iHeartMedia, Inc.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

(Rule 14a-101)

INFORMATION REQUIRED IN PROXY STATEMENT

SCHEDULE 14A INFORMATION

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the Securities Exchange Act of 1934 (Amendment No. )

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IHEARTMEDIA, INC.

(Name of Registrant as Specified In Its Charter)

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LETTER FROM OUR INDEPENDENT DIRECTORS

Dear Fellow Stockholders:

On behalf of the independent directors of the Board of Directors (the "Board") of iHeartMedia, Inc. (the “Company”), thank you for your continued investment and confidence in the Company. We recognize that our primary responsibility is to you, and we are committed to maintaining and evolving our governance processes and independent oversight over the Company.

In connection with the 2026 Annual Meeting of Stockholders, we want to share with you some of the highlights of the work of the Board over the past year.

In 2025, the Board provided meaningful oversight and guidance to management during the Company's continued transformation driven by innovation and supported by data and technology. That Board oversight and interaction has helped reinforce the Company’s position as the number one audio company in the United States, reaching 9 out of 10 Americans every month.

Financial Discipline and Modernization

Throughout 2025, the Board engaged in consistent and transparent dialogue with management regarding strategic initiatives, capital management and our continuing commitment to rigorous financial discipline. The comprehensive debt refinancing completed in late 2024 provided the Company with flexibility to execute its strategy in 2025. This execution included the implementation of cost savings initiatives announced in 2024 which resulted in over $150 million of net cost savings this past year. We also announced cost savings initiatives which are expected to generate an additional $100 million of annual cost savings in 2026. The Board is pleased by the continued year-over-year growth of our Digital Audio Group segment, including our industry-leading podcast division, and wholeheartedly supports the Company’s strategic modernization initiative in our Multiplatform Group to introduce our broadcast radio advertising inventory into existing programmatic digital buying platforms.

Executive Leadership Continuity

This past summer, the Board approved extensions of the employment agreements for our Chairman and Chief Executive Officer, Robert Pittman, and our President and Chief Operating Officer, Richard Bressler, securing continuity in key leadership roles through 2029. These extensions reflect the Board’s belief in the strength and stability of the leadership team and are a signal of our confidence in leadership’s plans and long-term direction. The Board approved an important executive leadership transition with the appointment of Michael McGuinness as Chief Financial Officer, effective January 1, 2026. Mike’s elevation into the Chief Financial Officer role follows years of service within the organization as Deputy Chief Financial Officer and supports the Company’s long-term planning, capital structure management and disciplined financial stewardship. The Board also invited three senior members of the Company’s management team, including the Company’s newly hired Chief Business Officer, to attend all scheduled Board meetings in order for our directors to interact directly with key day-to-day leaders who report to our CEO and President.

Board Composition and Stockholder Engagement

The Board continues to focus on its collective skills and expertise that, taken together, promote effective corporate governance. Our highly qualified Board consists of eight directors (six of whom are independent) who have a complementary mix of tenures, backgrounds, skills and experiences that facilitate strong and independent oversight.

The Board prioritizes stockholder feedback and remains committed to maintaining an open line of communication with our stockholders. Over the past several years, we have increased the frequency and scope of our stockholder engagement activities, and we value the candid feedback we received during these meetings. During 2025, the Company reached out to stockholders representing approximately 72% of the Company’s outstanding Class A common stock for governance-focused engagement, including 23 of our top 30 institutional stockholders, with active participation from independent directors including our Lead Independent Director. Dialogue with stockholders has yielded valuable perspectives that the Board considered, alongside our voting results from the 2025 Annual Meeting, in its discussions on strategic, governance and executive compensation matters. As part of our demonstrated efforts to be responsive to stockholders, in 2026, the Performance Stock Units awarded to management have a three-year performance period only and do not include any shorter term (e.g., one-year) metrics. We also have enhanced the disclosure of the evolution of our compensation program in the Executive Compensation section of this Proxy Statement to illustrate our continued alignment with execution against our key financial and strategic goals.

Commitment to Long-Term Value Creation

Looking ahead, we believe the Company is well positioned to continue to build long-term value for our stockholders. iHeartMedia’s leadership in the audio category, coupled with a focus on growth across digital platforms and strategic shifts toward operational modernization and technological development provide a strong foundation for the future. We remain committed to supporting the execution of the Company’s long-term strategy, providing effective oversight and representing the interests of all stockholders with diligence and integrity.

We appreciate your ongoing trust and support and look forward to the year ahead.

Sincerely,

James A. Rasulo, Lead Independent Director

Samuel E. Englebardt

Robert Millard

Cheryl Mills

Graciela Monteagudo

Kamakshi Sivaramakrishnan

NOTICE OF 2026 ANNUAL MEETING OF STOCKHOLDERS

To Be Held on June 4, 2026

Dear Fellow Stockholder:

The 2026 Annual Meeting of Stockholders (the “Annual Meeting”) of iHeartMedia, Inc., a Delaware corporation (the “Company”), will be held on Thursday, June 4, 2026, at 10:00 a.m. Eastern Time. The Annual Meeting will be a completely virtual meeting, which will be conducted via live webcast. You will be able to attend the Annual Meeting online and submit your questions during the meeting by visiting www.virtualshareholdermeeting.com/IHRT2026 and entering your 16-digit control number included on your Notice of Internet Availability of Proxy Materials or your proxy card. The Annual Meeting will be held for the following purposes:

While all of the Company’s stockholders are invited to attend the Annual Meeting, only holders of record of our outstanding shares of Class A common stock at the close of business on April 7, 2026, are entitled to notice of and to vote at the Annual Meeting, or any continuation, postponement or adjournment of the Annual Meeting. A complete list of these stockholders will be available for examination by any stockholder during the ten days prior to the Annual Meeting for a purpose germane to the meeting by sending an email to InvestorRelations@iHeartMedia.com, stating the purpose of the request and providing proof of ownership of Company stock. The Annual Meeting may be continued or adjourned from time to time without notice other than by announcement at the Annual Meeting. The holders of our Class B common stock and the holders of our Special Warrants are not entitled to notice of or to vote on any matter before the Annual Meeting.

Important Information for Holders of Class A Common Stock It is important that your shares be represented regardless of the number of shares you may hold as of the Record Date. Whether or not you plan to attend the Annual Meeting, we urge you to vote your shares via the toll-free telephone number or over the Internet, as described in the enclosed materials. If you received a copy of the proxy card by mail, you may sign, date and mail the proxy card in the enclosed return envelope, which is addressed for your convenience and needs no postage if mailed in the United States. We encourage stockholders to submit their proxy by mail or via telephone or over the Internet. Promptly voting your shares will ensure the presence of a quorum at the Annual Meeting and will save us the expense of further solicitation. Submitting your proxy now will not prevent you from voting your shares at the Annual Meeting if you desire to do so, as your proxy is revocable at your option. The Company asks your cooperation in promptly submitting your proxy. YOUR VOTE IS IMPORTANT

If you would like to attend the Annual Meeting, please refer to the logistical information in the section titled “Questions and Answers About the 2026 Annual Meeting of Stockholders.”

By Order of the Board of Directors,

David A. Hillman

Executive Vice President, Chief Legal Officer

and Secretary

TABLE OF CONTENTS

Forward-Looking Statements

Certain statements herein constitute “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. Such forward-looking statements involve known and unknown risks, uncertainties and other important factors that may cause the actual results, performance or achievements of iHeartMedia, Inc. and its subsidiaries to be materially different from any future results, performance or achievements expressed or implied by such forward-looking statements. The words or phrases “guidance,” “believe,” “expect,” “anticipate,” “estimates,” “forecast,” "goal," "commitment" and similar words or expressions are intended to identify such forward-looking statements. In addition, any statements that refer to expectations or other characterizations of future events or circumstances, such as statements about capital and cost savings initiatives, future financial results and long-term value creation, executive leadership continuity and succession planning, stockholder engagement activities, and our business plans, strategies and initiatives, including our Corporate Responsibility initiatives, are forward-looking statements. These statements are not guarantees of future performance and are subject to certain risks, uncertainties and other important factors, some of which are beyond our control and are difficult to predict. Various risks that could cause future results to differ from those expressed by the forward-looking statements included herein include, but are not limited to: risks associated to global economic or political uncertainty and our dependence on advertising revenues; competition, including increased competition from alternative media platforms and technologies; dependence upon our brand and the performance of on-air talent, program hosts and management; fluctuations in operating costs and other factors beyond our control; technological and industry changes and innovations; shifts in population and other demographics; risks related to our use of artificial intelligence; impact of acquisitions, dispositions and/or other strategic transactions; risks related to our indebtedness; legislative or regulatory requirements; impact of legislation and royalty audits on music licensing and royalties; regulations and concerns regarding privacy and data protection and breaches of information security measures; risks related to scrutiny and regulation of Corporate Responsibility matters; risks related to our Class A common stock; and regulations impacting our business and the ownership of our securities. Other unknown or unpredictable factors also could have material adverse effects on the Company’s future results, performance or achievements. In light of these risks, uncertainties, assumptions and factors, the forward-looking events discussed herein may not occur. You are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the date stated, or if no date is stated, as of the date hereof. Additional risks that could cause future results to differ from those expressed by any forward-looking statement are described in the Company’s reports filed with the U.S. Securities and Exchange Commission, including in the section entitled “Item 1A. Risk Factors” of iHeartMedia, Inc.’s Annual Reports on Form 10-K and Quarterly Reports on Form 10-Q. The Company does not undertake any obligation to publicly update or revise any forward-looking statements because of new information, future events or otherwise. Additionally, various disclosures made herein or elsewhere (including our website) are informed by third-party frameworks or other stakeholder expectations. Such information may not, and should not be interpreted as necessarily being "material" for purposes of our filings with the U.S. Securities and Exchange Commission, even if we use the words "material" or "materiality" herein or in other documents discussing such matters.

Corporate Responsibility disclosures in particular are often informed by frameworks that define materiality in a way that may differ from, and is often more expansive than, the definition for U.S. federal securities laws. Moreover, given the long timelines and uncertainties associated with certain matters, materiality can be difficult to predict in advance. The methodologies and data associated with such disclosures also continue to evolve, and we cannot guarantee that our approach will align with the preferences of any particular stakeholder. Even when we leverage frameworks for certain of our disclosures, we cannot guarantee, and no language of "alignment." "accordance," or similar should be taken to mean strict adherence and compliance to these frameworks. Our disclosures, whether based on such frameworks or otherwise, may change due to a variety of factors, including revisions in framework requirements, availability and quality of information, changes in our business or applicable government policy, or other factors, some of which may be beyond our control.

iHeartMedia, Inc.

20880 Stone Oak Parkway

San Antonio, TX 78258