DEF 14A

Annual Meeting Information:

How to Vote:

Date and Time

Tuesday, May 5, 2026

9:00 a.m. Eastern Time

Vote by Internet

Go to www.proxyvote.com

until 11:59 p.m. Eastern Time on May 4, 2026.

Vote by Phone

Call toll-free 1-800-690-6903

until 11:59 p.m. Eastern Time on May 4, 2026.

Vote by Mail

Complete, sign and date the latest proxy/voting instruction card and return it in the postage-paid envelope the Company has provided.

Virtual Meeting Website:

www.virtualshareholdermeeting.com/LSTR2026

Record Date:

Close of business

March 10, 2026

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

(Rule

14a-101)

INFORMATION REQUIRED IN PROXY STATEMENT

SCHEDULE 14A INFORMATION

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

Filed by the Registrant ☒ Filed by a party other than the Registrant ☐

Check the appropriate box:

☐	Preliminary Proxy Statement

☐	Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

☒	Definitive Proxy Statement

☐	Definitive Additional Materials

☐	Soliciting Material Pursuant to §240.14a-12

Landstar System, Inc.

(Name of Registrant as Specified in its Charter)

Not applicable.

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check all boxes that apply):



☒		No fee required.

☐		Fee paid previously with preliminary materials.

☐		Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11.

LOGO

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:

(1)	To elect nine (9) members of the Board of Directors;

(2)	To ratify the appointment of KPMG LLP as the Company’s independent registered public accounting firm for fiscal year 2026;

(3)	To hold an advisory vote on executive compensation; and

(4)	To transact such other business as may properly come before the meeting or any adjournment thereof.

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

LOGO

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.

The proxy statement and annual report are available at: www.landstar.com and www.proxyvote.com

We are furnishing our proxy materials to all of our stockholders over the Internet rather than in paper form. We believe that this delivery
process lowers the costs of printing and distributing our proxy materials and reduces our environmental impact, without impacting our
stockholders’ timely access to this important information. Accordingly, stockholders of record at the close of business on March 10, 2026
will receive a Notice of Internet Availability of Proxy Materials (the “Notice of Internet Availability”) and may vote at the meeting.
Such stockholders will also receive notice of any postponements or adjournments of the meeting.
The Notice of Internet Availability is being distributed to stockholders on or about March 23, 2026.

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


Proxy Summary			4

Letter From Our President and Chief Executive Officer			4

Introduction			6

Record Date			6

Proxies			6

Proxy Solicitation			6

Stockholder Communications with the Board of Directors			7

Voting Securities			7

Proposal Number One - Election of Directors			8

Directors of the Company			9

Information Regarding Board of Directors and Committees			14

Attendance at Annual Meetings			14

Attendance at Board Meetings			14

Independent Directors			14

Structure and Committees of the Board			14

Director Qualities, Skills, and Diversity			23

Core Competencies			23

Important Skills and Attributes			23

Board Diversity			24

Compensation of Directors			25

Report of the Audit Committee			27

Executive Compensation Table of Contents			29

Executive Officers of the Company			30

Compensation Discussion and Analysis			32

Overall Philosophy and Guiding Principles			32

Letter from the Chairman of the Compensation Committee			33

Stockholder Engagement on Executive Compensation Topics			35

CEO Transition Process and the Hiring of Mr. Lonegro			36

Letter Agreement with Mr. Lonegro			36

Compensation Programs			39

2025 Compensation Decisions and Outcomes			45

Changes to Performance-Based Compensation Programs for 2026			49

Compensation Policies and Practices			50


Compensation Committee Report			54


Compensation of Named Executives			55

Summary Compensation Table			55

Grants of Plan-Based Awards			56

Stock Vested			57

Outstanding Equity Awards at Fiscal Year End			57

Nonqualified Deferred Compensation			58

Potential Payment Upon Termination or Change in Control			58

Pay Ratio			60

Pay Versus Performance			61

Security Ownership by Management and Others			66

Section 16(a) Beneficial Ownership Reporting Compliance			67

Proposal Number Two-Ratification of Appointment of Independent Registered Public Accounting Firm			68

Proposal Number Three-Advisory Vote to Approve Executive Compensation			69

Stockholder Proposals			71

Delivery of Documents to Security Holders Sharing an Address			71

Other Matters			72

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


Proposals						Board Recommendation

PROPOSAL NUMBER ONE Election of Directors						FOR ü
PROPOSAL NUMBER ONE Election of Directors						See pages 8-13

PROPOSAL NUMBER TWO Ratification of Appointment of Independent Registered Public Accounting Firm						FOR ü
						See page 69

PROPOSAL NUMBER THREE Advisory Vote to Approve Executive Compensation						FOR ü
						See pages 70-71

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.

LOGO

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.

•

We continue to invest in our agent community through programs such as Grow Your Star, which pairs established agents with emerging entrepreneurs to foster mentorship, knowledge transfer, and long-term network strength.

•

When it comes to our BCO community, targeted retention initiatives have contributed to a trailing 12-month truck turnover rate of 31% at year-end 2025, among the best in our industry (where many large truckload fleets have annual driver turnover rates of over 100%), underscoring the stability of our capacity base.

•

At the same time, building the leadership team of the future remains a priority. Our executive and vice president leadership group – our “Top 60” – includes many leaders who are new to their roles or newly promoted, bringing fresh perspectives and energy while remaining aligned around our core commitment to Safety, Security, and Service.

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.

•

For more than 35 years, Landstar has hosted its monthly Safety Thursday call, bringing together independent agents, business capacity owners, and employees in a shared forum dedicated to safety awareness and continuous improvement. At Landstar, ownership of safety begins at the highest levels of the organization, which is why this call has always been led by the Chief Executive Officer – a longstanding tradition that reinforces accountability and reflects Landstar’s unwavering commitment to a safety-first culture.

•

For the second consecutive year, Landstar was recognized by the Truckload Carriers Association (TCA) as an Elite Fleet Certified Carrier, a distinction that underscores our prioritization of safety, driver support, compensation, and innovative practices that enhance the professional driving experience.

•

I am proud of our continued progress in strengthening risk management capabilities, resulting in a lower DOT accident frequency in 2025 compared with our most recent five-year average and a reduction in cargo theft events despite a significant increase in cargo fraud across the broader transportation industry. Together, these results underscore the strength of Landstar’s safety culture and the collective commitment across our network to protect people, freight, and the integrity of the supply chain.

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,

LOGO

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.

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


	Audit Committee	Compensation Committee	Corporate Governance, Nominating and Sustainability Committee	Safety and Risk Committee	Strategic Planning Committee

Homaira Akbari	●	●	●	«	●

David G. Bannister	●	«	●	●	●

J. Barr Blanton	●	●	●	●	●

Melanie M. Hart	●	●	●	●	●

James L. Liang	●	●	●	●	●

Frank A. Lonegro				●	●

Diana M. Murphy	●	●	«	●	●

George P. Scanlon	●	●	●	●	«

SEC Form DEF 14A filed by Landstar System Inc.