PENN Entertainment Inc

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a)

of the Securities Exchange Act of 1934

(Amendment No. )

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PENN ENTERTAINMENT, INC.

(Name of Registrant as Specified In Its Charter)

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A LETTER TO OUR SHAREHOLDERS

Dear Fellow Shareholders:

I am proud of the significant operational and financial milestones PENN Entertainment achieved in 2023 as our brands and businesses further evolved to meet the needs of our growing customer base. We executed across our retail footprint, transformed our digital business, invested in high growth projects, pioneered new technology, and advanced our corporate social responsibility (“CSR”) priorities. Our performance is underpinned by our talented team’s unwavering dedication to delivering superior integrated entertainment, casino and online sports betting and gaming experiences to our customers.

Best-in-Class Retail Operations Empower Our Growth Strategy

The continued strength and health of our retail business was evident in 2023, as we generated more than $2 billion in property-level EBITDAR. We delivered on our strategic targets and met our margin goals, all while navigating an uncertain macroeconomic environment. Led by our best-in-class operators, our regional gaming assets continue to deliver impressive and consistent results, providing a foundation for growth initiatives that are key to our long-term omnichannel strategy.

In 2023, we broke ground on four exciting new retail growth projects with an estimated overall budget of approximately $850 million. We are expanding our offerings at two of our best performing properties, Hollywood Columbus in Ohio and the M Resort in Las Vegas, Nevada, with the addition of a hotel at Columbus and a second hotel tower at the M Resort. In the Chicagoland market, we are relocating our riverboat licenses in Aurora and Joliet to create new best-in-class regional destinations in superior locations. We expect to complete these projects in the first half of 2026 and anticipate that expanding and modernizing these key properties will generate a strong return on our investment and create long-term value for our shareholders.

Transformative Strategic Alliance with ESPN Expands Our Value Proposition

After thoughtful deliberation and consideration of various alternatives by our Board, we made a significant pivot in our digital strategy in 2023, leading to our exclusive strategic alliance with ESPN, the undisputed leader in U.S. sports media. This transformative deal and the subsequent launch of ESPN BET™ last November, in alliance with ESPN, has already propelled our online business, delivering impressive download volumes, new registrations, and betting activity. While we are still in the early innings, ESPN BET is helping us reach new demographics of sports fans and grow the overall sports betting market in the U.S. We are now live in 18 states, and ESPN BET will be available to approximately 46% of the U.S. population following our launch in New York, which is expected in the second half of 2024. The early success of ESPN BET has also expanded our digital database by over 50% and bolstered our Hollywood-branded iCasino business through in-app cross-sell opportunities. We continue to see a growing convergence between sports media and sports betting, and our alliance with ESPN provides us with a compelling opportunity to fully capitalize on our investments in technology to create a differentiated sports betting and media experience, a truly unique and seamless value proposition for sports fans.

While we are pleased with the early ESPN BET adoption and engagement results, our primary focus in 2024 will be expanding our product offerings and introducing bespoke features to deliver a best-in-class experience for ESPN BET users. This will come from a combination of deep media and fantasy app integrations with ESPN, something no competitor in the industry can replicate, coupled with more expansive parlay and same game parlay offerings and an enhanced Hollywood-branded iCasino product. Strong execution in these areas will result in higher retention, share of wallet and spend per user.

Our Technology Investments and Growing Database Bolster Our Omnichannel Growth Strategy

Prior to the ESPN BET launch, our Interactive division achieved a major milestone in July with the full-scale migration of our U.S. online business to our proprietary technology platform. We acquired this technology platform in connection with our acquisition of theScore in 2021 and subsequently went live in 2022 in Ontario with strong results under theScore BET® brand. This seamless technology migration in the U.S. marked the culmination of a multi-year effort to bring all aspects of our North American online sports betting and iCasino operations in-house, and it would not have been possible without our strong team of talented engineers and product managers. Operating on our own technology has improved our efficiency, streamlined our ability to quickly introduce new features, and most importantly, provided us with complete control over our product roadmap as we work with ESPN to provide a best-in-class, fully integrated media and betting experience.

A LETTER TO OUR SHAREHOLDERS

The launch of ESPN BET has further bolstered our industry-leading loyalty program, PENN Play™, which now includes more than 29 million members. Nearly one third of new customers acquired through the initial launch of ESPN BET are located within 50 miles of one or more of our 43 properties – underpinning the advantages of our omnichannel-focused strategy. Our investments in technology have also led to the success of our market leading 3C’s (cashless, cardless, contactless) offering, which is now deployed at 21 properties across the nation, representing approximately 70% of our retail EBITDAR.

World-Class Technology Leadership Team and Valuable Board Refreshment

To help accelerate our technology and product improvements, we recently announced the hiring of Aaron LaBerge as the Company’s first-ever Chief Technology Officer. Mr. LaBerge brings more than 20 years of experience at The Walt Disney Company, most recently serving as President and Chief Technology Officer for both Disney Entertainment and ESPN. In his new role, he will be responsible for driving technology strategy and execution for PENN, while leading a multinational team of technologists and serving as the key business leader for the Company’s Interactive division. To help guide and inform our growing technology initiatives, we recently appointed Anuj Dhanda as an independent director. Mr. Dhanda serves as EVP, Chief Technology & Transformation Officer for Albertsons Companies, and he brings extensive technology, cybersecurity and business transformation experience to our Board.

Focused on Driving Sustainable Shareholder Value Creation

Our Company has a long-term track record of creating shareholder value through a relentless focus on delivering best-in-class margins, accretive M&A, organic growth and return on invested capital. While we are disappointed with our recent stock performance, we remain confident that the strategic investments we have made in our Interactive business, together with our four retail growth projects, are key to fortifying our omnichannel strategy, providing us with a solid foundation for future growth and long-term shareholder value.

Lastly, our Company’s success relies on the quality and development of our over 23,000 team members and our reputation as a well-regarded member of the communities in which we operate. I’m extremely proud of the strides we have collectively made to further our CSR objectives. Across the Company we donated more than $8 million in support of local charities and veterans-focused organizations in 2023, and our team members throughout North America volunteered over 9,500 hours with organizations that serve our local communities. We also continued to advance our sustainability initiatives by completing our first Scope 3 greenhouse gas emissions inventory, one of the many steps we are taking to ensure that we remain good stewards of our planet’s natural resources.

On behalf of myself, our Board and our leadership team, I would like to thank you, our valued shareholders, for your continued investment, support and confidence. 2024 is sure to be another exciting year at PENN Entertainment.

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

Voting Matters

At or before the 2024 Annual Meeting of Shareholders (“Annual Meeting”), we ask that you vote on the following items:

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

Important Notice Regarding the Availability of Proxy Material for the Annual Meeting to be Held on June 4, 2024.

Please note that we are furnishing proxy materials and access to this Proxy Statement to our shareholders via our website instead of mailing printed copies. This reduces our impact on the environment and helps us save costs.

Beginning on April 23, 2024, we will make available to each of our shareholders a Notice of Internet Availability of Proxy Materials, which contains instructions on how to access our proxy materials and vote online. If you attend the Annual Meeting virtually, you may withdraw your proxy and vote online during the Annual Meeting.

Your vote is important. We encourage you to vote promptly, regardless of whether you plan to attend the Annual Meeting.

By Order of the Board of Directors,

Christopher Rogers

Executive Vice President, Chief Strategy Officer and Secretary

Wyomissing, Pennsylvania, April 23, 2024

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING TO BE HELD ON JUNE 4, 2024: Our Proxy Statement and 2023 Annual Report are available free of charge on our website at https://investors. pennentertainment.com/reports-filings/sec-filings. In addition, our shareholders may access this information, as well as submit their voting instructions, at www.proxyvote.com by having their proxy card and related instructions in hand.