SEC Form DEF 14A filed by Landstar System Inc.

LETTER FROM OUR NON-EXECUTIVE CHAIRMAN OF THE BOARD

To the Stockholders of Landstar System, Inc.:   On behalf of the entire Board of Directors of Landstar System, Inc., we are pleased to invite you to attend the Annual Meeting of Stockholders to be held on Tuesday, May 5, 2026, at 9:00 a.m. Eastern Time, in a virtual-only meeting format. A notice of meeting, a proxy card, the 2025 Annual Report on Form 10-K and a Proxy Statement containing information about the matters to be acted upon at the 2026 Annual Meeting are enclosed. We hope you will attend the meeting virtually or by proxy and encourage you to vote your shares prior to the Annual Meeting.   We are proud of how our organization has navigated one of the most prolonged freight downturns in recent history while continuing to execute against our long-term strategy. Under the leadership of our Chief Executive Officer, Frank Lonegro, we remain focused on enhancing the Landstar business model, strengthening the Landstar brand, investing in strategic growth opportunities, and delivering value for our stockholders. Notably, Landstar has accelerated its development of artificial intelligence tools and technologies that have the potential to transform the freight transportation industry and reinforce Landstar’s strategic positioning for long-term stockholder value creation.   Our dedication to good governance practices remains unwavering, with a specific emphasis in 2025 on stockholder engagement, executive compensation matters, and director succession efforts. Following our long-standing commitment to refreshment of the Board, we were delighted to appoint J. Barr Blanton and Melanie M. Hart to the Landstar System, Inc. Board in October of 2025. Blanton, a former partner in McKinsey & Company’s transformation and private equity practices and current Chief Executive Officer of Crosslake Technologies, brings valuable strategic insight to both the Board and management. Similarly, Hart’s experience as Chief Financial Officer of Pool Corporation (NASDAQ: POOL) contributes significant expertise to Board discussions on global supply chain dynamics amidst an evolving, often volatile, tariff and trade policy environment. We are also deeply grateful to Board member Anthony Orlando for his eleven years of highly commendable service to Landstar and wish him all the best in his retirement.   We are excited for the future and remain confident in the strength of the Landstar model and our ability to create enduring value for our stockholders.
		Sincerely,
		DIANA M. MURPHY Non-Executive Chairman of the Board   March 23, 2026
Landstar System, Inc. | 13410 Sutton Park Drive S. | Jacksonville, Florida 32224

NOTICE OF ANNUAL MEETING

OF STOCKHOLDERS

To Be Held May 5, 2026

Agenda:

Only stockholders of record at the close of business on March 10, 2026 will be entitled to notice of, and to vote at, the meeting. A list of stockholders eligible to vote at the meeting will be available during business hours from April 24, 2026 to the date of the meeting at the Company’s corporate headquarters located at 13410 Sutton Park Drive South, Jacksonville, Florida 32224.

The platform for the virtual 2026 Annual Meeting includes functionality that provides validated stockholders the same meeting participation rights and opportunities they would have at an in-person meeting. Instructions to access and log-in to the virtual Annual Meeting are provided below. Once admitted, stockholders may view reference materials, submit questions and vote their shares by following the instructions that will be available on the meeting website.

For admission to the 2026 Annual Meeting, stockholders may go to www.virtualshareholdermeeting.com/LSTR2026 and enter the 16-digit control number you received with your proxy materials. Online access to the 2026 Annual Meeting will open at 8:45 a.m., Eastern Time on the morning of the meeting to allow time for stockholders to log-in prior to the start of the live audio webcast of the 2026 Annual Meeting at 9:00 a.m. Eastern Time. Persons who do not have a control number may attend as guests and will be able to hear the audio webcast but will not be able to utilize the question, voting or other functionality noted above. A recording of the webcast will be available at www.virtualshareholdermeeting.com/LSTR2026, approximately 24 hours after the conclusion of the meeting.

All stockholders are cordially invited to attend the 2026 Annual Meeting. Whether you expect to attend the meeting or not, your proxy vote is very important. To assure your representation at the 2026 Annual Meeting, the Company encourages you to vote in advance of the meeting by using one of the methods set forth below, whether or not you plan to access the virtual meeting.

By Order of the Board of Directors

MICHAEL K. KNELLER

Vice President, General Counsel and Secretary

Jacksonville, Florida

March 23, 2026

Important Notice Regarding the Availability of Proxy Materials for the Stockholder meeting to be held on May 5, 2026:

The proxy statement and annual report to security holders are available at www.landstar.com and www.proxyvote.com.

		LANDSTAR SYSTEM, INC. 13410 Sutton Park Drive South Jacksonville, Florida 32224

In accordance with rules and regulations adopted by the U.S. Securities and Exchange Commission (the “SEC”), we are pleased to provide access to our proxy materials over the Internet to all of our stockholders rather than in paper form. Accordingly, a Notice of Internet Availability of Proxy Materials (the “Notice of Internet Availability”) has been mailed to our stockholders on or about March 23, 2026. Stockholders will have the ability to access the proxy materials on the websites listed above, or to request a printed set of the proxy materials be sent to them by following the instructions in the Notice of Internet Availability.

The Notice of Internet Availability also provides instructions on how you may request that we send future proxy materials to you electronically by e-mail or in printed form by mail. If you choose to receive future proxy materials by e-mail, you will receive an e-mail next year with instructions containing a link to those materials and a link to the proxy voting site. Your election to receive proxy materials by e-mail or in printed form by mail will remain in effect until you terminate it. We encourage you to choose to receive future proxy materials by e-mail, which will allow us to provide you with the information you need in a more timely manner, will save us the cost of printing and mailing documents to you and will conserve natural resources.

2  Landstar System, Inc. 2026 Proxy Statement

Table of Contents

TABLE OF CONTENTS

Landstar System, Inc. 2026 Proxy Statement  3

Proxy Summary

PROXY SUMMARY

This summary highlights information contained elsewhere in this Proxy Statement. This summary does not contain all the information you should consider, and you should read the entire Proxy Statement before voting.

Meeting Agenda

LETTER FROM OUR PRESIDENT AND CHIEF EXECUTIVE OFFICER

Dear Stockholders,

Over the past two years, we have established our strategic priorities – what we call The Five Points of the Star – to guide our business and position Landstar for sustainable growth.

At the top of the star is Accelerating the Model, centered on the success of our independent agents and business capacity owners (BCOs). When our entrepreneurial network is strong, growing, and equipped with the right tools and support, the Landstar model is uniquely positioned to deliver excellent service for our customers.

4  Landstar System, Inc. 2026 Proxy Statement

Proxy Summary

During 2025, we advanced our Strategic Growth initiatives, including Heavy Haul and U.S./Mexico Cross-border services, which together now represent approximately 20% of our business. Our strategies recognize Landstar’s distinguished history of ‘doing the hard things well’ and leverage our demonstrated ability to handle complex freight. To support our Cross-border and Heavy Haul growth strategies, we have added new leadership and expanded the network of agents offering those services. While Cross-border freight flows were impacted by geopolitics, tariffs, and trade uncertainties, we delivered record-setting Heavy Haul revenues in 2025. We continue to tap into additional strategic growth areas that require specialized capabilities, including Cold Chain and Hazardous Materials, further demonstrating Landstar’s ability to execute complex freight solutions and deliver value in highly specialized markets.

We remain focused on delivering every load, every day, with a safety-first mindset and continuously strengthening the security of the freight entrusted to us by our customers.

The Landstar balance sheet remains strong, and we once again generated significant free cash flow in 2025. We continue to emphasize financial discipline while also investing capital to improve and grow the Company, leveraging the strength of our asset-light model. This financial strength enables Landstar to continue its successful track record of returning capital to stockholders. Over the past two years, we returned approximately $261 million through share repurchases and $245 million in cash dividends. We remain committed to maintaining a disciplined capital allocation approach, balancing investments that strengthen and grow our business with meaningful returns to our stockholders.

Our steadfast focus on enhancing the support we provide to our independent agents, BCOs, and employees is key to our mutual success. In 2025, we continued to invest in tools, technologies, and artificial intelligence to increase sales productivity, drive operational efficiency, and enhance the user experience. Our newly launched web portal includes embedded agentic AI designed specifically for the needs of Landstar freight agents, and we are advancing additional AI-enabled initiatives across pricing, contact center capabilities, BCO retention, trailer management, credit approvals, and our ERP deployment. Approximately half of our 2026 technology capital expenditures budget is dedicated to supporting AI-enabled solutions that strengthen the Landstar network and enhance our differentiated capabilities and competitiveness.

While the freight environment remains cyclical, the fundamentals of the Landstar model – an asset-light network of independent entrepreneurs empowered by Landstar’s culture of collaboration and accountability, tech-enabled support, and strong balance sheet – position us well for the future. We are confident that the strategic initiatives underway today and those we will discern in the years ahead support long-term value creation for our stockholders and continued success for the Landstar network.

Thank you for your continued trust and investment in Landstar.

Sincerely,

		FRANK A. LONEGRO President and Chief Executive Officer

Landstar System, Inc. 2026 Proxy Statement  5

Proxy Statement

PROXY STATEMENT

March 23, 2026

Introduction

This Proxy Statement (the “Proxy Statement”) has been made available on the Internet to the stockholders of Landstar System, Inc., a Delaware corporation (the “Company” or “Landstar”), in connection with the solicitation of proxies on behalf of the Board of Directors of the Company (the “Board”) to be voted at the 2026 Annual Meeting of Stockholders to be held on Tuesday, May 5, 2026, at 9:00 a.m. Eastern Time (the “2026 Annual Meeting”). The 2025 Annual Report to Stockholders (the “2025 Annual Report”) (which, notwithstanding anything herein to the contrary, does not form a part of the proxy solicitation material relating to this Proxy Statement), including the financial statements of the Company for fiscal year 2025, has also been made available on the Internet. This Proxy Statement, the form of proxy, the Notice of 2026 Annual Meeting and the 2025 Annual Report (collectively, the “proxy materials”) are being made available to the stockholders of the Company on or about March 23, 2026. Instructions on how to access the proxy materials over the Internet or to request a printed copy may be found in the Notice of Internet Availability. The mailing address of the principal executive offices of the Company is 13410 Sutton Park Drive South, Jacksonville, Florida 32224. Please note that information contained or connected to any website referenced in this Proxy Statement is not incorporated by reference in this Proxy Statement or any other report or document we file with the SEC, unless expressly so provided in this Proxy Statement.

Record Date

The Board has fixed the close of business on March 10, 2026 as the record date for the 2026 Annual Meeting. Only stockholders of record on that date will be entitled to vote at the 2026 Annual Meeting in person or by proxy.

Proxies

Shares cannot be voted at the 2026 Annual Meeting unless the owner thereof is present in person or by proxy. The proxies named on the proxy card were appointed by the Board to vote the shares of Common Stock of the Company, par value $0.01 per share (“Common Stock”), represented by the proxy card. If a stockholder does not return a signed proxy card with respect to any of his or her shares, such shares cannot be voted by proxy. Stockholders are urged to mark the boxes on the proxy card to show how his or her shares are to be voted. All properly executed and unrevoked proxies that are received in time for the 2026 Annual Meeting will be voted at the 2026 Annual Meeting or any adjournment thereof in accordance with any specification thereon, or if no specification is made, will be voted as follows: (i) “FOR” the election of the nine members of the Board nominated by the Board for re-election and named in this Proxy Statement; (ii) “FOR” the ratification of KPMG LLP as the independent registered public accounting firm for the Company; and (iii) “FOR” the proposal regarding an advisory vote on executive compensation. Each of these proposals is more fully described in this Proxy Statement. The proxy card also confers discretionary authority on the proxies to vote on any other matter not presently known to management that may properly come before the 2026 Annual Meeting.

Any proxy delivered pursuant to this solicitation is revocable at the option of the person(s) executing the same (i) upon receipt by the Company before such proxy is voted of a duly executed proxy bearing a later date, (ii) by written notice of the revocation of such proxy to the Secretary of the Company received before such proxy is voted or (iii) by such person(s) voting in person at the 2026 Annual Meeting.

The Board has selected Broadridge Investor Communication Solutions, Inc. as Inspector of Election (the “Inspector”) pursuant to Article I of the Company’s Bylaws, as amended and restated (the “Bylaws”). The Inspector shall ascertain the number of shares of Common Stock outstanding, determine the number of shares represented at the 2026 Annual Meeting by proxy or in person and count all votes. Each stockholder shall be entitled to one vote for each share of Common Stock held by such stockholder and such votes may be cast either in person or by proxy.

Proxy Solicitation

The cost of the preparation of proxy materials and the solicitation of proxies will be paid by the Company. The Company has engaged Georgeson LLC as the proxy solicitor for the 2026 Annual Meeting for a fee of approximately $12,500 plus

6  Landstar System, Inc. 2026 Proxy Statement

Proxy Statement

reasonable expenses. In addition to the use of the mails, certain directors, officers or employees of the Company may solicit proxies by telephone or personal contact. Upon request, the Company will reimburse brokers, dealers, banks and trustees, or their nominees, for reasonable expenses incurred by them in forwarding proxy materials to the beneficial owners of shares.

Stockholder Communications with the Board of Directors

A description of the procedures as to how stockholders may send communications to the Board or individual Board members is included on the Company’s website at https://investor.landstar.com/committee-details/shareholder-communications-board-directors.

Voting Securities

Shares of Common Stock are the only class of voting securities of the Company which are outstanding. On March 10, 2026, 33,967,110 shares of Common Stock were outstanding. At the 2026 Annual Meeting, each stockholder of record at the close of business on March 10, 2026 will be entitled to one vote for each share of Common Stock owned by such stockholder on that date as to each matter properly presented to the 2026 Annual Meeting. The holders of a majority of the total number of the issued and outstanding shares of Common Stock on such date shall constitute a quorum for purposes of the 2026 Annual Meeting (a “Quorum”).

Landstar System, Inc. 2026 Proxy Statement  7

Proposal Number One — Election of Directors

PROPOSAL NUMBER ONE — ELECTION OF DIRECTORS

There are currently ten members of the Board, whose terms will expire at the 2026 Annual Meeting.

As disclosed by the Company in a Current Report on Form 8-K filed with the U.S. Securities and Exchange Commission (the “SEC”) on October 30, 2025, the Board elected J. Barr Blanton and Melanie M. Hart to the Board, effective October 31, 2025. The current term of the appointments of Mr. Blanton and Ms. Hart will each expire at the 2026 Annual Meeting. In connection with the appointments of Mr. Blanton and Ms. Hart, the size of the Board was expanded from eight to ten members.

Mr. Anthony J. Orlando has informed the Board of his desire to retire from service as a Director of the Company upon the expiration of his current term as of the 2026 Annual Meeting. Following the 2026 Annual Meeting and Mr. Orlando’s retirement from service on the Board and each of the committees on which he serves, it is anticipated that the size of the Board will be reduced from ten directors to nine directors.

The Board has nominated Dr. Homaira Akbari, Mr. David G. Bannister, Mr. J. Barr Blanton, Ms. Melanie M. Hart, Mr. James L. Liang, Mr. Frank A. Lonegro, Ms. Diana M. Murphy, Mr. George P. Scanlon and Ms. Teresa L. White as Directors for election at the 2026 Annual Meeting. It is intended that the shares represented by the form of proxy will be voted at the 2026 Annual Meeting for the election of nominees Dr. Akbari, Mr. Bannister, Mr. Blanton, Ms. Hart, Mr. Liang, Mr. Lonegro, Ms. Murphy, Mr. Scanlon and Ms. White as Directors, unless the proxy specifies otherwise. Dr. Akbari, Mr. Bannister, Mr. Blanton, Ms. Hart, Mr. Liang, Mr. Lonegro, Ms. Murphy, Mr. Scanlon and Ms. White would each be elected for a term to expire at the 2027 Annual Meeting, and each has indicated his or her willingness to serve as a member of the Board, if elected.

If, for any reason not presently known, Dr. Akbari, Mr. Bannister, Mr. Blanton, Ms. Hart, Mr. Liang, Mr. Lonegro, Ms. Murphy, Mr. Scanlon or Ms. White is not available for election at the time of the 2026 Annual Meeting, the shares represented by the form of proxy may be voted for the election of one or more substitute nominee(s), if any, designated by the Board or a committee thereof, unless the proxy withholds authority to vote for such substitute nominee(s).

Assuming the presence of a Quorum, to be elected, a nominee must receive the affirmative vote of a majority of the votes cast by the holders of Common Stock with respect to that director’s election at the 2026 Annual Meeting. Abstentions from voting and broker non-votes will have no effect on the outcome of this proposal.

		PROPOSAL 1
		THE BOARD RECOMMENDS A VOTE FOR THIS PROPOSAL

8  Landstar System, Inc. 2026 Proxy Statement

Directors of the Company

DIRECTORS OF THE COMPANY

The following information describes the principal occupation or employment, other affiliations and business experience of each of the nominees named above for election as a Director at the 2026 Annual Meeting.

Landstar System, Inc. 2026 Proxy Statement  9

Directors of the Company

10  Landstar System, Inc. 2026 Proxy Statement

Directors of the Company

Landstar System, Inc. 2026 Proxy Statement  11

Directors of the Company

12  Landstar System, Inc. 2026 Proxy Statement

Directors of the Company

Landstar System, Inc. 2026 Proxy Statement  13

Information Regarding Board of Directors and Committees

INFORMATION REGARDING BOARD OF DIRECTORS AND COMMITTEES

The business of the Company is managed under the direction of the Board. The Board meets on a regularly scheduled basis four times a year to review significant developments affecting the Company and to act on matters requiring Board approval. It also holds special meetings and acts by written consent when matters require Board action between scheduled meetings. In addition, the Independent Directors (as defined below) of the Board meet regularly in executive session without any other members of management or the Board present.

Attendance at Annual Meetings

Each member of the Board is required to attend all meetings (whether special or annual) of the stockholders of the Company. In the case where a Director is unable to attend a special or annual stockholders’ meeting, such absence shall be publicly disclosed in the subsequent Proxy Statement filed by the Company with the SEC and an explanation for such absence shall be provided to the Company’s Corporate Governance, Nominating and Sustainability Committee. Any consideration of additional Company action, as appropriate, with respect to such absence shall be solely within the discretion of the Corporate Governance, Nominating and Sustainability Committee of the Board. All current Board members, other than Mr. Blanton and Ms. Hart, who were appointed to the Board in October 2025, attended the 2025 Annual Meeting of Stockholders (“2025 Annual Meeting”), which was held virtually.

Attendance at Board Meetings

During the Company’s 2025 fiscal year, the Board held thirteen meetings and did not act by written consent. During the Company’s 2025 fiscal year, each current Director who served on the Board in 2025 attended 75% or more of the total number of meetings of the Board and all committees of the Board on which such Director serves.

Independent Directors

Each of Homaira Akbari, David G. Bannister, J. Barr Blanton, Melanie M. Hart, James L. Liang, Diana M. Murphy, Anthony J. Orlando, George P. Scanlon and Teresa L. White is an “independent director,” as defined in Rule 5605(a)(2) of the Listing Rules of the NASDAQ Stock Market and Item 407(a) of Regulation S-K promulgated under the Securities Act and meets the requirements of Rule 5605(c)(2)(A) of such NASDAQ rules and Item 407(a) of Regulation S-K promulgated under the Securities Act (such Directors are, collectively, the “Independent Directors”). The Independent Directors held four meetings during fiscal year 2025, in each case in executive session without any other members of management or the Board present. During such meetings, which are led by Ms. Murphy as Non-Executive Chairman of the Board, the Independent Directors may discuss strategic, financial, operational, technology and compensation related issues, among other matters, and may engage outside advisors to present with respect to any of the foregoing. The Independent Directors typically have at least one “offsite” meeting annually amongst themselves, a portion of which the CEO may be invited to attend.

Structure and Committees of the Board

The Board has established an Audit Committee, a Compensation Committee, a Corporate Governance, Nominating and Sustainability Committee, a Safety and Risk Committee and a Strategic Planning Committee to devote attention to specific subjects. The functions of these committees and the number of meetings held during 2025 are described below. The Board does not currently have an Executive Committee. The Independent Directors have elected a non-executive Chairman, whose role is further described below. In addition, the Board has established a Disclosure Committee comprised of members of management, including one employee member of the Board, to establish and maintain certain disclosure controls and procedures to ensure accurate and timely disclosure in the Company’s periodic reports filed with the SEC, and a Management Risk Committee comprised of members of management, including one employee member of the Board, to identify, assess and manage significant risks and related policies and procedures of the Company. The Company has also established an Executive Risk Committee, comprised of the Chief Executive Officer, the Chief Financial Officer, the Chief Safety and Operations Officer and the General Counsel that focuses on enterprise risk management.

Each of the Audit Committee, Compensation Committee and Corporate Governance, Nominating and Sustainability Committee solely consist of the Independent Directors, with a different Independent Director serving as the Chairman for each such committee. In addition, Mr. Scanlon serves as the Chairman of the Strategic Planning Committee and Dr. Akbari

14  Landstar System, Inc. 2026 Proxy Statement

Information Regarding Board of Directors and Committees

serves as the Chairman of the Safety and Risk Committee, each of which is comprised of all of the Directors on the Board. Historically, each of the Audit Committee, Compensation Committee and Corporate Governance, Nominating and Sustainability Committee has typically invited the Chief Executive Officer, the Director who does not serve on those committees, to attend all regular meetings of these three committees, excluding any meetings of the Compensation Committee to the extent pertaining to the executive compensation arrangements of the Chief Executive Officer.

Leadership Structure of the Board

The leadership structure of the Board consists of: (i) a Non-Executive Chairman; (ii) an Independent Director serving as Chairman of the Audit Committee; (iii) an Independent Director serving as Chairman of the Compensation Committee; (iv) an Independent Director serving as Chairman of the Corporate Governance, Nominating and Sustainability Committee; (v) an Independent Director serving as Chairman of the Strategic Planning Committee; (vi) an Independent Director serving as Chairman of the Safety and Risk Committee; and (vii) an employee Director who also serves as the Company’s President and Chief Executive Officer. Each of the Audit Committee, the Compensation Committee and the Corporate Governance, Nominating and Sustainability Committee consists solely of Independent Directors.

The Board believes this leadership structure is appropriate for the Company as the Company’s Chief Executive Officer is responsible for leading the overall strategic direction of the enterprise; however, the Independent Directors, led by the Non-Executive Chairman of the Board, retain the decision-making authority of the Board because the Independent Directors consist of a majority of the members of the Board. In addition, the Independent Directors constitute the sole members of the Audit Committee, Compensation Committee and Corporate Governance, Nominating and Sustainability Committee and a majority of members of the Strategic Planning Committee and the Safety and Risk Committee. The Board also believes that its leadership structure is supported by Independent Directors serving as the Chairman of each committee of the Board, as the Chairman of each committee of the Board has responsibility for setting the agenda for each meeting of that committee. Ms. Murphy, as Non-Executive Chairman, sets the agenda for the meetings of the Board and the meetings of the Independent Directors. Further, the Company’s internal audit function reports directly to the Audit Committee. Finally, there are no meetings of the Board or any committee of the Board at which each Independent Director is not an invited member, the Independent Directors meet regularly in executive session without any members of management present, including the Chief Executive Officer, and the Independent Directors have significant input regarding the Board’s agenda and information flow.

Non-Executive Chairman

On May 19, 2015, the Board elected Diana M. Murphy to serve as Non-Executive Chairman of the Board for such term as the Board may determine. In appointing Ms. Murphy as the Non-Executive Chairman of the Board following the Company’s 2015 Annual Meeting, the Board considered Ms. Murphy’s extensive experience with the Company having served on the Board since 1998, including her service as Lead Independent Director since 2012 and her service at various times as Chairman of the Nominating and Corporate Governance Committee (subsequently renamed the Corporate Governance, Nominating and Sustainability Committee), the Strategic Planning Committee and the Compensation Committee.

The duties and responsibilities of the Non-Executive Chairman include: (i) to preside as the chairman at all meetings of the Board; (ii) to preside as the chairman at all meetings of the Independent Directors; (iii) to serve as a liaison between the Independent Directors and the Chief Executive Officer; (iv) to coordinate with the Chief Executive Officer to prepare meeting agendas and related materials for meetings of the Board; (v) to coordinate with the other Independent Directors of the Board to develop the agenda with respect to all meetings of the Independent Directors; (vi) to have the authority to call meetings of the Board and meetings of the Independent Directors; (vii) to approve the annual schedule of meetings of the Board; (viii) to ensure that the Board has adequate resources, including complete, timely information necessary to enable the members of the Board to perform their duties; and (ix) to communicate to management, as appropriate, the results of private discussions among the Independent Directors.

In addition to the aforementioned duties, the Non-Executive Chairman of the Board is also the Chairman of the Corporate Governance, Nominating and Sustainability Committee. In that capacity, Ms. Murphy leads the process by which potential new Independent Directors are identified and evaluated. The Board believes it is important to confer this responsibility on the Non-Executive Chairman in order to support a Board structure where the Independent Directors retain the decision-making authority of the Board.

Separation of the Roles of Chairman and Chief Executive Officer

Ms. Murphy, the former Lead Independent Director of the Company, was appointed Non-Executive Chairman of the Board, effective May 19, 2015. Historically, the Company has experienced periods during which the roles of Chairman of the Board

Landstar System, Inc. 2026 Proxy Statement  15

Information Regarding Board of Directors and Committees

and Chief Executive Officer have been combined and periods during which these roles have been separated. The Board believes that an analysis of whether the roles of Chairman of the Board and Chief Executive Officer should be separated is based on the facts and circumstances applicable at the time of the analysis and that it may not be appropriate under all circumstances to separate the roles of Chairman of the Board and Chief Executive Officer.

Declassification of the Board

The stockholders of the Company voted at the Company’s 2023 Annual Meeting to approve amendments to the Company’s Restated Certificate of Incorporation, to, among other things, declassify the Board over a two-year period beginning at the 2023 Annual Meeting. The process to declassify the Board was completed as of the 2025 Annual Meeting. The terms of all Directors will expire annually as of the 2026 Annual Meeting, and each Director nominee at our 2026 Annual Meeting will be elected for a one-year term expiring at the 2027 Annual Meeting of Stockholders.

16  Landstar System, Inc. 2026 Proxy Statement

Information Regarding Board of Directors and Committees

Committee Membership

« = Chairman

Landstar System, Inc. 2026 Proxy Statement  17

Information Regarding Board of Directors and Committees

18  Landstar System, Inc. 2026 Proxy Statement

Information Regarding Board of Directors and Committees

Landstar System, Inc. 2026 Proxy Statement  19

Information Regarding Board of Directors and Committees

20  Landstar System, Inc. 2026 Proxy Statement

Information Regarding Board of Directors and Committees

Landstar System, Inc. 2026 Proxy Statement  21

Information Regarding Board of Directors and Committees

22  Landstar System, Inc. 2026 Proxy Statement

Director Qualities, Skills, and Diversity

DIRECTOR QUALITIES, SKILLS, AND DIVERSITY

Core Competencies

Our Board believes that all Directors should possess certain core qualities that ensure their fitness to lead the Company, as described below. We believe that each of our Directors possesses the following skills:

Important Skills and Attributes

In addition to the core competencies noted above, our Board believes that the Company will be best served by Directors with a wide array of talents and perspectives to drive innovation, promote critical thinking and enhance discussion. Each of the following important skills and attributes meaningfully adds to our Board’s depth.

Landstar System, Inc. 2026 Proxy Statement  23

Director Qualities, Skills, and Diversity

Board Diversity

The following table provides information in a standardized matrix as of March 23, 2026: (i) the total number of Company board members and (ii) how those board members self-identify regarding gender, predefined race and ethnicity categories.

Definitions of the terms used in this table are as follows:

24  Landstar System, Inc. 2026 Proxy Statement

Report of the Audit Committee

REPORT OF THE AUDIT COMMITTEE

The Audit Committee of the Board is responsible for providing independent, objective oversight of the Company’s accounting functions and internal controls. The Audit Committee has the sole authority and responsibility to select, evaluate and, when appropriate, replace the Company’s independent registered public accounting firm. The Audit Committee is comprised of all of the Independent Directors. The Audit Committee operates under a written charter approved by the Board.

Management is responsible for the Company’s internal control over financial reporting. The independent registered public accounting firm is responsible for performing an independent audit of the Company’s consolidated financial statements in accordance with the standards of the Public Company Accounting Oversight Board (United States) and to issue a report thereon. The independent registered public accounting firm is also responsible for auditing the Company’s internal control over financial reporting. The Audit Committee is responsible for monitoring these processes. The Audit Committee is not, however, professionally engaged in the practice of accounting or auditing and does not provide any expert or other special assurance as to such financial statements concerning compliance with laws, regulations or generally accepted accounting principles or as to the independent registered public accounting firm’s independence. The Audit Committee relies, without independent verification, on the information provided to it and on presentations and statements of fact made by management, the internal auditors and the independent registered public accounting firm.

In connection with these responsibilities, as discussed elsewhere in this Proxy Statement, the Audit Committee held four meetings and six telephonic meetings during the Company’s 2025 fiscal year. These meetings were designed, among other things, to facilitate and encourage communication among the Audit Committee, management, the internal auditors and the independent registered public accounting firm. The Audit Committee discussed with representatives of the independent registered public accounting firm the overall scope and plans for these audits. The Audit Committee also met with representatives of KPMG, with and without management and the internal auditors present, to discuss the Company’s fiscal year 2025 financial statements and the Company’s internal control over financial reporting. The Audit Committee also reviewed and discussed the December 27, 2025 audited financial statements with management and reviewed and discussed the status of the Company’s internal control over financial reporting with management and the internal auditors. The Audit Committee also discussed with representatives of the independent registered public accounting firm the matters required to be discussed by Auditing Standard No. 1301, “Communications with Audit Committees,” adopted by the Public Company Accounting Oversight Board, and also received written disclosures and the letter from KPMG required by the Public Company Accounting Oversight Board regarding KPMG’s independence from the Company. The Audit Committee had discussions with representatives of the independent registered public accounting firm concerning the independence of the independent registered public accounting firm under the rules and regulations governing auditor independence promulgated under the Sarbanes-Oxley Act. The Audit Committee had discussions with management and the internal auditors concerning the process used to support certifications by the Company’s Chief Executive Officer and Chief Financial Officer that are required by the Securities and Exchange Commission (“SEC”) and the Sarbanes-Oxley Act to accompany the Company’s periodic filings with the SEC.

The Board has determined that Mr. Bannister, Ms. Hart, Mr. Liang, Mr. Orlando and Mr. Scanlon, each an independent director under the NASDAQ and SEC audit committee structure and membership requirements, meet the SEC criteria of an “audit committee financial expert” under the standards established by Item 407(d) of Regulation S-K under the Securities Act.

Landstar System, Inc. 2026 Proxy Statement  27

Report of the Audit Committee

During 2025, the Audit Committee preapproved the continuation of all non-audit services to be rendered to the Company by the independent registered public accounting firm in 2025 (which services are disclosed elsewhere in this Proxy Statement) and concluded that these services, if any, complied with maintaining the independence of the registered public accounting firm.

Based upon the Audit Committee’s discussions with management and the independent registered public accounting firm, and the Audit Committee’s review of the representations of management and the independent registered public accounting firm, the Audit Committee recommended that the Board include the audited consolidated financial statements in the 2025 Annual Report, filed with the SEC on February 20, 2026. The Audit Committee has also selected KPMG LLP as the Company’s independent registered public accounting firm for the fiscal year ending December 26, 2026 and has recommended to the Board that this selection be presented to the stockholders for ratification.

THE AUDIT COMMITTEE

Anthony J. Orlando, Chairman

Homaira Akbari

David G. Bannister

J. Barr Blanton

Melanie M. Hart

James L. Liang

Diana M. Murphy

George P. Scanlon

Teresa L. White

28  Landstar System, Inc. 2026 Proxy Statement

Executive Compensation

Executive Compensation

Landstar System, Inc. 2026 Proxy Statement  29

Executive Officers of the Company

EXECUTIVE OFFICERS OF THE COMPANY

The following table sets forth the name, age, principal occupation and business experience during the last five years of each of the executive officers (the “Executive Officers”) of the Company as of March 10, 2026. The Executive Officers of the Company serve at the discretion of the Board and until their successors are duly elected and qualified. For information regarding ownership of Common Stock by the Executive Officers of the Company, see “Security Ownership by Management and Others.” There are no family relationships among any of the Directors and Executive Officers of the Company or any of its subsidiaries.

		Frank A. Lonegro		Age: 57
		Executive Position: President and Chief Executive Officer		Director and Executive Officer of the Company since February 2024

30  Landstar System, Inc. 2026 Proxy Statement

Executive Officers of the Company

		Michael K. Kneller		Age: 51
		Executive Position: Vice President, General Counsel and Secretary		Executive Officer of the Company since June 2005

		Terri M. Lewis		Age: 55
		Executive Position: Vice President and Chief Human Resources Officer		Executive Officer of the Company since February 2026

		Matthew Miller		Age: 52
		Executive Position: Vice President and Chief Safety and Operations Officer		Executive Officer of the Company since December 2024

		James P. Todd		Age: 39
		Executive Position: Vice President and Chief Financial Officer		Executive Officer of the Company since July 2022

Landstar System, Inc. 2026 Proxy Statement  31

Compensation Discussion and Analysis

COMPENSATION DISCUSSION AND ANALYSIS

OVERALL PHILOSOPHY AND GUIDING PRINCIPLES

The Company’s executive compensation philosophy is to attract and motivate executive talent best suited to develop and implement the Company’s business strategy. These objectives are attained by tying a significant portion of each executive’s compensation to the Company’s success in meeting specified annual corporate financial performance goals and, through the grant of stock-based awards, aligning the interests of the executives whose compensation is detailed below (the “Named Executives”) to the interests of our stockholders. The Company’s philosophy is to recognize individual contributions while supporting a team approach in achieving overall business objectives and increasing shareholder value.

The key elements of the Company’s executive compensation consist of base salary, annual performance-based incentive payments and stock-based awards. The Company’s policies with respect to each of these elements, including the basis for the compensation awarded, are discussed below.

The Company’s philosophy is to pay annual compensation generally in cash, with long-term incentive compensation paid in the form of stock-based awards. Base salary is intended to constitute a modest percentage of total compensation. The annual incentive compensation program (the “ICP”) is designed to pay substantial compensation for superior performance. Stock-based awards have historically accounted for a significant portion of each Named Executive’s total compensation.

Short-Term and Long-Term Incentive Compensation – Guiding Principles

In 2025, the Company awarded both performance stock units and restricted stock to each of its Named Executives based on each individual’s level of responsibility and performance and to help align management’s future interests with that of the Company’s stockholders. The Company believes that its compensation practices align executive compensation with financial performance and, as such, executive compensation arrangements are generally aligned with the Company’s variable cost business model.

The Compensation Committee of the Board is solely responsible for decisions with respect to the compensation of the Company’s President and Chief Executive Officer. The Compensation Committee is also responsible, taking into consideration recommendations of the President and Chief Executive Officer, for decisions with respect to the compensation awarded to the Named Executives other than the Chief Executive Officer, subject to review by the entire Board.

32  Landstar System, Inc. 2026 Proxy Statement

Compensation Discussion and Analysis

Landstar System, Inc. 2026 Proxy Statement  33

Compensation Discussion and Analysis

Moreover, stockholders indicated that they were generally pleased with our compensation philosophy and program and our focus on pay for performance. For example, evidence of our use of challenging performance goals historically is that no cash bonuses based on achievement of our financial goals were paid to executive leadership with respect to 3 of the last 5 fiscal years, as the Company faced a challenging operating environment. Stockholders also expressed high regard and support for our President and CEO, Mr. Lonegro, and responded positively to our decision to recruit and hire him to Landstar. A few stockholders noted that the negative 2025 say-on-pay vote reflected a concern with the quantum of the one-time sign-on TSR-based RSU award made to Mr. Lonegro in February 2024, in connection with his hiring, even as such stockholders also acknowledged that this award was fully performance-based with a very challenging hurdle rate required for Mr. Lonegro to vest under this award. A number of stockholders also expressed a desire for additional disclosure regarding the process to identify and hire Mr. Lonegro as the Company’s President and Chief Executive Officer. We heard these concerns and have added substantial additional disclosure in this proxy statement to address this feedback. More information is provided below under “CEO Transition Process and the Hiring of Mr. Lonegro” and “Letter Agreement with Mr. Lonegro”. We believe Mr. Lonegro has already had a tremendous impact on Landstar since joining the Company in early 2024, and the letter from Mr. Lonegro towards the beginning of this Proxy Statement reflects a small sampling of that impact. We look forward to his continued leadership.

Following other feedback received from stockholders, as well as independent advice and input from a newly engaged compensation consultant, FW Cook (more information on our engagement of FW Cook is described below under “Compensation Consultants”), we made a number of modifications to our executive compensation programs, in both the short-term and long-term incentive programs. These changes are described below under “Changes to Performance-Based Compensation Programs for 2026”. As a result of this process, we believe that we have further improved a program that is supported by market practices and responsive to the feedback we received from you, while continuing to be competitive and incentivize our proven, successful and evolving executive team.

We believe that we have helped enable Landstar’s culture of accountability and collaboration where our employees work together to create solutions to the toughest freight transportation challenges and serve the current and future needs of our customers, agents, and capacity providers. Empowering our network of agents, BCOs and third-party carriers to safely serve our customers requires us to foster a culture of awareness and understanding of what our customers and network participants need, bold innovation to create solutions to meet those needs, and relentless execution to deploy those solutions. With the advent of a new generation of artificial intelligence tools and technologies that are transforming virtually every industry, including the freight transportation industry, we believe that it is even more imperative that we emphasize excellence in our executive team and have the ability to attract new talent when appropriate.

We are asking for your support of our executive compensation program. Thank you for your continued support and investment in Landstar.

         Sincerely,

 

		David G. Bannister Chairman of the Compensation Committee

34  Landstar System, Inc. 2026 Proxy Statement

Compensation Discussion and Analysis

Landstar System, Inc. 2026 Proxy Statement  35

Compensation Discussion and Analysis

CEO TRANSITION PROCESS AND THE HIRING OF MR. LONEGRO

During our stockholder engagement efforts following the 2025 Annual Meeting, a number of stockholders expressed interest in additional disclosure regarding the process to identify and hire Frank A. Lonegro as the Company’s President and Chief Executive Officer, to succeed James B. Gattoni in that role as of February 2, 2024. This section of the Proxy Statement is intended to address that feedback we received.

The Board regularly engages in succession planning discussions with the Company’s Chief Executive Officer regarding the role of the Chief Executive Officer as well as with respect to each of the other Executive Officer positions at the Company. During 2023, Mr. Gattoni informed the Board that he was interested in a discussion regarding his potential transition to retirement from his employment with the Company. Following this discussion with Mr. Gattoni, the Board initiated a formal process to identify a successor to Mr. Gattoni. This process was led by Diana M. Murphy, Non-Executive Chairman of the Board, and involved the consideration of internal and external candidates as well as the retention of Spencer Stuart, a well known executive search firm, to aid the Board in this process. Mr. Gattoni was involved throughout this process. During 2023, the Board engaged in numerous discussions in connection with this process and ultimately concluded that the Company would be best served by the hiring of an external candidate. The Company conducted an external, nationwide search process facilitated by Spencer Stuart during 2023 that involved discussions and interviews with multiple candidates. Ultimately, the Board focused on Mr. Lonegro, who was then employed as the Executive Vice President and Chief Financial Officer of Beacon Building Products, a Nasdaq-listed Fortune 500 building products distribution company serving customers throughout the U.S. and Canada. The Board recognized Mr. Lonegro’s broad strategic, financial, operational and technology leadership at large, publicly traded organizations and his impressive record of achievement as an experienced, solutions-oriented leader. The Board also believed Mr. Lonegro would be a strong cultural fit at Landstar, given his understanding of the fast-paced freight transportation industry, the critical importance of a safety-first culture and the Company’s commitment to the long-term success of Landstar agents, BCOs and other third-party capacity providers to continue to drive growth.

The process to negotiate the compensation arrangements with Mr. Lonegro was led by David G. Bannister, the Chairman of the Compensation Committee of the Board and approved by the Compensation Committee. During 2023, as previously disclosed, the Compensation Committee used the services of a compensation consultant, Compensation Strategies, Inc., to assist it in reviewing an appropriate peer group of other transportation and logistics companies, and benchmarking CEO executive compensation, including base salary, annual incentive compensation and long-term incentive compensation to that group. In determining an appropriate compensation package for Mr. Lonegro, we identified that Mr. Lonegro would need to forgo his 2023 bonus and certain equity-related arrangements with Beacon in connection with a transition to the Company on the timeline required by the Board. Moreover, the Board also considered that Mr. Lonegro would be required to relocate his family from Northern Virginia to Jacksonville, Florida in connection with his hiring by the Company.

LETTER AGREEMENT WITH MR. LONEGRO

As previously disclosed, on December 5, 2023, the Company announced the hiring of Mr. Lonegro as the Company’s next President and Chief Executive Officer, effective February 2, 2024. The Company entered into a letter agreement with Mr. Lonegro, dated December 4, 2023 (the “Lonegro Letter Agreement”), that provides Mr. Lonegro with an annual base salary of $800,000 and eligibility for a bonus under the Company’s annual ICP with a “threshold” target bonus percentage of 100% of his annual base salary.

The Lonegro Letter Agreement included certain compensatory items related to Mr. Lonegro’s requests for make-whole payments in lieu of compensatory arrangements in place with Beacon as well as relocation related costs associated with moving his family from Northern Virginia to Jacksonville, Florida. These make-whole awards included a sign-on bonus of $2,000,000 worth of restricted stock, granted on February 2, 2024, under the Company’s 2011 Landstar System, Inc. Equity Incentive Plan (the “Employee Equity Plan”) that vested in two equal annual installments on February 2, 2025 and February 2, 2026, and $800,000 in cash to compensate Mr. Lonegro for forgoing a 2023 bonus with his former employer to accommodate his start date with the Company, which amount would have been required to be repaid if Mr. Lonegro had been terminated for “cause” or had resigned without “good reason” prior to the first anniversary of his start date. The Lonegro Letter Agreement also provided for $400,000 in cash for relocation benefits.

From the perspective of the Compensation Committee, the most important element to consider in designing an appropriate compensation package for the next Chief Executive Officer of the Company was to create a significant potential opportunity for the new Chief Executive Officer to realize a substantial amount of compensation upon the achievement by the Company of a superior level of growth in shareholder return over a relatively long term period during the new Chief

36  Landstar System, Inc. 2026 Proxy Statement

Compensation Discussion and Analysis

Executive’s employment. Accordingly, the Lonegro Letter Agreement provided for a grant of $10,000,000 worth of performance-related restricted stock units (“TSR RSUs”), which will vest based on achievement in any measurement year of TSR of a CAGR of 9% relative to the base year, to be measured annually starting after the sixth anniversary of his start date and concluding after the tenth anniversary of his start date. In the event of a change in control of the Company occurring at any time, the TSR RSUs will vest based on achievement of a stock price that equals 125% of the stock price that achieves the TSR CAGR of 9%. The Compensation Committee believes that this significant sign-on grant of TSR RSUs was of the utmost importance with respect to the recruitment and hiring of Mr. Lonegro. Moreover, as further described below under “Compensation Discussion and Analysis – Stock-based Awards – Grants of TSR-based RSU Awards to Mr. Lonegro”, the sign-on grant of TSR RSUs to Mr. Lonegro will only vest upon achievement in any measurement year of a total shareholder return (“TSR”) compound annual growth rate (“CAGR”) of 9% relative to the base year, to be measured annually starting after the sixth anniversary of the grant date and concluding after the tenth anniversary of the grant date. The following chart sets forth the minimum implied stock price of a share of Common Stock and implied equity market capitalization of the Company (in both cases, based on the “Base TSR Value” of $188.74 determined under the award, which provides the starting point for the determination of performance under the award, and a TSR CAGR of 9% that would be required for the TSR RSUs granted under this award to vest during the life of the award, assuming constant share count and no dividends across the performance and potential vesting period):

Importantly, diluted earnings per share for the Company’s 2023 fiscal year, the year immediately prior to Mr. Lonegro’s start date in February 2024, was the third highest in the Company’s history, and the Base TSR Value is within 10% of the all-time high price of a share of Common Stock of $208.62 on July 26, 2023.

The Compensation Committee believes that the potential for performance-based vesting after the sixth anniversary of his start date and concluding after his tenth anniversary with the Company will help to align Mr. Lonegro’s long-term compensatory incentive arrangements with the long-term interests of the Company’s stockholders. Moreover, the Compensation Committee believes the TSR performance that would be required in order for any TSR RSUs under this award to vest would result in the creation of enormous stockholder value and more than justify the resulting compensation payable under this award to Mr. Lonegro.

Under the Lonegro Letter Agreement, Mr. Lonegro is also eligible for annual equity grants under the Employee Equity Plan, with initial grants in February 2024 of (i) $2,000,000 of Performance-Based Regular RSU Awards, the vesting of which is determined on the third, fourth and fifth anniversary of the grant date, (ii) $1,000,000 worth of Regular Restricted Stock Awards, which will vest in three equal annual installments on each of the first three anniversaries of the grant date and

Landstar System, Inc. 2026 Proxy Statement  37

Compensation Discussion and Analysis

(iii) $1,000,000 worth of TSR RSUs, which will vest (A) based on achievement in any measurement year of TSR with a CAGR of 9% relative to the Base TSR Value, to be measured annually starting after the sixth anniversary of the grant date of the award and concluding after the tenth anniversary of the grant date of the award or (B) in the event of a change in control occurring at any time, based on achievement of a stock price that equals 125% of the stock price that achieves the TSR CAGR of 9%.

Pursuant to the Lonegro Letter Agreement, the Company also entered into a Key Executive Employment Protection Agreement with Mr. Lonegro, which includes an applicable multiple for Mr. Lonegro of two times, and otherwise is consistent with the terms and provisions described below under “Compensation Discussion and Analysis – Key Executive Employment Protection Agreements”.

The Lonegro Letter Agreement does not have a fixed term and provides for compensation and benefits payable in the Company’s discretion. Either the Company or Mr. Lonegro may terminate his employment at any time. If the Company terminates Mr. Lonegro’s employment without “cause” other than in a situation where severance is payable under the Key Executive Employment Protection Agreement, the Company will pay Mr. Lonegro severance within 30 days of the one-year anniversary of his termination date in the amount of Mr. Lonegro’s annual base salary and “threshold” target annual bonus and will continue to cover his medical benefits for 12 months following his termination, subject, in each case, to Mr. Lonegro’s signing a release of claims in favor of the Company and its affiliates and continued compliance with applicable restrictive covenants.

38  Landstar System, Inc. 2026 Proxy Statement

Compensation Discussion and Analysis

COMPENSATION PROGRAMS

Base Salaries

Base salaries for Named Executives are initially determined by evaluating the responsibilities of the position held and the experience of the individual. Salary adjustments are determined by evaluating the performance of the Company and of each Named Executive, and also take into account the Named Executive’s assumption of, or changes in, responsibilities, if any. The financial results of the operating functions which report into a Named Executive or for which a Named Executive otherwise has responsibility are also considered. The base salaries of the five Named Executives are detailed in the Summary Compensation Table that follows.

Performance-Based Compensation

The Company maintains performance-based compensation programs that are designed to encourage the Company’s Named Executives to achieve various financial goals linked to operating objectives both for the Company’s upcoming fiscal year as well as for the longer term performance of the enterprise. The Company’s performance-based compensation programs include the Company’s annual ICP and stock-based awards program, each of which are further described below.

Annual Incentive Compensation Program (“ICP”)

The Company’s objective with respect to its annual ICP is to encourage the Company’s Named Executives to achieve various strategic and financial goals linked to operating objectives for the Company’s upcoming fiscal year. These annual goals are developed as part of the Company’s budgeting process and in general are aligned with the Company’s long-term strategic and financial objectives. For the 2025 fiscal year, the strategic goals incentive portion of the ICP represented 30% of each Named Executive’s bonus opportunity and the Diluted Earnings Per Share (“DEPS”) incentive portion of the ICP represented 70% of each Named Executive’s bonus opportunity under the ICP:

Landstar System, Inc. 2026 Proxy Statement  39

Compensation Discussion and Analysis

Each Named Executive has a “Participant’s Percentage Participation” or “PPP” under the ICP. The PPP multiplied by the Named Executive’s base salary is the “one-time” bonus payable to that Named Executive. The PPPs for the Named Executives in 2025 were as follows: Mr. Lonegro, 100%, Mr. Todd, 60%, Mr. Kneller, 60%, Mr. Coro, 60% and Mr. Miller, 60%, as illustrated below as a percentage of each Named Executive’s annual base salary.

Strategic Goals Incentive Portion of the ICP

The strategic goals incentive portion of the ICP was a new feature of the ICP in 2025. The Compensation Committee approved the establishment of Landstar’s 2025 Strategic Goals focused on growth, managing risk and enhancing support based on the Company’s “Five Points of the Star” framework and is intended to include a comprehensive set of discrete strategic goals and objectives for the Named Executives to execute upon during the applicable fiscal year. This framework was established following Mr. Lonegro’s appointment as CEO, with each point of the star weighted as follows for purposes of determining funding under this portion of the ICP:

40  Landstar System, Inc. 2026 Proxy Statement