Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

(Amendment No. )

Filed by the Registrant ☒

Filed by a party other than the Registrant  ☐

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

June 27, 2025

The directors and officers of MediaCo Holding Inc. join me in inviting you to attend the virtual annual meeting of our shareholders on Friday, August 8, 2025, at 9:00 a.m. Eastern time, via virtual conference using www.virtualshareholdermeeting.com/MDIA2025. As in recent years, in order to prioritize the health and safety of our shareholders and maximize efficiency, we have decided to hold the meeting solely by means of remote communication (i.e., a virtual-only meeting).

The formal notice of this annual meeting and the proxy statement appear on the following pages and are accompanied by a copy of our annual report on Form 10-K for the fiscal year ended December 31, 2024. After reading the proxy statement and other materials, please submit your proxy promptly by telephone or via the Internet in accordance with the instructions on the enclosed proxy card, or by marking, signing and returning a physical proxy card by mail, to ensure that your votes on the business matters of the meeting will be recorded.

We hope that you will dial in to attend this meeting. Whether or not you attend, we urge you to submit your proxy promptly. In light of the meeting being held virtually, we strongly recommend that you vote your shares in advance of the annual meeting even if you plan to attend. Instructions on how to vote or change your vote are found in the sections entitled “Questions and Answers About this Annual Meeting—How do I vote my shares before the annual meeting?” and “Questions and Answers About this Annual Meeting—How can I change my vote?”

We look forward to talking to you on Friday, August 8, 2025.

Sincerely,

/s/ Albert Rodriguez

Albert Rodriguez

This proxy statement is dated June 27, 2025, and we mailed to our shareholders of record as of June 18, 2025 (other than those who previously requested electronic or paper delivery of our proxy materials) a notice of internet availability of proxy materials on or about that date.

The annual meeting of the shareholders of MediaCo Holding Inc. will be held on Friday, August 8, 2025, at 9:00 a.m. Eastern time, via virtual conference using www.virtualshareholdermeeting.com/MDIA2025. As in recent years, in order to prioritize the health and safety of our shareholders and maximize efficiency, we have decided to hold the meeting solely by means of remote communication (i.e., a virtual-only meeting).

We describe each of these proposals in more detail in the accompanying proxy statement, which you should read in its entirety before voting.

Only shareholders of record at the close of business on June 18, 2025, are entitled to notice of and to vote at this meeting and any adjournments or postponements of this meeting.

By order of the Board of Directors,

/s/ Michelle Lee

Michelle Lee

New York, New York

June 27, 2025

MEDIACO HOLDING INC.

 

48 W. 25TH STREET, FLOOR 3

NEW YORK, NEW YORK 10010

PROXY STATEMENT

In this proxy statement, MediaCo Holding Inc. is referred to as “we,” “us,” “our,” “our Company,” “the Company” or “MediaCo.”

As a MediaCo shareholder, you received this proxy statement because our board of directors (the “Board” or “Board of Directors”) is soliciting your proxy to vote at the annual meeting of shareholders. The annual meeting will be held on Friday, August 8, 2025, at 9:00 a.m., Eastern time, via virtual conference using www.virtualshareholdermeeting.com/MDIA2025.

This proxy statement summarizes the information you need to know to vote on an informed basis at the annual meeting; however, you do not need to attend the annual meeting to vote your shares. For information regarding how to vote your shares, see “How do I vote my shares before the annual meeting?” We expect to begin sending or otherwise making available this proxy statement, the annual report, notice of annual meeting and the proxy card(s) on or about June 27, 2025, to all shareholders entitled to vote.

You are being asked to consider and vote on the following:

Holders of outstanding shares of MediaCo’s Class A Common Stock, par value $0.01 per share (“Class A Shares”) and holders of outstanding shares of MediaCo’s Class B Common Stock, par value $0.01 per share (“Class B Shares” and together with the Class A Shares, “Common Shares”) as of the close of business on June 18, 2025, the record date, are entitled to vote at the annual meeting. As of June 18, 2025, 48,264,309 Class A Shares and 5,413,197 Class B Shares were issued and outstanding. As of June 18, 2025, there were no shares of MediaCo’s Class C Common Stock, par value $0.01 per share, issued or outstanding.

The Board of Directors recommends that holders of Class A Shares vote FOR Colbert Cannon and that the holders of Class B Shares vote FOR Robert L. Greene and Deborah A. McDermott, the persons nominated by the Board to be elected as directors for terms of three years. The Board of Directors also recommends that holders of Common Shares vote FOR approval of the 2025 Equity Compensation Plan as set forth in Exhibit A to this proxy statement, FOR approval of an advisory resolution approving the compensation of our named executive officers, and FOR ratification of Deloitte & Touche LLP as our independent registered public accountants.

If you receive more than one proxy card, it means you hold Common Shares registered in more than one account. Sign and return ALL proxy cards to ensure that all your Common Shares are voted.

Each Class A Share is entitled to one vote and each Class B Share is entitled to ten votes. Generally, the holders of Class A and Class B Shares vote together as a single group. However, the two classes vote separately in connection with the election of certain directors, certain “going private” transactions and other matters as provided by law.

At this annual meeting, the Class A and Class B Shares, respectively, will vote separately on the election of t the director candidates, with Colbert Cannon (the “Class A Director”) to be voted upon by the holders of Class A Shares and Robert L. Greene and Deborah A. McDermott (each, a “Class B Director”) to be voted upon by the holders of Class B Shares. The Class A and Class B Shares will together on the election of directors, the approval of the 2025 Equity Compensation Plan, the advisory resolution approving the compensation of our named executive officers and the ratification of Deloitte & Touche LLP as our registered public accountants. The Company knows of no other business to be presented for consideration at the annual meeting other than the items indicated herein. If other matters are properly presented at the annual meeting, the persons designated as authorized proxies on your proxy card may vote on such matters in their discretion.

If you hold your shares in your own name, you may submit a proxy by telephone, via the Internet or by mail.

By casting your vote in any of the three ways listed above, you are authorizing the individuals listed on the proxy to vote your shares in accordance with your instructions. You may also attend the annual meeting and vote in person.

If your shares are held in the name of a bank, broker or other holder of record, then you are the beneficial owner of shares held in “street name.” The notice of annual meeting, proxy statement, and accompanying materials have been forwarded to you by your broker, bank, or other holder of record that is considered the “holder of record” of those shares. As the beneficial owner, you have the right to direct your broker, bank, or other holder of record in voting your shares and you will receive instructions from the holder of record that you must follow for your shares to be voted. The availability of telephonic or Internet voting will depend on the bank’s or broker’s voting process. Please check with your bank or broker and follow the voting procedures your bank or broker provides to vote your shares.

Stock exchange rules applicable to brokers grant your broker discretionary authority to vote your shares without receiving your instructions on certain matters. Your broker has discretionary voting authority under these rules to vote your shares on the ratification of Deloitte & Touche LLP as our independent registered public accountants. However, unless you provide voting instructions to your broker, your broker does not have discretionary authority to vote on the election of directors or the advisory resolution approving the compensation of our named executive officers. Therefore, it is particularly important that beneficial owners instruct their brokers how they wish to vote their shares.

If you provide specific voting instructions, your shares will be voted at the annual meeting in accordance with your instructions. If you return your signed proxy card but do not indicate your voting preferences, we will vote on your behalf FOR each of the nominees for election as director, FOR approval of the 2025 Equity Compensation Plan as set forth in Exhibit A to this proxy statement, FOR approval of an advisory resolution approving the compensation of our named executive officers and FOR the ratification of Deloitte & Touche LLP as our independent registered public accountants.

An “abstention” occurs when a shareholder sends in a proxy with explicit instructions to decline to vote regarding a particular matter. Abstentions are counted as present for purposes of determining a quorum. An abstention with respect to the election of directors is neither a vote cast “for” a nominee nor a vote cast “against” the nominee and, therefore, will have no effect on the outcome of the vote. Abstentions with respect to the advisory resolution approving the compensation of our named executive officers and the ratification of Deloitte & Touche LLP as our independent registered public accountants will also have no effect on the outcome of the vote.

A broker “non-vote” occurs when a broker or other nominee who holds shares for the beneficial owner is unable to vote those shares for the beneficial owner because the broker or other nominee does not have discretionary voting power for the proposal and has not received voting instructions from the beneficial owner of the shares. Brokers will have discretionary voting power to vote Common Shares for which no voting instructions have been provided by the beneficial owner only with respect to the ratification of Deloitte & Touche LLP as our independent registered public accountants. Brokers will not have discretionary voting power to vote Common Shares with respect to the election of directors, the approval of the 2025 Equity Compensation Plan or the advisory resolution approving the compensation of our named executive officers. Common Shares that are the subject of a broker non-vote are included for quorum purposes, but a broker non-vote with respect to a proposal will not be counted as a vote represented at the meeting and entitled to vote and, consequently, as a general matter, will have no effect on the outcome of the vote.

You may revoke your proxy at any time before it is exercised by:

Any written notice of revocation, or later dated proxy, should be delivered to:

MediaCo Holding Inc.

48 W. 25th Street, Floor 3

New York, New York 10010

Attention: Michelle Lee, Secretary

Alternatively, you may hand deliver a written revocation notice, or a later dated proxy, to the Secretary before we begin voting at the annual meeting.

If your shares are held by a bank, broker or other nominee, you must follow the instructions provided by the bank, broker or other nominee if you wish to change your vote.

Representatives of Broadridge Financial Solutions, Inc. will count the votes.

A majority of the combined voting power of the outstanding Class A and Class B Shares entitled to vote at the meeting constitutes a quorum for the items to be voted on by the Common Shares at the annual meeting (i.e., counting one vote for each share of outstanding Class A Shares and ten votes for each share of outstanding Class B Shares, present in person or represented by proxy), except that a majority of the outstanding Class A Shares entitled to vote at the meeting constitutes a quorum for the election of the Class A Director and a majority of the outstanding Class B Shares entitled to vote at the meeting constitutes a quorum for the election of the Class B Directors.

The Class A Director will be elected by a plurality of the votes cast by the holders of outstanding Class A Shares entitled to vote in the election who are present, in person or by proxy, at the meeting. Consequently, the director nominee receiving the most votes of the holders of Class A Shares will be elected to fill the Class A Director position. Only votes cast FOR a nominee will be counted.

The Class B Directors will be elected by a plurality of the votes cast by the holders of outstanding Class B Shares entitled to vote in the election who are present, in person or by proxy, at the meeting. Consequently, the director nominees receiving the most votes of the holders of Class B Shares will be elected to fill the Class B Director positions. Only votes cast FOR a nominee will be counted.

The approval of the advisory resolution approving the approval of the 2025 Equity Compensation Plan, the compensation of our named executive officers and the ratification of Deloitte & Touche LLP as our independent registered public accountants for the fiscal year ending December 31, 2025, require that the number of votes cast in favor of that proposal by holders of our outstanding Class A Shares and Class B Shares entitled to vote thereon, voting together, exceed the number of votes cast against the proposal by such holders of our outstanding Class A Shares and Class B Shares.

SG Broadcasting LLC (“SG Broadcasting”), is our largest single shareholder, beneficially owning approximately 80.0% of our Class A Shares and 100% of our Class B Shares as of June 18, 2025. Representatives of SG Broadcasting have informed us that they intend to vote for the nominees for election as Class B Director, for approval of the advisory resolution approving the compensation of our named executive officers and for the proposal regarding the ratification of the selection of Deloitte & Touche LLP as our independent registered public accountants. If SG Broadcasting does so, the election of each of the nominee for Class B Director, approval of the advisory resolution approving the compensation of our named executive officers and ratification of the selection of Deloitte & Touche LLP as our independent registered public accountants are expected to be approved because SG Broadcasting controls approximately 89.5% of the combined voting power of our outstanding Common Shares.

All directors and executive officers together own outstanding Class A Shares and Class B Shares representing less than 1% of the combined voting power of our outstanding Common Shares.

Yes. If you are a shareholder of record, you may, if you wish, receive future proxy statements and annual reports online. If you elect this feature, you will receive either a proxy card or an e-mail message notifying you when the materials are available, along with a web address for viewing the materials. You may sign up for electronic delivery by marking and signing the appropriate spaces on your proxy card or by contacting our Investor Relations Department by e-mail at ir@MediaCoHolding.com or toll-free by phone at (866) 366-4703. If you received these materials electronically, you do not need to do anything to continue receiving materials electronically in the future.

If you hold your shares in a brokerage account, you may also have the opportunity to receive proxy materials electronically. Please follow the instructions of your broker.

Electronic delivery saves MediaCo money by reducing printing and mailing costs. It will also make it convenient for you to receive your proxy materials online. MediaCo charges nothing for electronic delivery. You may, of course, incur the usual expenses associated with Internet access, such as telephone charges or charges from your Internet service provider.

You may discontinue electronic delivery at any time. For more information, contact our Investor Relations Department by e-mail at ir@MediaCoHolding.com or toll-free by phone at (866) 366-4703.

All shareholders of record as of June 18, 2025, as well as holders of shares held in street name, may attend by dialing into 1-800-690-6903.

We intend to hold our annual meeting via virtual conference using www.virtualshareholdermeeting.com/MDIA2025. As in recent years, in order to prioritize the health and safety of our shareholders and maximize efficiency, we have decided to hold the meeting solely by means of remote communication (i.e., a virtual-only meeting).

If you have any questions prior to the annual meeting, please contact our Investor Relations Department by e-mail at ir@MediaCoHolding.com or toll-free by phone at (866) 366-4703.

This proxy statement (this “proxy statement”) includes or incorporates forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended (the “Securities Act”), and Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). These forward-looking statements are based upon management's assumptions, expectations, projections, intentions and beliefs about future events. In some cases, predictive, future-tense or forward-looking words such as “intend,” “plan,” “may,” “will,” “project,” “estimate,” “anticipate,” “believe,” “expect,” “continue,” “potential,” “opportunity,” “forecast,” “should” and similar expressions, whether in the negative or affirmative, are intended to identify forward-looking statements, but are not the exclusive means of identifying such statements. Factors that could cause actual results to difference materially from the results anticipated in these forward-looking statements are contained in MediaCo Holding Inc.’s (the “Company”) periodic reports filed with the U.S. Securities and Exchange Commission (the “SEC”) under the heading “Risk Factors” and elsewhere, and other filings that the Company may make with the SEC. The Company cautions readers that the forward-looking statements included in this proxy statement represent our estimates and assumptions only as of the date of this proxy statement and are not intended to give any assurance as to future results. These forward-looking statements are not statements of historical fact and represent only our management's beliefs and expectations as of the date hereof, and involve risks and uncertainties that could cause actual results to differ materially and inversely from expectations expressed in or indicated by the forward-looking statements. New factors emerge from time to time, and it is not possible for us to predict all of these factors. Further, the Company cannot assess the effect of each such factor on our business or the extent to which any factor, or combination of factors, may cause actual results to be materially different from those contained in any forward-looking statement. Accordingly, you should not unduly rely on any forward-looking statements.

The Company undertakes no obligation to update or revise any forward-looking statements contained in this proxy statement, whether as a result of new information, future events, a change in our views or expectations or otherwise except as required by the federal securities laws.

Three directors are to be elected by the holders of Common Shares. Each of Colbert Cannon, Robert L. Greene and Deborah A. McDermott have each been nominated for a term of three years and until their respective successors have been elected and qualified. Mr. Cannon, the Class A Director, will be elected by the Class A Shares voting separately as a single class. Mr. Greene and Ms. McDermott, the Class B Directors, will be elected by the holder of the Class B Shares voting separately as a single class. All nominees are currently members of the Board of Directors.

On April 17, 2024, MediaCo consummated the transactions contemplated by that certain asset purchase agreement, dated April 17, 2024 (the “Asset Purchase Agreement”) with Estrella Broadcasting, Inc., a Delaware corporation (“Estrella”), and SLF LBI Aggregator, LLC, a Delaware limited liability company (“Aggregator”) and affiliate of HPS Investment Partners, LLC (“HPS”), pursuant to which MediaCo, through a wholly-owned subsidiary, MediaCo Operations LLC (“Purchaser”), purchased substantially all of the assets of Estrella and its subsidiaries (other than certain broadcast assets owned by Estrella and its subsidiaries, and assumed substantially all of the liabilities of Estrella and its subsidiaries. In connection with such transactions, MediaCo entered into a shareholders’ agreement with SG Broadcasting (“SG Broadcasting”) and Aggregator (the “Shareholders Agreement”) that, among other things, provides Aggregator the right to designate up to three individuals for election to our Board (each such designee, an “Investor Director Designee”), subject to reduction and termination based on certain MediaCo stock ownership requirements (including that such designation right falls away upon Aggregator ceasing to beneficially own at least ten percent (10%) of the fully diluted MediaCo common stock for ten consecutive days). Mr. Cannon, as well as Jacqueline Hernández¹ and Brett Pertuz, were designated by Aggregator pursuant to such rights and elected to the Board effective April 17, 2024.

If, at the time of the annual meeting, any nominee is unable or declines to serve, the discretionary authority provided in the proxy may be exercised to vote for a substitute or substitutes. The Board of Directors has no reason to believe that any substitute nominee or nominees will be required.

The Board believes that well-functioning boards consist of a diverse collection of individuals that bring a variety of complementary skills. Although the Board of Directors does not have a formal policy with regard to the consideration of diversity in identifying directors, diversity is one of the factors that the Board may, pursuant to its charter, take into account in identifying director candidates. Subject to any contractual commitments, the Board generally considers each director eligible for nomination in the broad context of the overall composition of our Board of Directors with a view toward constituting a board that, as a body, possesses the appropriate mix of skills and experience to oversee our business. The Board of Directors may actively seek candidates that embody elements of diversity in skills, ability, industry knowledge, experience, gender, race and ethnicity. The experience, qualifications, attributes, or skills that led the Board to conclude that each of the members of the Board of Directors should serve on the Board are generally described below

Name, Age, Principal Occupation(s) and Business Experience

As of June 18, 2025, there were 48,264,309 Class A Shares and 5,413,197 Class B Shares issued and outstanding. The Class A Shares are entitled to an aggregate of 48,264,309 votes and the Class B Shares are entitled to an aggregate of 54,131,970 votes. The following table shows, as of June 18, 2025, the number of shares and percentage of our Class A Shares and Class B Shares held by each person known to us to own beneficially more than five percent of the issued and outstanding Class A Shares or Class B Shares, by our named executive officers and our directors, and by our named executive officers and directors as a group. Unless otherwise specified, the address of each person listed is: c/o MediaCo Holding Inc., 48 W. 25th Street, Floor 3, New York, NY 10010.

Section 16(a) of the Exchange Act requires our directors and executive officers and any beneficial owner of more than 10% of any class of our equity securities to file with the Commission initial reports of beneficial ownership and reports of changes in ownership of any of our securities. These reports are made on documents referred to as Forms 3, 4 and 5. Our directors and executive officers must also provide us with copies of these reports. We have reviewed the copies of the reports that we have received and any written representations that no Form 5 was required from the individuals required to file the reports that we have received, as well as reviewed Forms 3, 4 and 5 filed with the Commission. Based on this review, we believe that during the year ended December 31, 2024, each of our directors and executive officers and beneficial owners of more than 10% of any class of our equity securities timely complied with applicable reporting requirements for transactions in our equity securities, except (i) Mr. Brian Kei was late in filing his Form 3 in connection with his service as an executive officer and (ii) Mr. Kudjo Sogadzi was late in filing his Form 4 in connection with a grant of shares as compensation for service on the Board in August 2023.

MediaCo aspires to the highest ethical standards for our employees, officers and directors, and remains committed to the interests of our shareholders and other constituents. We believe we can achieve these objectives only with a plan for corporate governance that clearly defines responsibilities, sets high standards of conduct and promotes compliance with the law. The Board has adopted formal corporate governance guidelines, as well as policies and procedures designed to foster the appropriate level of corporate governance. Some of these guidelines and procedures are discussed below. For further information, including electronic versions of our Code of Business Conduct and Ethics, our Corporate Governance Guidelines, our Audit Committee Charter, our Compensation Committee Charter, and our Complaint Procedure for Accounting and Auditing Matters, please visit the Corporate Governance section of our website (www.MediaCoHolding.com) located under the “Investors” heading.

 

Our Board currently consists of eight members. Of these, our Board has determined that seven (Mses. McAdaragh and McDermott, and Messrs. Cannon, Glaze, Greene, Pertuz and Thakrar) qualify as “independent directors” under the listing standards of Nasdaq. In addition, MediaCo is a “Controlled Company” as defined in the Nasdaq listing standards. The Company is, therefore, pursuant to Nasdaq Marketplace Rule 5615(c)(2), exempt from certain aspects of Nasdaq’s listing standards relating to independent directors.

Pursuant to the Nasdaq’s Board Diversity Rules, below is the Board Diversity Matrix outlining diversity statistics regarding our Board. In addition to gender and demographic diversity, we also recognize the value of other diverse attributes that directors may bring to our Board, including veterans of the U.S. Military. We are proud to report that of our eight current directors, one is also a military veteran.

MediaCo has adopted a Code of Business Conduct and Ethics to document the ethical principles and conduct we expect from our employees, officers and directors. A copy of our Code of Business Conduct and Ethics is available in the Corporate Governance section of our website (www.MediaCoHolding.com) located under the Investors heading.

We have adopted the MediaCo Securities Trading Policy, which governs the purchase, sale and other dispositions of our securities by all of our directors, officers and employees, as well as temporary employees, independent consultants and contractors, and their family members and any entities controlled by such insiders. Our securities trading policy is designed to promote compliance with insider trading laws, rules and regulations, as well as Nasdaq listing standards. In addition to the restrictions described above, it prohibits those who are subject to the policy from trading securities of any company, including MediaCo, while in possession of material non-public information, and from buying, selling or gifting our securities even if not in possession of such information during certain trading blackout periods, subject to limited exceptions. Our insider trading policy also imposes additional trading restrictions applicable to our directors, executive officers and certain employees. The foregoing summary of our securities trading policy does not purport to be complete and is qualified in its entirety by reference to the full text of the MediaCo Securities Trading Policy, a copy of which can be found as an exhibit to our Annual Report on Form 10-K for the fiscal year ended December 31, 2024.

MediaCo’s Corporate Governance Guidelines provide that the chair of the Board (“Board Chair”) is to meet the independence requirements under the applicable The Nasdaq Stock Market, Inc. (“Nasdaq”) listing standards. Our Board has determined that our Board Chair, Deborah McDermott, is an “independent director” under Nasdaq rules. As Board Chair, Ms. McDermott is responsible

for, among other matters: (i) setting the agenda for and leading executive sessions of the independent directors, unless a lead director is otherwise appointed by the Board Chair; (ii) briefing the Chief Executive Officer (“CEO”) on issues arising in the executive sessions; (iii) coordinating and developing the agenda for meetings of the Board, in collaboration with the CEO; (iv) convening meetings of the independent directors as necessary or appropriate; and (v) if requested and appropriate, being available for consultation with major shareholders. The Board believes that this structure provides strong independent leadership and oversight for our Company and our Board.

The Board expects the Company’s management to take primary responsibility for identifying material risks the Company faces and communicating them to the Board, developing and implementing appropriate risk management strategies responsive to those risks with oversight from the Board, and integrating risk management into the Company’s decision-making processes. The Board, through the Audit Committee on a quarterly basis and as a full Board at least annually, regularly reviews information regarding the Company’s credit, liquidity and operational risks, as well as strategies for addressing and managing such risks. In addition, the Compensation Committee monitors the Company’s compensation programs so that such programs do not encourage excessive risk-taking by Company employees.

Any employee, officer, shareholder or other interested party who has an interest in communicating with the Board Chair or any other MediaCo independent directors regarding any matter may do so by directing communication to Ms. McDermott addressed to Board Chair, c/o Corporate Secretary, MediaCo Holding Inc., 48 W. 25th Street, Floor 3, New York, New York 10010, by e-mail message to Chair@MediaCoHolding.com. The communication will be delivered to the independent directors as appropriate. For matters related to finance or auditing, a communication should specify that it is directed to the Audit Committee. For matters related to compensation, a communication should specify that it is directed to the Compensation Committee. Messages for any director or the Board as a whole may be delivered through the Board Chair as well.

The Board will consider and evaluate potential nominees submitted by holders of our Class A Common Stock, par value $0.01 per share (“Class A Shares”) to our corporate secretary on or before the date for shareholder nominations specified in the “Shareholder Proposals” section of the Company’s proxy statement. These potential nominees will be considered and evaluated using the same criteria as potential nominees obtained by the Board from other sources, subject to Aggregator’s rights to designate up to three individuals for election to the Board in accordance with the terms of the Shareholders Agreement.

In its assessment of each potential candidate, including those recommended by shareholders, the Board takes into account all factors it considers appropriate, which may include (a) ensuring that the Board, as a whole, is diverse and consists of individuals with various and relevant career experience, relevant technical skills, industry knowledge and experience, financial expertise (including expertise that could qualify a director as an “audit committee financial expert,” as that term is defined by the rules of the Commission), local or community ties, (b) minimum individual qualifications, including strength of character, mature judgment, familiarity with our business and related industries, independence of thought and an ability to work collegially, and (c) contractual and other obligations to nominate individuals recommended by SG Broadcasting. The Board also may consider the extent to which the candidate would fill a present need on the Board. After conducting an initial evaluation of a candidate, the Board would be expected to interview that candidate if it believes the candidate might be suitable to be a director and may ask the candidate to meet with certain directors and management. If the Board believes a candidate would be a valuable addition to the Board, it would expect to nominate that candidate as a director.

The standing committees of our Board are the Audit Committee and the Compensation Committee. MediaCo is a “controlled company” within the meaning of the Nasdaq listing standards. As such, we are exempt from Nasdaq’s requirement that director nominees be selected exclusively by independent directors constituting a majority of the independent directors of the Board or that MediaCo have a nominations committee comprised solely of independent directors. Accordingly, MediaCo does not have a separate standing nomination and corporate governance committee comprised of independent directors. The responsibilities and functions normally associated with such committee are instead carried out by the full Board.

Audit Committee. The Audit Committee’s primary responsibility is to engage our independent auditors and otherwise to monitor and oversee the audit process. The Audit Committee also undertakes other related responsibilities as summarized in the Report of the Audit Committee, included in the Original Filing, and detailed in the Audit Committee Charter, which is available in the Corporate

Governance section of our website (www.MediaCoHolding.com) located under the “Investors” heading. The Board has determined that the members of the Audit Committee, Robert L. Greene (chair), Deborah McDermott, Mary Beth McAdaragh, Brett Pertuz and Amit Thakrar, are independent directors under the Exchange Act and the Nasdaq listing standards. The Board has determined that Mr. Greene is an “audit committee financial expert” as defined in Item 407(d) of Regulation S-K. In making such determination, the Board took into consideration, among other things, the express provision in Item 407(d) of Regulation S-K that the determination that a person is an audit committee financial expert shall not impose any greater responsibility or liability on that person than the responsibility and liability imposed on such person as a member of the Audit Committee, nor shall it affect the duties and obligations of other Audit Committee members or the Board of Directors. The Audit Committee held four meetings during the last fiscal year.

Compensation Committee. The Compensation Committee reviews our compensation and benefit plans for executive officers to ensure that our corporate objectives are met, establishes compensation arrangements and approves compensation payments to members of our Board and our executive officers, and generally administers our equity incentive plans. The Compensation Committee’s charter is available in the Corporate Governance section of our website (www.MediaCoHolding.com) located under the “Investors” heading. The members of the Compensation Committee are Deborah McDermott (chair), Colbert Cannon, Amit Thakrar and Mary Beth McAdaragh, all of whom are independent directors under Nasdaq listing standards. The Compensation Committee held three meetings during the last fiscal year.

Additional Committees. The Company also has a Diversity, Equity and Inclusion Committee, the sole member of which is Andrew Glaze, who is an independent director under Nasdaq standards.

In 2024, our Board held four meetings, either in person or by telephone. Each director attended at least 75% of the aggregate of (1) the total number of meetings of our Board held while he or she was a director and (2) the total number of meetings held by all committees on which he or she served during the periods that he or she served on the committee.

We believe that communication between our shareholders and the members of our Board of Directors is enhanced by the opportunity for personal interaction at our annual meeting of shareholders. Accordingly, we encourage the members of our Board of Directors to attend our annual meeting of shareholders whenever possible. Each of our directors who was in office at the time attended the Company’s annual meeting of shareholders in 2024, which was held in a virtual-only format.

During 2021, the Compensation Committee authorized annual retainers of $75,000 for each director who is not an officer of Emmis, as well as the following retainers for certain committee chairs: $50,000 for Board Chair, $50,000 for Audit Committee Chair, $50,000 for Acquisition Committee Chair, $50,000 for Digital Committee Chair, $50,000 for COVID Committee Chair, and $100,000 for Diversity Committee Chair. However, these amounts remained subject to the previous decision by the directors, made in the summer of 2020, that each of the directors would reduce their annual $75,000 retainers by twenty percent, with Ms. McDermott reducing her retainer by forty percent. This reduction has remained in effect since that time and remains in effect for 2024, except that for 2024, the amount of the reduction is expected to be paid in Class A Shares upon the approval in the future of a new equity compensation plan. Mr. Cannon and Mr. Pertuz receive no compensation for their services on the Board.

On April 17, 2024, MediaCo and Purchaser, entered into the Asset Purchase Agreement, pursuant to which Purchaser purchased substantially all of the assets of Estrella and its subsidiaries (other than certain broadcast assets owned by Estrella and its subsidiaries (the “Estrella Broadcast Assets”)) (the “Purchased Assets”), and assumed substantially all of the liabilities (the “Assumed Liabilities”) of Estrella and its subsidiaries.

MediaCo provided the following consideration for the Purchased Assets:

The Class A Shares issuable upon the exercise of the Warrant and the shares of Class A Shares issuable upon the exercise of the Option Agreement (as defined below) represented approximately 43% of the outstanding shares of Class A Shares on a fully diluted basis (assuming the full exercise of the Warrant and the Option Agreement).

The Warrant, the shares of Series B Preferred Stock and the Second Lien Term Loan are initially held by an affiliate of HPS.

The Asset Purchase Agreement required MediaCo to prepare and file with the Commission a proxy statement to be sent to MediaCo shareholders relating to a special meeting of MediaCo shareholders (the “Shareholders Meeting”) to be held to consider approval of the issuance of shares of Class A Shares upon exercise of the Warrant and the issuance of shares of Class A Shares pursuant to the Option Agreement (the “Proposal”). The Board directed the Proposal be submitted to a vote at the Shareholders Meeting and recommended that MediaCo’s shareholders vote in favor of approval of the Proposal. On March 6, 2025, the shareholders voted to approve the Proposal.

The Asset Purchase Agreement includes representations, warranties and covenants of the parties customary for a transaction of this nature.

On April 17, 2024, in connection with the Transactions contemplated by the Asset Purchase Agreement (the “Transactions”), MediaCo and Purchaser entered into an Option Agreement (the “Option Agreement”) with Estrella and certain subsidiaries of Estrella pursuant to which (i) Purchaser was granted the option to purchase 100% of the equity interests of certain subsidiaries of Estrella holding the Estrella Broadcast Assets (the “Option Subsidiaries Equity”) in exchange for 7,051,538 shares of Class A Shares, and (ii) Estrella was granted the right to put the Option Subsidiaries Equity to Purchaser for the same consideration beginning six months after the date of the closing of the Transactions (the “Closing Date”).

On April 17, 2024, in connection with the Transactions, SG Broadcasting, the holder of shares of Class A Shares and Class B Shares representing a majority of the voting power of the shares of MediaCo, entered into a Voting and Support Agreement with MediaCo and Estrella (the “Voting and Support Agreement”), pursuant to which SG Broadcasting agreed to, among other things,

and subject to the terms and conditions set forth therein, at any meeting of MediaCo shareholders (including the Shareholders Meeting), or at any adjournment or postponement thereof, vote in favor of the Proposal and against any action or proposal that would reasonably be expected to prevent or materially delay consummation of the Proposal. The Voting Agreement also includes certain customary restrictions on SG Broadcasting’s ability to transfer its shares of MediaCo stock. The Voting Agreement will automatically terminate upon the date on which the Proposal is approved.

On April 17, 2024, in connection with the Transactions, MediaCo issued the Warrant, which provides for the purchase of up to 28,206,152 shares of Class A Shares (the “Warrant Shares”), subject to customary adjustments as set forth in the Warrant, at an exercise price per share of $0.00001. Subject to certain limitations, the Warrant also provides that the Warrant holder has the right to participate in distributions on Class A Shares on an as-exercised basis. The Warrant further provides that in no event shall the aggregate number of Warrant Shares issuable to the Warrant holder upon exercise of the Warrant exceed 19.9% of the aggregate number of shares of common stock of MediaCo outstanding, or the voting power of such outstanding shares of common stock, on the business day immediately preceding the issue date for such Warrant Shares, calculated in accordance with the applicable rules of Nasdaq, unless and until the Proposal has been approved.

In order to finance the Transactions, MediaCo and its direct and indirect subsidiaries entered into a maximum $45.0 million first lien term loan credit facility, dated April 17, 2024 (the “First Lien Credit Agreement”), with White Hawk Capital Partners, LP, as term agent thereunder, and the lenders party thereto. Under the terms of the First Lien Credit Agreement, MediaCo received an initial term loan of $35.0 million on April 17, 2024 (the “Initial Loan”) and was provided with a subsequent delayed draw facility of up to $10.0 million that may be provided for additional working capital purposes under certain conditions (the “Delayed Draw” and the loans thereunder, the “Delayed Draw Term Loans”). The Initial Loan and Delayed Draw Term Loans are collectively referred to as the “First Lien Term Loans.” The proceeds of the Initial Loan were used to finance the Transactions, pay off certain existing indebtedness in connection therewith and pay related fees and transaction costs. The Initial Loan will mature on April 17, 2029, and each Delayed Draw Term Loan will mature on the date that is two years after the drawing of such Delayed Draw Term Loan. First Lien Term Loans will be subject to monthly amortization payments equal to 0.8333% of the initial principal amount of the First Lien Term Loans, and monthly interest payments at a rate of SOFR + 6.00%. The First Lien Term Loans are subject to a borrowing base in accordance with the terms of the First Lien Credit Agreement.

In addition, MediaCo and its direct and indirect subsidiaries entered into a $30.0 million second lien term loan credit facility, dated April 17, 2024 (the “Second Lien Credit Agreement”), with HPS as term agent, and the lenders party thereto. Under the terms of the Second Lien Credit Agreement, MediaCo was deemed to receive the Second Lien Term Loan of $30.0 million on April 17, 2024 in exchange for the Transactions. The Second Lien Term Loan will mature on April 17, 2029 and will be subject to monthly interest payments at a rate of SOFR + 6.00%. The Second Lien Term Loans are subject to a borrowing base in accordance with the terms of the Second Lien Credit Agreement.

On April 17, 2024, in connection with the Transactions, MediaCo entered into a shareholders’ agreement with SG Broadcasting and Aggregator (the “Shareholders Agreement”). The Shareholders Agreement provides Aggregator (i) the right to designate up to three individuals for election to the Board (each such designee, an “Investor Director Designee”), subject to reduction and termination based on certain MediaCo stock ownership requirements (including that such designation right falls away upon Aggregator ceasing to beneficially own at least ten percent (10%) of the fully diluted MediaCo common stock for ten consecutive days), and (ii) certain consent rights over material actions taken by MediaCo.

On April 17, 2024, in connection with the Transactions, MediaCo entered into a registration rights agreement with SG Broadcasting and Aggregator (the “Registration Rights Agreement”), pursuant to which MediaCo has granted each of SG Broadcasting and Aggregator customary underwritten shelf takedown and piggyback rights with respect to the registration of shares of Class A Shares with the Commission under the Securities Act of 1933, as amended (the “Securities Act”). In addition, MediaCo has agreed to prepare and file within three months of the Closing Date a registration statement covering the sale or distribution of shares of Class A Shares held by SG Broadcasting and Aggregator.

On April 17, 2024, in connection with the Transactions, Purchaser entered into a Network Program Supply Agreement (the “Network Program Supply Agreement”) with certain subsidiaries of Estrella that operate radio broadcast stations (the “Radio Stations”). Pursuant to the Network Program Supply Agreement, Purchaser has agreed to license certain programs and other material to the Radio Stations for distribution on the Radio Stations’ broadcast channels.

On April 17, 2024, in connection with the Transactions, Purchaser entered into a Network Affiliation Agreement (the “Network Affiliation Agreement”) with certain subsidiaries of Estrella that operate television broadcast stations (the “TV Stations”). Pursuant to the Network Affiliation Agreement, Purchaser has agreed to license certain programs and other material to the TV Stations for distribution on the TV Stations’ broadcast channels.

MediaCo was formed by Emmis Communications Corporation (“Emmis”) in connection with a transaction (the “Emmis Transactions”) with SG Broadcasting that involved, among other things, Emmis conveying the assets of radio stations WBLS-FM and WQHT-FM (the “New York Radio Stations”) to MediaCo (the “Separation”) and distributing (the “Distribution”) all of MediaCo’s Class A Shares to all of Emmis’ shareholders pro rata. Emmis and the Company operate separately, each as an independent public company. In connection with the Separation, we and Emmis entered into certain agreements to affect the separation of our business from Emmis and govern our relationship with Emmis after the Separation. The following is a summary of the terms of the material agreements that we have entered into with Emmis. These summaries set forth the terms of the agreements that we believe are material and are qualified in their entirety by reference to the full text of such agreements.

On June 28, 2019, we entered into a certain Contribution and Distribution Agreement with Emmis and SG Broadcasting (the “Transaction Agreement”). The Transaction Agreement sets forth our agreements with Emmis and SG Broadcasting regarding the principal actions to be taken in connection with the Transactions. The Transaction Agreement identified assets to be transferred, liabilities to be assumed and contracts to be assigned to the Company as part of the separation, and it provided for when and how these transfers, assumptions and assignments will occur.

Initial Contribution, SG Broadcasting Investment, Purchase Price and Adjustment. At the closing of the Emmis Transactions and pursuant to the terms of the Transaction Agreement, SG Broadcasting made an investment in MediaCo (the “Initial SG Broadcasting Investment”) consisting of $41,500,000 plus the $6,250,000 for additional working capital purposes. As consideration for the SG Broadcasting Investment, MediaCo issued to SG Broadcasting a convertible promissory note payable by MediaCo in the amount of $6,250,000 (the “Original SG Broadcasting Promissory Note”) and issued to SG Broadcasting 5,359,753 Class B Shares, which constituted all of the issued and outstanding Class B Shares, representing in the aggregate an approximately 76.28% equity ownership interest and 96.98% of the outstanding voting interests of MediaCo immediately following the Emmis Transactions. Contemporaneously, Emmis contributed the assets of the NY Radio Stations to MediaCo and MediaCo paid to Emmis the sum of $91,500,000 (the “Purchase Price”), issued the Emmis Promissory Note, secured the use of $5,000,000 of working capital from Emmis which was required to be repaid within nine months following the closing of the Emmis Transactions (and was so repaid), and issued to Emmis 1,666,667 Class A Shares, which constituted all of the issued and outstanding Class A Shares and represented in the aggregate approximately 23.72% equity ownership interest and 3.02% of the outstanding voting interests of MediaCo immediately following the Emmis Transactions. In connection with the Distribution, Emmis was issued an additional 16,619 Class A Shares in order to enable 0.1265 Class A Shares to be distributed for each share of Emmis common stock outstanding, and SG Broadcasting was issued an additional 53,444 Class B Shares to enable SG Broadcasting to retain its proportionate ownership percentage in MediaCo.

Contemporaneously with the close of the Emmis Transactions, to fund the Purchase Price, the Company entered into a five-year senior secured term loan agreement (the “Senior Credit Facility”) by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent. The Senior Credit Facility originally provided for initial borrowings of up to $50,000,000, which net proceeds, along with the proceeds from the Initial SG Broadcasting and the Original SG Broadcasting Promissory Note, were paid to Emmis as consideration for the NY Radio Stations, as well as one tranche of additional borrowings of $25,000,000. On December 13, 2019, the Company entered into an amendment and restatement of the Senior Credit Facility (the “Amended and Restated Senior Credit Facility”) to provide for an additional approximately $23,500,000 in incremental term loans, the proceeds of which were used to fund the Company’s obligations in connection with the transactions.

On December 9, 2022, following the consummation of the transactions contemplated by the Purchase Agreement, the Company repaid in full, without penalty, all of its obligations under the Senior Credit Facility, which was terminated at that time.

Indemnification. The Transaction Agreement provides for releases with respect to pre closing claims arising from the Emmis Transactions, and with respect to post Distribution claims, except as otherwise provided in the Transaction Agreement, indemnifications principally designed to place financial responsibility for obligations and liabilities allocated to MediaCo under the Transaction Agreement with MediaCo and financial responsibility for obligations and liabilities allocated to Emmis under the Transaction Agreement with Emmis. Other than in limited circumstances, Emmis shall only be responsible for certain breaches of representations and warranties if losses exceed one percent (1%) and the maximum recovery is limited to ten percent (10%) of the Purchase Price.

Other Matters Governed by the Contribution and Distribution Agreement. Other matters governed by the Transaction Agreement include, without limitation, access to financial and other information, insurance, confidentiality and access to and provision of records.

The Emmis Convertible Promissory Note carries interest at a base rate equal to the interest on any senior credit facility of MediaCo, or if no senior credit facility is outstanding, of 6.00%, and an additional increase of 1.00% following the second anniversary of the date of issuance and additional increases of 1.00% following each successive anniversary thereafter. The Emmis Promissory Note has a maturity date of the fifth (5th) anniversary of its execution. Additionally, the Emmis Promissory Note will be payable in interest in kind through maturity, and will be convertible into Class A Shares at the option of Emmis beginning six (6) months after issuance and at a strike price equal to the thirty (30) day volume weighted average price of the Class A Shares on the date of conversion.

On August 19, 2022, Emmis exercised its right under the Emmis Convertible Promissory Note to convert thirty thousand dollars ($30,000.00) of the outstanding principal for 11,000 shares of the Company’s Class A Shares. On December 21, 2022, Emmis exercised its right under the Emmis Convertible Promissory Note to convert $0.9 million of the outstanding principal and $0.1 million of accrued but unpaid interest for 0.8 million shares of the Company’s Class A Shares.

The Emmis Convertible Promissory Note matured on November 25, 2024 and was settled in cash.

At closing of the Emmis Transactions, we entered into two Shared Services Agreements with Emmis. Historically, Emmis has operated radio stations WLIB AM and WEPN FM (which were retained by Emmis) from many of the same facilities and using many of the same personnel as used in the operation of NY Radio Stations. The Shared Services Agreements became operative as of the completion of the Separation to allow Emmis to continue to use MediaCo’s facilities, equipment and personnel consistent with past practices. Emmis is to reimburse MediaCo for all incremental out of pocket costs and expenses incurred by MediaCo in connection with this arrangement.

At closing of the Emmis Transactions, we entered into an Antenna Site Agreement with WLIB. Historically, WBLS FM has used the antenna site owned by WLIB in Lyndhurst, New Jersey as an emergency backup site from which to broadcast WBLS FM’s programs in the event its other broadcast antennas are unavailable. The Antenna Site Agreement allows WBLS FM antenna space

on the WLIB tower, as well as ground space for WBLS FM transmission equipment. The Antenna Site Agreement is to last for an initial term of 20 years, with two automatic renewal periods of 10 years each, unless MediaCo provides notice to WLIB of its intention to not renew the lease for an additional term. MediaCo is to pay to WLIB an annual license fee of ten dollars ($10.00).

At closing of the Emmis Transactions, MediaCo entered into an Employee Leasing Agreement, a Management Agreement and a Local Programming and Marketing Agreement with Emmis. All of such agreements were terminated by mutual agreement prior to 2022.

At the closing of the Emmis Transactions and pursuant to the terms of the Transaction Agreement, SG Broadcasting made the Initial SG Broadcasting Investment. As consideration for the Initial SG Broadcasting Investment, MediaCo issued to SG Broadcasting the Original SG Broadcasting Promissory Note and 5,359,753 Class B Shares, which constituted all of the issued and outstanding Class B Shares, representing in the aggregate an approximately 76.28% equity ownership interest and 96.98% of the outstanding voting interests of MediaCo immediately following the Emmis Transactions. Following closing of the Emmis Transactions, SG Broadcasting owns all of the issued and outstanding Class B Shares, representing an approximately 76.28% equity ownership interest and a 96.98% voting interest in MediaCo.

On February 28, 2020, MediaCo amended and restated the Original SG Promissory Note to allow SG Broadcasting to fund up to an additional $4 million (the “Amended and Restated SG Promissory Note”), and on March 27, 2020, further amended and restated the Amended and Restated SG Promissory Note to allow SG Broadcasting to fund up to an additional $9.75 million (the “Second Amended and Restated SG Promissory Note”). On September 30, 2020, SG Broadcasting loaned an additional $0.3 million to the Company pursuant to an additional SG Broadcasting Promissory Note (the “Second SG Promissory Note, and together with the Amended and Restated SG Promissory Note, the “SG Broadcasting Notes”). The SG Broadcasting Notes carry interest at a base rate equal to the interest on any senior credit facility, or if no senior credit facility is outstanding, of 6.00%, and an additional increase of 1.00% following the second anniversary of the date of issuance and additional increases of 1.00% following each successive anniversary thereafter. The SG Broadcasting Notes will have a maturity date of six (6) months after the fifth (5th) anniversary of execution of the Original SG Promissory Note. Additionally, the SG Broadcasting Notes will be payable in interest in kind through maturity. Subject to the Share Cap (as defined in Proposal 3), the SG Broadcasting Notes are convertible into Class A Shares at the option of SG Broadcasting at a strike price equal to the thirty (30) day volume weighted average price of the Class A Shares on the date of conversion. On July 28, 2022, SG Broadcasting exercised its right under the SG Broadcasting Promissory Notes to fully convert the outstanding principal and accrued but unpaid interest into the Company’s Class A Shares, and the 2019/2020 SG Broadcasting Promissory Notes were terminated at that time, while the May 2021 SG Broadcasting Promissory Note remains outstanding, but with no amounts outstanding as of December 31, 2022.

On April 17, 2024, SG Broadcasting entered into the Voting and Support Agreement. See “Transaction with Estrella” for more information.

On October 29, 2024, the Company and Standard Media Group LLC (“SMG”) entered into an Employee Leasing Agreement, effective as of October 1, 2024 (the “Leasing Agreement”). SMG is a wholly-owned subsidiary of Standard General. Standard General is an affiliate of the controlling shareholder of the Company, SG Broadcasting. Under the Leasing Agreement, the Company obtained the services of several SMG employees to serve various roles for the Company, including with respect to the legal, digital products, broadcast IT, and news operations function. The Leasing Agreement is an at-cost arrangement, with the Company paying only for a percentage of the actual cost of employing each leased employee, with no markup or service fees above the Company’s share of the actual fully-loaded cost of each leased employee.

The following Report of the Audit Committee shall not be deemed incorporated by reference by any general statement incorporating by reference this proxy statement into any of our filings under the Securities Act or the Exchange Act except to the extent that we specifically incorporate this information by reference, and shall not otherwise be deemed filed under such Acts.

The Audit Committee is a separately-designated, standing committee established in accordance with Section 3(a)(58)(A) of the Exchange Act. It is composed of five directors the Board of Directors has determined are “independent directors” as defined by Nasdaq listing standards. The Audit Committee’s responsibilities are set forth in its written charter approved by the Board of Directors. The charter is reviewed annually by the Audit Committee. A copy of the Audit Committee charter may be found in the Corporate Governance section of our website (www.MediaCoHolding.com) located under the Investors heading. As required by Nasdaq listing standards, the Audit Committee has determined that its charter is adequate. The Audit Committee has also determined that its members meet the financial literacy requirements of Nasdaq listing standards.

Management is responsible for the Company’s internal controls and the financial reporting process. The independent registered public accountants are responsible for performing an independent audit of the Company’s consolidated financial statements in accordance with auditing standards generally accepted in the United States of America and for issuing a report on the financial statements. The Audit Committee is responsible for the appointment, compensation, and oversight of the independent auditor. For the fiscal year ended December 31, 2024, the Audit Committee engaged Ernst & Young LLP to serve as the Company’s independent auditor, and Ernst & Young LLP served in such capacity with respect to the Company’s financial statements for that year. On May 7, 2025, the Company dismissed Ernst & Young LLP as the Company’s independent auditor and engaged Deloitte & Touche LLP to serve as the Company’s independent auditor for the fiscal year ending December 31, 2025.

The Audit Committee has met and held discussions with management and Ernst & Young LLP with respect to the Company’s financial statements for the fiscal year ended December 31, 2024. As part of these meetings and discussions, the Audit Committee (i) discussed with the Company’s internal auditor and Ernst & Young LLP the overall scope and plans for their respective audits, (ii) met with the Company’s internal auditor and Ernst & Young LLP, with and without management present, to discuss the results of their procedures and evaluations, and (iii) discussed with management the Company’s major financial risk exposures and the steps management has taken to monitor and control such exposures, including the Company’s risk assessment and risk management processes. Management represented to the Audit Committee that the Company’s consolidated financial statements as of and for the fiscal year ended December 31, 2024, were prepared in accordance with accounting principles generally accepted in the United States of America, and the Audit Committee has reviewed and discussed these consolidated financial statements with management. The Audit Committee also discussed with Ernst & Young LLP matters required to be discussed by their professional standards, including, among other things, matters related to the conduct of the audit of the Company's consolidated financial statements and the matters required to be discussed by the applicable requirements of the Public Company Accounting and Oversight Board (“PCAOB”) and the Securities and Exchange Commission.

The Board of Directors, upon the recommendation of the Audit Committee, has adopted an Auditor Independence Policy that, among other things, prohibits the Company’s independent auditor from performing certain non-audit services for the Company, requires prior approval of the Audit Committee for any services provided by the Company’s independent auditor, limits the hiring by the Company of former employees of the Company’s independent auditor who have worked on the MediaCo account and requires enhanced disclosure both to the Audit Committee and to shareholders of matters related to auditor independence.

The Audit Committee has received the written disclosures and the letter from Ernst & Young LLP required by applicable requirements of the PCAOB regarding Ernst & Young LLP’s communications with the Audit Committee concerning independence, and the Audit Committee has discussed with the independent registered public accountants that firm’s independence. In addition, the Audit Committee (or the chairman of the Audit Committee with respect to engagements of less than $100,000) approves in advance all engagements of the Company’s independent auditor. The Audit Committee determined that Ernst & Young LLP’s provision of non-audit services to the Company as described in “Matters Relating to Independent Registered Public Accountants” is compatible with maintaining that firm’s independence.

Based on these discussions and reviews, the Audit Committee determined that the audited financial statements for the Company’s last fiscal year should be included in our Company’s annual report on Form 10-K, and made a formal recommendation to the Board of Directors to that effect.

Robert L. Greene, Chair

Deborah McDermott

Mary Beth McAdaragh

Brett Pertuz

Amit Thakrar

During 2024, we experienced a transition of roles on our executive team following the transactions contemplated by the Asset Purchase Agreement. As of the end of 2024, we were managed by three executive officers: Albert Rodriguez, our Chief Executive Officer and President, who assumed that role on October 28, 2024; Debra DeFelice, our Chief Financial Officer, who assumed that role on September 26, 2024; and René Santaella, our Chief Operating Officer, who assumed that role on October 29, 2024. During 2024, we also had two other principial executive officers, who served on an interim basis and are listed in the following table based on applicable provisions of Regulation S-K: Jacqueline Hernández served as our principal executive officer from April 17, 2024 to October 28, 2024 and Kudjo Sogadzi served as our principal executive officer from October 11, 2023 through April 17, 2024. In addition, Brian Kei served as our Chief Operating Officer from April 18, 2024 through October 24, 2024, and is also listed in the following table based on applicable provisions of Regulation S-K.

The following table sets forth the compensation awarded to, earned by, or paid to Mr. Rodriguez, Ms. DeFelice, Mr. Santaella, Ms. Hernández and Mr. Sogadzi, as approved by the Compensation Committee of our Board, which has responsibility for establishing, implementing and continually monitoring adherence with the Company’s compensation philosophy. The Compensation Committee seeks to ensure that the total compensation paid to the executives is fair, reasonable and competitive

The Company sponsors a Section 401(k) retirement savings plan that is available to substantially all employees 18 years of age and older who have at least 30 days of service. Employees may make pre-tax contributions to the plan of up to the annual limit prescribed by the Internal Revenue Service (“IRS”). The Company may make discretionary matching contributions to the plans in the form of cash.

On June 20, 2025, our board of directors adopted the MediaCo Holding Inc. 2025 Equity Compensation Plan (the “2025 Plan”), subject to shareholder approval. The purpose of the 2025 Plan is to attract, retain, and motivate employees of, consultants and advisors to, and non-employee directors providing services to, the Company and its subsidiaries, and to promote the success of the Company’s business by providing participants with a proprietary interest in the performance of the Company and its subsidiaries. As of June 20, 2025, there were approximately ten (10) employees, seven (7) non-employee directors and two (2) consultants and advisors who would have been eligible for participation in the 2025 Plan.

The 2025 Plan is intended to replace the MediaCo Holding Inc. 2021 Equity Compensation Plan and MediaCo Holding Inc. 2020 Equity Compensation Plan (the “Prior Plans”). No additional grants will be made under either of the Prior Plans if the 2025 Plan is approved by our shareholders. Outstanding grants under the Prior Plans will continue in effect according to their terms as in effect before the effective date of the 2025 Plan (subject to such amendments as the plan administrator determines, consistent with the terms of the Prior Plans, as applicable). The shares underlying outstanding grants under the Prior Plans will not be issued or transferred under the 2025 Plan.

Our Board is seeking shareholder approval of the 2025 Plan in order to (a) meet the NASDAQ listing requirements, (b) allow incentive stock options that may be awarded under the 2025 Plan to meet the requirements of the Internal Revenue Code of 1986, as amended (the “Code”), and the regulations promulgated thereunder, (c) maintain a limit on annual compensation of non-employee directors, and (d) conform to good corporate governance practices.

The following summary of the principal provisions of the 2025 Plan is qualified by reference to the full text of the 2025 Plan, which is attached to this proxy statement as Exhibit A. The 2025 Plan, if approved by shareholders, permits the delivery of a maximum of five million (5,000,000) Class A Shares. The Board’s expectation is that these shares would satisfy MediaCo’s equity compensation needs for at least two years. As of June 20, 2025, the Class A Shares subject to the 2025 Plan had an aggregate market value of $5,350,000 based on a closing price of $1.07 per Class A Share.

Awards Generally: Pursuant to the 2025 Plan, we may grant to employees and other service providers equity awards in respect of our Class A Shares as well as awards in respect of cash amounts. Under the 2025 Plan, awards may be granted in the form of options, restricted stock, restricted stock units, stock appreciation rights, performance awards, dividend equivalent rights, cash-based awards and other share-based awards.

Administration: The 2025 Plan will be administered by the compensation committee of our board of directors, unless the board elects otherwise (such plan administrator, the “Administrator”). The Administrator will have the authority to determine the terms and conditions of any agreements evidencing any awards granted under the 2025 Plan and to adopt, alter and repeal rules, guidelines and practices relating to the 2025 Plan. The Administrator will have full discretion to administer and interpret the 2025 Plan and to adopt such rules, regulations and procedures as it deems necessary or advisable and to determine, among other things, the time or times at which the awards may be exercised and whether and under what circumstances an award may be exercised.

Plan Term: The 2025 Plan will terminate on the tenth (10th) anniversary of its effective date, unless terminated earlier by our board of directors.

Eligibility: Under the 2025 Plan, individuals entitled to receive awards, or “Eligible Individuals,” include non-employee directors, officers, employees, consultants, and certain advisors providing services to our Company or any of our subsidiaries, as well as any individual to whom our Company or one of our subsidiaries has extended a formal, written offer of employment; provided that any such prospective employee may not receive any payment or exercise any right relating to an award under the 2025 Plan until such person has commenced employment. “Eligible Individuals” also include holders of substitute awards (described further below). The Administrator will determine which Eligible Individuals will receive grants of awards.

Types of Awards Available: Under the 2025 Plan, the Administrator may grant any of the following types of awards to an Eligible Individual (to the extent permitted by applicable law): incentive stock options (“ISOs”) and nonqualified stock options (“NSOs,” together with ISOs, “Options”); stock appreciation rights (“SARs”); restricted stock; restricted stock units (“RSUs”); performance awards; dividend equivalent rights (“DERs”); cash-based awards; and other share-based awards (each, as described further below) (each type of award is considered an “Award”).

Shares Available: Subject to any adjustment as provided in the 2025 Plan, up to five million (5,000,000) Class A Shares may be issued pursuant to Awards granted under the 2025 Plan (the “Share Pool”). The Share Pool will not be subject to automatic increase.

Nonemployee Director Limit: The maximum aggregate dollar amount of cash and fair market value of Class A Shares that may be the subject of Awards granted to any non-employee director in any calendar year may not exceed $1,000,000 for the year of appointment and $300,000 for any subsequent year. The value of equity awards will be determined based on the grant date fair value of the Award.

Share Recycling: Class A Shares subject to an Award will become available again for issuance pursuant to the 2025 Plan if the shares (a) are not issued because the Award terminates by expiration, forfeiture, cancellation, or otherwise without the issuance of such shares; (b) are repurchased by our Company or an affiliate following the issuance for a price per share that is less than or equal to the price per share paid by the participant; (c) are tendered or withheld to pay the exercise price or to satisfy tax withholding obligations associated with any Award; or (d) are settled in cash (i.e., the participant receives cash rather than Class A Shares).

Substitute Awards: Awards may be granted under the 2025 Plan in assumption of, or in substitution for, outstanding awards previously granted by an entity directly or indirectly acquired by the Company or with which the Company combines. These substitute awards are not counted against the share limit.

Stock Options: The Administrator may grant Options (which may be ISOs or NSOs) to Eligible Individuals. An ISO is an Option intended to qualify for tax treatment applicable to ISOs under Section 422 of the Code. An ISO may be granted only to Eligible Individuals who are employees of our Company or any of our subsidiaries. No more than five million (5,000,000) Class A Shares may be issued under the 2025 Plan upon the exercise of ISOs. An NSO is an Option that is not subject to statutory requirements and limitations required for certain tax advantages allowed under Section 422 of the Code.

Vesting and Exercise Periods: Each Option granted under the 2025 Plan may be subject to certain vesting requirements and will become exercisable in accordance with the specific terms and conditions of the Option, as determined by the Administrator at the time of grant and set forth in an Award agreement. The term of an Option generally may not exceed ten (10) years from the date it is granted (five (5) years in the case of an ISO granted to a greater than ten percent (10%) shareholder). Each Option, to the extent it becomes exercisable, may be exercised at any time in whole or in part until its expiration or termination, unless otherwise provided in the applicable Award agreement.

Exercise Price; Method of Exercise: The purchase price per Class A Share with respect to any Option granted under the 2025 Plan will be determined by the Administrator, provided that (except as provided by the Administrator for substitute awards) it may not be less than 100% of the fair market value of a Class A Share on the date the Option is granted (110% in the case of an ISO granted to a greater than ten percent (10%) shareholder). The exercise price may be paid (a) in cash or its equivalent (e.g., a check), (b) if permitted by applicable law and the Administrator or set forth in the applicable Award agreement, by way of transfer, either actually or by attestation, to our Company of Class A Shares, such transfer to be upon such terms and conditions as determined by the Administrator or (c) if permitted by applicable law and the Administrator or set forth in the applicable Award agreement, in the form of a transfer of other property. In addition, (i) the Administrator may provide for the payment of the exercise price through withholding of Class A Shares as a result of which the number of shares issued upon exercise of an Option would be reduced by a number of shares having a fair market value (as defined in the 2025 Plan) equal to the exercise price; and (ii) an Option may be exercised through a registered broker-dealer pursuant to such cashless exercise procedures that are, from time to time, deemed acceptable by the Administrator. We will not issue fractional Class A Shares.

Limits on Incentive Stock Options: In order to comply with the requirements for ISOs in the Code, if any person holds ISOs granted under the 2025 Plan in respect of Class A Shares with an aggregate fair market value in excess of $100,000 (as determined on the applicable date of grant) that would be exercisable for the first time during any one calendar year, such Options will be treated as NSOs according to the order in which they were granted, such that the most recently granted Options are first treated as NSOs.

Stock Appreciation Rights: The Administrator may grant stock appreciation rights (“SARs”) to Eligible Individuals on terms and conditions determined by the Administrator at the time of grant and set forth in an Award agreement.

Vesting; Amount Payable: The Administrator will determine the terms by which a SAR will vest and become exercisable, which terms will be set forth in an Award agreement. A SAR is a right granted to a participant to receive an amount equal to the excess of the fair market value of a Class A Share on the date of exercise of such SAR over the fair market value of a Class A Share on the date the SAR was granted. A SAR may be settled or paid in cash, Class A Shares or a combination thereof, in accordance with its terms.

Duration: Each SAR will be exercisable or be forfeited or expire on such terms as the Administrator determines. Except in limited circumstances, a SAR may not have a term greater than ten (10) years.

Prohibition on Repricings: The Administrator will have no authority to (a) make any adjustment or amendment (other than in connection with certain changes in capitalization or certain corporate transactions in accordance with the terms of the 2025 Plan, as generally described below) that reduces, or would have the effect of reducing, the exercise price of an Option or the base price of a SAR previously granted under the 2025 Plan or (b) cancel for cash or other consideration any Option whose exercise price or SAR whose base price is greater than the fair market value per share, unless, in either case, our shareholders approve such adjustment or amendment.

Dividend Equivalent Rights: The Administrator may grant DERs, either in tandem with an Award or as a separate Award, to Eligible Individuals on terms and conditions determined by the Administrator at the time of grant and set forth in an Award agreement. DERs are rights to receive cash or Class A Shares based on the value of dividends that are paid with respect to the Class A Shares. Amounts payable in respect of DERs may be paid currently or may be deferred until the lapsing of restrictions on such DERs or until the vesting, exercise, payment, settlement or other lapse of restrictions on the Award to which the DERs relate; provided, however, that a DER granted in tandem with another Award that vests based on the achievement of performance goals will be subject to restrictions and risk of forfeiture to the same extent as the Awards with respect to which such dividends are payable. The Administrator will determine whether amounts payable in respect of DERs are to be held in cash or reinvested in Class A Shares or deemed (notionally) to be reinvested in Class A Shares. DERs may be settled in cash or Class A Shares or a combination thereof, in a single installment or multiple installments, as determined by the Administrator.

Performance Awards: The Administrator may grant Awards subject to performance-based vesting conditions (“Performance Awards”), including certain performance objectives enumerated in the 2025 Plan, on terms and conditions determined by the Administrator at the time of grant and set forth in an Award agreement. The value of the Award depends on the level of the participant’s and/or our achievement of the performance objectives during a specified period, as outlined in the Award agreement, or at such other time(s) as the Administrator may determine that the Performance Award has vested. The Administrator may adjust an Award’s performance objectives after the Award has been issued to reflect the impact of certain specified events. Each Performance Award represents the right of the participant to receive a payment upon vesting of either cash or Class A Shares equal to the fair market value of a Class A Share as of the date the Performance Award becomes vested according to the applicable Award agreement. A Performance Award may be settled or paid in cash, Class A Shares or a combination of each, as determined by the Administrator in its discretion.

Restricted Stock; RSUs: The Administrator may grant either unvested Class A Shares (“Restricted Stock”) or RSUs, in each case, subject to certain vesting requirements, on terms and conditions determined by the Administrator at the time of grant and set forth in an Award agreement.

Restricted Stock: To the extent Class A Shares are certificated, unless the Administrator determines otherwise, we will retain possession of the certificates for Class A Shares subject to an Award of Restricted Stock until all restrictions on such shares have lapsed. Unless held by us, each such certificate will contain a legend giving appropriate notice of the restrictions applicable to the Award. The Administrator may determine that we will not issue certificates for Awards of Restricted Stock until all restrictions on such Class A Shares have lapsed. Upon the lapse of all restrictions on an Award of Restricted Stock, the Administrator will cause a stock certificate or evidence of book entry shares (as applicable) to be delivered to the participant with respect to such shares of Restricted Stock, free of all restrictions. With regard to book entry shares, the Administrator may cause appropriate stop transfer instructions to be delivered to the account custodian, administrator, or our corporate secretary, as determined by the Administrator in its sole discretion.

Recipients of Restricted Stock will have all of the rights of a shareholder with respect to such Shares, including the right to receive any dividends paid or made with respect to the Class A Shares. At the time an Award of Restricted Stock is granted, the

Administrator may, in its discretion, determine that the payment of dividends, or a specified portion thereof, declared or paid on such Shares by the Company will accrue and be (a) deferred until the lapsing of the restrictions imposed upon such Shares, and (b) held by the Company until such time; provided, however, that a dividend that is accrued and payable in respect of Restricted Stock, prior to its vesting, if any, will be subject to such vesting conditions and a risk of forfeiture to the same extent as the Restricted Stock with respect to which such dividends are payable.

Restricted Stock Units: Each RSU will represent the right of the participant to receive a payment upon settlement of the RSU of an amount equal to the fair market value of a Class A Share as of the date the RSU settles according to the applicable Award agreement. An RSU may be settled or paid in cash, Class A Shares or a combination of each, as determined by the Administrator.

Cash-Based Awards: The Administrator may grant cash-based awards on such terms and conditions as determined by the Administrator at the time of grant. Each cash-based award will specify a cash-dominated payment amount, formula or payment ranges as determined by the Administrator.

Other Share-Based Awards: The Administrator may grant other awards based on Class A Shares on terms and conditions determined by the Administrator at the time of grant and set forth in an Award agreement. The Administrator may grant awards of fully-vested Class A Shares.

Adjustments upon Changes in Capitalization: In the event that the outstanding Class A Shares are increased or decreased in number or kind, or changed into or exchanged for a different number or kind of shares or other stock or securities or other equity interests of our Company or another corporation or entity, in each case by reason of a merger, amalgamation, consolidation, reorganization, recapitalization, reclassification, spin-off, split-up, stock dividend, stock split, reverse stock split, substitution or other similar corporate event or transaction, extraordinary or non-recurring cash dividend, property dividend, combination or exchange of Class A Shares, repurchase of Class A Shares, change in corporate structure, another similar corporate event or transaction, or any other equity restructuring, the Administrator will determine the appropriate adjustments, if any, to (a) the maximum number and type of shares of stock or other securities or other property that may thereafter be made the subject of Awards or be delivered under the 2025 Plan, (b) the maximum number and class of shares or other securities that may be issued upon exercise of ISOs, (c) the exercise price of outstanding Options and the base price of outstanding SARs, or the measure to be used to determine the amount of the benefit payable on an Award, (d) the performance objectives applicable to outstanding Performance Awards, and (e) any other adjustments the Administrator determines to be equitable, including cash payments to participants.

Effect of Change in Control or Certain Other Transactions: Except as otherwise provided in an Award agreement, all outstanding Awards will terminate upon the consummation of a Corporate Transaction (as defined below), unless provision is made in the sole discretion of the Administrator for the assumption or continuation of the Awards by, or the substitution for the Awards with new awards of, the surviving corporation or resulting entity, or a parent or subsidiary thereof, with such adjustments to the terms and underlying property of such awards as the Administrator determines appropriate.

For purposes of the 2025 Plan, “Corporate Transaction” means (a) a merger, amalgamation, consolidation, reorganization, recapitalization or other similar change in the capital stock of our Company, (b) a liquidation or dissolution of our Company, or (c) a Change in Control (as defined below).

For purposes of the 2025 Plan, “Change in Control” generally means the occurrence of any of the following events with respect to our Company: (a) an acquisition (other than directly from our Company) of any voting securities of our Company by any person or group, immediately after which such person or group first has beneficial ownership of more than fifty (50%) percent of the combined voting power of our Company’s then outstanding voting securities, other than a “non-control acquisition,” which includes an acquisition by (i) an employee benefit plan maintained by the Company or, a “related entity” (defined as any corporation or other person, the majority of the voting power, voting equity securities, or equity interest of which is owned, directly or indirectly, by the Company), (ii) the Company, any related entity or any “permitted holder” (defined as HPS Investment Partners LLC and/or funds or accounts or vehicles controlled, managed or advised thereby, and Standard General, L.P. and its affiliates), or any person in connection with a non-control transaction (as defined below); (b) a majority of the members of our board of directors is replaced by directors whose appointment or election is not endorsed by at least a majority of the members of our board of directors serving immediately prior to such appointment or election; (c) any merger, amalgamation, consolidation or reorganization (“Merger”), with or into our Company or pursuant to which securities of our Company are issued, in either case, other than a non-control transaction; (d) a complete liquidation or dissolution of our Company; or (e) a sale or disposition of all or substantially all of the assets of our Company and our subsidiaries. A “non-control transaction” generally includes any Merger in which (i) shareholders immediately before such transaction continue to own at least a majority of the combined voting power of the surviving corporation

or ultimate parent corporation following the transaction; (ii) a majority of the members of our board of directors immediately before such transaction continue to constitute at least a majority of the board of directors of the surviving corporation or the ultimate parent corporation following such transaction; (iii) with certain exceptions, no person other than any person who had beneficial ownership of fifty (50%) percent or more of the combined voting power of our Company’s then outstanding voting securities immediately prior to such transaction has beneficial ownership of fifty (50%) percent or more of the combined voting power of the surviving corporation’s or ultimate parent corporation’s outstanding voting securities immediately after such transaction; or (iv) one or more permitted holders, together, beneficially own following such Merger, more than fifty (50%) percent of the combined voting power of the outstanding voting securities or the surviving corporation or ultimate parent corporation.

Treatment of Options and SARs: If Options or SARs are to terminate in connection with a Corporate Transaction, the holders of vested Options or SARs will be provided either (a) fifteen days to exercise their Options or SARs or (b) payment (in cash or other consideration upon or immediately following the Corporate Transaction, or, to the extent permitted by Section 409A of the Code, on a deferred basis) in respect of each Class A Share covered by the Option or SAR being canceled in an amount equal to the per-share price to be paid to shareholders in the Corporate Transaction, where the value of any non-cash consideration will be determined by the Administrator in good faith, in each case less the exercise price or base price of the Option or SAR, as applicable. If the per-share price to be paid to shareholders in the Corporate Transaction is less than or equal to the exercise price of the Option or base price of the SAR, the Option or SAR may be terminated without payment of any kind. The holders of unvested Options or SARs may also receive payment, at the discretion of the Administrator, in the same manner as described above for vested Options and SARs. The Administrator may also accelerate the vesting on any unvested Option or SAR and provide holders of such Options or SARs a reasonable opportunity to exercise the Award.

Treatment Other Awards: If Awards other than Options and SARs are to terminate in connection with a Corporate Transaction, the holders of vested Awards will be provided, and holders of unvested Awards may be provided, at the discretion of the Administrator, payment (in cash or other consideration upon or immediately following the Corporate Transaction, or, to the extent permitted by Section 409A of the Code, on a deferred basis) in respect of each Class A Share covered by the Award being canceled in an amount equal to the per-share price to be paid to shareholders in the Corporate Transaction, where the value of any non-cash consideration will be determined by the Administrator in good faith.

The Administrator may, in its sole discretion, provide for different treatment for different Awards or Awards held by different parties, and where alternative treatment is available for a participant’s Awards, may allow the participant to choose which treatment will apply to his or her Awards.

Transferability: The 2025 Plan generally restricts the transfer of any Awards, except (a) transfers by will or the laws of descent and distribution, (b) to a beneficiary designated by the participant, to whom any benefit under the 2025 Plan is to be paid or who may exercise any rights of the participant in the event of the participant’s death before he or she receives any or all of such benefit or exercises an Award or (c) certain other specified events subject to the approval of the Administrator.

Amendment or Termination of the 2025 Plan: The 2025 Plan may be amended or terminated by our board of directors without shareholder approval, unless shareholder approval of the amendment or termination is required under applicable law, regulation or exchange requirement. The Administrator generally may not affect the repricing of Options or SARs without shareholder approval, as described further above in “Prohibition on Repricings.” No amendment may materially and adversely alter or materially impair any Award that had been granted under the 2025 Plan prior to the amendment without the impacted participant’s consent. No amendment may deprive any participant of any Class A Shares acquired through or as a result of the 2025 Plan, except as our board of directors deems necessary or appropriate to comply with applicable law or the rules and regulations of any government authority. The 2025 Plan will terminate on the tenth (10th) anniversary of its effective date; however, when the 2025 Plan terminates, any applicable terms will remain in effect for administration of any Awards outstanding at the time of the 2025 Plan’s termination.

Modification of Awards: The Administrator may also modify the terms of any Award under the 2025 Plan made to or held by a participant who is then a resident, or is primarily employed or providing services, outside of the United States in any manner deemed by the Administrator to be necessary or appropriate in order for such Award to conform to the laws, regulations, and customs of the country in which the participant is then a resident, or primarily employed or providing services, or to maintain the value of the Award. Additionally, the Administrator may adopt such procedures and sub-plans as are necessary or appropriate to permit participation in the 2025 Plan by persons who are foreign nationals or are primarily employed or providing services outside the United States.

Forfeiture Events; Clawback: The Administrator may specify in an Award agreement that the participant’s rights, payments, and benefits with respect to an Award will be subject to reduction, cancellation, forfeiture, clawback, or recoupment upon the occurrence of certain specified events or as required by law, regulation, or exchange requirement, in addition to any otherwise applicable forfeiture provisions that apply to the Award. Each Award will be subject to the terms of any clawback policy maintained by our Company or as required by law, regulation, or exchange requirement, as it may be amended from time to time.

The following is a general summary of the U.S. federal income tax consequences arising with respect to awards under the 2025 Plan. This summary is not a definitive explanation of the tax consequences of these awards and excludes the effect of state, local and non-U.S. tax laws.

Options. Options may be granted in the form of ISOs or NSOs. ISOs granted to employees are eligible for favorable federal income tax treatment that is provided under Section 422 of the Code if certain requirements are satisfied. An employee granted an ISO or NSO generally does not realize compensation income for U.S. federal income tax purposes upon the grant of the Option. The Company will generally be entitled to a deduction for U.S. federal income tax purposes at the time any compensation income is realized by the holder of an Option, as described below, in an amount equal to the amount of compensation income realized by the holder.

Nonqualified Stock Options. At the time of exercise of an NSO, the holder of the Option will realize taxable compensation income in the amount of the spread between the exercise price of the Option and the fair market value of the Class A Shares acquired on the date of exercise. Following the exercise of the Option, the holder’s later disposition of the Class A Shares acquired upon the exercise of the Option will ordinarily result in capital gain or loss to the option holder. Any gain will be subject to reduced long-term capital gains tax rates if the Class A Shares have been held for more than twelve (12) months.

Incentive Stock Options. An ISO must have an exercise price that is not less than the fair market value of the stock at the time the Option is granted and must be exercisable within ten (10) years from the date of grant. At the time of exercise of an ISO, no compensation income is realized by the holder of the Option other than tax preference income for purposes of the U.S. federal alternative minimum tax on individual income. If the Class A Shares acquired on exercise of an ISO are held for at least two years after grant of the Option and one year after exercise, the excess of the amount realized on sale over the exercise price will be taxed as capital gain. If the Class A Shares acquired on exercise of an ISO are disposed of within less than two years after grant or one year after exercise, the holder will realize taxable compensation income equal to the excess of the fair market value of the Class A Shares on the date of exercise or the date of sale, whichever is less, over the exercise price. Any additional amount realized will be taxed as capital gain which may be long-term or short-term capital gains, depending on how long the Class A Shares were held after exercise.

SARs. Upon the exercise of a SAR, an employee will generally realize taxable compensation income in an amount equal to the cash and/or the fair market value of the Class A Shares acquired pursuant to the exercise. The Company will be entitled to a U.S. federal income tax deduction at the time of and equal to the amount of compensation income the employee receives pursuant to the exercise of a SAR.

Restricted Stock, RSUs and Performance Awards. Employees granted Restricted Stock, RSUs and Performance Awards under the 2025 Plan generally recognize as taxable compensation income the fair market value of the Restricted Stock, RSUs, and Performance Awards on the date the restrictions lapse or the performance period ends and the Awards are settled, unless, in the case of Restricted Stock, the employee has elected to include the Restricted Stock in income at the time of grant under Section 83(b) of the Code. The Company is entitled to a corresponding U.S. federal income tax deduction at the same time. Any dividends or DERs paid to an employee during the restricted period are taxable compensation income to the employee and are deductible by the Company for U.S. federal income tax purposes, unless the employee has elected to include the Award in income when granted under Section 83(b) of the Code.

Cash-Based Awards and Other Shared-Based Awards. If Awards are in the nature of cash-based awards or other shared-based awards, they generally would be taxable as compensation income equal to the applicable amount of cash or the aggregate of the fair market value of the Class A Shares when the grant is not subject to a substantial risk of forfeiture. The Company would be entitled to a federal income tax deduction for the amount included in the participant’s income.

Code Section 280G. The effect of a Corporate Transaction on Options or other Awards, if any, may be set forth in an Award agreement, which may include accelerated vesting or lapse of restrictions with respect to Options or other Awards. Under certain

circumstances, the accelerated vesting or lapse of restrictions with respect to Options or other Awards in connection with a Corporate Transaction may be deemed an “excess parachute payment” for purposes of the golden parachute tax provisions of Section 280G of the Code. To the extent it is so considered, a participant may be subject to a 20% excise tax and the Company may be denied a U.S. federal income tax deduction.

Code Section 409A. Section 409A of the Code generally imposes an additional 20% income tax, as well as interest and penalties, on recipients of deferred compensation that does not comply with Section 409A of the Code. Subject to certain exceptions, “deferred compensation” for this purpose generally consists of compensation to which an individual has a legally binding right in a taxable year and which is to be paid in a later taxable year. In addition to the taxes, interest and penalties, deferred compensation that does not comply with Section 409A of the Code may be required to be taken into income earlier than is intended. If Awards under the 2025 Plan are subject to Section 409A of the Code and do not comply with Section 409A of the Code, participants may be liable for the tax, interest and penalties imposed by the statute.

Code Section 162(m). Section 162(m) of the Code limits the tax deduction the Company can take with respect to employees considered “covered employees” under Section 162(m) of the Code to compensation that does not exceed $1,000,000 on an annual basis. To the extent that a participant is considered a “covered employee” under Section 162(m) of the Code, income recognized by such covered employee that is over $1,000,000 on an annual basis as a result of the exercise of, or the vesting of, an Award, as applicable, will not be deductible by the Company.

Set forth below is information on awards of Restricted Stock that have been promised to be granted under the 2025 Plan, subject to the 2025 Plan being approved by shareholders in accordance with this Proposal 2. It is anticipated that these grants will be effective shortly after the annual meeting of shareholders, if this Proposal 2 is approved by shareholders. Other than as set forth in the table below, the future benefits to be allocated to any individual or to various groups of eligible participants are presently not determinable.

The following table gives information about Class A Shares that may be issued upon the exercise of options, warrants and rights under the Prior Plans as of December 31, 2024. Our shareholders have approved these plans.

Under the Dodd-Frank Wall Street Reform and Consumer Protection Act (the “Dodd-Frank Act”) and Section 14A of the Exchange Act, our shareholders are entitled to vote to approve, on an advisory basis, the compensation of our named executive officers as disclosed in this proxy statement in accordance with the rules of the Securities and Exchange Commission (the “SEC”). This vote is not intended to address any specific item of compensation, but rather the overall compensation of our named executive officers and the philosophy, policies and practices described in this proxy statement.

The compensation of our named executive officers subject to the vote is disclosed in the compensation tables, and the related narrative disclosure contained in this proxy statement. We believe that our compensation policies and decisions are designed to reward strong annual operating performance by the Company.

Accordingly, our Board is asking shareholders to indicate their support for the compensation of our named executive officers as described in this proxy statement by casting a non-binding, advisory vote “FOR” the following resolution:

“RESOLVED, that the shareholders approve, on an advisory basis, the compensation of the Company’s named executive officers, as disclosed pursuant to Item 402 of Regulation S-K, including the Compensation Discussion and Analysis, compensation tables and narrative discussion, in the Company’s Proxy Statement for the 2025 Annual Meeting of Shareholders.

Because the vote on this proposal is advisory in nature, it will not affect any compensation already paid or awarded to any named executive officer and will not be binding on or overrule any decisions by the Compensation Committee or the Board. Nevertheless, the views expressed by shareholders, whether through this vote or otherwise, are important to Company management and our Board and, accordingly, our Board and the Compensation Committee intend to consider the results of this vote in making determinations in the future regarding executive compensation arrangements. Your advisory vote serves as an additional tool to guide the Compensation Committee and our Board in continuing to align the Company’s executive compensation program with the interests of the Company and its shareholders and is consistent with our commitment to high standards of corporate governance.

This vote is not intended to express a view on any specific element of pay, but rather the overall compensation program and philosophy for our named executive officers described in the compensation tables, and the related narrative disclosure as set forth in the “Executive Compensation” section of this proxy statement. We encourage you to carefully review these disclosures and to indicate your support for our named executive officer compensation program.

The Audit Committee, a committee of the Board of Directors, has appointed Deloitte & Touche LLP to serve as our independent registered public accountants for the year ending December 31, 2025, subject to ratification by the holders of our Common Shares. Our financial statements for the year ended December 31, 2024, were certified by Ernst & Young LLP. Representatives of Deloitte & Touche LLP are expected to attend the annual meeting with the opportunity to make a statement if they desire to do so, and will be available to respond to appropriate questions.

Although our by-laws do not require that we seek shareholder ratification of the appointment of Deloitte & Touche LLP as our independent auditors, we are doing so as a matter of good corporate governance. If shareholders do not ratify the selection of Deloitte & Touche LLP as our independent registered public accountants, or if prior to our annual meeting of shareholders Deloitte & Touche LLP ceases to act as our independent registered public accountants, then the Audit Committee will reconsider the selection of independent registered public accountants.

The following table sets forth the fees (including cost reimbursements) paid to Ernst & Young LLP (Indianapolis, IN, PCAOB ID 42) for the years ended December 31, 2023 and 2024, for various categories of professional services they performed as our independent registered public accountants.

During the year ended December 31, 2024, prior to engaging the independent registered public accountants to render the above services and pursuant to its charter, the Audit Committee approved the engagement for each of the services and determined that the provision of such services by the independent registered public accountants was compatible with the maintenance of Ernst & Young LLP’s independence in the conduct of its auditing services. Under its current charter, it is the policy of the Audit Committee (or in certain instances, the chairman of the Audit Committee) to pre-approve the retention of the independent registered public accountants for any audit services and for any non-audit services, including tax services. No services were performed during the fiscal year ended December 31, 2024, under the de minimis exception in Rule 2-01(c) (7)(i)(C) of Regulation S-X.

To be considered for inclusion in the Company’s 2026 proxy solicitation materials, shareholder proposals submitted in accordance with SEC Rule 14a-8 of the Exchange Act, must be received in writing by our corporate secretary no later than February 27, 2026. Shareholders who wish to bring business before or nominate a person for election as a director at the Company’s 2026 annual meeting (other than through a shareholder proposal pursuant to Rule 14a-8 of the Exchange Act) must notify the corporate secretary in writing and provide the information required by the provisions of our by-laws dealing with shareholder proposals. Copies of our by-laws are available to shareholders free of charge upon request to our corporate secretary. The notice must be delivered to the corporate secretary at the principal executive offices of the Company not later than the close of business on the 90th day (May 10, 2026) nor earlier than the close of business on the 120th day (April 10, 2026) prior to the first anniversary of the 2025 annual meeting; provided, however, that in the event that the date of the 2026 annual meeting is more than 30 days before or more than 60 days after such anniversary date, notice by the shareholder, to be timely, must be delivered not earlier than the close of business on the 120th day prior to the 2026 annual meeting and not later than the close of business on the later of (i) the 90th day prior to the 2026 annual meeting or (ii) the 10th day following the day on which public announcement of the date of such meeting is first made. Any shareholder submitting a nomination of a person for election as director who intends to solicit proxies in support of such nominee must provide notice that sets forth the information required by Rule 14a-19 under the Exchange Act. Our Board of Directors will review any shareholder proposals that are filed as required and, with the assistance of the Company’s secretary, will determine whether such proposals meet applicable criteria for inclusion in our 2026 proxy solicitation materials or consideration at the 2026 annual meeting. In addition, we retain discretion to vote proxies on matters of which we are not properly notified at our principal executive offices on or before the close of business on the applicable 2026 shareholder proposal and nomination filing deadline, and also retain that authority under certain other circumstances.

A copy of our annual report on Form 10-K for the year ended December 31, 2024, is available in the Investors section of our website (www.MediaCoHolding.com). Certain shareholders who have previously given us their consent to receive materials electronically did not receive a physical copy of the annual report and can access the annual report from the Investors section of our website (www.MediaCoHolding.com). The annual report is not to be considered as proxy solicitation material.

Our Board of Directors knows of no other matters to be brought before this annual meeting. However, if other matters should come before the meeting, it is the intention of each person named in the proxy to vote such proxy in accordance with his or her judgment on such matters.

The Report of the Audit Committee and the information on the MediaCo website do not constitute soliciting material and should not be deemed filed or incorporated by reference into this proxy statement or any other MediaCo filing under the Securities Act or the Exchange Act, except to the extent MediaCo specifically incorporates the Report or website information therein by reference.

The entire expense of soliciting proxies, including preparing, assembling, printing and mailing the proxy form and the material used in the solicitation of proxies, will be paid by us. Solicitations may be made in person or by mail, telephone, facsimile or other means of electronic communication by our directors, officers and other employees, and none of those persons will receive any additional compensation in connection with the solicitation. We also will request record holders of shares beneficially owned by others to forward this proxy statement and related materials to the beneficial owners of such shares, and will reimburse those record holders for their reasonable expenses incurred in doing so.

We have adopted a procedure permitted by Securities and Exchange Commission rules that is commonly referred to as “householding.” Under this procedure, a single annual report, proxy statement and notice regarding the availability of proxy materials are delivered to multiple shareholders sharing an address unless we receive contrary instructions from any shareholder at that address. We will continue to send a separate proxy card to each shareholder of record. We have adopted this procedure because we believe it reduces the volume of duplicate information shareholders receive and helps to reduce our printing and postage costs. A number of brokers with account holders who are MediaCo shareholders will be “householding” our proxy materials and annual reports as well.

If, at any time, you no longer wish to participate in “householding” and would prefer to receive a separate proxy statement and annual report, please notify your broker if you hold your MediaCo shares through a broker, or notify us directly if you are a shareholder of record by sending us an e-mail at ir@MediaCoHolding.com, calling us toll-free at (866) 366-4703 or writing to us at MediaCo Holding Inc. Investor Relations, 48 W. 25th Street, Floor 3, New York, New York 10010. We will deliver promptly, upon written or oral request, a separate copy of the annual report, proxy statement, or notice regarding the availability of proxy materials, as applicable, to a shareholder at a shared address to which a single copy of the documents was delivered.

If you currently receive multiple copies of our proxy statement and annual report at your address and would like to request “householding” of your communications, you should contact your broker, or, if you are a record holder of MediaCo shares, you should submit a written request to our transfer agent, Equiniti Trust Company, LLC, Operations Center, 6201 15th Avenue, Brooklyn, New York 11219.

Exhibit A

Effective Date: June 20, 2025

Shareholder Approval Date: [August 8, 2025]