completion of the Landmark merger.

What will Triumph shareholders receive in the merger?

Based on the assumptions set forth below, at the time the Triumph merger is completed, which we refer to as the Triumph effective time, each share of Triumph common stock that is issued and outstanding immediately prior to the Triumph effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (i) [ ] shares of Simmons common stock, which we refer to as the Triumph stock consideration, with cash paid in lieu of fractional shares, and (ii) $[ ] in cash, which we refer to as the Triumph cash consideration, and together with the Triumph stock consideration,

the Triumph merger consideration. In the aggregate, Simmons expects to issue approximately [ ] shares of Simmons common stock and pay approximately $[ ] million (minus the cash payment for outstanding options to purchase shares of Triumph common stock, which we refer to as Triumph stock options) to Triumph shareholders upon completion of the Triumph merger, subject to certain conditions and potential adjustments under the Triumph merger agreement. The Triumph merger consideration is based on the assumption that (A) [ ] shares of Triumph common stock are issued and outstanding and (B) [ ] shares of Triumph common stock are subject to outstanding Triumph stock options with a weighted average exercise price of $[ ], in each case, immediately prior to the Triumph effective time. In addition, we have assumed that the Triumph/Simmons average closing price (as described below) is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

Simmons will not issue any fractional shares of Simmons common stock in the Triumph merger. Instead, Triumph shareholders who would otherwise be entitled to a fractional share of Simmons common stock will receive, in lieu thereof, an amount in cash, rounded up to the nearest whole cent (without interest), determined by multiplying (i) the fraction of a share (rounded to the nearest thousandth when expressed in decimal form) of Simmons common stock that such Triumph shareholder would otherwise be entitled to receive by (ii) the average of the daily closing prices of shares of Simmons common stock for the 20 consecutive full trading days on which shares are actually traded on Nasdaq, ending at the close of trading on the tenth business day prior to the Triumph effective time (or the immediately preceding day to the tenth business day prior to the Triumph effective time if shares of Simmons common stock are not actually traded on Nasdaq on such day), which we refer to as the Triumph determination date, and which average we refer to as the Triumph/Simmons average closing price.

If the mergers are both completed, existing Simmons shareholders would own approximately [ ]% of Simmons common stock immediately following completion of the mergers, while former Triumph shareholders would own approximately [ ]% and former Landmark shareholders would own approximately [ ]%. If the Triumph merger is completed, but the Landmark merger is not completed, existing Simmons shareholders and Triumph shareholders would own approximately [ ]% and [ ]%, respectively, of Simmons common stock upon completion of the Triumph merger.

Will the value of the merger consideration for the Landmark merger or the Triumph merger change between the date of this proxy statement/prospectus and the effective time of the mergers?

Yes. The amount of merger consideration for the mergers may increase or decrease if the number of fully diluted shares of Landmark common stock or Triumph common stock, as applicable, outstanding changes after the date hereof. Any change in the market price of Simmons common stock prior to the completion of the mergers will affect the market value of the merger consideration that Landmark shareholders and Triumph shareholders will receive upon completion of the respective mergers.

can be terminated by Triumph if, at any time during the five-day period commencing on the Triumph determination date, the Triumph/Simmons average closing price is less than $24.85 and the difference between the percentage change in the Nasdaq Bank Index and the percentage change in the Triumph/Simmons average closing price exceeds 20% over a designated measurement period, unless Simmons agrees to increase the Triumph cash consideration by a specified amount. See the section entitled “The Merger Agreements—Termination of the Merger Agreements.”

What will Simmons shareholders receive in the mergers?

If either or both of the mergers are completed, holders of Simmons common stock, or Simmons shareholders, will not receive any merger consideration and will continue to hold the number of shares of Simmons common stock that they currently hold. Following the mergers, shares of Simmons common stock will continue to be traded on Nasdaq under the symbol “SFNC.”

How will the mergers affect Landmark and Triumph stock options?

At the respective effective time, each Landmark stock option and each Triumph stock option, whether vested or unvested, outstanding immediately prior to the Landmark effective time or the Triumph effective time, respectively, and which we refer to collectively as the effective times, will be canceled and converted into the right to receive from Simmons a cash payment equal to the difference, if positive, between (i) the fully diluted per share value (as described below) and (ii) the exercise price of such Landmark stock option or Triumph stock option, as applicable, which we refer to as the Landmark stock option payout and the Triumph stock option payout, respectively.

Fully diluted per share value means with respect to Landmark or Triumph, as applicable, the quotient obtained by dividing (A) the sum of (i) the aggregate cash consideration, (ii) the product of (x) the aggregate stock consideration and (y) the average closing price and (iii) the product of (x) the total number of Landmark stock options or Triumph stock options, as applicable, outstanding immediately prior to the applicable effective time, and (y) the weighted average option exercise price for such stock options by (B) the sum of (i) the total number of shares of Landmark common stock or Triumph common stock, as applicable and (ii) the total number of shares of Landmark common stock or Triumph common stock, as applicable, underlying the Landmark stock options or Triumph stock options, respectively, outstanding, each as of immediately prior to the applicable effective time.

When do you expect to complete the mergers?

Each of Simmons, Landmark and Triumph expect to complete the applicable merger in the fourth quarter of 2021. However, Simmons, Landmark and Triumph cannot assure you of when or if the applicable merger will be completed. Landmark and Triumph must first obtain shareholder approval for the applicable merger, and the parties to the merger agreements also must obtain necessary regulatory approvals and satisfy certain other closing conditions. For further information, see the section entitled “The Merger Agreements—Conditions to Consummation of the Mergers.”

How does the Landmark board of directors recommend that Landmark shareholders vote at the Landmark special meeting?

The Landmark board of directors unanimously recommends that Landmark shareholders vote “FOR” the Landmark merger proposal and, if necessary or appropriate, “FOR” the Landmark adjournment proposal.

How does the Triumph board of directors recommend that Triumph shareholders vote at the Triumph special meeting?

The Triumph board of directors unanimously recommends that Triumph shareholders vote “FOR” the Triumph merger proposal and, if necessary or appropriate, “FOR” the Triumph adjournment proposal.

When and where are the special meetings?

The Landmark special meeting will be held on [ ], 2021, at [ ] Central Time, at [ ].

The Triumph special meeting will be held on [ ], 2021, at [ ] Central Time, at [ ].

What constitutes a quorum for the Landmark special meeting?

The presence at the Landmark special meeting, in person or by proxy, of holders of a majority of the shares of Landmark common stock issued, outstanding and entitled to vote at the Landmark special meeting will constitute a quorum.

What constitutes a quorum for the Triumph special meeting?

The presence at the Triumph special meeting, in person or by proxy, of holders of a majority of the outstanding shares of Triumph common stock entitled to vote at the Triumph special meeting will constitute a quorum.

Who is entitled to vote at the Landmark special meeting?

Holders of record of Landmark common stock at the close of business on [ ], which is the date that the Landmark board of directors has fixed as the record date for the Landmark special meeting, which we refer to as the Landmark record date, will be entitled to vote at the Landmark special meeting.

Who is entitled to vote at the Triumph special meeting?

Holders of record of Triumph common stock at the close of business on [ ], which is the date that the Triumph board of directors has fixed as the record date for the Triumph special meeting, which we refer to as the Triumph record date, will be entitled to vote at the Triumph special meeting.

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

Landmark merger proposal:

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

Effect of abstentions and broker non-votes: If you are a Landmark shareholder and mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Landmark merger proposal, it will have the same effect as a vote against the proposal.

Landmark adjournment proposal:

Standard: Approval of the Landmark adjournment proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock present or represented by proxy at the Landmark special meeting and entitled to vote on the proposal. A quorum is not required for a vote on the Landmark adjournment proposal.

Effect of abstentions and broker non-votes: If you are a Landmark shareholder and mark “ABSTAIN” on your proxy, it will have the same effect as a vote against the Landmark adjournment proposal. If you fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Landmark adjournment proposal, it will have no effect on the proposal.

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

Triumph merger proposal:

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

Effect of abstentions and broker non-votes: If you are a Triumph shareholder and mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Triumph merger proposal, it will have the same effect as a vote against the proposal.

Triumph adjournment proposal:

Standard: Approval of the Triumph adjournment proposal requires the votes cast by the outstanding shares of Triumph common stock present or represented by proxy at the Triumph special meeting and entitled to vote on the proposal favoring the approval to exceed the votes cast opposing the approval. A quorum is not required for a vote on the Triumph adjournment proposal.

Effect of abstentions and broker non-votes: If you are a Triumph shareholder and mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Triumph adjournment proposal, it will have no effect on the proposal.

Are there any voting agreements with existing Landmark shareholders or Triumph shareholders?

Yes. In connection with entering into the Landmark merger agreement, each of the directors and certain executive officers of Landmark, in their capacities as individuals, have separately entered into support and non-competition agreements, which we refer to as the Landmark voting agreements, pursuant to which they agreed to vote their beneficially owned shares of Landmark common stock in favor of the Landmark merger proposal and certain related matters and against alternative transactions. In connection with entering into the Triumph merger agreement, each of the directors and certain executive officers of Triumph, in their capacities as individuals, have separately entered into support and non-competition agreements, which we refer to as the Triumph voting agreements, pursuant to which they agreed to vote their beneficially owned shares of Triumph common stock in favor of the Triumph merger proposal and certain related matters and against alternative transactions. As of the Landmark record date, shares constituting approximately [ ]% of the Landmark common stock entitled to vote at the Landmark special meeting are subject to Landmark voting agreements; and as of the Triumph record date, shares constituting

approximately [ ]% of the Triumph common stock entitled to vote at the Triumph special meeting are subject to Triumph voting agreements. For further information, see the section entitled “The Merger Agreements—Voting Agreements.”

Why is my vote important?

If you do not vote, it will be more difficult for Landmark or Triumph to obtain the necessary quorum to hold their respective special meetings. In addition, each proposal must be approved by the voting requirements described above. The Landmark board of directors and the Triumph board of directors unanimously recommend that you vote “FOR” the Landmark merger proposal and “FOR” the Triumph merger proposal, respectively.

How many votes do I have?

Each holder of shares of Landmark common stock outstanding on the Landmark record date, and each holder of shares of Triumph common stock outstanding on the Triumph record date, will be entitled to one vote for each share held of record.

What do I need to do now?

After carefully reading and considering the information contained in this proxy statement/prospectus, including any documents incorporated into this proxy statement/prospectus by reference, and its annexes, Landmark shareholders and Triumph shareholders should complete, sign, date and return the applicable enclosed proxy and return it in the enclosed envelope as soon as possible so that your shares of Landmark common stock or Triumph common stock, as applicable, will be represented at the Landmark special meeting or the Triumph special meeting, respectively.

Please follow the instructions set forth on the applicable proxy or on the voting instruction form provided by the record holder if your shares are held in “street name” by a bank, broker or other nominee.

How do I vote?

If you hold your shares of Landmark common stock or Triumph common stock in your name as a shareholder of record, you may use one of the following methods to submit a proxy:

by mail by completing, signing, dating and returning the applicable proxy in the enclosed envelope, which requires no additional postage if mailed in the United States; or

in person at the Landmark special meeting or Triumph special meeting, as applicable.

If your shares are held in “street name” by a bank, broker or other nominee, that institution will send you separate instructions describing the procedure for voting your shares. You may not vote shares held in “street name” by returning a proxy directly to Landmark or Triumph, as applicable, or by voting at the Landmark special meeting or Triumph special meeting, as applicable, unless you provide a “legal proxy,” which you must obtain from your bank, broker or other nominee.

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

No. If your shares of Landmark common stock or Triumph common stock are held in “street name” by a bank, broker or other nominee, you must provide the record holder of your shares with instructions on how to vote your shares. Please follow the voting instructions provided by your bank, broker or other nominee. Please note that you may not vote shares held in “street name” by returning a proxy directly to Landmark or Triumph, as applicable, or by voting at the Landmark special meeting or Triumph special meeting, as applicable, unless you provide a “legal proxy,” which you must obtain from your bank, broker or other nominee.

Banks, brokers and other nominees who hold shares of Landmark common stock or Triumph common stock in “street name” for a beneficial owner of those shares typically have the authority to vote in their discretion on “routine” proposals when they have not received instructions from beneficial owners. However, banks, brokers and other nominees are not allowed to exercise voting discretion with respect to the approval of matters determined to be “non-routine,” without specific instructions from the beneficial owner. Landmark and Triumph expect that all proposals to be voted on at the special meetings will be “non-routine” matters. Broker non-votes are shares held by a bank, broker or other nominee with respect to which such entity is not instructed by the beneficial owner of such shares to vote on the particular proposal and the broker does not have discretionary voting power on such proposal.

If you are a Landmark shareholder or Triumph shareholder and you do not instruct your bank, broker or other nominee on how to vote your shares:

your bank, broker or other nominee may not vote your shares on the Landmark merger proposal or the Triumph merger proposal, as applicable, which broker non-votes will have the same effect as a vote against such proposal; and

your bank, broker or other nominee may not vote your shares on the Landmark adjournment proposal or the Triumph adjournment proposal, as applicable, which broker non-votes will have no effect on such proposal.

What if I abstain or do not vote?

For purposes of the special meetings, an abstention occurs when a shareholder attends a special meeting, either in person or represented by proxy, but abstains from voting on one or more proposals.

With respect to the Landmark merger proposal or the Triumph merger proposal, if you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the applicable special meeting, or if you fail to instruct your bank, broker or other nominee how to vote, it will have the same effect as a vote against the applicable merger proposal. With respect to the Landmark adjournment proposal, if you mark “ABSTAIN” on your proxy, it will have the same effect as a vote against the proposal, and if you fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote, it will have no effect on the proposal. With respect to the Triumph adjournment proposal, if you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting, or if you fail to instruct your bank, broker or other nominee how to vote, it will have no effect on the proposal.

What will happen if I return my proxy without indicating how to vote?

If any proxy is returned without indication as to how to vote, the shares of Landmark common stock or Triumph common stock represented by the proxy will be voted in favor of both the Landmark merger proposal and the Landmark adjournment proposal, in the case of Landmark common stock, or in favor of both the Triumph merger proposal and the Triumph adjournment proposal, in the case of Triumph common stock.

Can I attend the Landmark special meeting or the Triumph special meeting and vote my shares in person?

Yes. All shareholders of Landmark and Triumph, including shareholders of record and shareholders who hold their shares through banks, brokers, nominees or any other holder of record, are invited to attend their respective special meeting. Holders of record of Landmark common stock and Triumph common stock can vote in person at the Landmark special meeting and Triumph special meeting, respectively. If you are not a shareholder of record, you must obtain a proxy, executed in your favor, from the record holder of your shares, such as a broker, bank or other nominee, to be able to vote in person at the applicable special meeting.

May I change my vote after I have delivered my proxy?

Yes. You may change your vote at any time before your proxy is voted at the Landmark special meeting or the Triumph special meeting, as applicable. You may do so in one of three ways:

by completing, signing, dating and returning a proxy with a later date;

by delivering a written revocation letter to Landmark’s head of investor relations or Michael J. McCarver at Triumph, as applicable; or

by voting in person at the applicable special meeting.

If your shares are held in “street name” by a bank, broker or other nominee, you should follow the instructions of your bank, broker or other nominee regarding the revocation of voting instructions.

Are Landmark shareholders or Triumph shareholders entitled to dissenters’ rights?

Landmark shareholders and Triumph shareholders who do not vote in favor of the Landmark merger proposal or the Triumph merger proposal, as applicable, and follow certain procedural steps will be entitled to dissenters’ rights under the provisions of Section 48-23-101 et seq. of the Tennessee Business Corporation Act, or the TBCA. For further information, see the section entitled “The Mergers—Appraisal and Dissenters’ Rights.” In addition, a copy of Section 48-23-101 through Section 48-23-302 of the TBCA is attached as Annex G to this proxy statement/prospectus.

What are the material U.S. federal income tax consequences of the Landmark merger to Landmark shareholders and of the Triumph merger to Triumph shareholders?

Each of the Landmark merger and the Triumph merger is intended to qualify as “reorganization” within the meaning of Section 368(a) of the Internal Revenue Code of 1986, or the Code. If the Landmark merger and the Triumph merger so qualify, a U.S. holder of Landmark common stock or Triumph common stock, as applicable, receiving a combination of Simmons common stock and cash in exchange for such

	Landmark common stock or Triumph common stock will (1) not recognize any loss upon surrendering its Landmark common stock or Triumph common stock and (2) recognize gain upon surrendering its Landmark common stock or Triumph common stock equal to the excess, if any, of (a) the sum of any cash consideration received plus the fair market value (determined as of the effective time of the applicable merger) of the Simmons common stock received over (b) such U.S. holder’s aggregate tax basis in the shares of Landmark common stock or Triumph common stock surrendered, but only to the extent of the amount of any cash consideration received.

	U.S. holders of Landmark common stock or Triumph common stock receiving cash in lieu of fractional shares of Simmons common stock will generally recognize gain or loss equal to the difference between the amount of cash received instead of a fractional share and the basis in its fractional share of Simmons common stock.

For further information, see the section entitled “Material United States Federal Income Tax Consequences of the Mergers.”

The U.S. federal income tax consequences described above may not apply to all holders of Landmark common stock or holders of Triumph common stock. Your tax consequences will depend on your individual situation. Accordingly, we strongly urge you to consult your independent tax advisor for a full understanding of the particular tax consequences of the applicable merger to you.

If I am a Landmark shareholder or a Triumph shareholder, should I send in my Landmark or Triumph stock certificates now?

No. Landmark shareholders and Triumph shareholders SHOULD NOT send in any stock certificates now. If either or both of the mergers are approved by such shareholders, transmittal materials with instructions for their completion will be provided to Landmark shareholders and Triumph shareholders, as applicable, after the Landmark effective time or the Triumph effective time, respectively, and under separate cover and the applicable stock certificates should be sent at that time.

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

If the Landmark merger occurs, you are not required to take any special additional action to receive the Landmark merger consideration if your shares of Landmark common stock are held in book-entry form. After the completion of the Landmark merger, shares of Landmark common stock held in book-entry form will be exchanged automatically for the Landmark merger consideration, including shares of Simmons common stock in book-entry form, the applicable cash consideration and any cash to be paid in exchange for fractional shares in the Landmark merger.

Whom may I contact if I cannot locate my stock certificate(s)?

Landmark shareholders: If you are unable to locate your original Landmark stock certificate(s), you should contact Deborah R. Fields, telephone: (901) 457-3127, email: lcbinvestorrrelations@landmarkbanktn.com.

Triumph shareholders: If you are unable to locate your original Triumph stock certificate(s), you should contact Katie Hargett at 5699 Poplar Avenue, Memphis, Tennessee 38119, telephone: (901) 333-8852, email: katie.hargett@triumphbank.com.

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

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

What happens if I sell my shares of Landmark common stock or Triumph common stock after the applicable record date but before the applicable special meeting?

The Landmark record date and the Triumph record date are earlier than the date of the Landmark special meeting and the Triumph special meeting, respectively, and earlier than the date that the mergers are expected to be completed. If you transfer your shares of Landmark common stock or Triumph common stock after the applicable record date but before the date of the applicable special meeting, you will retain your right to vote at such special meeting (provided that such shares remain outstanding on the date of such special meeting), but you will not have the right to receive any applicable merger consideration for the transferred shares of Landmark common stock or Triumph common stock. You will only be entitled to receive the applicable merger consideration in respect of shares of Landmark common stock or Triumph common stock, as applicable, that you hold at the Landmark effective time or the Triumph effective time, respectively.

Are there risks involved in undertaking the mergers?

Yes. You should read and carefully consider the risk factors set forth in the section entitled “Risk Factors” beginning on page 32 of this proxy statement/prospectus.

What happens if the mergers are not completed?

If either or both of the mergers are not completed, holders of Landmark common stock or Triumph common stock, as applicable, will not receive any merger consideration for their shares in connection with the applicable merger. Instead, Landmark, Triumph or both will remain an independent company. In addition, if either or both of the merger agreements are terminated in certain circumstances, a termination fee may be required to be paid to Simmons by Landmark or Triumph, as applicable. See the section entitled “The Merger Agreements—Termination Fees” for a discussion of the circumstances under which termination fees will be required to be paid.

Whom should I call with questions?

Landmark shareholders: If you need assistance in completing your proxy, have questions regarding the Landmark special meeting, or would like additional copies of this proxy statement/prospectus, please contact James P. “Jake” Farrell, telephone: (901) 457-3111, email: jakefarrell@landmarkbanktn.com; or Charles E. “Buddy” Dickey, telephone: (901) 457-3123, email: cdickeylandmarkbanktn.com.

Triumph shareholders: If you need assistance in completing your proxy, have questions regarding the Triumph special meeting, or would like additional copies of this proxy statement/prospectus, please contact Michael J. McCarver and William J. Chase, Jr., 5699 Poplar Avenue, Memphis, Tennessee 38119, telephone: (901) 333-8801.

Where can I find more information about Simmons, Landmark and Triumph?

You can find more information about Simmons, Landmark and Triumph from the various sources described in the section entitled “Where You Can Find More Information.”

SUMMARY

The following summary highlights selected information in this proxy statement/prospectus and may not contain all the information that may be important to you. You should read carefully this entire proxy statement/prospectus, including any document incorporated by reference into this proxy statement/prospectus, and its annexes, because this section may not contain all of the information that may be important to you in determining how to vote. For a description of, and instructions as to how to obtain, this information, see the section entitled “Where You Can Find More Information.” Each item in this summary refers to the page of this proxy statement/prospectus on which that subject is discussed in more detail.

Information About the Companies (page 53)

Simmons

Simmons First National Corporation

P.O. Box 7009

Pine Bluff, Arkansas 71611

Telephone: (870) 541-1000

Simmons is a financial holding company registered under the Bank Holding Company Act of 1956, as amended, or the BHC Act. Simmons is headquartered in Arkansas and as of March 31, 2021, had, on a consolidated basis, total assets of $23.3 billion, total net loans of $12.0 billion, total deposits of $18.2 billion and total shareholders’ equity of $2.9 billion. Simmons conducts its banking operations through its subsidiary bank, Simmons Bank, in approximately 200 financial centers as of March 31, 2021, located throughout market areas in Arkansas, Kansas, Missouri, Oklahoma, Tennessee and Texas. Simmons common stock is traded on Nasdaq under the symbol “SFNC.”

Additional information about Simmons and its subsidiaries is included in documents incorporated by reference into this proxy statement/prospectus. See the section entitled “Where You Can Find More Information.”

Landmark

Landmark Community Bank

5880 Ridge Bend Road

Memphis, Tennessee 38120

Telephone: (901) 850-0555

Landmark is a Tennessee state-chartered bank. Landmark operates out of a main office in Collierville, Tennessee, with seven other branch offices located in the Memphis and Nashville, Tennessee metropolitan areas. As of March 31, 2021, Landmark had total assets of $1.0 billion, total net loans of $0.8 billion, total deposits of $0.8 billion, and total shareholders’ equity of $102 million. Landmark does not have a class of securities registered under Section 12 of the Exchange Act and is not subject to the reporting requirements of Section 13(a) or 15(d) of the Exchange Act, and, accordingly, does not file documents or reports with the SEC.

Triumph

Triumph Bancshares, Inc.

5699 Poplar Avenue

Memphis, Tennessee 38119

Telephone: (901) 333-8800

Triumph is a bank holding company registered under the BHC Act. Triumph was incorporated in Tennessee in 2005 to serve as the bank holding company for and sole shareholder of Triumph Bank, which was incorporated as a Tennessee state-chartered bank in 2006. Triumph Bank is headquartered in Memphis, Tennessee, and currently operates from nine office locations (including six full-service branches and three loan production offices) in Arlington, Brentwood, Collierville, Germantown, Memphis, Nashville, and Union City in Tennessee. As of March 31, 2021, Triumph had consolidated total assets of $895.5 million, total net loans of $702.9 million, total deposits of $750.0 million, and total shareholders’ equity of $89.1 million. Triumph does not have a class of securities registered under Section 12 of the Exchange Act, is not subject to the reporting requirements of Section 13(a) or 15(d) of the Exchange Act, and, accordingly, does not file documents or reports with the SEC.

The Landmark Merger (page 56)

Terms of the Landmark Merger (page 56)

The terms and conditions of the Landmark merger are contained in the Landmark merger agreement, which is attached to this proxy statement/prospectus as Annex A. We urge you to read the Landmark merger agreement carefully and in its entirety, as it is the legal document governing the Landmark merger. All descriptions in this summary and elsewhere in this proxy statement/prospectus of the terms and conditions of the Landmark merger are subject to, and qualified in their entirety by reference to, the Landmark merger agreement.

Under the terms and subject to the conditions of the Landmark merger agreement, among other things, Landmark will merge with and into Simmons Bank, with Simmons Bank as the surviving bank in the Landmark merger.

Based on the assumptions set forth below, at the Landmark effective time, each share of Landmark common stock that is issued and outstanding immediately prior to the Landmark effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (i) [ ] shares of Simmons common stock, with cash in lieu of fractional shares, and (ii) $[ ] in cash. In the aggregate, Simmons expects to issue approximately [ ] shares of Simmons common stock and pay approximately $[ ] million (minus the cash payment for outstanding Landmark stock options) to Landmark shareholders upon completion of the Landmark merger, subject to certain conditions and potential adjustments under the Landmark merger agreement. The Landmark merger consideration is based on the assumption that (i) [ ] shares of Landmark common stock are issued and outstanding and (ii) [ ] shares of Landmark common stock are subject to outstanding Landmark stock options with a weighted average exercise price of $[ ], in each case, immediately prior to the Landmark effective time. In addition, we have assumed that the Landmark/Simmons average closing price is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

The market value of the Landmark merger consideration will fluctuate with the price of Simmons common stock, and at the time of the Landmark special meeting, Landmark shareholders will not know or be able to calculate the value of the Landmark merger consideration to be received upon completion of the Landmark merger. Other than as described in this proxy statement/prospectus, there will be no adjustment to the Landmark merger consideration based upon changes in the market price of Simmons common stock or Landmark common stock prior to the time the Landmark merger is completed, and the Landmark merger agreement cannot be

terminated due to a change in the price of Simmons common stock. For further information, see the section entitled “The Merger Agreements—The Merger Consideration.”

Based on the closing sale price per share of Simmons common stock on June 4, 2021, the last trading day before the public announcement of the signing of the Landmark merger agreement, and on [ ], 2021, the last practicable trading day prior to printing this proxy statement/prospectus, and on certain assumptions as described elsewhere in this proxy statement/prospectus, the implied value of the aggregate Landmark merger consideration payable for each share of Landmark common stock is approximately $[ ], or $[ ] per share of Landmark common stock, and approximately $[ ], or $[ ] per share of Landmark common stock, respectively.

Treatment of Equity Awards—Landmark Stock Options (page 104)

At the Landmark effective time, each Landmark stock option, whether vested or unvested, outstanding immediately prior to the Landmark effective time, will be canceled and converted into the right to receive from Simmons a cash payment equal to the difference, if positive, between (1) the fully diluted per share value and (2) the exercise price of such Landmark stock option, which we refer to as the Landmark stock option payout. Any such Landmark stock option with an exercise price per share that equals or exceeds the amount set forth in (1) will be canceled with no consideration paid to the optionholder less any required withholding for taxes.

Landmark’s Reasons for the Landmark Merger and Recommendation of the Landmark Board of Directors (page 59)

The Landmark board of directors has approved the Landmark merger agreement and recommends that Landmark shareholders vote “FOR” the Landmark merger proposal and, if necessary or appropriate, “FOR” the adjournment proposal. See the section entitled “The Landmark Merger—Landmark’s Reasons for the Landmark Merger and Recommendation of the Landmark Board of Directors” for a more detailed discussion of the factors considered by the Landmark board of directors in reaching its decision to approve the Landmark merger agreement and the transactions contemplated thereby.

Opinion of Landmark’s Financial Advisor (page 61)

In connection with the Landmark merger, Landmark’s financial advisor, Olsen Palmer LLC, which we refer to as Olsen Palmer, delivered a written opinion, dated June 4, 2021, to the Landmark board of directors as to the fairness, from a financial point of view and as of the date of the opinion, to the holders of Landmark common stock of the Landmark merger consideration. The full text of the opinion, which describes the procedures followed, assumptions made, matters considered, and qualifications and limitations on the review undertaken by Olsen Palmer in preparing the opinion, is attached as Annex E to this proxy statement/prospectus.

The opinion was for the information of, and was directed to, the Landmark board of directors (in its capacity as such) in connection with its consideration of the financial terms of the Landmark merger. The opinion does not address the underlying business decision of Landmark to engage in the Landmark merger or enter into the Landmark merger agreement or constitute a recommendation to the Landmark board of directors in connection with the Landmark merger, and it does not constitute a recommendation to any holder of Landmark common stock or any shareholder of any other entity as to how to vote in connection with the Landmark merger or any other matter.

For a description of the Olsen Palmer opinion, see the section entitled “The Landmark Merger—Opinion of Landmark’s Financial Advisor.”

Simmons’ Reasons for the Landmark Merger (page 70)

The Simmons board of directors adopted and approved the Landmark merger agreement. See the section entitled “The Landmark Merger—Simmons’ Reasons for the Landmark Merger” for a more detailed discussion of the factors considered by the Simmons board of directors in reaching its decision to approve the Landmark merger agreement, including the Landmark merger and all transactions contemplated thereby.

The Landmark Special Meeting (page 41)

The Landmark special meeting will be held on [ ], 2021, at [ ] Central Time, at [ ]. At the Landmark special meeting, Landmark shareholders will be asked to consider and vote on the Landmark merger proposal and, if necessary or appropriate, the Landmark adjournment proposal.

Landmark has set the close of business on [ ], 2021 as the Landmark record date to determine which Landmark shareholders will be entitled to receive notice of and vote at the Landmark special meeting. Each holder of shares of Landmark common stock outstanding on the Landmark record date will be entitled to one vote for each share held of record. As of the Landmark record date, there were [ ] shares of Landmark common stock outstanding and entitled to vote at the Landmark special meeting. As of the Landmark record date, the directors and executive officers of Landmark and their affiliates beneficially owned and were entitled to vote approximately [ ] shares of Landmark common stock, representing approximately [ ]% of the shares of Landmark common stock outstanding on that date.

Approval of the Landmark merger proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock entitled to vote on the Landmark merger proposal. Approval of the adjournment proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock present or represented by proxy at the Landmark special meeting and entitled to vote on the Landmark adjournment proposal. A quorum is not required for a vote on the Landmark adjournment proposal.

With respect to the Landmark merger proposal, if you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote, it will have the same effect as a vote against the proposal. With respect to the Landmark adjournment proposal, if you mark “ABSTAIN” on your proxy, it will have the same effect as a vote against the proposal, and if you fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote, it will have no effect on the proposal.

Interests of Landmark’s Directors and Executive Officers in the Landmark Merger (page 72)

In considering the recommendation of the Landmark board of directors that Landmark shareholders vote “FOR” the Landmark merger proposal, Landmark shareholders should be aware that some of Landmark’s executive officers and directors have interests in the Landmark merger, which may be considered to be different from, or in addition to, the interests of the Landmark shareholders generally. The Landmark board of directors was aware of these interests and considered them, among other matters, in reaching its decision to approve the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement and to recommend that Landmark shareholders vote “FOR” the Landmark merger proposal.

These interests are described in more detail in the section entitled “The Landmark Merger—Interests of Landmark’s Directors and Executive Officers in the Landmark Merger.”

The Triumph Merger (page 74)

Terms of the Triumph Merger (page 74)

The terms and conditions of the Triumph merger are contained in the Triumph merger agreement, which is attached to this proxy statement/prospectus as Annex B. We urge you to read the Triumph merger agreement carefully and in its entirety, as it is the legal document governing the Triumph merger. All descriptions in this summary and elsewhere in this proxy statement/prospectus of the terms and conditions of the Triumph merger are subject to, and qualified in their entirety by reference to, the Triumph merger agreement.

Under the terms and subject to the conditions of the Triumph merger agreement, among other things, Triumph will merge with and into Simmons, with Simmons as the surviving corporation in the Triumph merger. Immediately following the Triumph merger, Triumph Bank will merge with and into Simmons Bank, with Simmons as the surviving bank.

Based on the assumptions set forth below, at the Triumph effective time, each share of Triumph common stock that is issued and outstanding immediately prior to the Triumph effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, (i) [ ] shares of Simmons common stock, with cash in lieu of fractional shares, and (ii) $[ ] in cash. In the aggregate, Simmons expects to issue approximately [ ] shares of Simmons common stock and pay approximately $[ ] million (minus the cash payment for outstanding Triumph stock options) to Triumph shareholders upon completion of the Triumph merger, subject to certain conditions and potential adjustments under the Triumph merger agreement. The Triumph merger consideration is based on the assumption that (i) [ ] shares of Triumph common stock are issued and outstanding and (ii) [ ] shares of Triumph common stock are subject to outstanding Triumph stock options with a weighted average exercise price of $[ ], in each case, immediately prior to the Triumph effective time. In addition, we have assumed that the Triumph/Simmons average closing price is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

Simmons will not issue any fractional shares of Simmons common stock in the Triumph merger. Instead, a Triumph shareholder who would otherwise be entitled to a fractional share of Simmons common stock upon the completion of the Triumph merger will receive, in lieu thereof, an amount in cash, rounded up to the nearest whole cent (without interest), determined by multiplying (i) the fraction of a share (rounded to the nearest thousandth when expressed in decimal form) of Simmons common stock that such Triumph shareholder would otherwise be entitled to receive by (ii) the Triumph/Simmons average closing price.

The market value of the Triumph merger consideration will fluctuate with the price of Simmons common stock, and at the time of the Triumph special meeting, Triumph shareholders will not know or be able to calculate the value of the Triumph merger consideration to be received upon completion of the Triumph merger. If, as of the Triumph determination date, (i) the Triumph/Simmons average closing price is greater than $37.28 and (ii) the difference between the percentage change in the Nasdaq Bank Index and the percentage change in the Triumph/Simmons average closing price exceeds 20% over a designated measurement period, the Triumph stock consideration will be adjusted. See the section entitled “The Merger Agreements—The Merger Consideration.” In addition, the Triumph merger agreement can be terminated by Triumph if, at any time during the five-day period commencing on the Triumph determination date, the Triumph/Simmons average closing price is less than $24.85 and the difference between the percentage change in the Nasdaq Bank Index and the percentage change in the Triumph/Simmons average closing price exceeds 20% over a designated measurement period, unless Simmons agrees to increase the Triumph cash consideration by a specified amount.”

Based on the closing sale price per share of Simmons common stock on June 4, 2021, the last trading day before the public announcement of the signing of the Triumph merger agreement, and on [ ], 2021, the last

practicable trading day prior to printing this proxy statement/prospectus, and on certain assumptions as described elsewhere in this proxy statement/prospectus, the implied value of the aggregate Triumph merger consideration payable for each share of Triumph common stock is approximately $[ ], or $[ ] per share of Triumph common stock, and approximately $[ ], or $[ ] per share of Triumph common stock, respectively.

Treatment of Equity Awards—Triumph Stock Options (page 104)

At the Triumph effective time, each Triumph stock option, whether vested or unvested, outstanding immediately prior to the Triumph effective time, will be canceled and converted into the right to receive from Simmons a cash payment equal to the difference, if positive, between (1) the fully diluted per share value and (2) the exercise price of such Triumph stock option, which we refer to as the Triumph stock option payout. Any such Triumph stock option with an exercise price per share that equals or exceeds the amount set forth in (1) will be canceled with no consideration paid to the optionholder less any required withholding for taxes.

Triumph’s Reasons for the Triumph Merger and Recommendation of the Triumph Board of Directors (page 78)

The Triumph board of directors has approved the Triumph merger agreement and recommends that Triumph shareholders vote “FOR” the Triumph merger proposal and, if necessary or appropriate, “FOR” the Triumph adjournment proposal. See the section entitled “The Triumph Merger—Triumph’s Reasons for the Triumph Merger and Recommendation of the Triumph Board of Directors” for a more detailed discussion of the factors considered by the Triumph board of directors in reaching its decision to approve the Triumph merger agreement and the transactions contemplated thereby.

Opinion of Triumph’s Financial Advisor (page 82)

In connection with the Triumph merger, Triumph’s financial advisor, Southard Financial, LLC, which we refer to as Southard Financial, delivered a written opinion, dated June 4, 2021, to the Triumph board of directors as to the fairness, from a financial point of view and as of the date of the opinion, to the holders of Triumph common stock of the Triumph merger consideration. The full text of the opinion, which describes the procedures followed, assumptions made, matters considered, and qualifications and limitations on the review undertaken by Southard Financial in preparing the opinion, is attached as Annex F to this proxy statement/prospectus.

The opinion was for the information of, and was directed to, the Triumph board of directors (in its capacity as such) in connection with its consideration of the financial terms of the Triumph merger. The opinion does not address the underlying business decision of Triumph to engage in the Triumph merger or enter into the Triumph merger agreement or constitute a recommendation to the Triumph board of directors in connection with the Triumph merger, and it does not constitute a recommendation to any holder of Triumph common stock or any shareholder of any other entity as to how to vote in connection with the Triumph merger or any other matter.

For a description of Southard Financial’s opinion, see the section entitled “The Triumph Merger—Opinion of Triumph’s Financial Advisor.”

Simmons’ Reasons for the Triumph Merger (page 91)

The Simmons board of directors adopted and approved the Triumph merger agreement. See the section entitled “The Triumph Merger—Simmons’ Reasons for the Triumph Merger” for a more detailed discussion of the factors considered by the Simmons board of directors in reaching its decision to approve the Triumph merger agreement, including the Triumph merger and all transactions contemplated thereby.

The Triumph Special Meeting (page 47)

The Triumph special meeting will be held on [ ], 2021, at [ ] Central Time, at [ ]. At the Triumph special meeting, Triumph shareholders will be asked to consider and vote on the Triumph merger proposal and, if necessary or appropriate, the Triumph adjournment proposal.

Triumph has set the close of business on [ ], 2021 as the Triumph record date to determine which Triumph shareholders will be entitled to receive notice of and vote at the Triumph special meeting. Each holder of shares of Triumph common stock outstanding on the Triumph record date will be entitled to one vote for each share held of record. As of the Triumph record date, there were [ ] shares of Triumph common stock outstanding and entitled to vote at the Triumph special meeting. As of the Triumph record date, the directors and executive officers of Triumph and their affiliates beneficially owned and were entitled to vote approximately [ ] shares of Triumph common stock, representing approximately [ ]% of the shares of Triumph common stock outstanding on that date.

Approval of the Triumph merger proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Triumph common stock entitled to vote on the Triumph merger proposal. Approval of the Triumph adjournment proposal requires the votes cast by the outstanding shares of Triumph common stock present or represented by proxy at the Triumph special meeting and entitled to vote on the proposal favoring the approval to exceed the votes cast opposing the approval. A quorum is not required for a vote on the Triumph adjournment proposal.

With respect to the Triumph merger proposal, if you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting, or if you fail to instruct your bank, broker or other nominee how to vote, it will have the same effect as a vote against the proposal. With respect to the Triumph adjournment proposal, if you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting, or if you fail to instruct your bank, broker or other nominee how to vote, it will have no effect on the proposal.

Interests of Triumph’s Directors and Executive Officers in the Triumph Merger (page 92)

In considering the recommendation of the Triumph board of directors that Triumph shareholders vote “FOR” the Triumph merger proposal, Triumph shareholders should be aware that some of Triumph’s executive officers and directors have interests in the Triumph merger, which may be considered to be different from, or in addition to, the interests of the Triumph shareholders generally. The Triumph board of directors was aware of these interests and considered them, among other matters, in reaching its decision to approve the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement and to recommend that Triumph shareholders vote “FOR” the Triumph merger proposal.

These interests are described in more detail in the section entitled “The Triumph Merger—Interests of Triumph’s Directors and Executive Officers in the Triumph Merger.”

The Mergers (page 95)

Board of Directors and Management of Simmons and Simmons Bank After the Mergers (page 95)

Public Trading Markets (page 95)

Simmons common stock is listed on Nasdaq under the symbol “SFNC.” The Simmons common stock issuable in the mergers will be listed on Nasdaq.

Accounting Treatment (page 95)

The mergers will be accounted for as acquisitions by Simmons using the acquisition method of accounting in accordance with FASB ASC Topic 805, “Business Combinations.” The result of this is that (1) the recorded assets and liabilities of Simmons will be carried forward at their recorded amounts, (2) Simmons historical operating results will be unchanged for the prior periods being reported on, and (3) the assets and liabilities of each of Landmark and Triumph will be adjusted to fair value at the respective dates Simmons assumes control of the combined entity, or the respective merger dates. In addition, all identifiable intangibles will be recorded at fair value and included as part of the net assets acquired. The amount by which the purchase price for each merger, consisting of the value of cash and shares of Simmons common stock to be issued to former Landmark shareholders and Triumph shareholders, respectively, and the value of cash and shares of Simmons common stock to be issued to former holders of Landmark and Triumph equity awards, respectively, exceeds the fair value of the net assets, including identifiable intangibles, of Landmark and Triumph, respectively, at the applicable merger date will be reported as goodwill. In accordance with current accounting guidance, goodwill is not amortized and will be evaluated for impairment at least annually. Identified intangibles will be amortized over their estimated lives. Further, the acquisition method of accounting results in the operating results of each of Landmark and Triumph being included in the operating results of Simmons from the applicable merger date going forward.

Appraisal and Dissenters’ Rights (page 95)

Landmark shareholders and Triumph shareholders who do not vote in favor of the applicable merger proposal and follow certain procedural steps will be entitled to dissenters’ rights under the provisions of Section 48-23-101 et seq. of the TBCA. These procedural steps include, among others: (1) delivering to Landmark or Triumph, as applicable, before the vote at the applicable special meeting is taken, written notice of such shareholder’s intent to demand payment for such shareholder’s shares of Landmark common stock or Triumph common stock if the applicable merger is effectuated, (2) not voting, or causing or permitting to be voted, such shareholder’s shares of Landmark common stock or Triumph common stock in favor of the applicable merger and (3) demanding payment and depositing with Simmons such shareholder’s stock certificates representing such holder’s shares of Landmark common stock or Triumph common stock, as applicable, in accordance with the terms of the written dissenters’ notice sent by Simmons following the applicable merger, which notice will set forth where and when to send the payment demand.

For more information, see the section entitled “The Mergers—Appraisal and Dissenters’ Rights.”

Regulatory Approvals Required for the Mergers and the Triumph Bank Merger (page 99)

The completion of the mergers and the Triumph Bank merger are subject to prior receipt of certain approvals and consents required to be obtained from, or waived by, applicable governmental and regulatory authorities. These approvals include approvals from, among others, the Board of Governors of the Federal Reserve System, or the Federal Reserve Board, the Tennessee Department of Financial Institutions, or the TDFI, and the Arkansas State Bank Department, or the ASBD. Simmons, Landmark and Triumph have agreed to use their reasonable best efforts and cooperate to promptly prepare and file all necessary documentation and to obtain as promptly as practicable all regulatory approvals necessary or advisable to complete the transactions contemplated by the merger agreements. Although Simmons, Landmark and Triumph believe that the mergers do not raise significant regulatory concerns and that they will be able to obtain all requisite regulatory approvals, none of Simmons, Landmark or Triumph can assure you that all of the regulatory approvals described above will be obtained and, if

obtained, cannot assure you as to the timing of any such approvals, the parties’ ability to obtain the approvals on satisfactory terms or the absence of any litigation challenging such approvals.

The Merger Agreements (page 102)

Agreement Not to Solicit Other Offers (page 117)

Each of Landmark and Triumph has agreed that it and its respective subsidiaries will not, and will cause their respective representatives not to, directly or indirectly:

solicit, initiate, encourage (including by providing information or assistance), facilitate or induce any acquisition proposal (as defined in the section entitled “The Merger Agreements—Agreement Not to Solicit Other Offers”);

engage or participate in any discussions or negotiations regarding, or furnish or cause to be furnished to any person any confidential or nonpublic information or data with respect to, or take any other action to facilitate any inquiries or the making of any offer or proposal that constitutes, or may reasonably be expected to lead to, an acquisition proposal;

adopt, approve, agree to, accept, endorse or recommend any acquisition proposal;

approve, agree to, accept, endorse or recommend, or propose to approve, agree to, accept, endorse or recommend any acquisition agreement (as defined in the section entitled “The Merger Agreements—Agreement Not to Solicit Other Offers”) contemplating or otherwise relating to any acquisition transaction (as defined in the section entitled “The Merger Agreements—Agreement Not to Solicit Other Offers”); or

otherwise cooperate in any way with, or assist or participate in, or facilitate or encourage any effort or attempt by any person to do or seek to do any of the foregoing.

Conditions to Consummation of the Mergers (page 120)

The respective obligations of each party to consummate the applicable merger and the other transactions contemplated by the applicable merger agreement are subject to the satisfaction or waiver at or prior to the effective time of the applicable merger of the following conditions:

the approval of the applicable merger proposal by the Landmark shareholders or Triumph shareholders, as applicable;

the receipt of all required regulatory permits or consents from the Federal Reserve Board, the ASBD, or the TDFI, the Federal Deposit Insurance Corporation, or the FDIC, and any other regulatory authority, and any other regulatory permits or consents contemplated by the applicable merger agreement, the failure of which to obtain would reasonably be expected to have, either individually or in the aggregate, a material adverse effect on Simmons, Simmons Bank and Landmark, in the case of the Landmark merger, or Simmons and Triumph, in the case of the Triumph merger, in each case, considered as a consolidated entity, in each case required to consummate the transactions contemplated by the applicable merger agreement, including the applicable merger, and expiration of all related statutory waiting periods, which we refer to as the requisite regulatory approvals, without the imposition of a burdensome condition as determined by Simmons in its sole discretion;

the absence of any law or order (whether temporary, preliminary or permanent) by any court or regulatory authority of competent jurisdiction prohibiting, restricting or making illegal the consummation of the transactions contemplated by the applicable merger agreement (including the applicable merger);

the effectiveness of the registration statement of which this proxy statement/prospectus is a part under the Securities Act, and there being no stop order, action, suit, proceeding or investigation by the SEC to suspend the effectiveness of the registration statement initiated and continuing;

the approval of the listing on Nasdaq of the Simmons common stock to be issued pursuant to the applicable merger, subject to official notice of issuance (if such approval is required by Nasdaq);

the receipt by each party of a written opinion of Covington & Burling LLP, or Covington, in form reasonably satisfactory to such parties to the effect that the applicable merger will qualify as a “reorganization” within the meaning of Section 368(a) of the Code;

the accuracy of the representations and warranties of the other party in the applicable merger agreement as of the date of such merger agreement and as of the effective time of the applicable merger, subject to the materiality standards provided in the applicable merger agreement;

the performance by the other party in all material respects of all agreements and covenants of such party required to be performed or complied with pursuant to the applicable merger agreement and other agreements contemplated by such merger agreement prior to the effective time of the applicable merger; and

the receipt of (1) a certificate from the other party to the effect that the two conditions described immediately above have been satisfied and (2) certified copies of resolutions duly adopted by the other party’s board of directors and shareholders evidencing the taking of all corporate action necessary to authorize the execution, delivery and performance of the applicable merger agreement, and the consummation of the transactions contemplated thereby, all in such reasonable detail as the other party and its counsel may request.

In addition, Simmons’ obligation to consummate the applicable merger and the other transactions contemplated by the applicable merger agreement is subject to the satisfaction or waiver at or prior to the effective time of the applicable merger of the following conditions:

as reflected in Landmark’s and Triumph’s, as applicable, closing financial statements, subject to certain exceptions, (a) Landmark and Triumph Bank’s, as applicable, delinquent loans shall not exceed 0.90% and 0.30% of all loans, respectively, (b) Landmark and Triumph Bank’s, as applicable, non-performing loans shall not exceed 1.00% and 0.50% of total loans, respectively, (c) Landmark and Triumph Bank’s, as applicable, ratio of non-performing assets to total assets shall not be in excess of 0.90% and 0.50%, respectively, (d) Landmark’s and Triumph Bank’s, as applicable, ratio of classified assets to Tier 1 capital plus allowance for loan and lease losses, or ALLL, shall not be in excess of 12.50% and 18.00%, respectively, (e) Landmark and Triumph Bank’s, as applicable, non-performing assets shall not exceed $8,500,000 and $2,000,000, respectively, (f) Landmark and Triumph Bank’s, as applicable, classified assets shall not exceed $14,000,000 and $10,000,000, respectively, and (g) Landmark’s and Triumph Bank’s, as applicable, ALLL to total loans ratio shall exceed 0.75% and 1.50%, respectively;

holders of not more than five percent of the outstanding shares of Landmark common stock or Triumph common stock, as applicable, having demanded, properly and in writing, appraisal for such shares under the TBCA;

as reflected in Landmark’s and Triumph’s, as applicable, closing financial statements, subject to certain exceptions, (a) Landmark and Triumph Bank, as applicable, being “well capitalized” as defined under applicable law, (b) Landmark and Triumph Bank, as applicable, having a Tier 1 leverage ratio of not less than 9.75% and 9.25%, respectively, (c) Landmark and Triumph Bank, as applicable, having a Tier 1 risked-based capital ratio of not less than 13.75% and 9.50%, respectively, (d) Landmark and Triumph Bank, as applicable, having a total risked-based capital ratio of not less than 14.5% and 11.0%, respectively, (e) Landmark and Triumph Bank, as applicable, having a common equity Tier 1 ratio of not less than 13.75% and 10.00%, respectively, and (f) Landmark and Triumph Bank, as applicable, having not received any notification from the TDFI or FDIC, with respect to Landmark, or the Federal Reserve Board, with respect to Triumph, to the effect that the capital of Landmark or Triumph, as applicable, is insufficient to permit it to engage in all aspects of its business and its currently proposed businesses without material restrictions, including the imposition of a burdensome condition, which condition we refer to as the regulatory capital condition;

Landmark and Triumph, as applicable, having delivered evidence satisfactory to Simmons in its discretion that certain contracts have been terminated;

no requisite regulatory approval contains, shall have resulted in or would reasonably be expected to result in, the imposition of a burdensome condition; and

Landmark and Triumph, as applicable, having delivered to Simmons and Simmons Bank, as applicable, a certificate, dated as of the respective closing, and signed on its behalf by its respective chief executive officer and its chief financial officer (and in such reasonable detail as Simmons, Simmons Bank and their counsel shall request), to the effect that it has fulfilled its obligations to archive documents associated with loans or the underwriting, servicing, administration, or monitoring thereof under the applicable merger agreement in all material respects.

Termination of the Merger Agreements (page 122)

Each of the merger agreements may be terminated and the applicable merger abandoned at any time prior to the effective time of the applicable merger (notwithstanding the approval of the applicable merger agreement by Landmark shareholders or Triumph shareholders, as applicable) by mutual written agreement, or by any party in the following circumstances:

(a) any regulatory authority denies a requisite regulatory approval, and such denial has become final, or has advised any party that it will not grant (or intends to rescind or revoke if previously approved) a requisite regulatory approval or (b) any regulatory authority shall have requested that Simmons, Simmons Bank, Landmark or Triumph, as applicable, or any of their respective affiliates withdraw (other than for technical reasons), and not be permitted to resubmit within 60 days, any application with respect to a requisite regulatory approval, unless in each case the failure to obtain the requisite regulatory approval shall be due to the failure of the party seeking to terminate the applicable merger agreement to perform or observe the obligations, covenants and agreements of such party under such merger agreement;

any law or order permanently restraining, enjoining or otherwise prohibiting the consummation of the transactions contemplated by the applicable merger agreement becomes final and nonappealable, so long as the party seeking to terminate the applicable merger agreement has used its reasonable best efforts to contest, appeal and change or remove such denial, law or order;

the Landmark shareholders or Triumph shareholders, as applicable, fail to vote their approval of the respective merger proposal (taking into account any adjournment or postponement thereof as required by the applicable merger agreement), subject to the terminating party’s compliance with its obligation to use reasonable best efforts to restructure the transaction in the event of such failure, which we refer to as a no-vote termination;

the applicable merger has not been consummated by March 1, 2022, which we refer to as the outside date, if the failure to consummate the transactions contemplated by the applicable merger agreement on or before such date is not caused by the terminating party’s breach of the applicable merger agreement, which we refer to as an outside date termination; or

if there was a breach of any of the covenants or agreements or any of the representations or warranties (or any such representation or warranty ceases to be true) set forth in the applicable merger agreement on the part of Landmark or Triumph, as applicable, in the case of a termination by Simmons or Simmons Bank, as applicable, or Simmons or Simmons Bank, as applicable, in the case of a termination by Landmark or Triumph, as applicable, which breach or failure to be true, either individually or in the aggregate with all other breaches by such party (or failures of such representations or warranties to be true), would constitute, if occurring or continuing on the closing date, the failure of a Simmons, Simmons Bank, as applicable, or Landmark or Triumph, as applicable, condition to closing, respectively, and is not cured within 45 days following written notice or by its nature or timing cannot be cured during such period (or such fewer days as remain prior to the outside date); provided, that the terminating party is not then in material breach of any representation, warranty, covenant or other agreement contained in the applicable merger agreement, which we refer to as a breach termination.

In addition, Simmons or Simmons Bank, as applicable, may terminate the merger agreements if:

the Landmark board of directors or Triumph board of directors, as applicable, fails to recommend that Landmark shareholders or Triumph shareholders, respectively, approve the applicable merger proposal, effects a change in recommendation, breaches its non-solicitation obligations with respect to acquisition proposals in any respect adverse to Simmons or Simmons Bank, as applicable, or fails to call, give notice of, convene and/or hold the Landmark special meeting or Triumph special meeting, respectively, in accordance with the applicable merger agreement, which, collectively, we refer to as a board breach termination; or

if any regulatory authority grants a requisite regulatory approval but such requisite regulatory approval contains, results or would reasonably be expected to result in, the imposition of a burdensome condition.

In addition, Triumph may terminate the Triumph merger agreement if:

the Triumph board of directors so determines by a vote of at least two-thirds of the members of the entire Triumph board of directors at any time during the five-day period commencing on the Triumph determination date and (i) the Triumph/Simmons average closing price is less than $24.85 and (ii) the difference between the percentage change in the Nasdaq Bank Index and the percentage change in the Triumph/Simmons average closing price exceeds 20%; provided, that Simmons may prevent the Triumph merger agreement from being terminated by electing to increase the aggregate Triumph cash consideration such that the total value of the aggregate Triumph merger consideration is not less than $106,142,186.98.

Termination Fees (page 123)

Landmark and Triumph, as applicable, will pay Simmons a termination fee of $7,000,000 and $6,500,000, respectively, if:

(1) any party to the applicable merger agreement effects an outside date termination or a no-vote termination, or (2) Simmons effects a breach termination and, in each case, within 12 months of such termination, Landmark or Triumph, as applicable, consummates an acquisition transaction or enters into an acquisition agreement with respect to an acquisition transaction, whether or not such acquisition transaction is subsequently consummated; or

Simmons or Simmons Bank, as applicable, effects a board breach termination.

If Landmark or Triumph, as applicable, fails to pay such termination fee when due, then such party must pay to Simmons its costs and expenses (including attorneys’ fees) in connection with collecting such fee, together with interest on the amount of such fee at the prime rate of Citibank, N.A. from the date such payment was due under the applicable merger agreement until the date of payment.

Voting Agreements (page 124)

In connection with entering into the Landmark merger agreement, each of the directors and certain executive officers of Landmark, in their capacities as individuals, have separately entered into Landmark voting agreements, pursuant to which they agreed to vote their beneficially owned shares of Landmark common stock in favor of the Landmark merger proposal and certain related matters and against alternative transactions. In connection with entering into the Triumph merger agreement, each of the directors and certain executive officers of Triumph, in their capacities as individuals, have separately entered into Triumph voting agreements, pursuant to which they agreed to vote their beneficially owned shares of Triumph common stock in favor of the Triumph merger proposal and certain related matters and against alternative transactions. As of the Landmark record date, shares constituting approximately [ ]% of the Landmark common stock entitled to vote at the Landmark special meeting are subject to Landmark voting agreements; and as of the Triumph record date, shares constituting approximately [ ]% of the Triumph common stock entitled to vote at the Triumph special meeting are subject to Triumph voting agreements. For further information, see the section entitled “The Merger Agreements—Voting Agreements.”

Material United States Federal Income Tax Consequences of the Mergers (page 126)

The respective obligations of Simmons and Landmark to complete the Landmark merger are contingent upon Simmons and Landmark receiving a legal opinion from Covington that the Landmark merger will qualify as a “reorganization” within the meaning of Section 368(a) of the Code. Similarly, the respective obligations of Simmons and Triumph to complete the Triumph merger are conditioned upon Simmons and Triumph receiving a legal opinion from Covington to the effect that the Triumph merger will qualify as a “reorganization” within the meaning of Section 368(a) of the Code. None of Simmons, Landmark or Triumph currently intends to waive this condition to the consummation of the Landmark merger or the Triumph merger, as applicable. If any party waives this condition after this registration statement is declared effective by the SEC, and if the tax consequences of the Landmark merger to Landmark shareholders or the Triumph merger to Triumph shareholders have materially changed, Simmons and Landmark or Triumph, as applicable, will recirculate appropriate soliciting materials to resolicit the votes of Landmark shareholders or Triumph shareholders.

Each of the Landmark merger and the Triumph merger is intended to qualify as “reorganization” within the meaning of Section 368(a) of the Code. If the Landmark merger and the Triumph merger so qualify, a U.S. holder of Landmark common stock or Triumph common stock, respectively, receiving a combination of Simmons common stock and cash in exchange for such Landmark common stock or Triumph common stock will (1) not

recognize any loss upon surrendering its Landmark common stock or Triumph common stock and (2) recognize gain upon surrendering its Landmark common stock or Triumph common stock equal to the excess, if any, of (a) the sum of any cash consideration received plus the fair market value (determined as of the effective time of the applicable merger) of the Simmons common stock received over (b) such U.S. holder’s aggregate tax basis in the shares of Landmark common stock or Triumph common stock surrendered, but only to the extent of the amount of any cash consideration received.

U.S. holders of Landmark common stock or Triumph common stock receiving cash in lieu of fractional shares of Simmons common stock will generally recognize gain or loss equal to the difference between the amount of cash received instead of a fractional share and the basis in its fractional share of Simmons common stock.

The U.S. federal income tax consequences described above may not apply to all holders of Landmark common stock or Triumph common stock. Your tax consequences will depend on your individual situation. Accordingly, we strongly urge you to consult your independent tax advisor for a full understanding of the particular tax consequences of the merger to you.

Comparison of Shareholders’ Rights of Simmons and Landmark, and Simmons and Triumph (pages 129 and 143)

The rights of Landmark shareholders are currently governed by the charter of Landmark, as amended, which we refer to as the Landmark charter, and the bylaws of Landmark, which we refer to as the Landmark bylaws. The rights of Triumph are currently governed by the amended and restated charter of Triumph, as amended, which we refer to as the Triumph charter, and the amended and restated bylaws of Triumph, which we refer to as the Triumph bylaws. Upon completion of the mergers, the rights of former holders of Landmark common stock and Triumph common stock will be governed by the Amended and Restated Articles of Incorporation of Simmons, which we refer to as the Simmons charter, and the As Amended By-Laws of Simmons, which we refer to as the Simmons bylaws. Simmons is organized under Arkansas law, while Landmark and Triumph are organized under Tennessee law. The rights associated with Landmark common stock and Triumph common stock are different from the rights associated with Simmons common stock. See the sections entitled “Comparison of Shareholders’ Rights of Simmons and Landmark” and “Comparison of Shareholders’ Rights of Simmons and Triumph” for a discussion of the different rights associated with Simmons common stock.

Risk Factors (page 32)

Before voting at the Landmark special meeting or Triumph special meeting, you should carefully consider all of the information contained in or incorporated by reference into this proxy statement/prospectus, including the risk factors set forth in the section entitled “Risk Factors” and described in Simmons’ Annual Report on Form 10-K for the year ended on December 31, 2020, Quarterly Report on Form 10-Q for the quarter ended March 31, 2021, and other reports filed by Simmons with the SEC, which are incorporated by reference into this proxy statement/prospectus. See the section entitled “Where You Can Find More Information.”

MARKET PRICE AND DIVIDENDS

Simmons common stock trades on Nasdaq under the symbol “SFNC.” Neither Landmark nor Triumph common stock is listed on a public exchange. As of [ ], 2021 there were approximately [ ] registered Simmons shareholders, approximately [ ] Landmark shareholders of record and approximately [ ] Triumph shareholders of record. There is no established public trading market for Landmark common stock or Triumph common stock. Shares of Landmark common stock and Triumph common stock are sold from time to time in isolated transactions that are privately negotiated between the purchasers and the sellers of such shares. If sales do occur, they are not subject to any reporting system. Shares of Landmark common stock and Triumph common stock are not traded frequently and the prices at which transactions involving such shares have occurred may not necessarily reflect the price that would be paid for Landmark common stock or Triumph common stock in an active market. The management of Landmark is aware of the following separate, isolated transactions: (i) in the third quarter of 2019, a total of 14,098 shares of Landmark common stock were transferred in three transactions at prices ranging from $5.10 to $5.30 per share; (ii) in the fourth quarter of 2019, a total of 36,283 shares of Landmark common stock were transferred in six transactions at prices ranging from $5.00 to $5.60 per share; (iii) in the second quarter of 2020, 7,000 shares of Landmark common stock were transferred at a price of $5.40 per share; (iv) in the fourth quarter of 2020, a total of 45,300 shares of Landmark common stock were transferred in three transactions at prices ranging from $5.00 to $5.40 per share; (v) in the first quarter of 2021, a total of 28,796 shares of Landmark common stock were transferred in three transactions at prices ranging from $5.10 to $5.40 per share; and (vi) in the second quarter of 2021, a total of 20,000 shares of Landmark common stock were transferred in two transactions at a price of $5.25 per share. Because there have been no recent private sales of Triumph common stock of which Simmons or Triumph is aware, no recent price data regarding Triumph common stock is available.

Landmark has a history of paying semi-annual cash dividends on Landmark common stock and intends to continue to pay such dividends in the future; however, there can be no assurance with respect to the amount, if any, of dividends that might be declared and paid in the future. Triumph does not regularly pay dividends on Triumph common stock and there can be no assurance with respect to the amount, if any, of dividends that might be declared and paid in the future.

The following table sets forth the closing sale price per share of Simmons common stock as reported on Nasdaq on June 4, 2021, the last trading day before the public announcement of the signing of the Landmark merger agreement and the Triumph merger agreement, and on [ ], 2021, the last practicable trading day prior to printing this proxy statement/prospectus. The table also shows (i) the applicable cash consideration payable for each share of Landmark common stock and Triumph common stock, (ii) the implied value of the applicable stock consideration payable for each share of Landmark common stock and Triumph common stock on June 4, 2021 and [ ], 2021, the last practicable trading day prior to printing this proxy statement/prospectus and (iii) the implied value of the Landmark merger consideration and Triumph merger consideration, in each case using the assumptions described in this proxy statement/prospectus.

	Simmons Common Stock		Cash Consideration Per Share of Landmark Common Stock		Implied Value of Stock Consideration Per Share of Landmark Common Stock		Implied Value of Per Share Landmark Merger Consideration
June 4, 2021	$	30.96	$	[ ]	$	[ ]	$	[ ]
[ ], 2021	$	[ ]	$	[ ]	$	[ ]	$	[ ]

	Simmons Common Stock		Cash Consideration Per Share of Triumph Common Stock		Implied Value of Stock Consideration Per Share of Triumph Common Stock		Implied Value of Per Share Triumph Merger Consideration
June 4, 2021	$	30.96	$	[ ]	$	[ ]	$	[ ]
[ ], 2021	$	[ ]	$	[ ]	$	[ ]	$	[ ]

We urge you to obtain current market quotations for Simmons common stock. The market value of the Landmark merger consideration and the Triumph merger consideration will fluctuate with the price of Simmons common stock. At the time of the special meetings of Landmark shareholders and Triumph shareholders, the Landmark shareholders and Triumph shareholders will not know or be able to calculate the value of the applicable merger consideration to be received upon completion of the Landmark merger or the Triumph merger, respectively.

CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

Certain statements contained in or incorporated by reference into this proxy statement/prospectus may not be based on historical facts and should be considered “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. These forward-looking statements may be identified by reference to a future period(s) or by the use of forward-looking terminology, such as “anticipate,” “believe,” “budget,” “contemplate,” “continue,” “estimate,” “expect,” “foresee,” “intend,” “indicate,” “plan,” “positions,” “potential,” “predict,” “project,” “prospects,” or “target,” by future conditional verbs such as “could,” “may,” “might,” “should,” “will,” or “would,” or by variations of such words or by similar expressions. These forward-looking statements include, without limitation, those relating to the benefits of the mergers, the impact Simmons, Landmark and Triumph expect the mergers to have on the combined entity’s operations, financial condition and financial results, and Simmons’ expectations about its ability to successfully integrate the combined businesses and the amount of cost savings and other benefits Simmons expects to realize as a result of the mergers. The forward-looking statements may also include, without limitation, statements relating to Simmons’ and the combined entity’s future growth, revenue, expenses, assets, asset quality, profitability, earnings, accretion, customer service, investment in digital channels, critical accounting policies, net interest margin, non-interest revenue, market conditions related to Simmons’ common stock repurchase program, consumer behavior and liquidity, the adequacy of the allowance for credit losses, the impacts of the COVID-19 pandemic and the ability of Simmons to manage the impacts of the COVID-19 pandemic, the impacts of Simmons’ and its customers’ participation in the Paycheck Protection Program, the expected performance of COVID-19 loan modifications, income tax deductions, credit quality, the level of credit losses from lending commitments, net interest revenue, interest rate sensitivity, loan loss experience, liquidity, Simmons’ expectations regarding actions by the Federal Home Loan Bank (“FHLB”) including with respect to the FHLB’s option to terminate FHLB Owns the Option advances, capital resources, market risk, plans for investments in securities, effect of future litigation, including the results of the overdraft fee litigation against Simmons, acquisition strategy, legal and regulatory limitations and compliance and competition.

These forward-looking statements are based on various assumptions (some of which may be beyond Simmons’ control) and involve substantial risks and uncertainties. There are many factors that may cause actual results to differ materially from those contemplated by such forward-looking statements. In addition to the factors disclosed by Simmons in the section entitled “Risk Factors” and elsewhere in this proxy statement/prospectus, and to factors previously disclosed by Simmons’ reports filed with the SEC and incorporated by reference herein, the following factors, among others, could cause actual results to differ materially and adversely from Simmons’ forward-looking statements:

the businesses of Simmons, Landmark and Triumph may not be integrated successfully or such integration may be more difficult, time-consuming or costly than expected;

expected revenue synergies and cost savings from the mergers may not be fully realized or realized within the expected timeframe;

revenues following the mergers may be lower than expected;

customer and employee relationships and business operations may be disrupted by the mergers;

management’s time and attention may be diverted to merger-related issues;

the potential dilutive effect of shares of Simmons common stock to be issued in the mergers;

Simmons’, Landmark’s and/or Triumph’s ability to obtain regulatory, shareholder or other approvals or other conditions to closing on a timely basis or at all, the ability to close the mergers on the expected timeframe, or at all;

the closing of the mergers may be more difficult, time-consuming or costly than expected;

Simmons’, Landmark’s and/or Triumph’s customers, employees, vendors and counterparties may have varied or negative reactions to the mergers;

changes in general business, economic and market conditions;

changes in fiscal and monetary policies, and laws and regulations;

changes in interest rates, inflation rates, deposit flows, loan demand and real estate values;

a deterioration in credit quality and/or a reduced demand for, or supply of, credit;

the impact of the COVID-19 pandemic on Simmons’, Landmark’s and/or Triumph’s businesses, the ability to complete the mergers and/or any of the other foregoing risks;

volatility in the securities markets generally or in the market price of Simmons common stock specifically; and

other factors, which could cause actual results to differ materially from future results expressed or implied by such forward-looking statements.

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

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 in the section entitled “Cautionary Statement Regarding Forward-Looking Statements,” and the matters discussed under the captions “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” sections of Simmons’ Annual Report on Form 10-K for the year ended December 31, 2020 and any updates to those risk factors set forth in Simmons’ Quarterly Reports on Form 10-Q, Current Reports on Form 8-K and other filings, which have been filed with the SEC, Landmark shareholders and Triumph shareholders should carefully consider the following factors in deciding whether to vote for the proposals presented in this proxy statement/prospectus. See also the section entitled “Where You Can Find More Information.”

Risks Relating to the Mergers

Because the market price of Simmons common stock will fluctuate, the value of the Landmark stock consideration to be received by Landmark shareholders and the value of the Triumph stock consideration to be received by Triumph shareholders is uncertain.

Based on the assumptions set forth herein, upon completion of the Landmark merger, each share of outstanding Landmark common stock (except for shares of Landmark common stock held directly or indirectly by Landmark or Simmons and any dissenting shares) will be converted into the right to receive the Landmark stock consideration, with cash paid in lieu of any remaining fractional shares, and the Landmark cash consideration. Based on the assumptions set forth herein, upon completion of the Triumph merger, each share of outstanding Triumph common stock (except for shares of Triumph common stock held directly or indirectly by Triumph or Simmons and any dissenting shares) will be converted into the right to receive the Triumph stock consideration, with cash paid in lieu of any remaining fractional shares, and the Triumph cash consideration. Any change in the market price of Simmons common stock prior to the completion of the mergers will affect the market value of the Landmark stock consideration and the Triumph stock consideration that Landmark shareholders and Triumph shareholders, respectively, will receive upon completion of the applicable merger. At the time of the Landmark special meeting and the Triumph special meeting, you will not know or be able to calculate the value of the Simmons common stock that you will receive upon completion of the applicable merger. Stock price changes may result from a variety of factors, including general market and economic conditions, changes in the respective businesses, operations and prospects of Simmons, Landmark or Triumph, and regulatory considerations, among other things. Many of these factors are beyond the control of Simmons, Landmark and Triumph. You should obtain current market quotations for shares of Simmons common stock before voting your shares at the applicable special meeting.

Other than as described in this proxy statement/prospectus, there will be no adjustment to the Landmark merger consideration based upon changes in the market price of Simmons common stock or Landmark common stock prior to the time the Landmark merger is completed, and the Landmark merger agreement cannot be terminated due to a change in the price of Simmons common stock. The Triumph stock consideration will be adjusted if the Triumph/Simmons average closing price is greater than $37.28 and the difference between the percentage change in the Nasdaq Bank Index and the percentage change in the Triumph/Simmons average closing price exceeds 20% over a designated measurement period. See the section entitled “The Merger Agreements—The Merger Consideration.” In addition, the Triumph merger agreement can be terminated by Triumph if, at any time during the five-day period commencing on the Triumph determination date, the Triumph/Simmons average closing price is less than $24.85 and the difference between the percentage change in the Nasdaq Bank Index and the percentage change in the Triumph/Simmons average closing price exceeds 20% over a designated measurement period, unless Simmons agrees to increase the Triumph cash consideration by a specified amount. See the section entitled “The Merger Agreements—Termination of the Merger Agreements.”

Regulatory approvals may not be received, may take longer than expected or may impose conditions that are not presently anticipated or cannot be met.

Before either merger may be completed, various approvals must be obtained from bank regulatory authorities. In determining whether to grant these approvals, the applicable regulatory authorities consider a variety of factors, including the competitive impact of the applicable proposal in the relevant geographic markets; financial, managerial and other supervisory considerations, including the future prospects, of each party; potential effects of the applicable merger on the convenience and needs of the communities to be served and the record of the insured depository institutions under the Community Reinvestment Act of 1977 and the regulations promulgated thereunder, or the Community Reinvestment Act, including the insured depository institutions’ respective overall compliance records and recent fair lending examinations; effectiveness of the parties in combatting money laundering activities; the extent to which the applicable proposal would result in greater or more concentrated risks to the stability of the United States banking or financial system; and whether Simmons controls or would after consummation of the applicable merger control deposits in excess of certain limits. These regulatory authorities may impose conditions on the granting of such approvals. Such conditions or changes and the process of obtaining regulatory approvals could have the effect of delaying completion of either merger or of imposing additional costs or limitations on the combined company following either merger. The regulatory approvals may not be received at all, may not be received in a timely fashion, or may contain conditions on the completion of either merger that are not anticipated or cannot be met. Furthermore, such conditions or changes may constitute a burdensome condition that may allow Simmons to terminate either merger agreement and if so, Simmons may exercise its right to terminate either merger agreement. If the consummation of either merger is delayed, including by a delay in receipt of necessary regulatory approvals, the business, financial condition and results of operations of each party to the applicable merger may also be materially and adversely affected. See the section entitled “The Mergers—Regulatory Approvals Required for the Mergers and the Triumph Bank Merger.”

Failure of either merger to be completed, the termination of either merger agreement or a significant delay in the consummation of either merger could negatively impact Simmons and Landmark or Triumph, as applicable.

Each merger agreement is subject to a number of conditions which must be fulfilled in order to complete the applicable merger. Please see the section entitled “The Merger Agreements—Conditions to Consummation of the Mergers.” These conditions to the consummation of the mergers may not be fulfilled and, accordingly, either merger may not be completed. In addition, if either the Landmark merger or Triumph merger is not completed by March 1, 2022, either Simmons or Landmark, in the case of the Landmark merger, and either Simmons or Triumph, in the case of the Triumph merger, may choose to terminate the applicable merger agreement at any time after such date if the failure to consummate the transactions contemplated by such merger agreement is not caused by any breach of such merger agreement by the party electing to terminate such merger agreement, before or after shareholder approval of the applicable merger.

If either merger is not consummated, the ongoing business, financial condition and results of operations of each party may be materially adversely affected and the market price of Simmons common stock may decline significantly, particularly to the extent that the current market price reflects a market assumption that the mergers will be consummated. If the consummation of either merger is delayed, including by the receipt of a competing acquisition proposal, the business, financial condition and results of operations of each party may be materially adversely affected.

In addition, each party to the mergers has incurred and will incur substantial expenses in connection with the negotiation and completion of the transactions contemplated by the applicable merger agreement, as well as the costs and expenses of filing, printing and mailing this proxy statement/prospectus and all filing and other fees paid to the SEC and other regulatory agencies in connection with the applicable merger. If either merger is not completed, the parties would have to recognize these expenses without realizing the expected benefits of

the applicable merger. Any of the foregoing, or other risks arising in connection with the failure of or delay in consummating either merger, including the diversion of management attention from pursuing other opportunities and the constraints in the applicable merger agreement on the ability to make significant changes to each party’s ongoing business during the pendency of the applicable merger, could have a material adverse effect on each party’s business, financial condition and results of operations.

Additionally, Simmons’, Landmark’s or Triumph’s business may have been adversely impacted by the failure to pursue other beneficial opportunities due to the focus of management on the applicable merger, without realizing any of the anticipated benefits of completing the applicable merger, and the market price of Simmons common stock might decline to the extent that the current market price reflects a market assumption that the mergers will be completed. If either merger agreement is terminated and a party’s board of directors seeks another merger or business combination, such party’s shareholders cannot be certain that such party will be able to find a party willing to engage in a transaction on more attractive terms than the applicable merger.

Some of the conditions to each merger may be waived by Simmons or Landmark, in the case of the Landmark merger, or Simmons or Triumph, in the case of the Triumph merger, without resoliciting shareholder approval of the applicable merger agreement.

Some of the conditions to the Landmark merger and the Triumph merger set forth in the applicable merger agreement may be waived by Simmons or Landmark, with respect to the Landmark merger agreement, or Simmons or Triumph, with respect to the Triumph merger agreement, subject to the agreement of the other party in specific cases. See the section entitled “The Merger Agreements—Conditions to Consummation of the Mergers.” If any such conditions are waived, Simmons and Landmark or Triumph, as applicable, will evaluate whether an amendment of this proxy statement/prospectus and solicitation of proxies is warranted. In the event that the Landmark board of directors or Triumph board of directors, as applicable, determines that solicitation of Landmark shareholders or Triumph shareholders, respectively, is not warranted, Simmons and Landmark, in the case of the Landmark merger, and Simmons and Triumph, in the case of the Triumph merger, will have the discretion to complete the applicable merger without seeking further shareholder approval.

Simmons, Landmark and Triumph will be subject to business uncertainties and contractual restrictions while the mergers are pending.

Uncertainty about the effect of the mergers on employees, customers (including depositors and borrowers), suppliers and vendors may have an adverse effect on the business, financial condition and results of operations of the parties to each merger. These uncertainties may impair Simmons’, Landmark’s or Triumph’s ability to attract, retain and motivate key personnel and customers (including depositors and borrowers) pending the consummation of the mergers, as such personnel and customers may experience uncertainty about their future roles and relationships following the consummation of the mergers. Additionally, these uncertainties could cause customers (including depositors and borrowers), suppliers, vendors and others who deal with Simmons, Landmark and/or Triumph to seek to change existing business relationships with Simmons, Landmark and/or Triumph or fail to extend an existing relationship with Simmons, Landmark and/or Triumph. In addition, competitors may target each party’s existing customers by highlighting potential uncertainties and integration difficulties that may result from the mergers.

The pursuit of the mergers and the preparation for the integration may place a burden on each party’s management and internal resources. Any significant diversion of management attention away from ongoing business concerns and any difficulties encountered in the transition and integration process could have a material adverse effect on each party’s business, financial condition and results of operations.

In addition, each merger agreement restricts each party thereto from taking certain actions without the other party’s consent while the applicable merger is pending. These restrictions could have a material adverse effect

on each party’s business, financial condition and results of operations. See the section entitled “The Merger Agreements—Covenants and Agreements” for a description of the restrictive covenants applicable to Simmons and Landmark, in the case of the Landmark merger agreement, and to Simmons and Triumph, in the case of the Triumph merger agreement.

Landmark’s and Triumph’s respective directors and executive officers have interests in the applicable merger that may be different from the interests of Landmark shareholders and Triumph shareholders, respectively.

Landmark’s and Triumph’s respective directors and executive officers have interests in the applicable merger that may be different from, or in addition to, the interests of Landmark shareholders and Triumph shareholders, respectively. The Landmark board of directors and Triumph board of directors were aware of these applicable interests and considered them, among other matters, in approving the Landmark merger agreement and Triumph merger agreement, respectively, and the transactions contemplated by the applicable merger agreement and recommending to the Landmark shareholders and Triumph shareholders, respectively, that they vote to approve the applicable merger proposal. These interests are described in more detail in the sections entitled “The Landmark Merger—Interests of Landmark’s Directors and Executive Officers in the Landmark Merger” and “The Triumph Merger—Interests of Triumph’s Directors and Executive Officers in the Triumph Merger.”

The merger agreements contain provisions that may discourage other companies from pursuing, announcing or submitting a business combination proposal to Landmark, in the case of the Landmark merger agreement, and Triumph, in the case of the Triumph merger agreement, that might result in greater value to Landmark shareholders or Triumph shareholders, respectively.

The merger agreements contain provisions that may discourage a third party from pursuing, announcing or submitting a business combination proposal to Landmark, in the case of the Landmark merger agreement, and Triumph, in the case of the Triumph merger agreement, that might result in greater value to Landmark shareholders or Triumph shareholders, respectively, than the applicable merger. These provisions include a general prohibition on Landmark and Triumph, respectively, from soliciting or entering into discussions with any third party regarding any acquisition proposal or offers for competing transactions, as described in the section entitled “The Merger Agreements—Agreement Not to Solicit Other Offers.” Furthermore, if the Landmark merger agreement or the Triumph merger agreement is terminated, under certain circumstances, Landmark may be required to pay Simmons a termination fee equal to $7,000,000 upon termination of the Landmark merger agreement, and Triumph may be required to pay Simmons a termination fee equal to $6,500,000 upon termination of the Triumph merger agreement, as described in the section entitled “The Merger Agreements—Termination Fees.” Each of Landmark and Triumph also has an unqualified obligation to submit its respective merger-related proposals to a vote by its respective shareholders, including if Landmark or Triumph, as applicable, receives an unsolicited proposal that the Landmark board of directors or Triumph board of directors, respectively, has determined in good faith is superior to the applicable merger. See the section entitled “The Merger Agreements—Special Meetings and Recommendations of the Board of Directors of Landmark and Triumph.”

In connection with the Landmark merger agreement, each of the directors and certain executive officers of Landmark, in their capacities as individuals, have separately entered into Landmark voting agreements pursuant to which they agreed to vote their beneficially owned shares of Landmark common stock in favor of the Landmark merger proposal and certain related matters and against alternative transactions. In connection with the Triumph merger agreement, each of the directors and certain executive officers of Triumph, in their capacities as individuals, have separately entered into Triumph voting agreements pursuant to which they agreed to vote their beneficially owned shares of Triumph common stock in favor of the Triumph merger proposal and certain related matters and against alternative transactions. As of the Landmark record date, shares constituting approximately [ ]% of the Landmark common stock entitled to vote at the Landmark special meeting are subject to Landmark

voting agreements; and as of the Triumph record date, shares constituting approximately [ ]% of the Triumph common stock entitled to vote at the Triumph special meeting are subject to Triumph voting agreements. For further information, see the section entitled “The Merger Agreements—Voting Agreements.”

Each of the Landmark merger and the Triumph merger is expected to, but may not, qualify as a reorganization under Section 368(a) of the Code.

The parties expect that and intend for each of the Landmark merger and the Triumph merger to be treated as a “reorganization” within the meaning of Section 368(a) of the Code. The respective obligations of Simmons and Landmark to complete the Landmark merger are contingent upon Simmons and Landmark receiving a legal opinion from Covington that the Landmark merger will qualify as a “reorganization” within the meaning of Section 368(a) of the Code. Similarly, the respective obligations of Simmons and Triumph to complete the Triumph merger are conditioned upon Simmons and Triumph receiving a legal opinion from Covington to the effect that the Triumph merger will qualify as a “reorganization” within the meaning of Section 368(a) of the Code. These tax opinions represent the legal judgment of counsel rendering the opinions and are not binding on the United States Internal Revenue Service, or the IRS, or the courts. The expectations that each of the mergers will be treated as a “reorganization” within the meaning of Section 368(a) of the Code reflect assumptions and takes into account the relevant information available to Simmons and Landmark or Triumph, as applicable, at the time. However, this information is not a fact and should not be relied upon as necessarily indicative of future results. Furthermore, such expectation constitutes a forward-looking statement. For information on forward-looking statements, see the section entitled “Cautionary Statement Regarding Forward-Looking Statements.”

If either the Landmark merger or the Triumph merger does not qualify as a “reorganization” within the meaning of Section 368(a) of the Code, then a holder of Landmark common stock or Triumph common stock, depending on whether the failed merger is the Landmark merger or the Triumph merger, may be required to recognize gain or loss equal to the difference between (1) the sum of the fair market value of Simmons common stock received by the Landmark shareholder or Triumph shareholder, as applicable, in the merger and the amount of cash, if any, received by the Landmark shareholder or Triumph shareholder in the merger, and (2) the Landmark shareholder or Triumph shareholder’s adjusted tax basis in the shares of Landmark common stock or Triumph common stock, respectively, exchanged therefor. For further information, please refer to the section entitled “Material United States Federal Income Tax Consequences of the Mergers.” You should consult your tax advisor to determine the particular tax consequences to you.

The opinions of the respective financial advisors to the Landmark board of directors and the Triumph board of directors prior to the signing of the applicable merger agreement will not reflect changes in circumstances after the respective dates of the opinions.

The Landmark board of directors received a written opinion from Olsen Palmer, dated June 4, 2021, which is attached as Annex E to this proxy statement/prospectus. The Triumph board of directors received a written opinion from Southard Financial, dated June 4, 2021, which is attached hereto as Annex F to this proxy statement/prospectus. For a description of these opinions, see the sections entitled “The Landmark Merger—Opinion of Landmark’s Financial Advisor” and “The Triumph Merger—Opinion of Triumph’s Financial Advisor.” Such opinions have not been updated as of the date of this proxy statement/prospectus and will not be updated at, or prior to, the time of the completion of the mergers. Changes in the operations and prospects of Simmons, Landmark or Triumph, general market and economic conditions and other factors that may be beyond the control of Simmons, Landmark and Triumph may alter the value of Simmons, Landmark or Triumph or the prices of shares of Simmons common stock, Landmark common stock or Triumph common stock by the time the mergers are completed. The opinions do not speak as of the time the mergers are completed or as of any other date than the date of the opinions. Further, the Olsen Palmer and Southard Financial opinions regarding the Landmark merger and Triumph merger, respectively, do not take the Triumph merger or Landmark merger, respectively, into consideration. For a description of the other factors considered by the Landmark board

of directors in determining to approve the Landmark merger and the Triumph board of directors in determining to approve the Triumph merger, see the sections entitled “The Landmark Merger—Landmark’s Reasons for the Landmark Merger and Recommendation of the Landmark Board of Directors” and “The Triumph Merger—Triumph’s Reasons for the Triumph Merger and Recommendation of the Triumph Board of Directors.”

Litigation against Landmark, Triumph or Simmons, or the members of the Landmark, Triumph or Simmons board of directors, could prevent or delay the completion of the mergers.

While Simmons, Landmark and Triumph believe that any claims that may be asserted by purported shareholder plaintiffs related to the mergers would be without merit, the results of any such potential legal proceedings are difficult to predict and could delay or prevent the mergers from being competed in a timely manner. The existence of litigation related to the Landmark merger or the Triumph merger could affect the likelihood of obtaining the required approval from Landmark shareholders or Triumph shareholders, respectively. Moreover, any litigation could be time consuming and expensive, could divert Simmons, Landmark and Triumph management’s attention away from their regular business, and any lawsuit adversely resolved against Landmark, Triumph, Simmons or members of the Landmark, Triumph or Simmons board of directors, could have a material adverse effect on each party’s business, financial condition and results of operations.

One of the conditions to the consummation of each merger is the absence of any law or order (whether temporary, preliminary or permanent) by any court or regulatory authority of competent jurisdiction prohibiting, restricting or making illegal consummation of the transactions contemplated by the applicable merger agreement (including the applicable merger). Consequently, if a settlement or other resolution is not reached in any lawsuit that is filed or any regulatory proceeding and a claimant secures injunctive or other relief or a regulatory authority issues an order or other directive prohibiting, restricting or making illegal consummation of the transactions contemplated by either of the merger agreements (including the applicable merger), then such injunctive or other relief may prevent such merger from becoming effective in a timely manner or at all.

The COVID-19 pandemic may delay and adversely affect the completion of the mergers.

The COVID-19 pandemic has created economic and financial disruptions that have adversely affected, and are likely to continue to adversely affect, the business, financial condition, liquidity, capital and results of operations of Simmons, Landmark and Triumph. If the effects of the COVID-19 pandemic cause continued or extended decline in the economic environment and the financial results of Simmons, Landmark or Triumph, or the business operations of Simmons, Landmark or Triumph are disrupted as a result of the COVID-19 pandemic, efforts to complete the mergers and integrate the businesses of Landmark and Triumph with Simmons may also be delayed and adversely affected. Additional time may be required to obtain the requisite regulatory approvals, and regulatory authorities may impose additional requirements on Simmons, Landmark or Triumph that must be satisfied prior to completion of the mergers, which could delay and adversely affect the completion of the mergers.

Risks Relating to the Combined Company’s Business Following the Mergers

The shares of Simmons common stock to be received by holders of Landmark common stock and holders of Triumph common stock as a result of the Landmark merger and Triumph merger, respectively, will have different rights from the shares of Landmark common stock and Triumph common stock, respectively.

The rights of Landmark shareholders are currently governed by the Landmark charter and the Landmark bylaws. The rights of Triumph are currently governed by the Triumph charter and the Triumph bylaws. Upon completion of the mergers, the rights of former holders of Landmark common stock and Triumph common stock will be governed by the Simmons charter and the Simmons bylaws. Simmons is organized under Arkansas law, while Landmark and Triumph are organized under Tennessee law. The rights associated with Landmark common

stock and Triumph common stock are different from the rights associated with Simmons common stock. See the sections entitled “Comparison of Shareholders’ Rights of Simmons and Landmark” and “Comparison of Shareholders’ Rights of Simmons and Triumph” for a discussion of the different rights associated with Simmons common stock.

Sales of substantial amounts of Simmons common stock in the open market by former holders of Landmark common stock and/or Triumph common stock could depress Simmons’ stock price.

Shares of Simmons common stock that are issued to holders of Landmark common stock in the Landmark merger and holders of Triumph common stock in the Triumph merger will be freely tradable without restrictions or further registration under the Securities Act. Simmons currently expects to issue 4,500,000 shares of Simmons common stock in connection with the Landmark merger and 4,164,839 shares of Simmons common stock in connection with the Triumph merger. If the mergers are completed and if Landmark’s and/or Triumph’s former shareholders sell substantial amounts of Simmons common stock in the public market following completion of the mergers, the market price of Simmons common stock may decrease. These sales might also make it more difficult for Simmons to sell equity or equity-related securities at a time and price that it otherwise would deem appropriate.

Combining Landmark and Triumph with Simmons may be more difficult, costly or time consuming than expected and the anticipated benefits and cost savings of the mergers may not be realized.

The success of the mergers will depend on, among other things, the combined company’s ability to combine the businesses of Landmark and Triumph with Simmons. If the combined company is not able to successfully achieve this objective, the anticipated benefits of the mergers may not be realized fully, or at all, or may take longer to realize than expected.

Simmons, Landmark and Triumph have operated and, until the completion of the mergers, will continue to operate, independently. The success of the mergers, including anticipated benefits and cost savings, will depend, in part, on the successful combination of the businesses of Landmark and Triumph with Simmons. To realize these anticipated benefits and cost savings, after the completion of the mergers, Simmons expects to integrate Landmark’s and Triumph’s businesses into its own. It is possible that the integration process could result in the loss of key employees, the disruption of each company’s ongoing businesses or inconsistencies in standards, controls, procedures and policies that adversely affect the combined company’s ability to maintain relationships with clients, customers, depositors and employees or to achieve the anticipated benefits and cost savings of the mergers. The loss of key employees could have an adverse effect on the companies’ financial results and the value of their common stock. If Simmons experiences difficulties with the integration process, the anticipated benefits of the mergers may not be realized fully, or at all, or may take longer to realize than expected. As with any merger of financial institutions, there also may be business disruptions that cause Simmons, Landmark and/or Triumph to lose current customers or cause current customers to remove their accounts from Simmons, Landmark and/or Triumph and move their business to competing financial institutions. Integration efforts will also divert management attention and resources. These integration matters could have an adverse effect on each of Simmons, Landmark or Triumph during this transition period and for an undetermined period after consummation of the mergers.

The combined company expects to incur substantial expenses related to the mergers.

The combined company expects to incur substantial expenses in connection with consummation of the mergers and combining the business, operations, networks, systems, technologies, policies and procedures of Landmark and Triumph with Simmons. Although Simmons, Landmark and Triumph have assumed that a certain level of transaction and combination expenses would be incurred, there are a number of factors beyond their control that could affect the total amount or the timing of their combination expenses. Many of the expenses that

will be incurred, by their nature, are difficult to estimate accurately at the present time. Due to these factors, the transaction and combination expenses associated with the mergers could, particularly in the near term, exceed the savings that the combined company expects to achieve from the elimination of duplicative expenses and the realization of economies of scale and cost savings related to the combination of the businesses following the consummation of the mergers. As a result of these expenses, each of Simmons, Landmark and Triumph expects to take charges against their earnings before and after the completion of the mergers. The charges taken in connection with the mergers are expected to be significant, although the aggregate amount and timing of such charges are uncertain at present.

Holders of Simmons, Landmark and Triumph common stock will have a reduced ownership and voting interest after the mergers and will exercise less influence over management.

Holders of Simmons common stock, Landmark common stock and Triumph common stock currently have the right to vote for the election of the directors and on other matters affecting Simmons, Landmark and Triumph, respectively. Upon the completion of the mergers, each holder of Landmark common stock and each holder of Triumph common stock who receives shares of Simmons common stock will become a shareholder of Simmons with a percentage ownership of Simmons common stock that is smaller than such shareholder’s percentage ownership of Landmark common stock or Triumph common stock, respectively. Following completion of both of the mergers, it is currently expected that former holders of Landmark common stock as a group will own approximately [ ]% of the combined company’s common stock, former holders of Triumph common stock as a group will own approximately [ ]% of the combined company’s common stock, and existing holders of Simmons common stock as a group will own approximately [ ]% of the combined company’s common stock. As a result, Landmark shareholders and Triumph shareholders will have less influence on the management and policies of the combined company than they now have on the management and policies of Landmark and Triumph, respectively, and existing Simmons shareholders may have less influence than they now have on the management and policies of Simmons.

Risks Relating to an Investment in Simmons Common Stock

The market price of Simmons common stock may decline as a result of the mergers.

The market price of Simmons common stock may decline as a result of the mergers if Simmons does not achieve the perceived benefits of the mergers or the effect of the mergers on Simmons’ financial results is not consistent with the expectations of financial or industry analysts. In addition, upon completion of the mergers, Simmons, Landmark and Triumph shareholders will own interests in a combined company operating an expanded business with a different mix of assets, risks and liabilities. Existing Simmons, Landmark and Triumph shareholders may not wish to continue to invest in the combined company, or for other reasons may wish to dispose of some or all of their shares of the combined company.

The market price of the common stock of the combined company after the mergers may be affected by factors different from those currently affecting the shares of Simmons, Landmark or Triumph common stock.

Upon the completion of the mergers, Simmons shareholders, Landmark shareholders and Triumph shareholders will become shareholders of the combined company. Simmons’ business differs from that of each of Landmark and Triumph, and, accordingly, the results of operations of the combined company and the market price of the combined company’s shares of common stock may be affected by factors different from those currently affecting the independent results of operations of each of Simmons, Landmark and Triumph. For a further discussion of the businesses of Simmons, Landmark and Triumph, see the section entitled “Information about the Companies.” For a discussion of the businesses of Simmons and of certain factors to consider in connection with such business, please see the documents incorporated by reference into this proxy statement/prospectus and referred to in the section entitled “Where You Can Find More Information.”

Simmons’ management will have broad discretion as to the use of assets acquired from the mergers, and Simmons may not use these assets effectively.

Simmons’ management will have broad discretion in the application of the assets from the mergers and could utilize the assets in ways that do not improve Simmons’ results of operations or enhance the value of its common stock. Holders of Landmark common stock and holders of Triumph common stock will not have the opportunity, as part of their investment decision, to assess whether these acquired assets are being used appropriately. Simmons’ failure to utilize these assets effectively could have a material adverse effect on the combined company’s business, financial condition and results of operations and cause the price of Simmons common stock to decline.

Simmons’ rights and the rights of Simmons shareholders to take action against Simmons’ directors and officers are limited.

The Simmons charter eliminates Simmons’ directors’ liability to Simmons and its shareholders for money damages for breach of fiduciary duties as a director to the fullest extent permitted by Arkansas law. Arkansas law provides that an officer has no liability in that capacity if he or she performs his or her duties in good faith, in a manner he or she reasonably believes to be in Simmons’ best interests and with the care that an ordinarily prudent person in a like position would use under similar circumstances.

The Simmons charter, Simmons bylaws and indemnification agreements with Simmons’ directors and executive officers also require Simmons to indemnify Simmons’ directors and officers for liability resulting from actions taken by them in those capacities to the maximum extent permitted by Arkansas law. As a result, Simmons shareholders and Simmons may have more limited rights against Simmons’ directors and officers than might otherwise exist under common law. In addition, Simmons may be obligated to fund the defense costs incurred by Simmons’ directors and officers.

THE LANDMARK SPECIAL MEETING

This section contains information for Landmark shareholders about the Landmark special meeting. Landmark is mailing or otherwise delivering this proxy statement/prospectus to you, as a Landmark shareholder, on or about [ ], 2021. This proxy statement/prospectus is also being delivered to Landmark shareholders as Simmons’ prospectus for its offering of Simmons common stock in connection with the Landmark merger. This proxy statement/prospectus is accompanied by a notice of the Landmark special meeting and a proxy that the Landmark board of directors is soliciting for use by Landmark shareholders at the Landmark special meeting and at any adjournments or postponements of the Landmark special meeting. References to “you” and “your” in this section are to Landmark shareholders.

Date, Time and Place of the Landmark Special Meeting

The Landmark special meeting will be held on [ ], 2021 at [ ] Central Time, at [ ]. On or about [ ], 2021, Landmark commenced mailing or otherwise delivering this proxy statement/prospectus and the enclosed form of proxy to its shareholders entitled to vote at the Landmark special meeting.

Matters to Be Considered

At the Landmark special meeting, you will be asked to consider and vote upon the following proposals:

the Landmark merger proposal; and

the Landmark adjournment proposal, if necessary or appropriate.

Recommendation of the Landmark Board of Directors

The Landmark board of directors has approved the Landmark merger agreement and unanimously recommends that you vote “FOR” the Landmark merger proposal and, if necessary or appropriate, “FOR” the Landmark adjournment proposal. See the section entitled “The Landmark Merger—Landmark’s Reasons for the Landmark Merger and Recommendation of the Landmark Board of Directors” for a more detailed discussion of the factors considered by the Landmark board of directors in reaching its decision to approve the Landmark merger agreement, including the Landmark merger and all transactions contemplated thereby.

Completion of the Landmark merger is conditioned upon the approval of the Landmark merger proposal, but is not conditioned upon the approval of the Landmark adjournment proposal. Neither the closing of the Landmark merger nor the closing of the Triumph merger is conditioned upon closing of the other merger.

Record Date and Quorum

The Landmark board of directors has fixed the close of business on [ ], 2021 as the Landmark record date for determination of Landmark shareholders entitled to notice of and to vote at the Landmark special meeting. Only Landmark shareholders at the close of business on the Landmark record date will be entitled to notice of, and to vote at, the Landmark special meeting. As of the Landmark record date, there were [ ] shares of Landmark common stock outstanding and entitled to notice of, and to vote at, the Landmark special meeting, held by approximately [ ] Landmark shareholders of record. Each Landmark shareholder will be entitled to one vote for each share of Landmark common stock held of record.

Landmark shareholders that are present at the Landmark special meeting in person or by proxy and holding a majority of the shares of Landmark common stock issued, outstanding and entitled to be voted at Landmark special meeting, will constitute a quorum at the Landmark special meeting. All shares of Landmark common

stock present at the Landmark special meeting in person or by proxy, including abstentions, if any, will be treated as present for purposes of determining the presence or absence of a quorum for all matters voted on at the Landmark special meeting.

Under the Landmark bylaws, if a quorum is not present at the Landmark special meeting, a majority in voting interest of those present in person or by proxy and entitled to vote at the Landmark special meeting may adjourn the meeting from time to time without notice to the Landmark shareholders until Landmark shareholders holding the amount of stock required for a quorum are present or represented. In the absence of all of the Landmark shareholders, any officer entitled to preside at, or to act as presiding officer of, the Landmark special meeting may adjourn the meeting from time to time without notice to the Landmark shareholders until Landmark shareholders holding the amount of stock required for a quorum are present or represented.

Vote Required; Treatment of Abstentions; Broker Non-Votes and Failure to Vote

Landmark merger proposal:

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

Effect of abstentions and broker non-votes: If you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Landmark merger proposal, it will have the same effect as a vote against the proposal.

Landmark adjournment proposal:

Vote required: Approval of the Landmark adjournment proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock present or represented by proxy at the Landmark special meeting and entitled to vote on the proposal. A quorum is not required for a vote on the Landmark adjournment proposal.

Effect of abstentions and broker non-votes: If you mark “ABSTAIN” on your proxy, it will have the same effect as a vote against the Landmark adjournment proposal. If you fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Landmark adjournment proposal, it will have no effect on the proposal.

Shares Held by Directors and Executive Officers

As of the Landmark record date, there were [ ] shares of Landmark common stock outstanding and entitled to vote at the Landmark special meeting. As of the Landmark record date, the directors and executive officers of Landmark and their affiliates beneficially owned and were entitled to vote approximately [ ] shares of Landmark common stock, representing approximately [ ]% of the shares of Landmark common stock outstanding on that date. Landmark currently expects that the shares of Landmark common stock beneficially owned by its directors and executive officers will be voted in favor of the Landmark merger proposal and the Landmark adjournment proposal. In connection with the Landmark merger agreement, each of the directors and certain executive officers of Landmark, in their capacities as individuals, have separately entered into Landmark voting agreements pursuant to which they agreed to vote their beneficially owned shares of Landmark common stock in favor of the Landmark merger proposal and certain related matters and against alternative transactions. For further information, see the section entitled “The Merger Agreements—Voting Agreements.”

Voting of Proxies; Incomplete Proxies

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

by mail by completing, signing, dating and returning the proxy in the enclosed envelope, which requires no additional postage if mailed in the United States; or

in person at the Landmark special meeting.

When a properly executed proxy is returned, the shares of Landmark common stock represented by it will be voted at the Landmark special meeting in accordance with the instructions contained on the proxy. If any proxy is returned without indication as to how to vote, the shares of Landmark common stock represented by the proxy will be voted in favor of both the Landmark merger proposal and the Landmark adjournment proposal.

For Landmark shareholders whose shares are registered in the name of a bank, broker or other nominee, please consult the voting instructions provided by your bank, broker or other nominee.

If your shares are held in “street name” by a bank, broker or other nominee, you should check the voting form used by that firm to determine how to vote. You may not vote shares held in “street name” by returning a proxy directly to Landmark or by voting at the Landmark special meeting unless you provide a “legal proxy,” which you must obtain from your bank, broker or other nominee.

Every Landmark shareholder’s vote is important. Accordingly, you should complete, sign, date and return the enclosed proxy, whether or not you plan to attend the Landmark special meeting. Sending in your proxy will not prevent you from voting your shares personally at the Landmark special meeting, since you may revoke your proxy at any time before it is voted.

Shares Held in “Street Name”

If your shares are held in “street name” by a bank, broker or other nominee, you must provide the record holder of your shares with instructions on how to vote your shares. Banks, brokers and other nominees who hold shares of Landmark common stock in “street name” for a beneficial owner of those shares typically have the authority to vote in their discretion on “routine” proposals when they have not received instructions from beneficial owners. However, banks, brokers and other nominees are not allowed to exercise voting discretion with respect to the approval of matters determined to be “non-routine,” without specific instructions from the beneficial owner. Landmark expects that all proposals to be voted on at the Landmark special meeting will be “non-routine” matters. Broker non-votes are shares held by a bank, broker or other nominee with respect to which such entity is not instructed by the beneficial owner of such shares to vote on the particular proposal and the broker does not have discretionary voting power on such proposal. If your bank, broker or other nominee holds your shares of Landmark common stock in “street name,” such entity will vote your shares of Landmark common stock only if you provide instructions on how to vote by complying with the voter instruction form sent to you by your bank, broker or other nominee with this proxy statement/prospectus.

Revocability of Proxies and Changes to a Landmark Shareholder’s Vote

If you hold stock in your name as a shareholder of record, you may change your vote or revoke any proxy at any time before it is voted by (1) completing, signing, dating and returning a proxy with a later date, (2) delivering a written revocation letter to Landmark’s head of investor relations, or (3) voting in person at the

Landmark special meeting. If you choose to send a completed proxy bearing a later date than your original proxy, the new proxy must be received before the beginning of the Landmark special meeting.

Any Landmark shareholder entitled to vote at the Landmark special meeting may vote regardless of whether or not a proxy has been previously given, but simply attending the Landmark special meeting (without notifying Landmark’s head of investor relations) will not constitute revocation of a previously given proxy.

Written notices of revocation and other communications about revoking your proxy should be addressed to:

Landmark Community Bank
5880 Ridge Bend Road
Memphis, Tennessee 38120
Attention: Deborah R. Field

Solicitation of Proxies

Landmark is soliciting proxies from its shareholders in conjunction with the Landmark merger. Landmark will bear the entire cost of soliciting proxies from Landmark shareholders. In addition to solicitation of proxies by mail, Landmark will request that banks, brokers, nominees and other record holders send proxies and proxy materials to the beneficial owners of Landmark common stock and secure their voting instructions. Landmark will reimburse the record holders for their reasonable expenses in taking those actions. If necessary, Landmark may use its directors, officers or employees, who will not be specially compensated, to solicit proxies from Landmark shareholders, either personally or by telephone, facsimile, letter or electronic means.

Attending the Landmark Special Meeting

If you are a Landmark shareholder as of the Landmark record date, you may vote your shares in person at the Landmark special meeting. Even if you currently plan to attend the Landmark special meeting, it is recommended that you also submit your proxy as described below, so your vote will be counted if you later decide not to attend the Landmark special meeting. If you submit your vote by proxy and later decide to vote at the Landmark special meeting, the vote you submit at the Landmark special meeting will override your proxy vote. If your shares of Landmark common stock are held in “street name” by a bank, broker or other nominee, please follow the instructions on the voting instruction form provided by the record holder. “Street name” shareholders who wish to vote in person at the Landmark special meeting will need to obtain a legal proxy from the institution that holds their shares.

Assistance

If you need assistance in completing your proxy, have questions regarding the Landmark special meeting, or would like additional copies of this proxy statement/prospectus, please contact James P. “Jake” Farrell, telephone: (901) 457-3111, email: jakefarrell@landmarkbanktn.com; or Charles E. “Buddy” Dickey, telephone: (901) 457-3123, email: cdickeylandmarkbanktn.com.

THE LANDMARK PROPOSALS

Proposal 1: Landmark Merger Proposal

Landmark is asking Landmark shareholders to approve the Landmark merger agreement, including the Landmark merger and all transactions contemplated thereby. For a detailed discussion of the terms and conditions of the Landmark merger agreement, see the section entitled “The Merger Agreements.” Landmark shareholders should read this proxy statement/prospectus, including any documents incorporated by reference into this proxy statement/prospectus, and its annexes, carefully and in their entirety for more detailed information concerning the Landmark merger agreement and the Landmark merger. A copy of the Landmark merger agreement is attached to this proxy statement/prospectus as Annex A.

As discussed in the section entitled “The Landmark Merger—Landmark’s Reasons for the Landmark Merger and Recommendation of the Landmark Board of Directors,” after careful consideration, the Landmark board of directors approved the Landmark merger agreement and declared the Landmark merger agreement and the transactions contemplated thereby, including the Landmark merger, to be advisable and in the best interest of Landmark and Landmark shareholders.

Required Vote

Approval of the Landmark merger proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock entitled to vote on the proposal. If you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Landmark merger proposal, it will have the same effect as a vote against the proposal.

The Landmark board of directors recommends that Landmark shareholders vote “FOR” the Landmark merger proposal.

Proposal 2: Landmark Adjournment Proposal

Landmark is asking Landmark shareholders to approve one or more adjournments of the Landmark special meeting, if necessary or appropriate, to solicit additional proxies in favor of approval of the Landmark merger proposal if there are insufficient votes at the time of such adjournment to approve the Landmark merger proposal.

If, at the Landmark special meeting, there is an insufficient number of shares of Landmark common stock present or represented by proxy and voting in favor of the Landmark merger proposal, Landmark will move to adjourn the Landmark special meeting in order to enable the Landmark board of directors to solicit additional proxies in favor of the Landmark merger proposal. If the Landmark shareholders approve the Landmark adjournment proposal, Landmark may adjourn the Landmark special meeting and use the additional time to solicit additional proxies, including the solicitation of proxies from Landmark shareholders who have previously voted. Notice need not be given of the adjourned meeting if the time and place of the adjourned meeting are announced at the Landmark special meeting. If the meeting is adjourned to a date more than four months after the date fixed for the original meeting, Landmark must fix a new record date. Even if a quorum is not present, the Landmark special meeting may be adjourned by the affirmative vote of a majority in voting interest of those present in person or by proxy and entitled to vote at the Landmark special meeting until Landmark shareholders holding the amount of stock required for a quorum are present or represented. In the absence of all the Landmark shareholders, any officer entitled to preside at, or to act as presiding officer of, the Landmark special meeting may adjourn the meeting from time to time without notice to the Landmark shareholders until Landmark shareholders holding the amount of stock required for a quorum are present or represented.

Required Vote

Approval of the Landmark adjournment proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Landmark common stock present or represented by proxy at the Landmark special meeting and entitled to vote on the proposal. A quorum is not required for a vote on the Landmark adjournment proposal. If you mark “ABSTAIN” on your proxy, it will have the same effect as a vote against the Landmark adjournment proposal. If you fail to submit a proxy or vote in person at the Landmark special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Landmark adjournment proposal, it will have no effect on the proposal.

The Landmark board of directors recommends that Landmark shareholders vote “FOR” the Landmark adjournment proposal.

Other Matters to Come Before the Landmark Special Meeting

As of the date of this proxy statement/prospectus, the Landmark board of directors is not aware of any matters that will be presented for consideration at the Landmark special meeting other than as described in this proxy statement/prospectus. If, however, the Landmark board of directors properly brings any other matters before the Landmark special meeting, the persons named in the proxy will vote the shares represented thereby in accordance with the recommendation of the Landmark board of directors on any such matter.

THE TRIUMPH SPECIAL MEETING

This section contains information for Triumph shareholders about the Triumph special meeting. Triumph is mailing or otherwise delivering this proxy statement/prospectus to you, as a Triumph shareholder, on or about [ ], 2021. This proxy statement/prospectus is also being delivered to Triumph shareholders as Simmons’ prospectus for its offering of Simmons common stock in connection with the Triumph merger. This proxy statement/prospectus is accompanied by a notice of the Triumph special meeting and a proxy that the Triumph board of directors is soliciting for use by Triumph shareholders at the Triumph special meeting and at any adjournments or postponements of the Triumph special meeting. References to “you” and “your” in this section are to Triumph shareholders.

Date, Time and Place of the Triumph Special Meeting

The Triumph special meeting will be held on [ ], 2021 at [ ] Central Time, at [ ]. On or about [ ], 2021, Triumph commenced mailing or otherwise delivering this proxy statement/prospectus and the enclosed form of proxy to its shareholders entitled to vote at the Triumph special meeting.

Matters to Be Considered

At the Triumph special meeting, you will be asked to consider and vote upon the following proposals:

the Triumph merger proposal; and

the Triumph adjournment proposal, if necessary or appropriate.

Recommendation of the Triumph Board of Directors

The Triumph board of directors has approved the Triumph merger agreement and unanimously recommends that you vote “FOR” the Triumph merger proposal and, if necessary or appropriate, “FOR” the Triumph adjournment proposal. See the section entitled “The Triumph Merger—Triumph’s Reasons for the Triumph Merger and Recommendation of the Triumph Board of Directors” for a more detailed discussion of the factors considered by the Triumph board of directors in reaching its decision to approve the Triumph merger agreement, including the Triumph merger and all transactions contemplated thereby.

Completion of the Triumph merger is conditioned upon the approval of the Triumph merger proposal, but is not conditioned upon the approval of the Triumph adjournment proposal. Neither the closing of the Triumph merger nor the closing of the Landmark merger is conditioned upon closing of the other merger.

Record Date and Quorum

The Triumph board of directors has fixed the close of business on [ ], 2021 as the Triumph record date for determination of Triumph shareholders entitled to notice of and to vote at the Triumph special meeting. Only Triumph shareholders at the close of business on the Triumph record date will be entitled to notice of, and to vote at, the Triumph special meeting. As of the Triumph record date, there were [ ] shares of Triumph common stock outstanding and entitled to notice of, and to vote at, the Triumph special meeting, held by approximately [ ] Triumph shareholders of record. Each Triumph shareholder will be entitled to one vote for each share of Triumph common stock held of record.

Triumph shareholders that are present at the Triumph special meeting in person or by proxy and holding a majority of the outstanding shares of Triumph common stock entitled to be voted at Triumph special meeting, will constitute a quorum at the Triumph special meeting. All shares of Triumph common stock present at the

Triumph special meeting in person or by proxy, including abstentions, if any, will be treated as present for purposes of determining the presence or absence of a quorum for all matters voted on at the Triumph special meeting.

Under the TBCA, if a quorum is not present at the Triumph special meeting, the chair of the meeting or the holders of a majority of the shares of those present in person or by proxy and entitled to vote at the Triumph special meeting may adjourn the meeting from time to time without notice to the Triumph shareholders until Triumph shareholders holding the amount of stock required for a quorum are present or represented.

Vote Required; Treatment of Abstentions; Broker Non-Votes and Failure to Vote

Triumph merger proposal:

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

Effect of abstentions and broker non-votes: If you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Triumph merger proposal, it will have the same effect as a vote against the proposal.

Triumph adjournment proposal:

Vote required: Approval of the Triumph adjournment proposal requires the votes cast by the outstanding shares of Triumph common stock present or represented by proxy at the Triumph special meeting and entitled to vote on the proposal favoring the approval to exceed the votes cast opposing the approval. A quorum is not required for a vote on the Triumph adjournment proposal.

Effect of abstentions and broker non-votes: If you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting, or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Triumph adjournment proposal, it will have no effect on the proposal.

Shares Held by Directors and Executive Officers

As of the Triumph record date, there were [ ] shares of Triumph common stock outstanding and entitled to vote at the Triumph special meeting. As of the Triumph record date, the directors and executive officers of Triumph and their affiliates beneficially owned and were entitled to vote approximately [ ] shares of Triumph common stock, representing approximately [ ]% of the shares of Triumph common stock outstanding on that date. Triumph currently expects that the shares of Triumph common stock beneficially owned by its directors and executive officers will be voted in favor of the Triumph merger proposal and the Triumph adjournment proposal. In connection with the Triumph merger agreement, each of the directors and certain executive officers of Triumph, in their capacities as individuals, have separately entered into Triumph voting agreements pursuant to which they agreed to vote their beneficially owned shares of Triumph common stock in favor of the Triumph merger proposal and certain related matters and against alternative transactions. For further information, see the section entitled “The Merger Agreements—Voting Agreements.”

Voting of Proxies; Incomplete Proxies

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

by mail by completing, signing, dating and returning the proxy in the enclosed envelope, which requires no additional postage if mailed in the United States; or

in person at the Triumph special meeting.

When a properly executed proxy is returned, the shares of Triumph common stock represented by it will be voted at the Triumph special meeting in accordance with the instructions contained on the proxy. If any proxy is returned without indication as to how to vote, the shares of Triumph common stock represented by the proxy will be voted in favor of both the Triumph merger proposal and the Triumph adjournment proposal.

For Triumph shareholders whose shares are registered in the name of a bank, broker or other nominee, please consult the voting instructions provided by your bank, broker or other nominee.

If your shares are held in “street name” by a bank, broker or other nominee, you should check the voting form used by that firm to determine how to vote. You may not vote shares held in “street name” by returning a proxy directly to Triumph or by voting at the Triumph special meeting unless you provide a “legal proxy,” which you must obtain from your bank, broker or other nominee.

Every Triumph shareholder’s vote is important. Accordingly, you should complete, sign, date and return the enclosed proxy, whether or not you plan to attend the Triumph special meeting. Sending in your proxy will not prevent you from voting your shares personally at the Triumph special meeting, since you may revoke your proxy at any time before it is voted.

Shares Held in “Street Name”

If your shares are held in “street name” by a bank, broker or other nominee, you must provide the record holder of your shares with instructions on how to vote your shares. Banks, brokers and other nominees who hold shares of Triumph common stock in “street name” for a beneficial owner of those shares typically have the authority to vote in their discretion on “routine” proposals when they have not received instructions from beneficial owners. However, banks, brokers and other nominees are not allowed to exercise voting discretion with respect to the approval of matters determined to be “non-routine,” without specific instructions from the beneficial owner. Triumph expects that all proposals to be voted on at the Triumph special meeting will be “non-routine” matters. Broker non-votes are shares held by a bank, broker or other nominee with respect to which such entity is not instructed by the beneficial owner of such shares to vote on the particular proposal and the broker does not have discretionary voting power on such proposal. If your bank, broker or other nominee holds your shares of Triumph common stock in “street name,” such entity will vote your shares of Triumph common stock only if you provide instructions on how to vote by complying with the voter instruction form sent to you by your bank, broker or other nominee with this proxy statement/prospectus.

Revocability of Proxies and Changes to a Triumph Shareholder’s Vote

If you hold stock in your name as a shareholder of record, you may change your vote or revoke any proxy at any time before it is voted by (1) completing, signing, dating and returning a proxy with a later date, (2) delivering a written revocation letter to Michael J. McCarver of Triumph, or (3) voting in person at the Triumph

special meeting. If you choose to send a completed proxy bearing a later date than your original proxy, the new proxy must be received before the beginning of the Triumph special meeting.

Any Triumph shareholder entitled to vote at the Triumph special meeting may vote regardless of whether or not a proxy has been previously given, but simply attending the Triumph special meeting (without notifying Michael J. McCarver) will not constitute revocation of a previously given proxy.

Written notices of revocation and other communications about revoking your proxy should be addressed to:

Triumph Bancshares, Inc.

5699 Poplar Avenue

Memphis, Tennessee 38119

Attention: Michael J. McCarver

Solicitation of Proxies

Triumph is soliciting proxies from its shareholders in conjunction with the Triumph merger. Triumph will bear the entire cost of soliciting proxies from Triumph shareholders. In addition to solicitation of proxies by mail, Triumph will request that banks, brokers, nominees and other record holders send proxies and proxy materials to the beneficial owners of Triumph common stock and secure their voting instructions. Triumph will reimburse the record holders for their reasonable expenses in taking those actions. If necessary, Triumph may use its directors, officers or employees, who will not be specially compensated, to solicit proxies from Triumph shareholders, either personally or by telephone, facsimile, letter or electronic means.

Attending the Triumph Special Meeting

If you are a Triumph shareholder as of the Triumph record date, you may vote your shares in person at the Triumph special meeting. Even if you currently plan to attend the Triumph special meeting, it is recommended that you also submit your proxy as described below, so your vote will be counted if you later decide not to attend the Triumph special meeting. If you submit your vote by proxy and later decide to vote at the Triumph special meeting, the vote you submit at the Triumph special meeting will override your proxy vote. If your shares of Triumph common stock are held in “street name” by a bank, broker or other nominee, please follow the instructions on the voting instruction form provided by the record holder. “Street name” shareholders who wish to vote in person at the Triumph special meeting will need to obtain a legal proxy from the institution that holds their shares.

Assistance

If you need assistance in completing your proxy, have questions regarding the Triumph special meeting, or would like additional copies of this proxy statement/prospectus, please contact Michael J. McCarver, 5699 Poplar Avenue, Memphis, Tennessee 38119, telephone: (901) 333-8802.

THE TRIUMPH PROPOSALS

Proposal 1: Triumph Merger Proposal

Triumph is asking Triumph shareholders to approve the Triumph merger agreement, including the Triumph merger and all transactions contemplated thereby. For a detailed discussion of the terms and conditions of the Triumph merger agreement, see the section entitled “The Merger Agreements.” Triumph shareholders should read this proxy statement/prospectus, including any documents incorporated by reference into this proxy statement/prospectus, and its annexes, carefully and in their entirety for more detailed information concerning the Triumph merger agreement and the Triumph merger. A copy of the Triumph merger agreement is attached to this proxy statement/prospectus as Annex B.

As discussed in the section entitled “The Triumph Merger—Triumph’s Reasons for the Triumph Merger and Recommendation of the Triumph Board of Directors,” after careful consideration, the Triumph board of directors approved the Triumph merger agreement and declared the Triumph merger agreement and the transactions contemplated thereby, including the Triumph merger, to be advisable and in the best interest of Triumph and Triumph shareholders.

Required Vote

Approval of the Triumph merger proposal requires the affirmative vote of holders of at least a majority of the outstanding shares of Triumph common stock entitled to vote on the Triumph merger proposal. If you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting or fail to instruct your bank, broker or other nominee how to vote with respect to the Triumph merger proposal, it will have the same effect as a vote against the Triumph merger proposal.

The Triumph board of directors recommends that Triumph shareholders vote “FOR” the Triumph merger proposal.

Proposal 2: Triumph Adjournment Proposal

Triumph is asking Triumph shareholders to approve one or more adjournments of the Triumph special meeting, if necessary or appropriate, to solicit additional proxies in favor of approval of the Triumph merger proposal if there are insufficient votes at the time of such adjournment to approve the Triumph merger proposal.

If, at the Triumph special meeting, there is an insufficient number of shares of Triumph common stock present or represented by proxy and voting in favor of the Triumph merger proposal, Triumph will move to adjourn the Triumph special meeting in order to enable the Triumph board of directors to solicit additional proxies in favor of the Triumph merger proposal. If the Triumph shareholders approve the Triumph adjournment proposal, Triumph may adjourn the Triumph special meeting and use the additional time to solicit additional proxies, including the solicitation of proxies from Triumph shareholders who have previously voted. Notice need not be given of the adjourned meeting if the time and place of the adjourned meeting are announced at the Triumph special meeting. If the meeting is adjourned to a date more than four months after the date fixed for the original meeting, Triumph must fix a new record date. Under the TBCA, if a quorum is not present at the Triumph special meeting, the chair of the meeting or the holders of a majority of the shares of those present in person or by proxy and entitled to vote at the Triumph special meeting may adjourn the meeting from time to time without notice to the Triumph shareholders until Triumph shareholders holding the amount of stock required for a quorum are present or represented.

Required Vote

Approval of the Triumph adjournment proposal requires the votes cast by the outstanding shares of Triumph common stock present or represented by proxy at the Triumph special meeting and entitled to vote on the proposal favoring the approval to exceed the votes cast opposing the approval. A quorum is not required for a vote on the Triumph adjournment proposal. If you mark “ABSTAIN” on your proxy, fail to submit a proxy or vote in person at the Triumph special meeting or if you fail to instruct your bank, broker or other nominee how to vote with respect to the Triumph adjournment proposal, it will have no effect on the proposal.

The Triumph board of directors recommends that Triumph shareholders vote “FOR” the Triumph adjournment proposal.

Other Matters to Come Before the Triumph Special Meeting

As of the date of this proxy statement/prospectus, the Triumph board of directors is not aware of any matters that will be presented for consideration at the Triumph special meeting other than as described in this proxy statement/prospectus. If, however, the Triumph board of directors properly brings any other matters before the Triumph special meeting, the persons named in the proxy will vote the shares represented thereby in accordance with the recommendation of the Triumph board of directors on any such matter.

INFORMATION ABOUT THE COMPANIES

Simmons First National Corporation

P.O. Box 7009

Pine Bluff, Arkansas 71611

Telephone: (870) 541-1000

Simmons is a financial holding company registered under the BHC Act. Simmons is headquartered in Arkansas and as of March 31, 2021, had, on a consolidated basis, total assets of $23.3 billion, total net loans of $12.0 billion, total deposits of $18.2 billion and total shareholders’ equity of $2.9 billion. Simmons conducts its banking operations through its subsidiary bank, Simmons Bank, in approximately 200 financial centers as of March 31, 2021, located throughout market areas in Arkansas, Kansas, Missouri, Oklahoma, Tennessee and Texas.

Simmons seeks to build shareholder value by focusing on strong asset quality, maintaining strong capital, managing its liquidity position, improving its operational efficiency and opportunistically growing its business, both organically and through acquisitions of financial institutions.

Simmons’ business philosophy centers on building strong, deep customer relationships through excellent customer service and integrity in its operations. While Simmons has grown in recent years into a regional financial institution and one of the largest bank/financial holding companies headquartered in the State of Arkansas, Simmons continues to emphasize, where practicable, a community-based mindset focused on local associates responding to local banking needs and making business decisions in the markets they serve. Those efforts, though, are buttressed by experienced, centralized support functions in select, critical areas. While Simmons serves a variety of customers and industries, Simmons is not dependent on any single customer or industry.

Simmons common stock is traded on Nasdaq under the symbol “SFNC.”

Additional information about Simmons may be found in the documents incorporated by reference into this proxy statement/prospectus. See the section entitled “Where You Can Find More Information.”

Landmark Community Bank

5880 Ridge Bend Road

Memphis, Tennessee 38120

Telephone: (901) 850-0555

Landmark is a Tennessee state-chartered bank. Landmark operates out of a main office in Memphis, Tennessee, with seven other branch offices located in in the Memphis and Nashville, Tennessee metropolitan areas. As of March 31, 2021, Landmark had total assets of $1.0 billion, total net loans of $0.8 billion, total deposits of $0.8 billion, and total shareholders’ equity of $102 million. Landmark does not have a class of securities registered under Section 12 of the Exchange Act and is not subject to the reporting requirements of Section 13(a) or 15(d) of the Exchange Act, and, accordingly, does not file documents or reports with the SEC.

Landmark conducts a full-service banking business in its service area, emphasizing the banking needs of individuals and small to medium-sized businesses. Landmark draws most of its customer deposits and conducts most of its lending transactions from and within a primary service area in Shelby County, the western area of Fayette County, Davidson County, and Williamson County, Tennessee.

The principal business of Landmark is to accept deposits from the public and to make loans and other investments. The principal sources of funds for Landmark’s loans and investments are demand, time, savings,

money market deposits, retirement accounts and other deposits (including negotiable order of withdrawal or NOW accounts). In addition, Landmark receives funds from amortization and prepayment of loans, sales to other lenders or institutions of loans or participations in loans, fees received from other lenders or institutions for servicing loans sold to such lenders or institutions, and borrowings. The principal sources of income for Landmark are interest and fees collected on loans, including fees received for servicing loans sold to other lenders or institutions, and, to a lesser extent, interest and dividends collected on other investments. The primary expenses of Landmark are interest paid on savings and other deposits (including NOW accounts), interest paid on other borrowings by Landmark, employee compensation, office expenses, and other overhead expenses.

The profitability of Landmark depends primarily on the extent to which Landmark’s earnings, primarily interest collected on loans, exceed Landmark’s expenses, primarily interest paid by Landmark on deposits used to fund its loans. The extent to which Landmark will be able to produce and maintain a positive spread between its income and expenses will be affected by, among other things, the actions of its competitors and changes in applicable laws and regulations, monetary control policies, general economic conditions, and the extent to which Landmark makes relatively short-term loans or makes long-term loans with variable or adjustable interest rates.

Landmark is authorized to make both secured and unsecured loans to individuals, partnerships, corporations, and other entities. Landmark’s lending business consists principally of making consumer loans to individuals and commercial loans to medium-sized business and professional concerns. Landmark may also emphasize the extension of relatively short-term loans or, to the extent it makes long-term loans, the extension of loans with variable or adjustable interest rates, in an effort to retain the flexibility to maintain a positive spread between its interest income and expense. The extent to which Landmark may be successful in implementing this lending policy, however, will depend in part upon consumer acceptance, the actions of Landmark’s competitors, and, to some extent, usury laws and other rules and regulations applicable to Landmark.

Historic financial information about Landmark is available from the FDIC on its website at www.fdic.gov. The website address of the FDIC is included as an inactive textual reference only. Except as specifically incorporated by reference into this proxy statement/prospectus, the information on this website is not a part of this proxy statement/prospectus and therefore is not incorporated by reference into this proxy statement/prospectus.

Triumph Bancshares, Inc.

5699 Poplar Avenue

Memphis, Tennessee 38119

Telephone: (901) 333-8800

Triumph is a bank holding company registered under the BHC Act. Triumph was incorporated in Tennessee in 2005 to serve as the bank holding company for and sole shareholder of Triumph Bank, which was incorporated as a Tennessee state-chartered bank in 2006. Triumph Bank is headquartered in Memphis, Tennessee, and currently operates from nine office locations (including six full-service branches and three loan production offices) in Arlington, Brentwood, Collierville, Germantown, Memphis, Nashville, and Union City in Tennessee. As of March 31, 2021, Triumph had consolidated total assets of $895.5 million, total net loans of $702.9 million, total deposits of $750.0 million, and total shareholders’ equity of $89.1 million. Triumph does not have a class of securities registered under Section 12 of the Exchange Act and is not subject to the reporting requirements of Section 13(a) or 15(d) of the Exchange Act, and, accordingly, does not file documents or reports with the SEC.

Triumph conducts a full-service banking business in its service area, emphasizing the banking needs of individuals and small to medium-sized businesses. Triumph draws most of its customer deposits and conducts most of its lending transactions from and within a primary service area in Shelby County, the western area of Fayette County, Davidson County, and Williamson County, Tennessee.

The principal business of Triumph is to accept deposits from the public and to make loans and other investments. The principal sources of funds for Triumph’s loans and investments are demand, time, savings, money market deposits, retirement accounts and other deposits (including NOW accounts). In addition, Triumph receives funds from amortization and prepayment of loans, sales to other lenders or institutions of loans or participations in loans, fees received from other lenders or institutions for servicing loans sold to such lenders or institutions, and borrowings. The principal sources of income for Triumph are interest and fees collected on loans, and, to a lesser extent, interest and dividends collected on other investments. The primary expenses of Triumph are interest paid on savings and other deposits (including NOW accounts), interest paid on other borrowings by Triumph, employee compensation, office expenses, and other overhead expenses.

The profitability of Triumph depends primarily on the extent to which Triumph’s earnings, primarily interest collected on loans, exceed Triumph’s expenses, primarily interest paid by Triumph on deposits used to fund its loans. The extent to which Triumph will be able to produce and maintain a positive spread between its income and expenses will be affected by, among other things, the actions of its competitors and changes in applicable laws and regulations, monetary control policies, general economic conditions, and the extent to which Triumph makes relatively short-term loans or makes long-term loans with variable or adjustable interest rates.

Triumph is authorized to make both secured and unsecured loans to individuals, partnerships, corporations, and other entities. Triumph’s lending business consists principally of making consumer loans to individuals and commercial loans to medium-sized business and professional entities.

Historic financial information about Triumph is available from the Federal Financial Institutions Examination Council, or the FFIEC, on its website at www.ffiec.gov. The website address of the FFIEC is included as an inactive textual reference only. Except as specifically incorporated by reference into this proxy statement/prospectus, the information on this website is not a part of this proxy statement/prospectus and therefore is not incorporated by reference into this proxy statement/prospectus.

THE LANDMARK MERGER

The following discussion contains material information regarding the Landmark merger. The discussion is subject to, and qualified in its entirety by reference to, the Landmark merger agreement, which is attached to this proxy statement/prospectus as Annex A and is incorporated by reference into this proxy statement/prospectus. The following is not intended to provide factual information about the parties or any of their respective subsidiaries or affiliates. This discussion does not purport to be complete and may not contain all of the information about the Landmark merger that is important to you. We urge you to read the Landmark merger agreement carefully and in its entirety, as it is the legal document governing the Landmark merger.

Terms of the Landmark Merger

Each of the Simmons board of directors, the Simmons Bank board of directors and the Landmark board of directors approved the Landmark merger agreement. The Landmark merger agreement provides that, among other things, Landmark will merge with and into Simmons Bank, with Simmons Bank as the surviving bank in the merger.

Based on the assumptions set forth below, at the Landmark effective time, each share of Landmark common stock that is issued and outstanding immediately prior to the Landmark effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, the Landmark merger consideration. In the aggregate, Simmons expects to issue approximately [ ] million shares of Simmons common stock and pay approximately $[ ] million (minus the cash payment for outstanding Landmark stock options) to Landmark shareholders upon completion of the Landmark merger, subject to certain conditions and potential adjustments under the Landmark merger agreement. The Landmark merger consideration is based on the assumption that (i) [ ] shares of Landmark common stock are issued and outstanding and (ii) [ ] shares of Landmark common stock are subject to outstanding Landmark stock options with a weighted average exercise price of $[ ], in each case, immediately prior to the Landmark effective time. In addition, we have assumed that the Landmark/Simmons average closing price is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

Landmark shareholders are being asked to approve the Landmark merger agreement, including the Landmark merger and all transactions contemplated thereby. See the section entitled “The Merger Agreements” for additional and more detailed information regarding the legal documents that govern the Landmark merger, including information about the conditions to consummation of the Landmark merger and the provisions for terminating or amending the Landmark merger agreement.

Background of the Landmark Merger

Landmark’s management and the Landmark board of directors periodically evaluate and consider various strategic alternatives, with the ultimate goal of optimizing shareholder value. Various options, such as enhancing organic growth, raising additional capital, acquiring loans or assuming deposits from other institutions, merging with a similar-sized organization, and selling Landmark are among the alternatives the Landmark board of directors has considered and evaluated on an on-going basis.

As a part of its on-going evaluations, and in light of national and regional market conditions in which Landmark operates, in the summer of 2017 the Landmark board of directors authorized Landmark’s chief executive officer to contact potential third parties to initiate preliminary discussions regarding whether there was any interest in pursuing a transaction. As a result of these preliminary inquiries, Landmark held more substantive discussions with four financial institutions over the course of 2018, including Simmons. None of the institutions other than Simmons expressed a desire for further discussions and none of these institutions other than Simmons entered into any non-disclosure agreements with Landmark.

In November 2018, Landmark and Simmons signed a customary non-disclosure agreement. The following month, Landmark’s Chief Executive Officer and Chief Financial Officer and Simmons’ Chief Executive Officer, Chief Financial Officer, Chief Banking Officer and Chief Administrative Officer held an in-person meeting in Memphis, Tennessee at an off-site location to discuss the potential for a transaction between the two parties.

In March 2019, Simmons made an oral offer to acquire Landmark for shares of Simmons common stock with the following terms: 100% stock offer, fixed price of $105 million, and shares would not exceed 4,000,000 or be less than 3,500,000. In April 2019, the Landmark board of directors met to consider the oral offer. At this meeting, a representative of Landmark’s financial advisor, Olsen Palmer, discussed with the Landmark board of directors the relative financial considerations with respect to such offer.

In April 2019, at the direction of the Landmark board of directors, a representative of Olsen Palmer, on behalf of Landmark, made a verbal counterproposal to Simmons with the following terms: 4.3 million shares of Simmons of common stock and $5.9 million in cash. Simmons verbally indicated its agreement to such counterproposal, but did not provide a written offer or letter of intent.

In May 2019, the Landmark board of directors met to further discuss the oral offer from Simmons. Following the meeting, Landmark offered three alternative counterproposals to Simmons: one proposal would be based on the same structure as Simmons’ prior verbal offer but with 0.2 million additional shares of Simmons common stock; one proposal would match Simmons’ prior verbal offer but include a special dividend of $0.25 per share of Landmark common stock payable to Landmark shareholders by Landmark between signing and closing; and one proposal would match Simmons’ prior verbal offer but include a floor mechanism such that the per share consideration to Landmark shareholders would not be less than $5.00. On the same date, Simmons communicated to Landmark that it was no longer interested in pursuing a transaction at that time, because it had other larger transactions it was pursuing.

In September 2019, Landmark engaged Olsen Palmer to assist Landmark in evaluating various strategic alternatives. During the remainder of 2019, Landmark had discussions with other financial institutions on a confidential basis, none of which were the financial institutions Landmark had discussions with in 2018. As a result of these conversations, several financial institutions signed non-disclosure agreements with Landmark and conducted preliminary diligence. None of these other financial institutions made an offer to acquire Landmark.

In January 2020, Simmons contacted the Chief Executive Officer of Landmark to schedule an additional meeting. Representatives of Landmark and Simmons met in February 2020 in Memphis at an off-site location and on February 12, 2020, Simmons and Landmark entered into a new non-disclosure agreement, which was substantially similar to the agreement signed in November 2018.

On February 15, 2020, Simmons submitted a new letter of intent to Landmark for its consideration, offering to acquire Landmark for a combination of 4.3 million shares of Simmons common stock and $10 million cash in aggregate transaction value. On February 18, 2020, the Landmark board of directors met and approved the terms of the letter of intent. On February 19, 2020, Landmark countersigned the letter of intent.

On March 4, 2020, Simmons withdrew its letter of intent from February 15, 2020, citing the concerns and uncertainty regarding the COVID-19 pandemic as the reason for its withdrawal.

Throughout the remainder of 2020, Landmark, its management and the Landmark board of directors, focused their energy on addressing the many challenges brought about due to the COVID-19 pandemic.

In January 2021, Simmons reached out to Landmark to schedule a follow-up meeting. The Chief Executive Officer of Landmark and the Chief Executive Officer of Simmons met in February 2021 in Memphis, Tennessee at an off-site location, and confirmed that the non-disclosure agreement entered into on February 12, 2020 remained binding and effective.

On February 12, 2021, Simmons submitted a new letter of intent to Landmark, offering to acquire Landmark for either $130 million cash or 4,650,000 shares of Simmons common stock valued at approximately $124.3 million. Landmark made a counterproposal for 4,650,000 shares of Simmons common stock and $15 million in cash consideration. Simmons provided a revised letter of intent on February 16, 2021, offering a combination of 4.5 million shares of Simmons common stock and $7 million in cash consideration in aggregate transaction value for the acquisition of Landmark, including the cash-out of stock options as part of the overall transaction offer.

On February 19, 2021, the Landmark board of directors met to consider the revised offer from Simmons. A representative of Olsen Palmer participated in the meeting and discussed with the Landmark board of directors this offer. After discussion among the Landmark board of directors, the board approved the terms set forth in Simmons’ letter of intent of February 12, 2021 and authorized Landmark management to countersign the letter of intent. Simmons submitted an expanded due diligence request list to Landmark on the same date.

In April 2021, Simmons submitted an initial draft of the Landmark merger agreement to Baker, Donelson, Bearman, Caldwell & Berkowitz, PC, Landmark’s counsel, which we refer to as Baker Donelson. During April and May 2021, the parties negotiated the terms of the Landmark merger agreement and the related transaction documents, including the Landmark voting agreements, and discussed such documentation with their legal and financial advisors. During this period, Landmark and Simmons exchanged several additional drafts of the Landmark merger agreement and the related transaction documents, including the Landmark voting agreements. In addition, during this time, Landmark’s management conducted diligence on Simmons, while Simmons continued its diligence on Landmark.

On May 25, 2021, the Landmark board of directors met to discuss the terms of the Landmark merger agreement and related transaction documents. A representative of Olsen Palmer attended this meeting and discussed the financial terms of the Landmark merger and provided its opinion orally 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 Olsen Palmer as set forth in its opinion, the Landmark merger consideration to be received by Landmark shareholders, as described in the section entitled “—Opinion of Landmark’s Financial Advisor,” in the proposed Landmark merger was fair, from a financial point of view, to the holders of Landmark common stock. For a description of the Olsen Palmer opinion, please refer to the section entitled “—Opinion of Landmark’s Financial Advisor.” Baker Donelson also attended this meeting and discussed the key terms of the Landmark merger agreement with the Landmark board of directors.

After listening to the presentations by its advisors and discussing the terms of the proposed Landmark merger agreement, the terms of the Landmark voting agreements, and the matters discussed during that meeting and prior meetings of the Landmark board of directors, including the factors described in the section entitled “—Landmark’s Reasons for the Landmark Merger and Recommendations of the Landmark Board of Directors,” upon a motion duly made and seconded, the Landmark board of directors determined that the Landmark merger agreement, including the Landmark merger and the other transactions contemplated thereby, was in the

best interests of Landmark and its shareholders, and approved the Landmark merger agreement, including the Landmark merger and the other transactions contemplated by the Landmark merger agreement and recommended that the shareholders of Landmark approve the Landmark merger.

On June 4, 2021, the Simmons board of directors held a meeting to consider the terms of the proposed Landmark merger and Landmark merger agreement. At the meeting, members of Simmons’ management reported on the status of due diligence and negotiations with Landmark. Also at the meeting, Simmons’ financial advisor reviewed with the Simmons board of directors financial aspects of the proposed Landmark merger. At the meeting, Simmons’ internal legal counsel reviewed with the Simmons board of directors its fiduciary duties and reviewed the key terms of the Landmark merger agreement and related agreements (including the Landmark voting agreements), as described elsewhere in this proxy statement/prospectus, including a summary of the provisions relating to governance of the combined company and the provisions relating to employee matters.

After considering the proposed terms of the Landmark merger agreement, the terms of the Landmark voting agreements, and taking into consideration the matters discussed during that meeting and prior meetings of the Simmons board of directors, including the factors described in the section entitled “—Simmons’ Reasons for the Landmark Merger,” the Simmons board of directors determined that the Landmark merger was consistent with Simmons’ business strategies and in the best interests of Simmons and Simmons shareholders and the Simmons board of directors voted to approve and adopt the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement.

Following the board meetings of Landmark and Simmons, on June 4, 2021, Landmark and Simmons signed the Landmark merger agreement; each of the directors and certain executive officers of Landmark signed the Landmark voting agreements; and Olsen Palmer provided the Landmark board of directors its written opinion. On June 7, 2021, the parties issued a joint press release announcing the execution of the Landmark merger agreement.

Landmark’s Reasons for the Landmark Merger and Recommendation of the Landmark Board of Directors

At the special board meeting held on May 25, 2021, the Landmark board of directors approved the Landmark merger agreement, the Landmark merger and the transactions contemplated by the Landmark merger agreement, determining that the Landmark merger is advisable and fair to, and in the best interest of, Landmark and its shareholders.

In reaching its decision to approve the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement and to recommend that Landmark shareholders vote “FOR” the Landmark merger proposal, the Landmark board of directors evaluated the Landmark merger in consultation with Landmark’s management, as well as Landmark’s financial, legal, and other professional advisors. The Landmark board of directors considered a number of factors including, without limitation, the following:

information with respect to the businesses, earnings, operations, financial conditions, prospects, capital levels, and asset qualities of Landmark and Simmons, both individually and after giving effect to the Landmark merger;

the market value of Simmons common stock prior to the execution of the Landmark merger agreement, the prospects for future appreciation of Simmons common stock, and the history of dividends payable by Simmons to holders of Simmons common stock;

the market for and trading liquidity of Simmons common stock;

the value to be received by Landmark shareholders in the Landmark merger as compared to potential Landmark shareholder value for Landmark as a stand-alone entity;

the opinion dated June 4, 2021, of Olsen Palmer to the Landmark board of directors as to the fairness, from a financial point of view and as of the date of the opinion, to the holders of Landmark common stock of the Landmark merger consideration to be received by such holders in the proposed Landmark merger, as more fully described below in the section entitled “—Opinion of Landmark’s Financial Advisor”;

the perceived risks and uncertainties attendant to Landmark’s operation as an independent banking organization, including the risks and uncertainties related to competition in market areas of Landmark Bank, increased operating and regulatory costs, interest rate environments, and potentially increased capital requirements;

the expected impact of the Landmark merger on constituencies served by Landmark, including its borrowers, depositors, and communities;

the effects of the Landmark merger on Landmark’s employees, including the ability of those employees to participate in Simmons’ benefit plans;

the understanding that the structure and terms of the Landmark merger would result in favorable tax consequences to the shareholders of Landmark;

the review of potential strategic affiliation partners other than Simmons, the prospects of such other potential strategic affiliation partners, and the (lack of) likelihood of a more favorable transaction with such potential affiliation partners;

consideration of the alternatives to the Landmark merger, including remaining independent and growing organically and then selling to or merging with another institution at a future time, attempting to raise outside capital through a public sale of Landmark securities, and engaging in a merger transaction with a similarly-sized financial institution;

the current environment in the financial services industry, including national, regional, and local economic conditions, the interest rate environment, continued consolidation, uncertainties in the regulatory climate for financial institutions, the current environment for community banks, including in the western and middle Tennessee markets where Landmark operates, and current financial market conditions and the likely effects of these factors on Landmark’s and Simmons’ potential growth, development, productivity, and strategic options;

that a portion of the aggregate Landmark merger consideration would be paid through a fixed number of shares of Simmons common stock, such that the nominal value of the aggregate Landmark merger consideration would increase or decrease with the fluctuation of the day-to-day market price of Simmons common stock;

the possible disruption to Landmark’s business that could result from the announcement of the Landmark merger and the resulting distraction of management’s attention from the day-to-day operations of Landmark’s business;

that the Landmark merger agreement restricts the conduct of Landmark’s business prior to the completion of the Landmark merger which, subject to specific exceptions, could delay or prevent Landmark from undertaking business opportunities that may arise or any other action it would otherwise take with respect to the operations of Landmark absent the pending Landmark merger;

the risks associated with the provision in the Landmark merger agreement that Landmark is not permitted to solicit or respond to any acquisition proposals, except for the limited right to terminate the Landmark merger agreement and pay a termination fee in the event Landmark receives an unsolicited superior offer, which fee may deter others from proposing an alternative transaction that may be more advantageous to the Landmark shareholders;

the risk that, while Landmark expects that the Landmark merger will be consummated, there can be no assurance that all conditions to the parties’ obligations to complete the Landmark merger will be satisfied, including the risk that Landmark shareholder approval might not be obtained and, as a result, the Landmark merger may not be consummated; and

the anticipated benefits to Landmark of being acquired by a larger financial institution that would be better equipped to respond to economic and industry developments and to develop and build on their positions in existing markets.

The foregoing discussion of the information and factors considered by the Landmark board of directors is not intended to be exhaustive, but, rather, includes all material factors considered by the Landmark board of directors. In reaching its decision to approve the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement, the Landmark board of directors did not quantify, rank or otherwise assign any relative weights to the factors considered, and individual directors may have given different weights to different factors. The Landmark board of directors considered all these factors as a whole, including through its discussions with and questioning of, Landmark’s management and Landmark’s financial, legal and other professional advisors, and overall considered the factors to be favorable to, and supportive of its determination to approve the Landmark merger agreement and the transactions contemplated thereby, including the Landmark merger.

The Landmark board of directors collectively made its determination with respect to the Landmark merger based on the conclusion reached by its members, based on the factors that each of them considered appropriate, that the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement are in the best interests of Landmark and its shareholders and that the benefits expected to be achieved from the Landmark merger outweigh the potential risks and vulnerabilities.

This explanation of the Landmark 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.”

For the reasons set forth above, the Landmark board of directors approved the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement, determining that they are advisable and fair to, and in the best interest of, Landmark and its shareholders and recommends that Landmark shareholders vote “FOR” the Landmark merger proposal.

Each of the directors and certain executive officers of Landmark, in their capacities as individuals, entered into Landmark voting agreements with Simmons and Landmark pursuant to which they agreed to vote “FOR” the Landmark merger proposal and “FOR” any other matters required to be approved by the Landmark shareholders in furtherance of the Landmark merger proposal. For more information regarding the Landmark voting agreements, please see the section entitled “The Merger Agreements—Voting Agreements.”

Opinion of Landmark’s Financial Advisor

Landmark retained Olsen Palmer to render financial advisory and investment banking services and to act as the exclusive financial advisor to Landmark in connection with a potential strategic combination. Olsen Palmer is an investment banking firm specializing in community bank mergers and acquisitions. Landmark selected Olsen Palmer as

its financial advisor on the basis of its experience and expertise in representing community banks in similar transactions and its familiarity with Landmark. Olsen Palmer, as part of its investment banking services, is regularly engaged in the valuation of financial institutions and their securities in connection with mergers and acquisitions.

In its capacity as financial advisor, Olsen Palmer provided an opinion to the Landmark board of directors in connection with the Landmark merger. At the meeting of the Landmark board on May 25, 2021, Olsen Palmer provided an oral opinion to the Landmark board of directors (which was subsequently confirmed in writing by delivery of Olsen Palmer’s written opinion dated June 4, 2021) that, based upon and subject to the various factors, assumptions and limitations set forth in such opinion, Olsen Palmer representatives’ experience as investment bankers, Olsen Palmer’s work as described in such opinion and other factors Olsen Palmer deemed relevant, as of such date, the Landmark merger consideration to be received by Landmark shareholders in the proposed Landmark merger was fair, from a financial point of view, to Landmark shareholders. The Olsen Palmer written opinion, dated June 4, 2021, is sometimes referred to as the Olsen Palmer opinion. The full text of the Olsen Palmer opinion, which sets forth, among other things, the assumptions made, procedures followed, matters considered and limitations on the review undertaken by Olsen Palmer in rendering its opinion, is attached to this proxy statement/prospectus as Annex E. The summary of the Olsen Palmer opinion set forth herein is qualified in its entirety by reference to the full text of the opinion. Landmark shareholders should read the full text of the Olsen Palmer opinion carefully and in its entirety.

The Olsen Palmer opinion is addressed to the Landmark board of directors, is directed only to the fairness, from a financial point of view, to the Landmark shareholders of the Landmark merger consideration to be received by Landmark shareholders in the Landmark merger with Simmons, and does not constitute a recommendation to any shareholder as to how such shareholder should vote or act on any matters relating to the Landmark merger. Olsen Palmer expressed no opinion as to the fairness of the Landmark merger consideration to the creditors or other constituencies of Landmark. The Olsen Palmer opinion is directed only to the fairness, from a financial point of view, of the Landmark merger consideration to the Landmark shareholders and does not address the underlying business decision of Landmark to engage in the Landmark merger or the relative merits of the Landmark merger as compared to any other alternative business strategies that might exist for Landmark. Olsen Palmer did not express any opinion as to the fairness of the amount or nature of the compensation to be received in the Landmark merger by any officer, director, or employee, or class of such persons, relative to the compensation to be received in the Landmark merger by any other shareholder. The Olsen Palmer opinion should not be construed as creating any fiduciary duty on the part of Olsen Palmer to any party or person. The Olsen Palmer opinion was not reviewed or issued by a fairness opinion committee. Olsen Palmer has not been requested to opine as to, and the Olsen Palmer opinion does not express an opinion as to or otherwise address, among other things: (i) the fairness of any portion or aspect of the Landmark merger to any one class or group of Landmark or any other party’s security holders or other constituents vis-à-vis any other class or group of Landmark’s or such other party’s security holders or other constituents (including, without limitation, the allocation of any consideration amongst or within such classes or groups of security holders or other constituents), or (ii) the fairness, financial or otherwise, of the amount, nature or any other aspect of any compensation to or consideration payable to or received by any officers, directors or employees of any party to the Landmark merger, any class of such persons or any other party, relative to the Landmark merger consideration or otherwise. Olsen Palmer expressed no opinion as to the actual value of Simmons common stock when issued in the Landmark merger or the prices at which Landmark common stock or Simmons common stock will trade following announcement of the Landmark merger or at any future time.

In performing its review, and for purposes of rendering its opinion, Olsen Palmer relied upon the accuracy and completeness of all of the financial and other information that was available to it from public sources, that was provided to Olsen Palmer by Landmark, its representatives or representatives of Simmons or that was otherwise reviewed by Olsen Palmer and has assumed, without independent verification, such accuracy and completeness of all such information. Olsen Palmer further relied on the assurances of the management of Landmark that they are not aware of any facts or circumstances that would make any of such information inaccurate or misleading. Olsen Palmer has not been asked to and has not undertaken an independent verification of any of such information and does not assume any responsibility or liability for the accuracy or completeness

thereof. With Landmark’s consent, Olsen Palmer relied upon the advice Landmark has received from its legal, accounting and tax advisors as to all legal, accounting and tax matters relating to the Landmark merger that is contemplated by the Landmark merger agreement and Olsen Palmer assumed that all such advice is correct.

In connection with its opinion, Olsen Palmer made such reviews, analyses and inquiries as it deemed necessary and appropriate under the circumstances. Among other things, Olsen Palmer reviewed:

a draft version of the Landmark merger agreement;

certain financial statements and other historical financial information of Landmark and Simmons that Olsen Palmer deemed relevant;

internal financial projections for Landmark for the year ending December 31, 2021 and estimated long-term annual earnings and balance sheet growth rates for the years ending December 31, 2022, December 31, 2023, December 31, 2024, December 31, 2025, and December 31, 2026 as provided by Landmark;

publicly available “street estimates” for Simmons, as well as assumed long-term dividends, and growth rates for Simmons, as discussed with representatives of Simmons;

a comparison of certain financial information for Landmark with similar institutions for which publicly available information is available;

the financial terms of certain recent business combinations in the commercial banking industry, to the extent publicly available;

an analysis of the relative contribution that Landmark and Simmons will make to the combined company;

an estimated range of the intrinsic value of Landmark based on internal financial projections for Landmark as provided by Landmark;

the estimated pro forma financial impact of the Landmark merger, based on assumptions relating to transaction expenses, acquisition accounting adjustments, and cost savings as communicated to Olsen Palmer by representatives of Simmons;

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

such other information, financial studies, analyses and investigations and financial, economic and market criteria as Olsen Palmer considered relevant.

Olsen Palmer also discussed with certain members of senior management of Landmark and its representatives the business, financial condition, results of operations and prospects of Landmark. Olsen Palmer held similar discussions with representatives of Simmons regarding the business, financial condition, results of operations, and prospects of Simmons.

The Olsen Palmer opinion is necessarily based on financial, economic, market and other conditions as in effect on, and the information made available to it as of June 4, 2021. Events occurring after June 4, 2021 could materially affect the Olsen Palmer opinion. Olsen Palmer has not undertaken to update, revise, reaffirm or withdraw its opinion or otherwise comment upon events occurring after June 4, 2021.

Several analytical methodologies have been employed and no one method of analysis should be regarded as critical to the overall conclusion reached by Olsen Palmer. Each analytical technique has inherent strengths

and weaknesses, and the nature of the available information may further affect the value of particular techniques. The overall conclusions Olsen Palmer reached are based on all the analysis and factors presented, taken as a whole, and also on application of Olsen Palmer’s own experience and judgment. Such conclusions may involve significant elements of subjective judgment and qualitative analysis. Olsen Palmer therefore gives no opinion as to the value or merit standing alone of any one or more parts of the analyses.

The following summarizes the material financial analyses that were considered by Olsen Palmer in rendering its opinion. The summary below is not a complete description of the analyses underlying the Olsen Palmer opinion or the presentation made by Olsen Palmer to the Landmark board of directors, but is a summary of all material analyses performed and presented by Olsen Palmer. No company or transaction used in the analyses described below is identical or directly comparable to Landmark, Simmons, or the contemplated merger.

Summary of Financial Terms of Landmark Merger Agreement. The financial terms of the Landmark merger agreement provide that Landmark shareholders shall be entitled to receive 4,500,000 shares of Simmons common stock and $7,000,000 in cash. Based on Simmons’s closing price on June 3, 2021 of $30.86, the implied deal value per fully diluted share equaled $6.50 and the aggregate transaction value approximated $145.9 million. Olsen Palmer calculated that the aggregate transaction value of $145.9 million represented:

143 percent of Landmark’s March 31, 2021 tangible book value;

14.0 times Landmark’s March 31, 2021 last twelve months earnings;

10.9 times Landmark’s March 31, 2021 last twelve months earnings plus cost savings;

14.5 percent of Landmark’s March 31, 2021 total assets; and

7.0 percent premium to Landmark’s March 31, 2021 core deposits.

Simmons Selected Companies Analysis. As part of its analysis, Olsen Palmer reviewed publicly available information to compare selected financial and market trading information for Simmons and a group of eight financial institutions which (i) were banks with common stock listed on the Nasdaq or the New York Stock Exchange, or NYSE; (ii) were headquartered in the United States; (iii) had total assets as of March 31, 2021 between $17.5 and $25.0 billion; (iv) had return on average assets over the twelve months ended March 31, 2021 between 0.75% and 1.25%; and (v) had nonperforming assets as a percentage of total assets as of March 31, 2021 of less than 1.0%. These eight financial institutions were as follows:

·	Atlantic Union Bankshares Corporation	·	First Interstate BancSystem, Inc.
·	Bank of Hawaii Corporation	·	Heartland Financial USA, Inc.
·	Customers Bancorp, Inc.	·	United Community Banks, Inc.
·	First Hawaiian, Inc.	·	Washington Federal, Inc.

Olsen Palmer noted the following selected financial measures, in each case as of and for the relevant period ended March 31, 2021:

	Total Assets ($ billions)		LTM Return on Average Assets			Nonperforming Assets to Total Assets
Median	$	19.2		1.01	%		0.37	%
Mean	$	19.9		1.00	%		0.39	%
Low	$	18.2		0.82	%		0.21	%
High	$	23.5		1.23	%		0.64	%
Simmons	$	23.3		1.11	%		0.56	%

Olsen Palmer analyzed various financial multiples for each company as calculated by S&P Global Market Intelligence, based on trading prices as of June 3, 2021 and financial metrics for the relevant period ended March 31, 2021, including trading price per share to last twelve months’ earnings per share, trading price per share to tangible common equity per share, trading price per share to total assets, and the core deposit premium implied by the market capitalization. Olsen Palmer reviewed the mean, median, high, and low values for each metric of the selected companies. The results of the selected companies analysis are summarized below:

	Price to LTM Earnings per Share			Price to Tangible Common Equity per Share			Price to Total Assets			Core Deposit Premium
Median		16.1	x		199.2	%		15.8	%		5.4	%
Mean		15.3	x		195.2	%		14.0	%		6.4	%
Low		8.5	x		134.0	%		7.0	%		2.8	%
High		19.8	x		270.0	%		16.3	%		11.0	%
Simmons		13.7	x		191.3	%		14.3	%		10.0	%

Landmark Selected Companies Analysis. Olsen Palmer analyzed the relative valuation multiples as calculated by S&P Global Market Intelligence of 15 publicly-traded banks which (i) were banks with common stock listed on the Nasdaq or NYSE; (ii) were headquartered in the U.S.; (iii) had total assets as of March 31, 2021 between $500 million and $1.5 billion; (iv) had a return on average assets over the twelve months ended March 31, 2021 between 0.75% to 1.25%; and (v) had nonperforming assets as a percentage of total assets as of March 31, 2021 less than 1.0%. Merger targets were excluded from the selected companies. These 15 financial institutions were as follows:

·	Auburn National Bancorporation, Inc.	·	IF Bancorp, Inc.
·	Community West Bancshares	·	Limestone Bancorp, Inc.
·	Cortland Bancorp	·	Ohio Valley Banc Corp.
·	Emclaire Financial Corp	·	OP Bancorp
·	First Capital, Inc.	·	Richmond Mutual Bancorporation, Inc.
·	First Community Corporation	·	Salisbury Bancorp, Inc.
·	First National Corporation	·	Virginia National Bankshares Corporation
·	Home Federal Bancorp, Inc. of Louisiana

Olsen Palmer noted the following selected financial measures, in each case as of and for the relevant period ended March 31, 2021:

	Total Assets ($ millions)		LTM Return on Average Assets			Nonperforming Assets to Total Assets
Median	$	1,056		0.97	%		0.48	%
Mean	$	1,084		0.97	%		0.46	%
Low	$	563		0.76	%		0.08	%
High	$	1,492		1.21	%		0.99	%
Landmark	$	1,007		1.04	%		0.66	%

Olsen Palmer analyzed various financial multiples for each company as calculated by S&P Global Market Intelligence, based on trading prices as of June 3, 2021 and financial metrics for the relevant period ended March 31, 2021, including trading price per share to last twelve months’ earnings per share, trading price per share to tangible common equity per share, trading price per share to total assets, and the core deposit premium implied by the market capitalization. Olsen Palmer reviewed the mean, median, high, low, 40th percentile, and 60th percentile values for each metric of the selected companies. The results of the selected companies analysis are summarized below:

	Price to LTM Earnings per Share			Price to Tangible Common Equity per Share			Price to Total Assets			Core Deposit Premium Implied by Market Capitalization
Median		11.1	x		114.0	%		10.3	%		1.5	%
Mean		12.0	x		115.3	%		11.0	%		2.3	%
Low		8.8	x		86.3	%		7.4	%		-3.0	%
High		17.9	x		148.9	%		16.5	%		13.1	%
40^thPercentile		11.0	x		112.7	%		9.8	%		1.4	%
60^thPercentile		11.7	x		117.4	%		10.3	%		1.9	%

Landmark Selected Transactions Analysis. Olsen Palmer analyzed publicly available information relating to 11 acquisitions of banks that satisfied the following selected search criteria: transactions (i) which were announced between January 1, 2020 and June 4, 2021; (ii) where targets were headquartered in the U.S.; (iii) where targets had total assets between $550 million and $1.5 billion; (iv) where targets had a return on average assets over the twelve months prior to the transaction announcement between 0.50% and 1.50%; and (v) where targets had nonperforming assets as a percentage of total assets as of March 31, 2021 less than 1.50%. The selected transactions consisted of the following (buyer / seller):

·	United Community Banks, Inc./Aquesta Financial Holdings, Inc.	·	BancorpSouth Bank/National United Bancshares, Inc.
·	Equity Bancshares, Inc./American State Bancshares, Inc.	·	First Mid Bancshares, Inc./LINCO Bancshares, Inc.
·	Bank of Marin Bancorp/American River Bankshares	·	Dollar Mutual Bancorp/Standard AVB Financial Corp.
·	Shore Bancshares, Inc./Severn Bancorp, Inc.	·	Hanover Bancorp Inc./Savoy Bank
·	Stock Yards Bancorp, Inc./Kentucky Bancshares, Inc.	·	Enterprise Financial Services Corp/Seacoast Commerce Banc Holdings
·	First Busey Corporation/Cummins-American Corp.

Olsen Palmer noted the following selected financial measures of the targets, in each case as of prior to the transaction announcement and for Landmark as of March 31, 2021:

	Total Assets ($ millions)		LTM Return on Average Assets			Nonperforming Assets to Total Assets
Median	$	953		0.91	%		0.76	%
Mean	$	984		0.93	%		0.73	%
Low	$	597		0.58	%		0.15	%
High	$	1,395		1.31	%		1.26	%
Landmark	$	1,007		1.04	%		0.66	%

Olsen Palmer analyzed various financial multiples for each transaction as calculated by S&P Global Market Intelligence including deal value to last twelve months’ earnings plus cost savings prior to transaction announcement, deal value to tangible common equity, deal value to total assets, and the core deposit premium implied by the deal value. Olsen Palmer reviewed the mean, median, high, low, 40^th percentile, and 60^th percentile values for each such metric of the acquired institution in each such transaction. The results of the selected transactions analysis are summarized below:

	Deal Value to LTM Earnings Plus Cost Savings			Deal Value to Tangible Common Equity			Deal Value to Total Assets			Core Deposit Premium Implied by the Deal Value
Median		8.4	x		149.2	%		15.2	%		1.5	%
Mean		9.4	x		148.3	%		13.6	%		3.5	%
Low		5.7	x		106.6	%		9.8	%		1.1	%
High		12.3	x		214.3	%		17.2	%		7.0	%
40^thPercentile		8.2	x		139.9	%		12.4	%		1.4	%
60^thPercentile		11.0	x		156.3	%		15.3	%		3.4	%

Relative Contribution Analysis. Olsen Palmer analyzed the relative standalone contribution of Simmons and Landmark to various pro forma balance sheet and income statement items and the combined market capitalization of the combined entity. This analysis did not include purchase accounting adjustments or cost savings. To perform this analysis, Olsen Palmer used (i) balance sheet and income statement data for Simmons and Landmark as of or for the 12-month period ended March 31, 2021 and (ii) 2019 and 2020 net income. The results of Olsen Palmer’s analysis are set forth in the following table:

	Simmons First National Corporation % of Total			Landmark % of Total
Balance Sheet:
Total Assets		95.9	%		4.1	%
Gross Loans Held for Investment		93.9	%		6.1	%
Deposits		95.6	%		4.4	%
Tangible Common Equity		94.5	%		5.5	%
Total Equity		96.6	%		3.4	%
Income Statement:
Net Income – 2019		96.3	%		3.7	%
Net Income – 2020		96.2	%		3.8	%
Net Income – LTM		95.9	%		4.1	%

Landmark Discounted Cash Flow Analysis. Olsen Palmer analyzed the discounted present value of Landmark projected free cash flows for the years ending December 31, 2021 through December 31, 2026. Olsen Palmer estimated cash flows based on dividendable common equity, defined as Tier 1 Capital in excess of a minimum Tier 1 Capital ratio of 9.0%. Olsen Palmer applied a range of price to earnings multiples of 10.3x to 12.3x, based on review of price/earnings multiples for relevant indices of publicly traded bank stocks, to Landmark estimated calendar year 2026 net income to derive a terminal value.

The projected cash flows and terminal values were discounted using an estimated cost of equity capital for Landmark derived by the Duff & Phelps discount rate build-up method consisting of the sum of a risk-free rate, equity risk premium, size premium, and industry risk premium. Olsen Palmer applied a range of discount rates of 13.5% to 15.5%.

The calculations resulted in a rage of implied values of $138.3 million to $166.4 million.

The discounted cash flow analysis is a widely used valuation methodology that relies on numerous assumptions, including asset growth rates, earnings growth rates, discount rates, and terminal multiples, and the results of such methodology are highly dependent on these assumptions. The financial forecasts from 2021 – 2026 were provided by Landmark management.

Financial Impact Analysis. Olsen Palmer performed a pro forma financial impact analysis that combined projected income statement and balance sheet information of Simmons and Landmark. Using (i) publicly available consensus “street estimates” for Simmons and assumed long-term dividends, and growth rates for Simmons as provided by its representatives, (ii) pro forma assumptions regarding the impact of the Landmark merger, based on assumptions relating to transaction expenses, acquisition accounting adjustments, and cost savings as communicated to Olsen Palmer by representatives of Simmons, and (iii) financial forecasts and projections relating to the net income and tangible common equity of Landmark provided by Landmark management, Olsen Palmer analyzed the potential financial impact of the Landmark merger on certain projected financial results of Simmons. This analysis indicated that the Landmark merger is expected to be accretive to Simmons’s estimated earnings per share beginning in 2022. The analysis also indicated that the Landmark merger is expected to be accretive to tangible book value per share for Simmons and that Simmons would maintain capital ratios in excess of those required for Simmons to be considered well-capitalized under existing regulations. For all of the above analyses, the actual results achieved by Landmark and Simmons prior to and following the Landmark merger will vary from the projected results, and the variations may be material.

Olsen Palmer’s Compensation and Other Relationships with Landmark and Simmons. No limitations were imposed by the Landmark board of directors on Olsen Palmer with respect to the investigations made or procedures followed in rendering its opinion. Neither Olsen Palmer nor the individuals involved in providing the Olsen Palmer opinion has any present or contemplated future ownership interest in Landmark. Olsen Palmer is acting as Landmark’s financial advisor in connection with the Landmark merger and will receive a cash fee equal to 1.50% of the aggregate Landmark merger consideration, $150,000 of which became payable to Olsen Palmer with rendering of its opinion and the balance of which is contingent upon the closing of the Landmark merger. Landmark has also agreed to indemnify Olsen Palmer against certain claims and liabilities arising out of Olsen Palmer’s engagement and to reimburse Olsen Palmer for certain of its out-of-pocket expenses incurred in connection with Olsen Palmer’s engagement.

Olsen Palmer has not provided investment banking and financial advisory services to Landmark or Simmons during the two-year period prior to June 4, 2021, except with respect to the Landmark merger. Olsen Palmer may provide investment banking, financial advisory and other financial services to Landmark and/or Simmons in the future, for which Olsen Palmer may receive compensation.

Certain Prospective Financial Information

Simmons and Landmark 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 of any such projections. However, Landmark is including in this proxy statement/prospectus certain unaudited prospective financial information that was used by Olsen Palmer for the purpose of Olsen Palmer performing its financial analysis in connection with rendering its opinion to the Landmark board of directors, as described in the section entitled “—Opinion of Landmark’s Financial Advisor.” The unaudited prospective financial information of Landmark included in this proxy statement/prospectus, which we refer to as the Landmark prospective information, was made available by Landmark to Olsen Palmer. The Landmark prospective information was prepared solely by Landmark management and was not prepared, provided to, reviewed or approved by Simmons management or the Simmons board of directors. The unaudited prospective financial information of Simmons included in this proxy statement/prospectus, which we refer to as the Simmons prospective information (and, together with the Landmark prospective information, the prospective information) was not prepared, provided to, reviewed or approved by Landmark management, the Landmark board of directors, Simmons management or the Simmons board of directors. By inclusion of this prospective information, the respective managements and boards of directors of Landmark and Simmons, and Landmark’s financial advisor, assume no responsibility for the prospective information. The inclusion of this prospective information should not be regarded as an indication that any of Landmark, Simmons, Olsen Palmer, their

respective representatives or any other recipient of this prospective 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.

The Landmark prospective information was prepared solely by Landmark management for internal use, and certain of the assumptions related to the impact of the merger were discussed between representatives of Simmons, Landmark and Olsen Palmer. The prospective information is subjective in many respects. While presented with numeric specificity, the prospective information reflects numerous estimates and assumptions made solely by Landmark management with respect to business, economic, market, competition, regulatory and financial conditions and matters specific to Landmark’s and Simmons’ respective businesses, all of which are difficult to predict and many of which are beyond Landmark’s and Simmons’ control. The prospective information reflects both assumptions solely by Landmark management as to certain business decisions that are subject to change and, in many respects, subjective judgment solely by Landmark management, and thus is susceptible to multiple interpretations and periodic revisions based on actual experience and business developments. No assurance can be given that the prospective information and the underlying estimates and assumptions will be realized. Actual results may differ materially from those set forth below, and important factors that may affect actual results and cause the prospective information to be inaccurate include, but are not limited to, risks and uncertainties relating to Landmark’s and Simmons’ respective businesses, industry performance, general business and economic conditions, competition, customer requirements and adverse changes in applicable laws, regulations or rules. For other factors that could cause actual results to differ, see the sections entitled “Risk Factors” and “Cautionary Statement Regarding Forward-Looking Statements” in this proxy statement/prospectus and in Simmons’ Annual Report on Form 10-K for the fiscal year ended December 31, 2020, as well as the other reports filed by Simmons with the SEC.

The prospective information was not prepared by Landmark management with a view toward public disclosure, nor was it prepared with a view toward compliance with 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 prospective information requires significant estimates and assumptions that make it inherently less comparable to the similarly titled GAAP measures in Landmark’s and Simmons’ respective historical GAAP financial statements. Neither Landmark’s nor Simmons’ independent public accountants nor any other independent accountants, have compiled, examined or performed any procedures with respect to the prospective information contained herein, nor have they expressed any opinion or any other form of assurance on such information or its achievability.

Furthermore, the prospective information does not take into account any circumstances or events occurring after the date it was prepared. No assurance can be given that, had the prospective information been prepared as of the date of this proxy statement/prospectus, similar estimates and assumptions would be used. Neither Landmark nor Simmons intends to, and expressly disclaims any obligation to, make publicly available any update or other revision to the prospective information to reflect circumstances existing since their preparation or to reflect the occurrence of unanticipated events, even in the event that any or all of the underlying assumptions are shown to be in error, or to reflect changes in general economic or industry conditions. The prospective information does not take into account the possible financial and other effects on Landmark or Simmons of the Landmark merger and does not attempt to predict or suggest future results of the surviving company. The prospective information does not give effect to the Landmark merger, including the impact of negotiating or executing the Landmark merger agreement, the expenses that may be incurred in connection with consummating the Landmark merger, the potential synergies that may be achieved by the surviving company as a result of the Landmark merger, the effect on Landmark or Simmons of any business or strategic decision or action that has been or will be taken as a result of the Landmark merger agreement having been executed, or the effect of any business or strategic decisions or actions that would likely have been taken if the Landmark merger agreement had not been executed, but which were instead altered, accelerated, postponed or not taken in anticipation of

the Landmark merger. Further, the Landmark prospective information does not take into account the effect on Landmark of any possible failure of the Landmark merger to occur.

None of Landmark, Simmons, Olsen Palmer, or their respective affiliates, officers, directors, advisors or other representatives has made, makes or is authorized in the future to make any representation to any shareholder of Landmark or Simmons or other persons regarding Landmark’s or Simmons’ ultimate performance compared to the information contained in the prospective information or that the projected results will be achieved. The summary of the prospective information included below is not being included to influence your decision whether to vote for the Landmark merger proposal, but is being provided solely because it was used by Olsen Palmer in connection with rendering the Olsen Palmer opinion.

In light of the foregoing, and considering that the Landmark special meeting will be held many months after the prospective information was prepared, as well as the uncertainties inherent in any forecasted information, Landmark shareholders are cautioned not to place unwarranted reliance on such information, and all Landmark shareholders are urged to review the other information contained elsewhere in this proxy statement/prospectus for a description of Simmons’ and Landmark’s respective businesses as well as Simmons’ most recent SEC filings for a description of Simmons’ reported financial results. See the section entitled “Where You Can Find More Information.”

The following tables present the Landmark prospective information, prepared solely by Landmark management, and the Simmons prospective information, in each case, approved for Olsen Palmer’s use by the Landmark board of directors for Olsen Palmer’s financial analysis in connection with rendering the Olsen Palmer opinion to the Landmark board of directors, as described in the section entitled “—Opinion of Landmark’s Financial Advisor.”

Landmark Prospective Information

	As of or For the Years Ended December 31,
	2021		2022		2023		2024		2025		2026
Landmark Net Income ($ millions)	$	11.3	$	12.6	$	14.0	$	15.3	$	16.6	$	18.0
Landmark Total Assets ($ millions)	$	1,012	$	1,062	$	1,112	$	1,162	$	1,212	$	1,262

Simmons Prospective Information

	Assumed Long-Term Growth Rates for Simmons
Earnings (%)		7	%
Total Assets (%)		7	%

Simmons’ Reasons for the Landmark Merger

In reaching its decision to adopt and approve the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement, the Simmons board of directors evaluated the Landmark merger agreement and the Landmark merger in consultation with Simmons’ management, as well as Simmons’ financial and legal advisors, and considered a number of factors, including, without limitation, the following material factors, which are not presented in order of priority:

the anticipation that the Landmark merger is expected to enhance the scale and expand the footprint of the combined company in the attractive Tennessee banking market;

each of Simmons’, Landmark’s and the combined company’s business, operations, financial condition, asset quality, earnings and prospects;

the fact that Landmark’s business and operations complement those of Simmons and that the Landmark merger would result in a combined company with a diversified revenue stream from diversified geographic markets, a well-balanced portfolio and an attractive funding base;

its existing knowledge of Landmark’s business and its review and discussions with Simmons’ management concerning the additional due diligence examination of Landmark conducted in connection with the Landmark merger;

the perceived complementary nature of the cultures and the shared core technology operating systems of the two companies, which Simmons’ management believes should facilitate integration and implementation of the Landmark merger;

the complementary branch networks of Simmons and Landmark;

Landmark’s market position within the Tennessee banking market, particularly Landmark’s market share in the Memphis market;

its understanding of the current and prospective environment in which Simmons and Landmark operate, including national, regional and local economic conditions, the competitive environment for financial institutions generally and the likely effect of these factors on Simmons both with and without the Landmark 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 terms of the Landmark merger agreement, including the Landmark merger consideration, expected tax treatment, deal protection and termination fee provisions, which the Simmons board of directors reviewed with Simmons’ management and Simmons’ financial and legal advisors;

Simmons’ successful operating and acquisition track record, specifically Simmons’ history of efficiently closing and integrating acquisitions;

its belief that the Landmark merger is likely to provide substantial value to Simmons shareholders;

the potential risks associated with achieving anticipated cost synergies and savings and successfully integrating Landmark’s business, operations and workforce with those of Simmons;

the potential risk of diverting management attention and resources from the operation of Simmons’ business and towards the completion of the Landmark merger;

certain anticipated Landmark merger-related costs;

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

the potential risk of losing other acquisition opportunities while Simmons remains focused on completing the Landmark merger; and

the nature and amount of payments and other benefits to be received by Landmark management in connection with the Landmark merger.

The foregoing discussion of the information and factors considered by the Simmons board of directors is not intended to be exhaustive, but, rather, includes the material factors considered by the Simmons board of directors. In reaching its decision to adopt and approve the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement, the Simmons board of directors did not quantify or assign any relative weights to the factors considered, and individual directors may have given different weights to different factors. The Simmons board of directors considered all these factors as a whole, and overall considered the factors to be favorable to, and to support, its determination to adopt and approve the Landmark merger agreement and the transactions contemplated thereby, including the Landmark merger.

This explanation of the Simmons 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.”

Interests of Landmark’s Directors and Executive Officers in the Landmark Merger

In considering the recommendation of the Landmark board of directors that Landmark shareholders vote “FOR” the Landmark merger proposal, Landmark shareholders should be aware that some of Landmark’s executive officers and directors have interests in the Landmark merger, which may be considered to be different from, or in addition to, the interests of the Landmark shareholders generally. These interests are described below. The Landmark board of directors was aware of these interests and considered them, among other matters, in reaching its decision to approve the Landmark merger agreement, the Landmark merger and the other transactions contemplated by the Landmark merger agreement and to recommend that Landmark shareholders vote “FOR” the Landmark merger proposal.

Employment Agreements

Landmark has entered into employment agreements with the following executives which provide for severance obligations upon a termination of employment in connection with a change in control transaction: Charles Dickey, James Farrell and Mike Russell. These severance benefits provide for a severance payment equal to (1) 2.99 times the executive’s base salary, plus (2) an amount equal to the greater of the bonus paid to the executive for the previous year, if any, or the bonus that would have been paid to executive for the year in which the termination occurred, based on an annualized basis and in good faith, and (3) any unpaid vacation pay, expense reimbursements and other amounts due to the executive but not yet paid. In addition, for 36 months following the termination of employment, the executive and the executive’s spouse and dependents shall be eligible for a continuation of employee benefits or alternatively, if continuation of such benefits is not permitted under applicable law or regulations, cash in lieu of such benefits continuation. The employment agreements with each of Messrs. Dickey, Farrell, and Russell provide that if payments would constitute excess parachute payments within the meaning of Section 280G of the Code, payments will be reduced to the extent necessary in order to prevent payments from constituting an excess parachute payment. Whether any of the individual’s payments will be subject to reduction under this provision will depend on a number of factors, including each individual’s post-closing arrangements and compensation with Simmons. As of the date of this proxy statement/prospectus, Mr. Farrell has been offered employment by Simmons but Simmons intends that Mr. Farrell will remain eligible for the severance benefits described above even if he accepts the offered employment.

Stock Option Plan Acceleration

Landmark’s Non-Qualified Stock Option Plan provides that any unvested options automatically vest upon the occurrence of a change in control transaction. At the Landmark effective time, each Landmark stock option, whether vested or unvested, outstanding immediately prior to the Landmark effective time, will be canceled and converted into the right to receive from Simmons a cash payment equal to the difference, if positive, between (1) the fully diluted per share value and (2) the exercise price of such Landmark stock option.

Indemnification

The Landmark merger agreement provides that, for a period of six years after the Landmark effective time, Simmons will indemnify, defend and hold harmless each of the present and former directors or officers of Landmark against all liabilities arising out of actions or omissions arising out of such person’s services as director or officers of Landmark, or at Landmark’s request, of another corporation, partnership, joint venture, trust or other enterprise, occurring at or prior to the effective time to the fullest extent permitted under the Landmark charter and the Landmark bylaws in effect on the date of the Landmark merger agreement (subject to applicable law), including provisions relating to the advancement of expenses incurred in the defense of any litigation, provided that, in the case of an advancement of expenses, any indemnified party to whom expenses are advanced provides a written undertaking to repay such advances if it is ultimately determined that such indemnified party is not entitled to indemnification.

THE TRIUMPH MERGER

The following discussion contains material information regarding the Triumph merger. The discussion is subject to, and qualified in its entirety by reference to, the Triumph merger agreement, which is attached to this proxy statement/prospectus as Annex B and is incorporated by reference into this proxy statement/prospectus. The following is not intended to provide factual information about the parties or any of their respective subsidiaries or affiliates. This discussion does not purport to be complete and may not contain all of the information about the Triumph merger that is important to you. We urge you to read the Triumph merger agreement carefully and in its entirety, as it is the legal document governing the Triumph merger.

Terms of the Triumph Merger

Each of the Simmons board of directors and the Triumph board of directors approved the Triumph merger agreement. The Triumph merger agreement provides that, among other things, Triumph will merge with and into Simmons, with Simmons as the surviving corporation in the merger. Immediately following the Triumph merger, Triumph Bank will merge with and into Simmons Bank, with Simmons Bank as the surviving bank.

Based on the assumptions set forth below, at the Triumph effective time, each share of Triumph common stock that is issued and outstanding immediately prior to the Triumph effective time, excluding certain specified shares, will be converted into the right to receive, subject to possible adjustment, the Triumph merger consideration. In the aggregate, Simmons expects to issue approximately [ ] shares of Simmons common stock and pay approximately $[ ] million (minus the cash payment for outstanding Triumph stock options) to Triumph shareholders upon completion of the Triumph merger, subject to certain conditions and potential adjustments under the Triumph merger agreement. The Triumph merger consideration is based on the assumption that (i) [ ] shares of Triumph common stock are issued and outstanding and (ii) [ ] shares of Triumph common stock are subject to outstanding Triumph stock options with a weighted average exercise price of $[ ], in each case, immediately prior to the Triumph effective time. In addition, we have assumed that the Triumph/Simmons average closing price is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

Simmons will not issue any fractional shares of Simmons common stock in the Triumph merger. Instead, a Triumph shareholder who would otherwise be entitled to a fractional share of Simmons common stock upon completion of the Triumph merger will receive, in lieu thereof, an amount in cash, rounded up to the nearest whole cent (without interest), determined by multiplying (i) the fraction of a share (rounded to the nearest thousandth when expressed in decimal form) of Simmons common stock that such shareholder would otherwise be entitled to receive by (ii) the Triumph/Simmons average closing price.

Triumph shareholders are being asked to approve the Triumph merger agreement, including the Triumph merger and all transactions contemplated thereby. See the section entitled “The Merger Agreements” for additional and more detailed information regarding the legal documents that govern the Triumph merger, including information about the conditions to consummation of the Triumph merger and the provisions for terminating or amending the Triumph merger agreement.

Background of the Triumph Merger

As part of the ongoing consideration and evaluation of Triumph’s long-term prospects and strategies over the years, the Triumph board of directors has regularly reviewed and assessed Triumph’s business strategies and objectives, including assessments of potentially available strategic growth opportunities, as part of Triumph’s efforts to enhance value for its shareholders and deliver the best possible services to its customers and communities.

The Triumph board of directors at its offsite retreat held on July 17, 2020, at Shelby Group International, Inc. d/b/a MCR Safety, which is located in Collierville, Tennessee, discussed possible next steps and growth of Triumph and Triumph Bank. During this Triumph board of directors’ retreat, business strategies and objectives were discussed as part of the continued effort to increase shareholder value and to deliver quality services to Triumph’s customers and to enhance the communities in which we live, work and play. Discussions ensued on the financial services markets in Memphis and Nashville, the regulatory environment, the economy generally and in these markets, Triumph’s ability to compete attracting talent, its pricing and service to Triumph’s customers.

The Triumph board of directors also discussed the benefits and risks to Triumph and its shareholders to continue to build organically through the opening of new branches or to consider combining with one or more financial institutions. The Triumph board of directors requested Mr. John A. Bobango of the law firm, Farris Bobango, PLC, Triumph’s counsel, which we refer to as Farris Bobango, and Mr. William J. Chase, Jr., Triumph’s President and Chief Executive Officer, to review and consider financial institutions to approach on behalf of Triumph for a discussion regarding potential opportunities. Over the next several days, Mr. Chase and Mr. Bobango discussed potential financial institutions to consider.

During July and August of 2020 and in the midst of the COVID-19 pandemic, Mr. Bobango had brief discussions with representatives of two financial institutions. The conversations were positive; however, after Mr. Chase and Mr. Bobango had discussions with Mr. Hilliard Crews, chair of the Triumph board of directors, and Mr. Mike McCarver, Triumph’s Executive Vice-President and Chief of Operations Officer, Mr. Chase and Mr. Bobango delayed further discussions due to the COVID-19 pandemic.

At the meeting of the Triumph board of directors on November 18, 2020, Mr. Bobango mentioned that now may be a better time to open discussions with financial institutions and Simmons would be a good candidate. Mr. Crews asked Mr. Bobango to connect with Mr. George Makris, Jr., Chairman and Chief Executive Officer of Simmons. On November 21, 2020, Mr. Bobango contacted Mr. Makris regarding the potential opportunity of a business combination with Simmons. Mr. Bobango and Mr. Makris agreed it would be useful to meet in person the next time Mr. Makris was in Memphis to explore a possible business combination.

Over the following three months Triumph entered into a mutual non-disclosure agreement with another financial institution, which resulted in preliminary discussions regarding a merger with Triumph. During this time, Triumph discussed, but did not enter into, a non-disclosure agreement with one additional financial institution.

On March 5, 2021, Mr. Makris called Mr. Bobango to inquire about Triumph’s interest in discussing a merger between the two companies. Mr. Bobango suggested Mr. Makris and other representatives of Simmons meet with representatives of Triumph.

On March 6, 2021, Mr. Bobango briefed Messrs. Crews, Chase and McCarver regarding his conversation with Mr. Makris and the opportunity of exploring a potential transaction with Simmons. Messrs. Crews, Chase and McCarver discussed that a meeting with Mr. Makris would be the next step and expressed their support for Mr. Bobango to contact Mr. Makris to arrange an in-person meeting between representatives of Triumph and Simmons to discuss a potential merger in greater detail. Over the next several days, Mr. Crews communicated with the other members of the Triumph board of directors regarding the initial discussions with Simmons.

On March 12, 2021, Messrs. Bobango, Crews, Chase and McCarver met with a representative of another financial institution to discuss potential strategic advantages of a merger.

On March 19, 2021, Messrs. Bobango, Crews, Chase and McCarver met with representatives of Simmons, which included Mr. Makris; Robert Fehlman, who was, at that time, Simmons’ Chief Financial Officer and Chief Operating Officer; and Stephen Massanelli, Simmons’ Chief Administrative Officer, which meeting was held at the offices of Farris Bobango in Memphis, Tennessee. The parties discussed the potential strategic advantages of a merger, each company’s philosophy, credit and underwriting, and

the financial and operational benefits of a combination of the two companies. At the meeting, the Triumph and Simmons representatives expressed interest in continuing discussions regarding a merger of the two companies. Following this meeting and over the next several days, Mr. Crews briefed other members of the Triumph board of directors on the discussions with Simmons.

From March 19, 2021 to March 24, 2021, Mr. Crews had informal discussions with the Triumph board of directors to outline the next steps with Simmons.

On March 24, 2021, at the Triumph board meeting, Mr. Crews discussed the meeting on March 19, 2021 with representatives from Simmons and the potential strategic advantages of a merger with Simmons. The Triumph board of directors also discussed the March 12, 2021 meeting of Triumph representatives with the other financial institution. After discussing the advantages and disadvantages of a strategic merger, the Triumph board of directors decided to pursue discussions with Simmons. The board of directors also discussed engaging Southard Financial to advise and issue a fairness opinion.

On March 26, 2021, Triumph and Simmons executed a customary mutual nondisclosure agreement in order to facilitate more detailed discussions of a potential business combination and reciprocal due diligence efforts.

On March 29, 2021, Simmons delivered an indication of interest to the Triumph board of directors to acquire Triumph for shares of Simmons common stock of approximately $132,047,500 in aggregate transaction value and based on the 20-trading day average closing price of Simmons common stock as of March 29, 2021.

On March 31, 2021, the Triumph board of directors held a special meeting to discuss the meeting with representatives of Simmons, the potential transaction with Simmons and the indication of interest delivered by Simmons. Mr. Bobango reviewed with the Triumph board of directors the directors’ fiduciary duties under Tennessee law and then discussed with the Triumph board of directors the terms for the potential transaction that were being discussed between Simmons and Triumph in the indication of interest. After a lengthy discussion, the Triumph board of directors expressed its support for continuing to explore the feasibility and potential benefits of a proposed transaction with Simmons and approved pursing a transaction with Simmons, provided Simmons submitted a revised bid with a “collar” based on the fluctuating price of the market value of Simmons common stock and a closing date early in the fourth quarter of 2021. The Triumph board of directors directed Messrs. Crews, Chase, McCarver and Bobango, to continue their discussions and negotiations with Simmons regarding such a transaction, and if the requested changes were made, authorized Mr. Crews to execute the revised indication of interest.

On April 1, 2021, Mr. Makris and Mr. Bobango discussed the terms set out in Simmons’ indication of interest and the changes requested by Triumph. Triumph requested a closing date in early October in the fourth quarter of 2021 and a right to terminate by Triumph if the price of the Simmons’ stock decreased beyond a certain level. Mr. Makris indicated he would discuss internally at Simmons.

On April 2, 2021, Simmons submitted a revised indication of interest that contained revisions acceptable to Triumph. The revised indication of interest was executed and dated by Mr. Crews on behalf of Triumph on April 2, 2021.

On April 10, 2021, Mr. McCarver communicated with its accounting advisor, Reynolds, Bone and Griesbeck, PLC, which we refer to as Reynolds, to assist with the financial analysis of the Triumph merger.

From April 13, 2021 to June 3, 2021, the parties engaged in mutual due diligence, including through a series of virtual due diligence meetings and telephone calls between the parties and their respective representatives to discuss relevant topics. Triumph made available to Simmons documents for their mutual due diligence, including through the use of a virtual data room. Triumph reviewed the public information available on Simmons and asked follow up questions to representatives of Simmons.

On May 10, 2021, Simmons delivered a first draft of the Triumph merger agreement to Farris Bobango. Between May 10, 2021 and June 1, 2021, the specific terms of the Triumph merger agreement were negotiated between the representatives of Simmons and Triumph and their respective outside counsel. During this period the representatives and their legal counsel also negotiated the terms of the Triumph voting agreements. During this period, Triumph and Simmons exchanged several additional drafts of the Triumph merger agreement and the related transaction documents, including the Triumph voting agreement. Additionally, during this time, Triumph continued to confer with Reynolds.

Throughout the day of June 2, 2021, the Triumph and Simmons management teams, with the assistance of the parties’ legal advisors, continued to finalize the Triumph merger agreement and Triumph voting agreements.

On June 3, 2021, the Triumph board of directors held a special meeting to review and discuss the potential transaction with Simmons, with representatives of Farris Bobango, Southard Financial, and Reynolds in attendance. Mr. Bobango updated the Triumph board of directors on the final negotiations with Simmons relating to the potential transaction and the final terms of the Triumph merger agreement, including the price terms, representations and warranties, negative covenants and closing conditions. Mr. Bobango then discussed with Triumph’s directors the terms of the Triumph voting agreements. The directors then asked management and Farris Bobango questions about the Triumph merger agreement. Following these questions from the Triumph board of directors, Mr. Bobango reviewed with the directors certain legal considerations, including the directors’ fiduciary duties in connection with their consideration of a potential transaction with Simmons.

Representatives of Southard Financial then reviewed and discussed with the Triumph board of directors, among other matters, certain preliminary financial analyses regarding the two companies and the financial aspects of the proposed transaction. Following the discussion, representatives of Southard Financial rendered to the Triumph board of directors its firm’s opinion, which was initially rendered orally and confirmed by a written opinion dated June 4, 2021, to the effect that, as of that date and subject to the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken as set forth in its opinion, the Triumph merger consideration was fair, from a financial point of view, to the holders of Triumph common stock as described in the section entitled “—Opinion of Triumph’s Financial Advisor.” For a description of Southard Financial’s opinion, please refer to the section entitled “—Opinion of Triumph’s Financial Advisor.”

There were further discussions, including comments and questions answered by Joseph Callicutt with Reynolds. After these discussions and considering various factors, including the interests of the Triumph shareholders, customers, employees and communities served by Triumph, as well as the factors described in the section entitled “—Triumph’s Reasons for the Triumph Merger and Recommendations of the Triumph Board of Directors,” the Triumph board of directors approved the Triumph merger agreement and the transactions contemplated thereby and determined that they were advisable and fair to and in the best interests of Triumph and its shareholders, and recommended that the Triumph shareholders approve and adopt the Triumph merger agreement.

On June 4, 2021, the Simmons board of directors held a meeting to consider the terms of the proposed Triumph merger and Triumph merger agreement. At the meeting, members of Simmons’ management reported on the status of due diligence and negotiations with Triumph. Also at the meeting, Simmons’ financial advisor reviewed with the Simmons board of directors financial aspects of the proposed Triumph merger. At the meeting, Simmons’ internal legal counsel reviewed with the Simmons board of directors its fiduciary duties and reviewed the key terms of the Triumph merger agreement and related agreements (including the Triumph voting agreements), as described elsewhere in this proxy statement/prospectus, including a summary of the provisions relating to governance of the combined company and the provisions relating to employee matters.

After considering the proposed terms of the Triumph merger agreement, the terms of the Triumph voting agreements, and taking into consideration the matters discussed during that meeting and prior meetings of the Simmons board of directors, including the factors described in the section entitled “—Simmons’ Reasons for the Triumph Merger,” the Simmons board of directors determined that the Triumph merger was consistent with Simmons’ business strategies and in the best interests of Simmons and Simmons shareholders and the Simmons board of directors voted to approve and adopt the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement.

Following the board meetings of Triumph and Simmons, on June 4, 2021, the Triumph merger agreement was signed by Triumph and Simmons and each of the directors and certain executive officers of Triumph signed the Triumph voting agreements. The transaction was announced in the morning of Monday, June 7, 2021, in a press release issued by Simmons.

Triumph’s Reasons for the Triumph Merger and Recommendation of the Triumph Board of Directors

After careful consideration, at a special meeting held on June 3, 2021, the Triumph board of directors (i) determined that the Triumph merger agreement and the transactions contemplated thereby, including the Triumph merger, are in the best interests of Triumph, its shareholders and other constituencies, (ii) declared the Triumph merger agreement advisable and (iii) approved the execution, delivery and performance of the Triumph merger agreement and the consummation of the transactions contemplated thereby, including the Triumph merger. Accordingly, the Triumph board of directors unanimously recommends that the Triumph shareholders vote “FOR” the Triumph merger proposal and “FOR” the Triumph adjournment proposal.

In reaching its decision to approve the Triumph merger agreement and the transactions contemplated thereby, including the Triumph merger, and to recommend that the Triumph shareholders approve the Triumph merger agreement, the Triumph board of directors evaluated the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement in consultation with Triumph’s management, as well as with Triumph’s financial and legal advisors, and considered a number of factors, including the following:

each of Triumph’s and Simmons’ business, operations, financial condition, stock performance, asset quality, earnings and prospects. In reviewing these factors, including the information obtained through due diligence, the Triumph board of directors considered that Simmons’ and Triumph’s respective business, operations and risk profile complement each other and that the companies’ separate earnings and prospects, and the synergies and scale potentially available in the proposed transaction, create the opportunity for the combined company to leverage complementary and diversified revenue streams and to have superior future earnings and prospects compared to Triumph’s earnings and prospects on a stand-alone basis;

the market value of Simmons common stock prior to the execution of the Triumph merger agreement, the prospects for future appreciation of Simmons common stock, and the history of dividends payable by Simmons to holders of Simmons common stock, and the trading liquidity of Simmons common stock;

the fact that the exchange ratio, as may be adjusted, and the cash consideration to be paid to Triumph shareholders was believed by Triumph board of directors to be consistent with market practice for transactions of this type and with the strategic purpose of the transaction;

Simmons’ broader products and services offerings, as well as its digital capabilities across its customer base;

the perceived risks and uncertainties attendant to Triumph’s operation as an independent banking organization, including the risks and uncertainties related to competition in market areas of Triumph Bank, increased operating and regulatory costs, interest rate environments, and potentially increased capital requirements;

the terms of the recent business combinations, including financial institutions, either announced or completed during the past year and the two quarters of this year in Tennessee and contiguous states and the effect of such combinations or competitive conditions and future opportunities in the Triumph market areas;

Triumph’s familiarity of the current and prospective environment in the financial services industry, including economic conditions and the interest rate and regulatory environments, possible effects of scale, increased operating costs resulting from regulatory and compliance mandates, increasing competition from both nationwide banks and non-bank financial and financial technology firms, and current financial market conditions and the likely effects of these factors on Triumph’s and the combined company’s potential growth, development productivity and strategic options, and the likely effect of these factors on Triumph both with and without the proposed Triumph merger;

Triumph’s views with respect to other strategic alternatives potentially available to Triumph, including continuing as a stand-alone company focused exclusively on organic growth, making smaller acquisitions of other banks, transformative transactions (including large acquisitions or a merger of equals) and a transaction involving the sale of Triumph and a transformative transaction with another potential acquiror or merger partner, and Triumph’s belief that a transaction with such other potential transaction partners would not deliver the financial and operational benefits that could be achieved in the proposed merger with Simmons;

Simmons’ past record of integrating acquisitions and realizing expected financial and other benefits of such acquisitions;

Triumph’s belief that the two companies’ corporate cultures are similar and compatible, which would facilitate integration and implementation of the transaction;

synergies and positive impact to local communities and minimize the loss of customers and employees and to further diversify the operating risk of Triumph on a stand-alone basis;

the fact that the Triumph shareholders will have an opportunity to vote on the approval of the Triumph merger agreement and the Triumph merger;

the fact that Simmons intends to retain as many employees of Triumph as feasible;

the fact that the Triumph shareholders would be entitled to appraisal or dissenters’ rights in connection with the Triumph merger;

the impact of the Triumph merger on Triumph’s employees, including the compensation and employee benefits agreed to be provided by Simmons pursuant to the Triumph merger agreement;

the expectation that the required regulatory approvals could be obtained in a timely fashion;

the expectation the Triumph merger will be generally tax-free for United States federal income tax purposes for Triumph shareholders;

the oral opinion of Southard Financial to the Triumph board of directors, subsequently confirmed in writing, to the effect that, as of June 4, 2021, the date of Southard Financial’s written opinion, and based upon and subject to the factors, qualifications and assumptions set forth in Southard Financial’s written opinion, the Triumph merger consideration was fair from a financial point of view to the holders (other than Simmons and its affiliates) of Triumph common stock, as more fully described below in the section entitled “—Opinion of Triumph’s Financial Advisor;” and

the terms of the Triumph merger agreement, which Triumph reviewed with its legal counsel, including the representations, covenants, deal protection, closing conditions and termination provisions.

The Triumph board of directors also considered the potential risks related to the transaction but concluded that the anticipated benefits of combining with Simmons were likely to outweigh these risks substantially. These potential risks include:

the potential for the value of the Triumph merger consideration to be received by Triumph shareholders to be adversely affected by a decrease in the trading price of Simmons’ common stock;

the possible diversion of management and resources from other strategic opportunities and operational matters while working to implement the transaction and integrate the two companies;

that Triumph’s directors and executive officers may have interests in the Triumph merger that are different from or in addition to those of its shareholders generally, as more fully described in the section entitled “—Interests of Triumph’s Directors and Executive Officers in the Triumph Merger;”

the nature and amount of payments and other benefits to be received by Triumph’s management in connection with the Triumph merger pursuant to existing Triumph plans and compensation arrangements and the Triumph merger agreement;

the risk of losing key Triumph employees during the pendency of the Triumph merger and thereafter;

the restrictions on the conduct of Triumph’s business during the period between execution of the Triumph merger agreement and the consummation of the Triumph merger, which could delay or prevent Triumph from undertaking business opportunities that might arise or certain actions it might otherwise take regarding its operations, if not for the pendency of the Triumph merger;

the potential effect of the Triumph merger on Triumph’s overall business, including its relationships with customers, employees, suppliers and regulators;

the risk that the Triumph merger may not be completed despite the combined efforts of Triumph and Simmons or that completion may be delayed;

the regulatory and other approvals required in connection with the Triumph merger and the merger of Triumph Bank with and into Simmons Bank and the risk that such regulatory approvals will not be received or will not be received in a timely manner or may impose burdensome or unacceptable conditions;

the potential for legal claims challenging the Triumph merger;

the potential risks associated with achieving anticipated efficiency improvements and cost reductions and savings and successfully integrating Triumph’s business, operations and workforce with those of Simmons;

the fact that Triumph may be obligated to pay Simmons a termination fee of $6.5 million in certain circumstances, as more fully described in the sections entitled “The Merger Agreements—Termination of the Merger Agreements” and “The Merger Agreements—Termination Fees,” may deter others from proposing an alternative transaction that may be more advantageous to the Triumph shareholders; and

the other risks described in the sections entitled “Risk Factors” and “Cautionary Statement Regarding Forward-Looking Statements.”

The foregoing discussion of the information and factors considered by the Triumph board of directors is not intended to be exhaustive, and may not include all of the material factors considered by the Triumph board of directors. In view of the variety of factors considered in connection with its consideration of the Triumph merger agreement and the other transactions contemplated thereby, including the Triumph merger and the complexity of these matters, the Triumph board of directors did not quantify or assign any relative weights to the factors considered, and individual directors may have given different weights to different factors. The above factors are not listed in any particular order of priority. The Triumph board of directors considered all these factors as a whole, including discussions with, and questioning of, Triumph’s senior management team and Triumph’s financial, legal advisors and accountants, in evaluating the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement.

For reasons set forth above, the Triumph board of directors determined that the Triumph merger agreement and the transactions contemplated by the Triumph merger agreement are advisable and fair to and in the best interests of Triumph and its shareholders, and approved the Triumph merger agreement and approved the Triumph merger and the other transactions contemplated by the Triumph merger agreement.

In considering the recommendation of the Triumph board of directors, you should be aware that certain directors and executive officers of Triumph may have interests in the Triumph merger that are different from, or in addition, to interests of the Triumph shareholders generally may create potential conflicts of interest. The Triumph board of directors was aware of these interests and considered them when evaluating and negotiating the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement, and in recommending to the Triumph shareholders that they vote in favor of the Triumph merger proposal. See the description of these interests in the section entitled “The Triumph Merger—Interests of Triumph’s Directors and Executive Officers in the Triumph Merger.”

This explanation of the reasoning of the Triumph board of directors 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.”

For the reasons set forth above, the Triumph board of directors unanimously recommends the holders of Triumph common stock vote “FOR” the Triumph merger proposal and “FOR” the Triumph adjournment proposal.

Each of the directors and certain executive officers of Triumph, in their capacities as individuals, entered into Triumph voting agreements with Simmons and Triumph pursuant to which they agreed to vote “FOR” the Triumph merger proposal and “FOR” any other matters required to be approved by the Triumph shareholders in furtherance of the Triumph merger proposal. For more information regarding the Triumph voting agreements, please see the section entitled “The Merger Agreements—Voting Agreements.”

Opinion of Triumph’s Financial Advisor

Southard Financial was retained by the Triumph board of directors in connection with the Triumph merger. Southard Financial is a business valuation and strategic financial management consulting firm founded in 1987. The team of professionals at Southard Financial has extensive business valuation experience. Southard Financial provides a variety of valuation services, including fairness opinions, and Southard Financial offers valuations for financial institutions, corporations, and partnerships for various purposes. Since its founding, Southard Financial has provided thousands of valuation opinions for companies in 43 states. Triumph selected Southard Financial as its financial advisor on the basis of its experience and expertise in representing community banks in similar transactions and its familiarity with Triumph.

In connection with the Triumph merger, the Triumph board of directors has requested that Southard Financial render a written opinion, which we refer to as the Southard Financial opinion, regarding the fairness of the Triumph merger consideration. Southard Financial rendered to the Triumph board of directors its firm’s opinion, which was initially rendered orally and confirmed by a written opinion dated June 4, 2021, to the effect that, as of that date and subject to the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken as set forth in each such its opinion, the consideration to be paid by Simmons pursuant to the Triumph merger agreement was fair, from a financial point of view, to the Triumph shareholders. The full text of the Southard Financial opinion, which sets forth, among other things, the assumptions made, procedures followed, matters considered and limitations on the review undertaken by Southard Financial in rendering its opinion, is attached to this proxy statement/prospectus as Annex F. The summary of the Southard Financial opinion set forth herein is qualified in its entirety by reference to the full text of the opinion. Triumph shareholders should read the full text of the Southard Financial opinion carefully and in its entirety.

Southard Financial provided the Southard Financial opinion for the information of the Triumph board of directors (solely in its capacity as such) in connection with, and for purposes of, its consideration of the Triumph merger agreement, and the Southard Financial opinion only addressed whether the consideration to be paid by Simmons pursuant to the Triumph merger agreement was fair, from a financial point of view, to the Triumph shareholders. The Southard Financial opinion does not address any other terms or aspect of the Triumph merger agreement or the Triumph merger contemplated thereby. The Southard Financial opinion does not constitute a recommendation to the Triumph board of directors or any holder of Triumph common stock as to how the Triumph board of directors, such shareholder, or any other person should vote or otherwise act concerning the Triumph merger or any other matter. Southard Financial does not express any opinion as to the likely trading range of Simmons’ common stock following the Triumph merger, which may vary depending on numerous factors that generally impact the price of securities or on the financial condition of Simmons at that time.

In connection with rendering the Southard Financial opinion, Southard Financial reviewed and considered, among other things:

a draft of the Triumph merger agreement, dated June 4, 2021;

certain publicly available financial statements and other historical financial information of Triumph that Southard Financial deemed relevant;

the publicly reported historical price and trading activity for Simmons common stock;

a comparison of certain financial information for Triumph with similar financial institutions for which information is publicly available;

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

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

other information, financial studies, analyses and investigations, financial, economic, and market criteria as Southard Financial considered relevant.

Southard Financial also discussed with certain members of Triumph management and its representatives the business, financial condition, results of operations, and prospects of Triumph.

In performing its review, Southard Financial relied upon the accuracy and completeness of all of the financial and other information available to and reviewed by Southard Financial. Southard Financial assumed such accuracy and completeness to render the Southard Financial opinion without any independent verification or investigation. Southard Financial relied on the assurances of Triumph management that they were not aware of any facts or circumstances that would make any of such information inaccurate or misleading. Southard Financial was not asked to and did not undertake independent verification of any of such information. Southard Financial did not assume any responsibility or liability for the accuracy or completeness thereof. Southard Financial 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 Triumph, nor was Southard Financial furnished with any such evaluations or appraisals. Southard Financial rendered no opinion or evaluation on the collectability of any assets or the future performance of any loans of Triumph. Southard Financial did not independently evaluate the adequacy of the allowance for loan losses of Triumph or the combined entity after the Triumph merger. Southard Financial did not review any individual credit files relating to Triumph. Southard Financial assumed that the allowances for loan loss provision at Triumph were adequate to cover such losses and would be sufficient on a pro forma basis for the combined entity.

Southard Financial also assumed, with Triumph’s consent, that (i) each of the parties to the Triumph merger agreement would comply in all material respects with all material terms of the Triumph 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 required to be performed by such party under the 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 Triumph merger, no delay, limitation, restriction or condition would be imposed that would have an adverse effect on Triumph, Simmons or the Triumph merger or any related transactions, and (iii) the Triumph merger and any related transactions would be consummated in accordance with the terms of the Triumph 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 Triumph’s consent, Southard Financial relied upon the advice that Triumph received from its legal, accounting, and tax advisors as to all legal, accounting, and tax matters relating to the Triumph merger and the other transactions contemplated by the Triumph merger agreement. Accordingly, Southard Financial expressed no opinion as to any such matters.

The Southard Financial opinion was necessarily based on financial, economic, regulatory, market, and other conditions as in effect on, and the information made available to Southard Financial as of the date of the Southard Financial opinion. Events occurring after the date of the Southard Financial opinion could materially affect the Southard Financial opinion. Southard Financial has not undertaken to update, revise, reaffirm or withdraw the Southard Financial opinion or otherwise comment upon events occurring after the date of the Southard Financial opinion. Southard Financial expresses no opinion as to the trading value of Simmons common stock at any time or what the value of Simmons common stock would be once it is received by Triumph shareholders.

In rendering the Southard Financial opinion, Southard Financial performed a variety of financial analyses. The summary below is not a complete description of the analyses underlying the Southard Financial opinion or the presentation made by Southard Financial to the Triumph board of directors. However, it is a summary of all material analyses performed and presented by Southard Financial. 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. Also, no company included in Southard Financial’s comparative analyses described below is identical to Triumph, and no transaction is identical to the Triumph 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 merger transaction values, as the case may be, of Triumph and the companies to which they are being compared. In arriving at the Southard Financial opinion, Southard Financial did not attribute any particular weight to any analysis or factor that it considered. Rather, Southard Financial made qualitative judgments as to the significance and relevance of each analysis and factor. Southard Financial did not form an opinion as to whether any individual analysis or factor (positive or negative) considered in isolation supported or failed to support the Southard Financial opinion; instead, Southard Financial made its determination as to the fairness of the Triumph merger based on its experience and professional judgment after considering the results of all its analyses taken as a whole.

In performing its analyses, Southard Financial also made numerous assumptions concerning industry performance, business and economic conditions, and various other matters, many of which are beyond the control of Triumph. Southard Financial prepared its analyses solely for purposes of rendering the Southard Financial opinion. Estimates of 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, Southard Financial’s analyses do not necessarily reflect the value of Triumph common stock or the prices at which Triumph common stock may be sold at any time. The analyses of Southard Financial and the Southard Financial opinion were among many factors taken into consideration by the Triumph board of directors in making its determination to approve the Triumph merger agreement. The type and amount of consideration payable in the Triumph merger were determined through negotiations between Triumph and Simmons.

Summary of Consideration and Implied Transaction Metrics

Southard Financial reviewed the financial terms of the Triumph merger. Under the terms of the Triumph merger agreement, Triumph shareholders are entitled to receive, in exchange for all outstanding shares of Triumph common stock, subject to adjustments outlined in the Triumph merger agreement, consideration equal to 4,164,839 shares of Simmons common stock and $2,645,938 in cash (in the aggregate, rounded, minus cash payment to optionholders of Triumph). The aggregate implied deal value as of June 4, 2021 is shown below.

Total Consideration	Announced*
Buyer Shares		4,164,839
SFNC Price Per Share	$	30.96

SFNC Share Consideration		128,943,415
Cash Consideration		2,645,938

Deal Value		131,589,353

* Based on Closing Price as of June 4, 2021

The implied deal ratios as reported by S&P Global, Inc., which reflect Triumph’s financial information for the twelve months ended December 31, 2020, are shown below.

Announcement Deal Ratios	Price/ Earnings			Price/ Book			Price/ Tang Book
Deal Value		131,589,353			131,589,353			131,589,353
Triumph Bancshares, Inc.		7,663,536			87,839,070			86,288,070

Multiple		17.17	x		149.81	%		152.50	%

The implied deal ratios based on Triumph’s financial information for the twelve months ended May 31, 2021 are shown below.

Current Deal Ratios	Price/ Earnings			Price/ Book			Price/ Tang Book
Deal Value		131,589,353			131,589,353			131,589,353
Triumph Bancshares, Inc.		7,366,575			90,036,217			88,486,060

Multiple		17.86	x		146.15	%		148.71	%

Selected National Mergers Analysis

Southard Financial analyzed publicly available information relating to 19 selected acquisitions of banking institutions with assets between $500 million and $2.5 billion and announced on or after October 1, 2020. In addition, transactions involving banks with unreported book value pricing multiples were excluded. The selected transactions used in the analysis included (buyer/seller):

Enterprise Financial Services Corp/First Choice Bancorp	HPS Investment Partners, LLC/Marlin Business Services Corp.
First Foundation Inc./TGR Financial, Inc.	Bank of Marin Bancorp/American River Bankshares
Peoples Bancorp Inc./Premier Financial Bancorp, Inc.	Virginia National Bankshares Corporation/Fauquier Bankshares, Inc.
First Bancorp/Select Bancorp, Inc.	BancorpSouth Bank/FNS Bancshares, Inc.
United Bankshares, Inc./Community Bankers Trust Corporation	Equity Bancshares, Inc./American State Bancshares, Inc.
Banc of California, Inc./Pacific Mercantile Bancorp	United Community Banks, Inc./Aquesta Financial Holdings, Inc.
VyStar Credit Union/Heritage Southeast Bancorporation Inc.	BancorpSouth Bank/National United Bancshares, Inc.
Nicolet Bankshares, Inc./Mackinac Financial Corporation	Colony Bankcorp, Inc./SouthCrest Financial Group, Inc.
First Busey Corporation/Cummins-American Corp.	Seacoast Banking Corporation of Florida/Legacy Bank of Florida
Stock Yards Bancorp, Inc./Kentucky Bancshares, Inc.

The following operating statistics were compiled for the guideline transaction group and Triumph Bank.

	Triumph			Whole Bank Transactions from S&P Global, Inc.
Financial Metric	Bank *			Low			25th Percent			Median			75th Percent			High
LTM Return on Average Equity		10.10	%		0.18	%		6.61	%		8.82	%		10.64	%		12.45	%
LTM Return on Average Assets		0.98	%		0.03	%		0.78	%		0.91	%		1.09	%		1.38	%
Non-Performing Assets/Total Assets		0.92	%		0.00	%		0.46	%		0.71	%		1.16	%		2.53	%
Total Assets		893,732			533,334			781,809			1,200,539			1,643,199			2,283,115

For Triumph Bank, reflects data through March 31, 2021 last twelve months (“LTM”) as reported by S&P Global, Inc.

The implied Triumph merger multiples and summary whole bank transaction multiples are shown below.

	Transaction			Multiples w/
	Announced			Updated Triumph			Whole Bank Transactions from S&P Global, Inc.
Valuation Metric	By S&P *			Data **			Low			25th Percent			Median			75th Percent			High
Price / Earnings		17.17	x		17.86	x		10.10	x		14.60	x		17.61	x		19.20	x		43.55	x
Price / Book		149.81	%		146.15	%		85.49	%		135.43	%		145.18	%		154.33	%		214.25	%
Price / Tangible Book		152.50	%		148.71	%		85.49	%		146.81	%		168.21	%		181.94	%		214.33	%

For Triumph Bancshares, Inc., reflects multiples as announced by S&P Global, Inc. (reflects Triumph data for the twelve months ended December 31, 2020)

For Triumph Bancshares, Inc., based on SFNC closing on June 4, 2021 and Triumph data for twelve months ended May 31, 2021

Based on the review conducted by Southard Financial, the implied Triumph merger pricing ratios are within the range of the whole bank pricing ratios shown above, supporting the fairness of the Triumph merger to the Triumph shareholders. It should be noted that Triumph’s earnings were well above historical levels in 2020 and 2021 year-to-date, largely due to the impact of Triumph Bank’s mortgage origination operations. Despite the substantial increase in earnings and the significant non-core mortgage origination income, Triumph’s implied price/earnings ratio is still near the median of the guideline transaction group reviewed by Southard Financial.

Selected Regional Mergers Analysis

Southard Financial analyzed publicly available information relating to a regional (southeastern United States) subset of the national group above. The 10 transactions used in the analysis included (buyer/seller):

First Foundation Inc./TGR Financial, Inc.	Virginia National Bankshares Corporation/Fauquier Bankshares, Inc.
Peoples Bancorp Inc./Premier Financial Bancorp, Inc.	BancorpSouth Bank/FNS Bancshares, Inc.
First Bancorp/Select Bancorp, Inc.	United Community Banks, Inc./Aquesta Financial Holdings, Inc.
United Bankshares, Inc./Community Bankers Trust Corporation	Colony Bankcorp, Inc./SouthCrest Financial Group, Inc.
VyStar Credit Union/Heritage Southeast Bancorporation Inc.	Seacoast Banking Corporation of Florida/Legacy Bank of Florida

The following operating statistics were compiled for the guideline transaction group and Triumph Bank.

	Triumph			Publicly Traded Bank Data from S&P Global, Inc.
Financial Metric	Bank *			Low			25th Percent			Median			75th Percent			High
LTM Return on Average Equity		10.10	%		3.16	%		7.44	%		9.71	%		11.30	%		12.45	%
LTM Return on Average Assets		0.98	%		0.31	%		0.79	%		0.95	%		1.13	%		1.28	%
Non-Performing Assets/Total Assets		0.92	%		0.00	%		0.42	%		0.63	%		0.86	%		1.31	%
Total Assets		893,732			533,334			760,832			1,205,738			1,798,949			2,273,916

For Triumph Bank, reflects data through March 31, 2021 LTM as reported by S&P Global, Inc.

The implied Triumph merger multiples and summary whole bank transaction multiples are shown below.

	Transaction			Multiples w/
	Announced			Updated Triumph			Whole Bank Transactions from S&P Global, Inc.
Valuation Metric	By S&P *			Data **			Low			25th Percent			Median			75th Percent			High
Price / Earnings		17.17	x		17.86	x		10.10	x		13.24	x		17.61	x		19.05	x		43.55	x
Price / Book		149.81	%		146.15	%		85.49	%		134.84	%		146.86	%		176.87	%		214.25	%
Price / Tangible Book		152.50	%		148.71	%		85.49	%		148.04	%		174.29	%		184.92	%		214.33	%

For Triumph Bancshares, Inc., reflects multiples as announced by S&P Global, Inc. (reflects Triumph data for the twelve months ended December 31, 2020)

For Triumph Bancshares, Inc., based on SFNC closing on June 4, 2021 and Triumph data for twelve months ended May 31, 2021

Comparable Company Analysis

Southard Financial analyzed publicly available information relating to publicly traded banking institutions with the following characteristics: (a) assets between $500 million and $2.5 billion; (b) LTM return on average assets of 0.5% to 1.5%; (c) LTM return on average equity of 5% to 15%; and (d) average daily trading volume of 1,000 shares or more. Further, institutions that are the target of an announced acquisition were excluded from the group. The 30 selected publicly traded banking institutions used in the analysis included:

Auburn National Bancorporation, Inc.	MainStreet Bancshares, Inc.
Bank of South Carolina Corporation	Mountain Commerce Bancorp, Inc.
Bank of the James Financial Group, Inc.	National Bankshares, Inc.
C&F Financial Corporation	New Peoples Bankshares, Inc.
Citizens Bancshares Corporation	Old Point Financial Corporation
Citizens Holding Company	Parkway Acquisition Corp.
Coastal Carolina Bancshares, Inc.	Peoples Bancorp of North Carolina, Inc.
Colony Bankcorp, Inc.	Prime Meridian Holding Company
F & M Bank Corp.	Professional Holding Corp.
First Community Corporation	South Atlantic Bancshares, Inc.
First IC Corporation	The Freedom Bank of Virginia
First National Corporation	Touchstone Bankshares Inc.
FVCBankcorp, Inc.	UB Bancorp
GrandSouth Bancorporation	United Bancorporation of Alabama, Inc.
John Marshall Bancorp, Inc.	Virginia National Bankshares Corporation

The following operating statistics were compiled for the publicly traded group and Triumph.

	Triumph			Publicly Traded Bank Data from S&P Global, Inc.
Financial Metric	Bank *			Low			25th Percent			Median			75th Percent			High
LTM Return on Average Equity		10.10	%		5.68	%		7.93	%		9.92	%		11.52	%		14.25	%
LTM Return on Average Assets		0.98	%		0.54	%		0.74	%		0.97	%		1.12	%		1.47	%
Non-Performing Assets/Total Assets		0.92	%		0.03	%		0.14	%		0.35	%		0.65	%		1.33	%
Total Assets		893,732			554,099			874,874			1,032,398			1,545,655			2,233,558

For Triumph Bank, reflects data through March 31, 2021 LTM as reported by S&P Global, Inc.

The implied Triumph merger multiples and summary market pricing multiples of the guideline group of publicly traded bank stocks are shown below.

	Transaction			Multiples w/
	Announced			Updated Triumph			Publicly Traded Bank Data from S&P Global, Inc.
Valuation Metric	By S&P *			Data **			Low			25th Percent			Median			75th Percent			High
Price / Earnings		17.17	x		17.86	x		5.57	x		11.03	x		12.50	x		14.00	x		18.33	x
Price / Book		149.81	%		146.15	%		54.21	%		101.39	%		113.21	%		120.68	%		209.12	%
Price / Tangible Book		152.50	%		148.71	%		54.59	%		105.87	%		114.91	%		130.56	%		209.12	%

For Triumph Bancshares, Inc., reflects multiples as announced by S&P Global, Inc. (reflects Triumph data for the twelve months ended December 31, 2020)

For Triumph Bancshares, Inc., based on SFNC closing on June 4, 2021 and Triumph data for twelve months ended May 31, 2021

Based on the review conducted by Southard Financial, the implied Triumph merger pricing ratios are near the high end of the range of the publicly traded pricing ratios shown above, supporting the fairness of the Triumph merger to the Triumph shareholders.

Present Value Analysis

Southard Financial performed an analysis of the present value of Triumph’s future earnings. The analysis is based on Triumph’s historical and projected financial results on a standalone basis with normalizing adjustments made by Southard Financial. Southard Financial utilized a single period model with earnings in the first year estimated as follows: (a) ongoing pre-tax return on average assets of 1.20% based on historical results and forecasted results, (b) forecasted 2021 average assets, (c) ongoing holding company net pre-tax expenses, and (d) an estimated tax rate of 26%.

Sensitivity Analysis ($000)
	Discount Rate
	11.00%		12.00%		13.00%		14.00%		15.00%
Terminal Value Growth
3.0%		105,437,500		93,712,850		84,350,000		76,674,150		70,263,550
3.5%		112,438,550		99,195,600		88,820,550		80,301,200		73,384,500
4.0%		120,536,150		105,437,500		93,712,850		84,350,000		76,674,150
4.5%		129,730,300		112,438,550		99,195,600		88,820,550		80,301,200
5.0%		140,611,450		120,536,150		105,437,500		93,712,850		84,350,000

As illustrated in the sensitivity analysis above, the valuation of Triumph ranged from $70.3 million to $140.6 million with a base case scenario valuation of $93.7 million. The consideration to be received by Triumph shareholders (approximately $132 million based on the closing price of Simmons common stock on June 4, 2021) generally represents a premium to the values shown above, supporting the fairness of the Triumph merger to the Triumph shareholders.

Liquidity

The proposed Triumph merger will create liquidity for the Triumph shareholders as the Triumph shareholders will own Simmons common stock following the Triumph merger, which is publicly traded stock with significant volume (median daily volume of approximately 470,000 shares in the year-to-date period ended June 4, 2021). The ability to hold publicly traded shares versus privately held stock is a significant positive factor for the Triumph shareholders.

Additional Considerations

The preparation of a fairness opinion is a complex process and is not susceptible to a partial analysis or summary description. Therefore, Southard Financial believes that its analyses must be considered as a whole and that selecting portions of its analyses would create an incomplete view of the process underlying the Southard Financial opinion without considering the analyses taken as a whole. In addition, Southard Financial considered the results of all such analyses and did not assign relative weights to any of the analyses, but instead made qualitative judgments as to the significance and relevance of each analysis and factor, so the ranges of valuations resulting from any particular analysis described above should not be taken to be the view of Southard Financial as to the actual value of Triumph.

In accordance with recognized professional ethics, Southard Financial’s professional fees for this service are not contingent upon the opinions expressed herein, and neither Southard Financial, nor any of its employees, has a present or intended financial relationship with or interest in Simmons, Triumph or Triumph Bank.

Certain Prospective Financial Information

Simmons and Triumph 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 of any such projections. However, Triumph is including in this proxy statement/prospectus certain unaudited prospective financial information that was made available by Triumph to Southard Financial for the purpose of Southard Financial performing its financial analysis in connection with rendering its opinion to the Triumph board of directors, as described in the section entitled “—Opinion of Triumph’s Financial Advisor.” This unaudited prospective financial information, which we refer to as the Triumph prospective information, was prepared solely by Triumph management and was not prepared, provided to, reviewed or approved by Simmons management or the Simmons board of directors. By inclusion of this information, the respective managements and boards of directors of Triumph and Simmons, and Triumph’s financial advisor, assume no responsibility for the Triumph prospective information. The inclusion of this information should not be regarded as an indication that any of Triumph, Simmons, Southard Financial, 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.

The Triumph prospective information was prepared solely by Triumph management for internal use and is subjective in many respects. While presented with numeric specificity, the Triumph prospective information reflects numerous estimates and assumptions made solely by Triumph management with respect to business, economic, market, competition, regulatory and financial conditions and matters specific to Triumph’s business,

all of which are difficult to predict and many of which are beyond Triumph’s control. The Triumph prospective information reflects both assumptions solely by Triumph management as to certain business decisions that are subject to change and, in many respects, subjective judgment solely by Triumph management, and thus is susceptible to multiple interpretations and periodic revisions based on actual experience and business developments. No assurance can be given that the Triumph prospective information and the underlying estimates and assumptions will be realized. Actual results may differ materially from those set forth below, and important factors that may affect actual results and cause the Triumph prospective information to be inaccurate include, but are not limited to, risks and uncertainties relating to Triumph’s business, industry performance, general business and economic conditions, competition, customer requirements and adverse changes in applicable laws, regulations or rules. For other factors that could cause actual results to differ, see the sections entitled “Risk Factors” and “Cautionary Statement Regarding Forward-Looking Statements” in this proxy statement/prospectus.

The Triumph prospective information was not prepared by Triumph management with a view toward public disclosure, nor was it prepared with a view toward compliance with 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 Triumph prospective information requires significant estimates and assumptions that make it inherently less comparable to the similarly titled GAAP measures in Triumph’s historical GAAP financial statements. Neither Triumph’s nor Simmons’ independent public accountants nor any other independent accountants, have compiled, examined or performed any procedures with respect to the Triumph prospective information contained herein, nor have they expressed any opinion or any other form of assurance on such information or its achievability.

Furthermore, the Triumph prospective information does not take into account any circumstances or events occurring after the date it was prepared. No assurance can be given that, had the Triumph prospective information been prepared as of the date of this proxy statement/prospectus, similar estimates and assumptions would be used. Neither Triumph nor Simmons intends to, and expressly disclaims any obligation to, make publicly available any update or other revision to the Triumph prospective information to reflect circumstances existing since their preparation or to reflect the occurrence of unanticipated events, even in the event that any or all of the underlying assumptions are shown to be in error, or to reflect changes in general economic or industry conditions. The Triumph prospective information does not take into account the possible financial and other effects on Triumph of the Triumph merger and does not attempt to predict or suggest future results of the surviving company. The Triumph prospective information does not give effect to the Triumph merger, including the impact of negotiating or executing the Triumph merger agreement, the expenses that may be incurred in connection with consummating the Triumph merger, the potential synergies that may be achieved by the surviving company as a result of the Triumph merger, the effect on Triumph of any business or strategic decision or action that has been or will be taken as a result of the Triumph merger agreement having been executed, or the effect of any business or strategic decisions or actions that would likely have been taken if the Triumph merger agreement had not been executed, but which were instead altered, accelerated, postponed or not taken in anticipation of the Triumph merger. Further, the Triumph prospective information does not take into account the effect on Triumph of any possible failure of the Triumph merger to occur.

None of Triumph, Simmons, Southard Financial, or their respective affiliates, officers, directors, advisors or other representatives has made, makes or is authorized in the future to make any representation to any shareholder of Triumph or Simmons or other persons regarding Triumph’s ultimate performance compared to the information contained in the Triumph prospective information or that the projected results will be achieved. The summary of the Triumph prospective information included below is not being included to influence your decision whether to vote for the Triumph merger proposal, but is being provided solely because it was made available to Southard Financial in connection with the Triumph merger.

In light of the foregoing, and considering that the Triumph special meeting will be held many months after the Triumph prospective information was prepared, as well as the uncertainties inherent in any forecasted information, Triumph shareholders are cautioned not to place unwarranted reliance on such information, and all Triumph shareholders are urged to review the other information contained elsewhere in this proxy statement/prospectus for a description of Simmons’ and Landmark’s respective businesses as well as Simmons’ most recent SEC filings for a description of Simmons’ reported financial results. See the section entitled “Where You Can Find More Information.”

The following tables present the Triumph prospective information, which was prepared solely by Triumph management and approved for Southard Financial’s use by the Triumph board of directors for Southard Financial’s financial analysis in connection with rendering the Southard Financial opinion to the Triumph board of directors, as described in the section entitled “—Opinion of Triumph’s Financial Advisor.”

	As of or For the Years Ended December 31,
	2021		2022		2023		2024			2025
Triumph Net Income ($ millions)	$	8.3	$	8.5	$	8.9	$	9.2		$	10.7
Triumph Total Assets ($ billions)		0.98		1.08		1.19		1.30			1.43

					Assumed Long-Term Growth Rates for Triumph
Earnings (%)								6.48	%
Total Assets (%)								9.88	%

Simmons’ Reasons for the Triumph Merger

In reaching its decision to adopt and approve the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement, the Simmons board of directors evaluated the Triumph merger agreement and the Triumph merger in consultation with Simmons’ management, as well as Simmons’ financial and legal advisors, and considered a number of factors, including, without limitation, the following material factors, which are not presented in order of priority:

the anticipation that the Triumph merger is expected to enhance the scale and expand the footprint of the combined company in the attractive Tennessee banking market;

each of Simmons’, Triumph’s and the combined company’s business, operations, financial condition, asset quality, earnings and prospects;

the fact that Triumph’s business and operations complement those of Simmons and that the Triumph merger would result in a combined company with a diversified revenue stream from diversified geographic markets, a well-balanced portfolio and an attractive funding base;

its existing knowledge of Triumph’s business and its review and discussions with Simmons’ management concerning the additional due diligence examination of Triumph conducted in connection with the Triumph merger;

the complementary branch networks of Simmons and Triumph;

Triumph’s market position within the Tennessee banking market, particularly Triumph’s market share in the Nashville market;

its understanding of the current and prospective environment in which Simmons and Triumph operate, including national, regional and local economic conditions, the competitive environment for financial institutions generally and the likely effect of these factors on Simmons both with and without the Triumph 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 terms of the Triumph merger agreement, including the Triumph merger consideration, expected tax treatment, deal protection and termination fee provisions, which the Simmons board of directors reviewed with Simmons’ management and Simmons’ financial and legal advisors;

Simmons’ successful operating and acquisition track record, specifically Simmons’ history of efficiently closing and integrating acquisitions;

its belief that the Triumph merger is likely to provide substantial value to Simmons shareholders;

the potential risks associated with achieving anticipated cost synergies and savings and successfully integrating Triumph’s business, operations and workforce with those of Simmons;

the potential risk of diverting management attention and resources from the operation of Simmons’ business and towards the completion of the Triumph merger;

certain anticipated Triumph merger-related costs;

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

the potential risk of losing other acquisition opportunities while Simmons remains focused on completing the Triumph merger; and

the nature and amount of payments and other benefits to be received by Triumph management in connection with the Triumph merger.

The foregoing discussion of the information and factors considered by the Simmons board of directors is not intended to be exhaustive, but, rather, includes the material factors considered by the Simmons board of directors. In reaching its decision to adopt and approve the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement, the Simmons board of directors did not quantify or assign any relative weights to the factors considered, and individual directors may have given different weights to different factors. The Simmons board of directors considered all these factors as a whole, and overall considered the factors to be favorable to, and to support, its determination to adopt and approve the Triumph merger agreement and the transactions contemplated thereby, including the Triumph merger.

Interests of Triumph’s Directors and Executive Officers in the Triumph Merger

In considering the recommendation of the Triumph board of directors that Triumph shareholders vote “FOR” the Triumph merger proposal, Triumph shareholders should be aware that some of Triumph’s executive officers and directors have interests in the Triumph merger, which may be considered to be different from, or in addition to, the interests of the Triumph shareholders generally. These interests are described below. The Triumph board of directors was aware of these interests and considered them, among other matters, in reaching its decision to approve the Triumph merger agreement, the Triumph merger and the other transactions contemplated by the Triumph merger agreement and to recommend that Triumph shareholders vote “FOR” the Triumph merger proposal.

Employment Agreements

Seven executive officers of Triumph are party to employment agreements with Triumph that contain change of control payments: William J. Chase, Jr., Michael J. McCarver, Scott A. Forman, Steven C. Mitchener, John N. Brignole, David Umsted, and William C. Menkel. Under these employment agreements, the Triumph merger would constitute a change in control, as defined in the agreements. Without a change in control, these seven executives are entitled to certain defined severance benefits if they are terminated by Triumph without cause, as cause is defined in their respective employment agreements. In the event of termination (without a change in control), (i) Messrs. Chase, McCarver, Brignole, Umsted and Menkel would be entitled to receive compensation equal to their annual base salary and 12 months of continued health coverage, and (ii) Messrs. Forman and Mitchener would be entitled to receive compensation equal to one-half of their annual base salary and six months of continued health coverage. In the event of resignation for good reason (without a change in control), (i) Mr. Menkel would be entitled to receive compensation equal to his annual base salary and 12 months of continued health coverage and (ii) Mr. Mitchener would be entitled one-half of his annual base salary and six months of continued health coverage. Upon a change of control, the seven executives may be due certain payments based on the terms and conditions of their employment agreements, as follows.

William J. Chase, Jr., Michael J. McCarver and William C. Menkel. In the event of a change of control, if any of Messrs. Chase, McCarver or Menkel is offered a new employment agreement that contains a “material reduction,” which is defined as (i) a material reduction in the executive’s duties, title, authority or responsibilities, and (ii) a reduction in the base salary of the executive, or (iii) a relocation of the executive’s principal place of work to more than 25 miles from a specified location in Tennessee, then he is due a payment equal to his annual base salary and 12 months of continued health coverage. If any of Messrs. Chase, McCarver or Menkel is terminated in anticipation of the change in control or is not offered a position after the change in control, then he is due a payment equal to two times his annual base salary in the case of Messrs. Chase and McCarver, and equal to his annual base salary in the case of Mr. Menkel, as well as 12 months of continued health coverage. Mr. Chase was offered a position that included a material reduction and as a result he will be eligible for a payment equal to his annual base salary and 12 months of continued health coverage.

David Umsted, Scott A. Forman and John N. Brignole. In the event of a termination without cause or resignation for good reason (either before or after a change of control), each of Messrs. Umsted, Forman and Brignole is entitled to receive 12 months of continued health coverage, Mr. Forman is entitled to receive a payment equal to one-half of his annual base salary and each of Messrs. Umsted and Brignole is entitled to receive a payment equal to his annual base salary. In the event of a change in control, (i) each of Mr. Brignole and Mr. Umsted is due a payment equal to one-half of his annual base salary and 12 months of continued health coverage, unless he is offered employment on at least similar terms and conditions as his current employment and he refuses to accept such employment, in which case, no change in control payment or continued benefits will be due and (ii) Mr. Forman is due a payment equal to one-half of his annual base salary and 12 months of continued health coverage, unless he is offered employment on at least similar terms and conditions as his current employment and he refuses to accept such employment, in which case, no change in control payment will be due. If any of Messrs. Umsted, Forman or Brignole is terminated in anticipation of the change in control, then he is due a payment equal to one-half of his annual base salary plus an amount equal to his pro-rata bonus earned through the date of termination and 12 months of continued health coverage.

Steven C. Mitchener. In the event of a change of control, Mr. Mitchener is entitled to receive a payment equal to one-half of his annual base salary if he is terminated in anticipation of the change in control or is not offered a position after the change in control that includes the same base salary, comparable duties, title authority and responsibilities.

As of the date of this proxy statement/prospectus, John Bobango has been offered an advisory position with Simmons for 18 months following the closing of the Triumph merger for a fee of $660,000.

The Triumph merger will also act to trigger accelerated vesting of outstanding options held by the seven executive officers named above (and others) under the Triumph 2006 Incentive and Non-Qualified Stock Option Plan, Triumph 2012 Incentive and Non-Qualified Stock Option Plan, and the Triumph 2017 Incentive and Non-Qualified Stock Option Plan. The amounts of the options will not be affected by the Triumph merger, but the timing of the vesting of the options will be accelerated.

Incentive Plans and Stock Options

The Triumph merger will trigger the vesting of all issued and outstanding options, including any options issued to executives and directors of Triumph, under the Triumph 2006 Incentive and Non-Qualified Stock Option Plan, Triumph 2012 Incentive and Non-Qualified Stock Option Plan, or Triumph 2017 Incentive and Non-Qualified Stock Option Plan.

Under the terms of the Triumph merger agreement, at the Triumph effective time, each Triumph stock option, whether vested or unvested, that is outstanding and unexercised immediately prior to the Triumph effective time will be canceled and converted into the right to receive from Simmons a cash payment per option share equal to the difference between (1) the fully diluted per share value and (2) the exercise price of such Triumph stock option.

Indemnification

The Triumph merger agreement provides that, for a period of six years after the Triumph effective time, Simmons will indemnify, defend and hold harmless each of the present and former directors or officers of Triumph and its subsidiaries against all liabilities arising out of actions or omissions arising out of such person’s services as director or officer of Triumph, or at Triumph’s request, of another corporation, partnership, joint venture, trust or other enterprise, occurring at or prior to the Triumph effective time to the fullest extent permitted under the Triumph charter and the Triumph bylaws in effect on the date of the Triumph merger agreement (subject to applicable law), including provisions relating to the advancement of expenses incurred in the defense of any litigation, provided that, in the case of an advancement of expenses, any indemnified party to whom expenses are advanced provides a written undertaking to repay such advances if it is ultimately determined that such indemnified party is not entitled to indemnification.

THE MERGERS

Board of Directors and Management of Simmons and Simmons Bank After the Mergers

The directors and officers of Simmons and Simmons Bank immediately prior to the effective time of each of the mergers will serve as the directors and officers of the surviving corporation and surviving bank from and after the effective time of each of the mergers in accordance with the bylaws of the surviving corporation and surviving bank. Information about the current members of the Simmons board of directors can be found in the documents listed in the section entitled “Where You Can Find More Information.”

Public Trading Markets

Simmons common stock is listed for trading on Nasdaq under the symbol “SFNC.” Neither Landmark common stock nor Triumph common stock is listed for trading on any securities exchange and there is no established public trading market for either Landmark common stock or Triumph common stock.

Under the merger agreements, Simmons will cause the shares of Simmons common stock to be issued in the mergers to be approved for listing on Nasdaq, subject to notice of issuance, and the merger agreements provide that Simmons and Landmark, in the case of the Landmark merger agreement, and Simmons and Triumph, in the case of the Triumph merger agreement, will not be required to complete the applicable merger if such shares have not been authorized for listing on Nasdaq.

Accounting Treatment

The mergers will be accounted for as acquisitions by Simmons using the acquisition method of accounting in accordance with FASB ASC Topic 805, “Business Combinations.” The result of this is that (1) the recorded assets and liabilities of Simmons will be carried forward at their recorded amounts, (2) Simmons historical operating results will be unchanged for the prior periods being reported on, and (3) the assets and liabilities of each of Landmark and Triumph will be adjusted to fair value at the respective dates Simmons assumes control of the combined entity, or the respective merger dates. In addition, all identifiable intangibles will be recorded at fair value and included as part of the net assets acquired. The amount by which the purchase price for each merger, consisting of the value of cash and shares of Simmons common stock to be issued to former Landmark and Triumph shareholders, respectively, and the value of cash and shares of Simmons common stock to be issued to former holders of Landmark and Triumph equity awards, respectively, exceeds the fair value of the net assets, including identifiable intangibles, of Landmark and Triumph, respectively, at the applicable merger date will be reported as goodwill. In accordance with current accounting guidance, goodwill is not amortized and will be evaluated for impairment at least annually. Identified intangibles will be amortized over their estimated lives. Further, the acquisition method of accounting results in the operating results of each of Landmark and Triumph being included in the operating results of Simmons from the applicable merger date going forward.

Appraisal and Dissenters’ Rights

Dissenters’ rights with respect to Landmark common stock and Triumph common stock are governed by the TBCA. Under the TBCA, Landmark shareholders as of the Landmark record date and Triumph shareholders as of the Triumph record date have the right to dissent from the Landmark merger or the Triumph merger, respectively, and to receive payment in cash for the fair value of such holders’ shares of Landmark common stock or Triumph common stock, respectively, in lieu of the consideration such holders would otherwise be entitled to pursuant to the applicable merger agreement. These rights are known as “appraisal rights” or “dissenters’ rights.” However, it is a condition to Simmons’ obligations under the Landmark merger agreement and the Triumph merger agreement that holders of not more than five percent of outstanding Landmark common stock or Triumph common stock, respectively, demand, properly and in writing, appraisal for such shares of outstanding common

stock. No Landmark shareholder or Triumph shareholder dissenting from the applicable merger will be entitled to the applicable merger consideration or any dividends or other distributions unless and until such shareholder fails to perfect or effectively withdraws or loses his or her right to dissent from the applicable merger agreement. Subject to the terms of the merger agreements, the Landmark board of directors or the Triumph board of directors could elect to terminate the applicable merger agreement even if it is approved by shareholders, thus cancelling dissenters’ rights.

The following is intended as a brief summary of the material provisions of the Tennessee statutory procedures required to be followed by a Landmark shareholder or Triumph shareholder in order to dissent from the Landmark merger or the Triumph merger, respectively, and perfect appraisal rights. This summary, however, is not a complete statement of all applicable requirements and is qualified in its entirety by reference to Section 48-23-101 through Section 48-23-302 of the TBCA, the full text of which appears in Annex G to this proxy statement/prospectus. Strict compliance with the statutory procedures is required to perfect appraisal rights under the TBCA. Neither Landmark nor Triumph can give any Landmark shareholder or Triumph shareholder legal advice. To completely understand this law, each Landmark shareholder and Triumph shareholder should read carefully Annex G to this proxy statement/prospectus in its entirety, and may want, and Landmark and Triumph encourage any Landmark shareholder or Triumph shareholder, as applicable, seeking to dissent, to consult with such shareholder’s legal advisor. Any Landmark shareholder or Triumph shareholder who wishes to dissent should not send in a signed proxy unless such shareholder marks such shareholder’s proxy to vote against the Landmark merger or the Triumph merger, as applicable, or such shareholder will lose the right to dissent.

In order to perfect dissenters’ rights with respect to the Landmark merger or the Triumph merger, a shareholder must satisfy each of the following conditions:

deliver to Landmark or Triumph, as applicable, before the vote at the applicable special meeting is taken, written notice of such shareholder’s intent to demand payment for such shareholder’s shares of Landmark common stock or Triumph common stock if the applicable merger is effectuated;

not vote, or cause or permit to be voted, such shareholder’s shares of Landmark common stock or Triumph common stock in favor of the applicable merger; and

demand payment and deposit with Simmons such shareholder’s stock certificates representing such shareholder’s shares of Landmark common stock or Triumph common stock, as applicable, in accordance with the terms of the written dissenters’ notice sent by Simmons following the merger, which notice will set forth where and when to send the payment demand.

Such written notification should be delivered either in person or by mail (certified mail, return receipt requested, being the recommended form of transmittal) to Landmark, with respect to Landmark shareholders, or Triumph, with respect to Triumph shareholders, at the following respective addresses:

Landmark Community Bank

5880 Ridge Bend Road

Memphis, Tennessee 38120

Attention: James P. “Jake” Farrell

Telephone: (901) 457-3111

Email: jakefarrell@landmarkbanktn.com

Attention: Charles E “Buddy” Dickey

Telephone: (901) 457-3123

Email: cdickey@landmarkbanktn.com

Triumph Bancshares, Inc.

5699 Poplar Avenue

Memphis, Tennessee 38119

Attention: Michael J. McCarver

Telephone: (901) 333-8802

Landmark and Triumph urge any Landmark shareholder or Triumph shareholder, respectively, who wishes to dissent to act carefully. Neither Landmark nor Triumph can, and neither Landmark nor Triumph does, accept the risk of late or undelivered notices or demands. A dissenting Landmark shareholder or Triumph shareholder may call the applicable telephone number above to receive confirmation that such shareholder’s notice or demand has been received. If such shareholder’s notices or demands are not timely received by Landmark or Triumph, as applicable, then such shareholder will not be entitled to exercise his or her dissenters’ rights. Landmark shareholders and Triumph shareholders bear the risk of non-delivery and of untimely delivery. If the applicable merger is completed, a shareholder who fails to satisfy delivery requirements will have no appraisal rights with respect to such holder’s shares of Landmark common stock or Triumph common stock, as applicable.

ANY LANDMARK SHAREHOLDER OR TRIUMPH SHAREHOLDER WHO WISHES TO EXERCISE DISSENTERS’ RIGHTS OR WHO WISHES TO PRESERVE SUCH SHAREHOLDER’S RIGHT TO DO SO SHOULD REVIEW ANNEX G CAREFULLY AND CONSULT SUCH SHAREHOLDER’S LEGAL ADVISOR. FAILURE TO TIMELY AND PROPERLY COMPLY WITH THE PROCEDURES SET FORTH THEREIN WILL RESULT IN THE LOSS OF SUCH RIGHTS. INVESTMENT BANKER OPINIONS AS TO THE FAIRNESS, FROM A FINANCIAL POINT OF VIEW, OF THE CONSIDERATION PAYABLE IN TRANSACTIONS SUCH AS THE MERGERS ARE NOT OPINIONS AS, AND DO NOT ADDRESS IN ANY RESPECT, FAIR VALUE UNDER THE TBCA.

No later than ten days after the completion of the applicable merger, Simmons, as the surviving corporation of such merger, must deliver to each Landmark shareholder and Triumph shareholder who filed a notice of intent to demand payment for such shareholder’s shares a written appraisal notice and an election form that, among other things:

specifies the first date of any public announcement of the principal terms of the applicable proposed merger;

requires the dissenting shareholder to certify whether beneficial ownership of their shares of Landmark common stock or Triumph common stock, as applicable, was acquired before the date of the public announcement regarding the applicable merger;

requires the dissenting shareholder to certify that such shareholder did not vote in favor of or consent to the applicable merger; and

states:

where to return the completed appraisal election form and such shareholder’s stock certificates representing such shareholder’s shares of Landmark common stock or Triumph common stock, as applicable, for deposit, and the date by which each must be received by Simmons or its agent, which may not be fewer than 40 nor more than 60 days after the written appraisal notice is sent to shareholders, and that such shareholder shall have waived the right to demand payment with respect to such shares unless the form is received by Simmons or its agent by such specified date;

Simmons’s estimate of the fair value of the shares of Landmark common stock or Triumph common stock, as applicable; and

that, if requested in writing, Simmons will provide to the shareholder so requesting, within ten days after the date set for receipt by Simmons of the appraisal election form, the number of Landmark shareholders or Triumph shareholders, as applicable, who return the forms by such date and the total number of shares owned by them;

and would need to be accompanied by a copy of Section 48-23-101 through Section 48-23-302 of the TBCA, if Landmark, Triumph or Simmons, as applicable, had not previously sent a copy of that chapter to the shareholder. The full text of Section 48-23-101 through Section 48-23-302 of the TBCA appears in Annex G to this proxy statement/prospectus.

Upon receipt of such notice, dissenting shareholders would become entitled to receive payment of their shares of Landmark common stock or Triumph common stock, as applicable, when they:

demand payment;

certify whether such shareholder acquired the shares of Landmark common stock or Triumph common stock, as applicable, prior to the date of the first public announcement of the applicable merger; and

deposit with Simmons such shareholder’s stock certificates representing such shareholder’s shares of Landmark common stock or Triumph common stock, as applicable, in accordance with the instructions set forth in the notice.

Such shareholder retains all other rights of a shareholder until these rights are canceled or modified by the effectuation of the applicable merger. A shareholder who does not demand payment or deposit such shareholder’s share certificates where required, each by the date set in the dissenters’ notice, is not entitled to payment for such shareholder’s Landmark common stock or Triumph common stock, as applicable.

Upon receipt of the payment demand described above or the date the applicable merger is effectuated, whichever is later, Simmons will pay to each Landmark shareholder and Triumph shareholder who complied with the requirements of the TBCA the amount Simmons estimates to be the fair value of each Landmark shareholder’s and Triumph shareholder’s shares, plus accrued interest. The payment will be accompanied by:

Simmons’ balance sheet as of the end of a fiscal year ending not more than 16 months before the date of payment, an income statement for that year, a statement of changes in shareholders’ equity for that year, and the latest available interim financial statements, if any;

an estimate of the fair value of the shares, which shall equal or exceed the estimate given in the dissenters’ notice;

an explanation of how the interest was calculated;

a statement of the dissenter’s right to demand payment in case of disagreements between the dissenter and Simmons regarding fair value; and

a copy of Section 48-23-101 through Section 48-23-302 of the TBCA, if Landmark, Triumph or Simmons, as applicable, had not previously sent a copy of that chapter to the shareholder. The full text of Section 48-23-101 through Section 48-23-302 of the TBCA is attached as Annex G to this proxy statement/prospectus.

A shareholder who does not demand payment or deposit the shareholder’s stock certificates where required, each by the date set in the dissenters’ notice, is not entitled to payment for such shareholder’s shares. A demand for payment filed by a dissenting shareholder may not be withdrawn without Landmark’s or Triumph’s consent, as applicable, or, after the completion of the applicable merger, Simmons’s consent. Upon valid withdrawal from the appraisal process, the right of such shareholder to be paid the fair value of such shareholder’s shares will cease, and such shareholder will be reinstated as a shareholder and will be entitled to receive the Landmark merger consideration or the Triumph merger consideration, as applicable.

A dissenting shareholder who is dissatisfied with Simmons’s estimate of the fair value of the shares of Landmark common stock or Triumph common stock, as applicable, must notify Simmons of such shareholder’s estimate of the fair value of such shareholder’s shares and demand payment of that estimate plus interest in the appraisal election form within one month after Simmons made or offered payment for such shareholder’s shares. A dissenting shareholder who fails to notify Simmons in writing of the shareholder’s demand to be paid its stated estimate of the fair value of the shares plus interest within the required time period waives the right to demand payment and will be entitled only to the payment offered by Simmons in the appraisal election form.

If a demand for payment from a dissenting shareholder who is dissatisfied with Simmons’s estimate of the fair value of such holder’s shares remains unsettled, then within two months after receipt of a payment demand from such shareholder, Simmons must petition a court of record having equity jurisdiction in the county where Simmons’s principal office is located, to determine the fair value of the shares and accrued interest. Simmons will be required to make all dissenting shareholders whose demands remain unsettled, parties to the proceeding. If Simmons does not commence the proceeding within the two-month period, it must pay each dissenting shareholder whose demand remains unsettled the amount demanded by such shareholder.

Failure to strictly comply with the applicable TBCA provisions will result in the loss of the right of appraisal. The right of a dissenting shareholder to be paid the fair value for such shareholder’s shares will also cease if the applicable merger agreement is terminated for any reason.

THE PRECEDING SUMMARY IS QUALIFIED IN ITS ENTIRETY BY THE TEXT OF THE APPRAISAL PROVISIONS OF TBCA SECTION 48-23-101 THROUGH SECTION 48-23-302. A COPY OF THESE STATUTES IS ATTACHED TO THIS PROXY STATEMENT/PROSPECTUS AS ANNEX G AND IS INCORPORATED HEREIN BY REFERENCE. TO THE EXTENT THERE ARE ANY INCONSISTENCIES BETWEEN THE FOREGOING SUMMARY AND THE APPLICABLE PROVISIONS OF THE TBCA, THE TBCA WILL CONTROL.

Regulatory Approvals Required for the Mergers and the Triumph Bank Merger

Completion of each of the Landmark merger, the Triumph merger, and the Triumph Bank merger is subject to prior receipt of certain approvals and consents required to be obtained from, or waived by, applicable governmental and regulatory authorities, without materially burdensome conditions or requirements being imposed by any governmental authority as part of a regulatory approval. Subject to the terms and conditions of the merger agreements, Simmons and Landmark, in the case of the Landmark merger agreement, and Simmons and Triumph, in the case of the Triumph merger agreement, have agreed to use their reasonable best efforts and cooperate to promptly prepare and file all necessary documentation and to obtain as promptly as practicable all regulatory approvals necessary or advisable to complete the transactions contemplated by the merger agreements. These approvals include, among others, approval from the Federal Reserve Board and the ASBD, with respect to each of the Landmark merger and the Triumph Bank merger. No assurance can be given that the necessary regulatory approvals will be received in time to effect the mergers in the fourth quarter of 2021.

Federal Reserve Board

Under Federal Reserve Board regulations, the transactions contemplated in the Landmark merger agreement are exempt from the requirement to submit an application to the Federal Reserve Board pursuant to the BHC Act.

The transactions contemplated by the Triumph merger agreement are subject to review and approval by the Federal Reserve Board pursuant to the BHC Act. Simmons has submitted to the Federal Reserve Board a request for waiver of this approval requirement with respect to the Triumph merger. If the Federal Reserve Board does not grant this waiver request, Simmons will be required to submit an application under Section 3 of the BHC Act to consummate the Triumph merger.

When acting on applications under Section 3 of the BHC Act, the Federal Reserve Board is required by statute and under its regulations to consider a number of factors. These factors include, but are not limited to, the following: (i) the financial and managerial resources (including consideration of the competence, experience and integrity of the officers, directors and principal shareholders, as well as the pro forma capital ratios) and future prospects of the combined organization; (ii) the supervisory records of the parties and compliance with federal banking laws and regulations (specifically including the effectiveness of the applicant in combatting money laundering); (iii) the ways in which the transaction would satisfy the convenience and needs of the communities served by the parties; (iv) the effect of the transaction on the concentration of deposits on a nationwide basis; (v) the extent to which the transaction would result in greater or more concentrated risks to the stability of the U.S. banking or financial system; (vi) the effect of the transaction on competition or on the concentration of resources in any banking market; and (vii) the record of performance of each of Simmons Bank and Triumph Bank in meeting the credit needs of the respective communities that they serve, including low and moderate income neighborhoods within such communities, under the Community Reinvestment Act. As of their most recent Community Reinvestment Act examinations, Simmons Bank and Triumph Bank each had Community Reinvestment Act ratings of “satisfactory.”

The Landmark merger and the Triumph Bank merger are also subject to review and approval by the Federal Reserve Board under Section 18(c) of the Federal Deposit Insurance Act, or the Bank Merger Act. Specifically, Simmons Bank has submitted applications under the Bank Merger Act seeking the prior approval of the Federal Reserve Board for Landmark to merge with and into Simmons Bank, and for Triumph Bank to merge with and into Simmons Bank. With respect to an application filed under the Bank Merger Act, the Federal Reserve Board is required to consider, among other factors: (i) whether the effect of the applicable transaction in any portion of the country would substantially lessen competition, tend to create a monopoly, or otherwise retrain trade; (ii) the financial and managerial resources and future prospects of the banking organizations, including the effect of the applicable transaction on such resources (including capital and pro forma capital ratios of the combined organization and its management expertise, internal controls and risk management systems); (iii) the supervisory records of the banking organizations, including records of compliance with Bank Secrecy Act and anti-money laundering laws; (iv) the extent to which the applicable transaction would result in greater or more concentrated risks to the stability of the U.S. banking or financial system; and (v) the effect of the applicable transaction on the convenience and needs of the communities served by the banking organizations, including consideration of the records of performance of the relevant insured banking organizations under the Community Reinvestment Act. As of their most recent Community Reinvestment Act examinations, Simmons Bank, Landmark and Triumph Bank each had Community Reinvestment Act ratings of “satisfactory.”

A transaction approved under the Bank Merger Act or BHC Act generally may not be completed until 30 days after the approval of the appropriate federal banking agency is received (here, the Federal Reserve Board), during which time the Department of Justice, which we refer to as the DOJ, may initiate legal action to prevent consummation of the transaction if the DOJ determines the transaction may have a significantly adverse effect on competition. With the approval of the applicable federal agency and the concurrence of the DOJ, the 30-day waiting period may be reduced to no less than 15 days. The commencement of an antitrust action would stay the effectiveness of such an approval unless a court specifically ordered otherwise. In reviewing either

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of the Landmark merger or the Triumph Bank merger, the DOJ could analyze the applicable merger’s effect on competition differently than the Federal Reserve Board, and thus it is possible that the DOJ could reach a different conclusion than the Federal Reserve Board regarding the transaction’s effects on competition. A determination by the DOJ not to object to either of these mergers may not prevent the filing of antitrust actions by private persons or state attorneys general.

Simmons is required to publish notice of its applications to the Federal Reserve Board and to provide the opportunity for public comment on these applications. The Federal Reserve Board takes into account the views of third-party commenters, particularly on the subject of the convenience and needs of the communities to be served. The Federal Reserve Board may upon request or upon its own initiative hold a public hearing or meeting to clarify facts or issues raised by the applications in order to aid in the Federal Reserve Board’s decision-making process. Any hearing, meeting or comments provided by third parties could prolong the period during which the applications are under review by the Federal Reserve Board.

State of Arkansas

Although no application is required to be filed with the ASBD in order to complete the Triumph merger, Simmons Bank is required to submit applications to, and receive approval from, the ASBD for the Landmark merger and Triumph Bank merger to complete such mergers. The ASBD will review the applications to determine whether the mergers comply with Arkansas law. Simmons Bank is required to publish notice of its applications to the ASBD and to provide the opportunity for public comment on these applications. The ASBD is required by law to hold a public hearing regarding each application. Any hearing, meeting or comments provided by third parties could prolong the period during which the applications are under review by the ASBD.

State of Tennessee

Although no application is required to be filed with the TDFI in order to complete the Landmark merger, the Triumph merger or the Triumph Bank merger, the TDFI requires that Simmons Bank notify the TDFI of the proposed mergers not later than the date on which the applications under the Bank Merger Act are filed with the Federal Reserve Board and provide to the TDFI a copy of the applications submitted to the Federal Reserve Board under the Bank Merger Act.

Additional Regulatory Approvals and Notices

Notifications and/or applications requesting approval may be submitted to various other federal and state regulatory authorities and self-regulatory organizations.

Simmons, Landmark and Triumph believe that the mergers do not raise significant regulatory concerns and that we will be able to obtain all requisite regulatory approvals. None of Simmons, Landmark or Triumph can assure you that all of the regulatory approvals described above will be obtained and, if obtained, we cannot assure you as to the timing of any such approvals, our ability to obtain the approvals on satisfactory terms or the absence of any litigation challenging such approvals. In addition, there can be no assurance that such approvals will not impose conditions or requirements that, individually or in the aggregate, would or could reasonably be expected to have a material adverse effect on the financial condition, results of operations, assets or business of the combined company.

Simmons, Landmark and Triumph are not aware of any material governmental approvals or actions that are required for completion of the mergers other than those described above. It is presently contemplated that if any such additional governmental approvals or actions are required, those approvals or actions will be sought. There can be no assurance, however, that any additional approvals or actions will be obtained.

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THE MERGER AGREEMENTS

The following describes certain material provisions of the merger agreements, but does not describe all of the terms of the merger agreements and may not contain all of the information about the merger agreements that is important to you. The following is not intended to provide factual information about the parties or any of their respective subsidiaries or affiliates. The following description of the merger agreements is subject to, and qualified in its entirety by reference to, the Landmark merger agreement, which is attached to this proxy statement/prospectus as Annex A, and the Triumph merger agreement, which is attached to this proxy statement/prospectus as Annex B, each of which is incorporated by reference into this proxy statement/prospectus. We urge you to read each of the merger agreements carefully and in their entirety, as they are the legal document governing the respective mergers.

Structure of the Mergers

Each of the Simmons board of directors, the Simmons Bank board of directors and the Landmark board of directors, and each of the Simmons board of directors and the Triumph board of directors, adopted and approved the Landmark merger agreement and the Triumph merger agreement, respectively. The Landmark merger agreement provides for the merger of Landmark with and into Simmons Bank, with Simmons Bank as the surviving bank in the merger. The Triumph merger agreement provides for (a) the merger of Triumph with and into Simmons, with Simmons as the surviving corporation in the merger and (b) immediately following the Triumph merger, the merger of Triumph Bank with and into Simmons Bank, with Simmons Bank as the surviving bank.

The Merger Consideration

Landmark Consideration

Based on the assumptions set forth below, at the Landmark effective time, each share of Landmark common stock that is issued and outstanding immediately prior to the Landmark effective time (excluding certain specified shares of Landmark common stock held directly or indirectly by Landmark or Simmons and any dissenting shares) will be converted into the right to receive, subject to possible adjustment, the Landmark merger consideration, comprised of (i) [ ] shares of Simmons common stock, with cash in lieu of fractional shares, and (ii) $[ ] in cash. In the aggregate, Simmons expects to issue approximately [ ] shares of Simmons common stock and pay approximately $[ ] million (minus the cash payment for outstanding Landmark stock options) to Landmark shareholders upon completion of the Landmark merger, subject to certain conditions and potential adjustments under the Landmark merger agreement. The Landmark merger consideration is based on the assumption that (i) [ ] shares of Landmark common stock are issued and outstanding and (ii) [ ] shares of Landmark common stock are subject to outstanding Landmark stock options with a weighted average exercise price of $[ ], in each case, immediately prior to the Landmark effective time. In addition, we have assumed that the Landmark/Simmons average closing price is equal to $[ ], which was the closing sales price of Simmons common stock on the last practicable trading day prior to printing this proxy statement/prospectus.

Triumph Consideration