DEF 14A of PENN Entertainment, Inc., Apr 27, 2026

DEF 14A of PENN Entertainment, Inc.

Filed Apr 27, 2026 · FY20250001140361-26-016846

Open on EDGAR

  1. Attendance at Meeting

    | FREQUENTLY REQUESTED INFORMATION | | | | | Board and Committee Membership | 7 | Director Compensation | 43 | | Board Qualifications, Skills and Experience | 8 | Executive Compensation Peer Group | 63 | | Cybersecurity Risk Oversight | 25 | CEO Pay Ratio | 85 | | Management Committees | 38 | Pay Versus Performance | 86 | | Response to Shareholder Engagement | 40 | | |

  2. Board of Directors

    Board of Directors

  3. Our Board of Directors

    Our Board of Directors We believe our Board brings the right combination of fresh perspectives and deep experience, both of which are critical to governing a Company operating in a highly regulated and complex industry. Five of our ten independent directors have been appointed since our 2025 Annual Meeting, contributing extensive finance, human capital and talent management, gaming, strategy, corporate governance and technology experience to effectively oversee our next phase of growth and execution of our refocused digital strategy. At the same time, we have preserved the essential long-term knowledge and sound judgment that seasoned directors provide — experience that deepens the Board’s understanding of the Company’s history, regulatory landscape, and strategic evolution, and strengthens its ability to oversee management effectively and drive sustainable, long-term success.

  4. DIRECTORS

    DIRECTORS

  5. DIRECTORS

    | Board Recommendation | | | | OUR BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE “FOR” EACH CLASS III DIRECTOR NOMINEE: (i) Marla Kaplowitz; (ii) Jane Scaccetti; (iii) Fabio Schiavolin; and (iv) Jay Snowden |

  6. Introduction

    Introduction Our Board of Directors currently consists of eleven members. The directors are organized into three classes, with each class elected to serve a three-year term. At the Annual Meeting, shareholders will be asked to elect each of the four Class III directors to serve until the annual meeting of shareholders of the Company to be held in 2029 and until their respective successors are duly elected and qualified. Our Board of Directors, upon the recommendation of our Nominating and Corporate Governance Committee, has nominated (i) Marla Kaplowitz; (ii) Jane Scaccetti; (iii) Fabio Schiavolin; and (iv) Jay Snowden to serve as Class III directors. Each of the nominated persons has consented to being named in this Proxy Statement and to serve as a Class III director, if elected. We believe that each of our Class III director nominees has the specific experience, qualifications, attributes, and skills necessary to serve as an effective director on our Board of Directors. A description of our process for identifying and evaluating director nominees, as well as our criteria for membership on our Board of Directors, is set forth under the heading “Director Candidate Qualification and Selection Process.”

  7. Introduction

    | PROXY STATEMENT - 2026 | 13 |

  8. Introduction

    | | KEY SKILLS AND EXPERTISE: Ms. Kaplowitz is an innovator and a proven leader in marketing and digital transformation, with a long track record of experience in business management, strategic planning and communications. She has successfully counseled companies through impacts of evolving technologies on consumer behavior, including risks and opportunities associated with digital consumer experiences and omnichannel growth strategies, which she contributes to Board discussions on PENN’s customer offerings and strategy. • Industry Experience (Gaming, Hospitality, Media) and Government Affairs: Gained over Ms. Kaplowitz's more than 35-year career in the media industry, including her prior role as Chief Executive Officer of 4As, a trade association for advertising agencies that serves corporate members representing more than 85% of total U.S. advertising spend. In that role, she worked with members of the U.S. Congress to address critical issues pertaining to the media and digital media ecosystem and the industry's evolving regulatory landscape. • Sales & Marketing: Acquired through her extensive career in marketing and communications, including executive leadership roles focused on identifying strategic growth areas to build consumer loyalty and strengthen brand equity. During Ms. Kaplowitz's nearly 25 years at media communication agencies, she led marketing campaigns for global high-profile brands across personal care, restaurant and financial services sectors. • Corporate Stewardship: Obtained through her leadership roles in advertising, marketing and media, which required understanding of the evolving impact of non-financial business risks on various industries and evolving consumer preferences. Ms. Kaplowitz's work has included advising global companies on the FTC's updated Green Guides on the use of environmental marketing claims, as well as navigating the shifting regulatory and legislative landscape across state jurisdictions. EXPERIENCE: 4As (American Association of Advertising Agencies) – Trade association serving more than 600 member agencies throughout the U.S. • President and CEO (2017-2025) MEC Global (now Wavemaker Global) – Global media agency • CEO of North America (2011-2017) MediaVest (now Spark Foundry) – Full-service media agency that provides marketing, content and technology solutions • EVP, Managing Director (2006-2011), SVP, Media Director (2003-2006), SVP, Group Media Director (1999-2002) Ammirati Puris Lintas – Advertising agency • SVP, Group Media Director (1996-1999) | | Marla Kaplowitz | | | Class III Director (Independent) Age: 60 Director Since: 2020 Committees: • Nominating and Corporate Governance, Chair • Compensation, Chair Education: • UC Santa Barbara: BA, Sociology | |

  9. Introduction

    | 14 | PROXY STATEMENT - 2026 |

  10. Introduction

    | | KEY SKILLS AND EXPERTISE: Ms. Scaccetti brings expertise in finance, tax, accounting, cyber risk oversight, strategic planning, M&A, risk management and human capital development, shaped by her career as a Certified Public Accountant (CPA) and extensive corporate governance expertise, developed through her service on the boards of leading public companies over the past three decades. She has guided strategic planning initiatives to drive value creation and transformative growth, while ensuring financial integrity and aligning talent strategies with organizational objectives. Her financial acumen, strategic vision and governance experience make her a critical contributor to PENN’s growth and risk management efforts. • Risk Management: Acquired during Ms. Scaccetti’s more than 45-year career as a practicing CPA, including at Drucker & Scaccetti, which she co-founded, and at Laventhol & Horwath, where she was the first female tax partner of any international accounting firm in Philadelphia. In these roles, she provided counsel to U.S. and international based companies on a wide range of complex tax planning, corporate transactions and business strategy matters. • Cybersecurity: Developed through her leadership role at Drucker & Scaccetti, where she oversaw the creation and continued evolution of information security systems and controls to safeguard the firm’s information infrastructure. Ms. Scaccetti’s expertise was further enhanced through her role as the chair of the audit committee at multiple public companies for over three decades and her service on the board of a $3B+ in revenue non-profit institution where cybersecurity is paramount to protecting personal health records and information and annual CPA continuing education requirements. • Strategic Planning / M&A: Skills gained from both her board service and work with complex clients, where Ms. Scaccetti has guided organizations through evaluating and executing detailed analysis of acquisition targets, assessing integration risks, determining optimal pathways for growth, assessing financial implications and aligning strategic initiatives with long-term goals to drive value creation. EXPERIENCE: Armanino LLP – Successor company of Drucker & Scaccetti, P.C. • Of Counsel/Ambassador (since 2022) Drucker & Scaccetti, P.C. – Public accounting and business advisory firm • Chief Executive Officer (2013-2021), Partner (1990-2021) Laventhol & Horwath – International accounting firm • Partner (1987-1990), Staff/Manager (1977-1987) | | Jane Scaccetti | | | Class III Director (Independent) Age: 72 Director Since: 2015 Committees: • Audit, Chair • Compensation • Nominating and Corporate Governance Public Board Directorships: • Myers Industries, Inc (2016-2021) • The Pep Boys (2002-2016) Education: • Temple University's Fox School of Business: BBA • Villanova University: MS, Taxation | |

  11. Introduction

    | PROXY STATEMENT - 2026 | 15 |

  12. Introduction

    | | KEY SKILLS AND EXPERTISE: Mr. Schiavolin is a recognized leader in gaming markets and omnichannel business development, bringing over 25 years of executive experience and deep M&A expertise to the Board. Over the course of his career, he has built and scaled integrated gaming businesses across land-based and retail operations, online gaming and sports betting. His track record of integrating digital platforms with physical operations and managing complex international businesses provides him with a deep understanding of the industry dynamics, which strengthens the oversight of PENN’s growth strategy, capital allocation and innovation priorities. • Industry Experience (Gaming, Hospitality, Media): As CEO and Co-Founder of Cogetech, an online gaming and gambling company, Mr. Schiavolin scaled the business and led its merger with Snaitech in 2015, expanding the company’s retail betting network to over 1,600 points of sale. Under his leadership, Snaitech became Italy’s largest publicly traded gaming and entertainment company, achieving market-leading positions in sports betting, gaming machines and horse racing. He began his career at Cirsa, a multinational casino and gaming machine operator. • Strategic Planning / M&A: At Snaitech, Mr. Schiavolin delivered durable operating performance and margin expansion. He led the company’s strategic initiatives, including the 2018 merger with Playtech Group, a global gaming technology company operating in more than 17 countries. His experience evaluating transactions, managing integrations, and executing value creation strategies supports effective board oversight of M&A activity. • Technology / Digital: Mr. Schiavolin brings extensive experience leading technology-enabled gaming platforms and omnichannel growth initiatives. He has overseen the development and expansion of digital-first offerings across online gaming, sports betting and broadcasting, successfully integrating technology with retail operations to build customer loyalty and engagement. EXPERIENCE: Snaitech S.p.A. – A leading Italian gaming and betting company • CEO (2015-2025) Cogetech S.p.A. – An Italian gaming company (acquired by Snaitech in 2015) • Co-Founder and CEO (2004-2015) Bottega del Caffe – An Italian coffee chain • CEO (2000-2003) Cirsa – A leading multinational gaming company • BU Director (1997-2000) • Branch Director (1995-1997) | | Fabio Schiavolin | | | Class III Director (Independent) Age: 56 Director Since: 2026 Education: • Università di Bologna: MA, Business Administration | |

  13. Introduction

    | 16 | PROXY STATEMENT - 2026 |

  14. Introduction

    | | KEY SKILLS AND EXPERTISE: Mr. Snowden is Chief Executive Officer and President of PENN Entertainment (“PENN”), North America’s leading provider of integrated entertainment, sports content and casino gaming experiences. PENN operates in 27 jurisdictions throughout North America, with a broadly diversified portfolio of casinos, racetracks and online sports betting and iCasino offerings under well-recognized brands including Ameristar, L’Auberge, Hollywood Casino and theScore Bet. As Chief Executive Officer and President, Mr. Snowden has led PENN’s expansion into sports media, entertainment and technology. Under his leadership the Company has transformed from a regional gaming operator into an omnichannel provider of entertainment experiences, focusing on leveraging best-in-class regional gaming assets into cross-sell opportunities that expand the customer ecosystem and brand awareness. His deep industry knowledge and best-in-class operational capabilities make him a valuable member of the Board. Mr. Snowden served as President and Chief Operating Officer beginning in March 2017, was appointed to the Board of Directors in August 2019, and has held various senior leadership roles since joining the Company in October 2011. Prior to joining PENN, Mr. Snowden held leadership positions with Caesars Entertainment Corporation in several markets, including Las Vegas, Nevada and Atlantic City, New Jersey. • Industry Experience (Gaming, Hospitality, Media): Gained from Mr. Snowden’s more than 25-year successful career in the highly regulated and rapidly evolving gaming and sports betting industry, and hospitality and entertainment sectors. Prior to being appointed as CEO in 2020, he served as PENN’s President and Chief Operating Officer and as SVP of Regional Operations. Mr. Snowden previously spent 12 years with Caesars Entertainment, where he acquired significant gaming industry management experience across several regional and destination markets, including as SVP and General Manager of both Caesars and Harrah’s Resorts in Atlantic City. • HR / Talent Management: Acquired through his executive leadership career overseeing human capital strategies at large corporations, including talent integration initiatives following strategic transactions. At PENN, Mr. Snowden oversaw the launch of the expansive talent development strategy designed to support the growth of the Interactive segment and attract and retain leading industry talent. • Technology / Digital: His deep industry knowledge and digital transformation expertise provide unique perspectives on the Company’s strategic navigation of its broader omnichannel expansion and customer engagement strategies. EXPERIENCE: PENN Entertainment • CEO and President (since 2020), President and Chief Operating Officer (2017-2019), Chief Operating Officer (2014-2017), Senior Vice President of Regional Operations (2011-2014) Caesars and Harrah's Resorts Atlantic City – Casino resort and hotel • Senior Vice President and General Manager (2010-2011) Caesars Entertainment Corporation – Leading global gaming and hospitality resort chain • Various leadership positions in St. Louis, San Diego and Las Vegas (1998-2010) | | Jay Snowden | | | Class III Director (Executive Director) Age: 50 Director Since: 2019 Education: • Harvard University: BA • Washington University in St. Louis: MBA | |

  15. Introduction

    | Board Recommendation | | | | OUR BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE “FOR” EACH CLASS III DIRECTOR NOMINEE: (i) Marla Kaplowitz; (ii) Jane Scaccetti; (iii) Fabio Schiavolin; and (iv) Jay Snowden |

  16. Introduction

    | PROXY STATEMENT - 2026 | 17 |

  17. Introduction

    | | KEY SKILLS AND EXPERTISE: Mr. Handler has over 30 years of investment banking experience advising clients on many of the largest and most transformative transactions in the technology sector. In 2022, he co-founded Tidal Partners, a strategic M&A advisory firm headquartered in Palo Alto, California. Mr. Handler is a strategy and transaction thought partner to CEOs and boards as they navigate through the rapidly changing and increasingly complex technology industry. His experience in the highly regulated gaming industry, especially given the impact of technology, provides invaluable contributions to the Board’s oversight of PENN’s growth and capital allocation strategies. • Financial (Capital Markets, Accounting & Tax): Acquired over his 30+ year career in investment banking where he successfully advised clients on significant business transformation initiatives to unlock shareholder value. • Strategic Planning / M&A: Gained through decades of guiding major technology industry players on large-scale, high-profile and industry-defining transactions. Mr. Handler's long-term exposure to the gaming and technology industries, including opportunities created by emerging technologies, is an especially valuable asset to the Board. • Technology / Digital: As a co-founder of an M&A advisory firm focused on the technology sector, Mr. Handler contributes to the Board deep strategic insights into the evolving industry landscape, expertise in effective risk oversight and the ability to identify strategic opportunities for PENN's omnichannel growth strategy. EXPERIENCE: Tidal Partners – Strategic M&A advisory firm focused on the technology industry • Co-Founder and Partner (since 2022) Centerview Partners – Investment banking and advisory firm • Partner, founding Head of the Technology Group (2008-2022) UBS – Global investment bank • Managing Director, Co-Head of Americas Technology Investment Banking (2006-2009) Bear Stearns & Company – Specialized financial services company and investment bank • Managing Director, Co-Head of Communications Technology Investment Banking (2000-2006) | | David Handler | | | Class I Director (Independent) Age: 61 Director Since: 1994 Board Chair Since: 2019 Committees: • Compensation • Nominating and Corporate Governance Education: • NYU Stern School of Business: BA, Marketing • NYU Stern School of Business: MBA, Finance | |

  18. Introduction

    | 18 | PROXY STATEMENT - 2026 |

  19. Introduction

    | | KEY SKILLS AND EXPERTISE: Ms. Black-Gupta contributes to the Board more than 25 years of executive leadership experience with a strong track record of leading successful product, consumer and digital marketing strategies for global brands, including Colgate-Palmolive, Equinox, Estée Lauder and Procter & Gamble. As a founder of her own skincare consumer brand, Ourself, and in her roles guiding brand development and digital engagement strategies, she has overseen regulatory compliance, strategic planning, talent management and sustainability initiatives, driving corporate growth and innovation. Ms. Black-Gupta was named to Women Inc.’s list of “2023 Most Influential Corporate Directors.” • Industry Experience (Gaming, Hospitality, Media): Acquired through Ms. Black-Gupta’s executive career in global marketing roles, including as Global Chief Marketing Officer at Equinox, where she led the enterprise-wide marketing strategy for over 300 Equinox sport clubs and a pipeline of 10 lifestyle Equinox hotels with a focus on customer experience and digital engagement that successfully elevated the brand, enhanced client loyalty and expanded omnichannel growth opportunities. • Sales & Marketing: Developed through her experience overseeing the digital marketing strategy for the $1 billion Bobbi Brown Cosmetics brand at Estée Lauder in over 150 countries, including the beauty industry’s first digital channel launch, and for Procter and Gamble’s Gillette Venus and Oral B brands. As Co-Founder of Ourself, Ms. Black-Gupta was responsible for driving proprietary innovation in bio-technology for the fast growing direct-to-consumer and professional brand. • Strategic Planning / M&A: Obtained throughout numerous executive leadership roles, where Ms. Black-Gupta was responsible for strategy development and M&A initiatives. At Estée Lauder, she worked closely with the corporate development team to support the company's M&A strategy to fuel brand innovation and shareholder value growth. EXPERIENCE: Colgate-Palmolive (NYSE: CL) – Global consumer products company • Executive Vice President, Innovation (since 2025) Ourself – Innovative biotech skincare brand • Chief Executive Officer and Co-Founder (Co-Founder beginning 2021, CEO 2022-2024) Equinox Fitness Club and Hotel – Luxury fitness company • Global Chief Marketing Officer (2017-2019) Bobbi Brown Cosmetics – Global premium beauty brand • Senior Vice President of Global Marketing (2013-2017) Estée Lauder – Multinational cosmetics company • Vice President Global Marketing Idea Bank (2008-2013) Procter & Gamble – Global consumer goods corporation • Global Marketing Director (2005-2007) • Various executive global marketing leadership roles for Gillette and Procter & Gamble (1997-2005) | | Vimla Black-Gupta | | | Class I Director (Independent) Age: 56 Director Since: 2021 Committees: • Compensation • Nominating and Corporate Governance • Audit Education: • Duke University: BA • Northwestern University’s Kellogg School of Management: MBA | |

  20. Introduction

    | PROXY STATEMENT - 2026 | 19 |

  21. Introduction

    | | KEY SKILLS AND EXPERTISE: Mr. Dhanda is a well-respected technology leader in the consumer sector, with over 30 years of experience in leading technology and business functions. He is known for building powerful and collaborative teams that keep pace with the rapidly evolving technology, AI and cybersecurity landscape, which enables him to contribute tremendous insights to Board discussions related to PENN’s customer-focused digital and omnichannel retail strategy. In recognition of his significant contributions to advancing the use of technology in business, Mr. Dhanda was inducted into the CIO Hall of Fame. • Technology / Digital: Obtained through numerous executive leadership roles with consumer- oriented and digitally-enabled businesses, with responsibilities for technological transformation efforts, including customer digital engagement and intelligence, application and supply chain modernization. At Albertsons Companies (NYSE: ACI), he led the shift to exclusively cloud-based operations and is currently focused on accelerating business growth through the use of AI. • Cybersecurity: Acquired through more than 15 years of service as Chief Information Officer with leading national retail and financial services companies, overseeing the security of IT architecture, application platforms and data, including in Mr. Dhanda’s current role with Albertsons Companies where he oversees the security and reliability of the payments platform that processes approximately $78 billion in sales annually. • Strategic Planning / M&A: Gained by serving in strategic planning roles at JP Morgan and executive roles with PNC Financial Services Group, which focused on leading business development in high potential markets and enterprise-wide transformation strategies. He played critical roles in leading business and technology functions across multiple mergers and acquisitions by PNC. At Albertsons Companies, Mr. Dhanda oversaw the post-acquisition integration of the company and Safeway to a common platform. EXPERIENCE: Albertsons Companies, Inc. (NYSE: ACI) – Leading Fortune 100 grocery store chain • EVP and Chief Technology and Transformation Officer (since 2023), EVP and Chief Information Officer (2015-2022) Giant Eagle, Inc. – American supermarket chain • SVP, Digital Commerce and Chief Information Officer (2013-2015) The PNC Financial Services Group, Inc. (NYSE: PNC) – Diversified U.S.-based financial services institution • EVP and CIO (2008-2013), SVP and CIO, PNC Bank (2005-2008), Various positions (1999-2013), SVP and Manager, Eastern Markets (1997-1999), Small Business Lending (1995-1997) JP Morgan Chase & Co. (NYSE: JPM) (formerly Chemical Bank) – Leading global financial services firm • SVP, Marketing and Business Planning Manager, Consumer Bank (1992-1995), Strategic Planning Officer, Regional Banking Operations Division (1989-1992), Management Consultant, Retail Operations and Technology (1988-1989) | | Anuj Dhanda | | | Class I Director (Independent) Age: 63 Director Since: 2024 Committees: • Audit Public Board Directorships: • BlueLinx Holdings (NYSE: BXC) (2023-Present) Education: • University of Delhi: BA, Commerce • Rutgers University: MBA • Rutgers University: PhD, Finance | |

  22. Introduction

    | 20 | PROXY STATEMENT - 2026 |

  23. Introduction

    | | KEY SKILLS AND EXPERTISE: Ms. Ace is a seasoned global executive leader with more than 20 years of experience aligning human capital, operations and capital deployment with long-term business strategy. She has held senior leadership roles at complex, multinational organizations where she partnered closely with boards and executive teams to drive enterprise transformation and support sustained value creation. Her experience as a former attorney further strengthens her perspective on governance and compliance, which is particularly valuable in PENN’s regulated operating environment. • Human Capital / Talent Management: As Executive Vice President and Chief Human Resources Officer of Qualcomm, Ms. Ace oversees the global workforce of ~50,000 employees and advises senior leadership on enterprise transformation, operating model design, executive compensation, leadership development and employee engagement. Her scope includes responsibility for aligning organizational structure and incentives with business strategy and long-term performance objectives. • Strategic Planning / M&A: Ms. Ace has extensive experience with corporate transactions from strategy planning through execution. As Director of Human Resources, M&A at Life Technologies, she guided due diligence, contract negotiations and integration planning across all transactions. At Volcano Corporation, she served as Business Integration Leader for the company’s $1.2 billion acquisition by Royal Philips (NYSE: PHG), overseeing enterprise-wide integration efforts and the execution of cost synergies during the critical first year post-merger. • Risk Management: Developed through her numerous executive leadership roles at global companies, Ms. Ace contributes deep expertise in enterprise risk management, including identifying and mitigating operational, regulatory and compliance risks. Her background as a partner at a legal advisory firm, where she practiced litigation and employment law, specializing in mergers and acquisitions, provides her with a deep understanding of regulatory frameworks and governance practices. EXPERIENCE: Qualcomm Incorporated (Nasdaq: QCOM) – A global semiconductor manufacturing company • Chief Human Resources Officer and EVP, Human Resources (since 2020) Dexcom, Inc. (Nasdaq: DXCM) – A medical device company • Chief Human Resources Officer & SVP Human Resources (2016-2020) Orexigen Therapeutics – A pharmaceutical company • Chief Human Resources Officer & EVP Global Human Resources (2016) Volcano Corporation – A global medical device company (former Nasdaq: VOLC) • Business Integration Leader (2015-2016) • Chief Human Resources Officer & EVP Global Human Resources (2012-2015) Life Technologies Corporation – A leading life sciences company (former Nasdaq: LIFE) • VP, HR Life Sciences (2011-2012) • Roles of increasing scope and responsibility (2004-2011) Gray Cary Ware & Freidenrich LLP – A law firm (acquired by DLA Piper in 2005) • Employment Law Partner / Associate (1996-2004) | | Heather Ace | | | Class II Director (Independent) Age: 56 Director Since: 2026 Education: • University of California, Santa Barbara: BA, Law & Society • Santa Clara School of Law: JD | |

  24. Introduction

    | PROXY STATEMENT - 2026 | 21 |

  25. Introduction

    | | KEY SKILLS AND EXPERTISE: Mr. Fox is an accomplished executive with a proven track record of increasing revenue, profitability and shareholder value through strategic leadership and operational excellence. He has led multiple strategic and operational transformations, delivering improved financial performance through disciplined capital allocation, strategic M&A and successful integrations. Mr. Fox brings deep operational, technology, capital markets and financial expertise to the Board, supporting its oversight of PENN’s long-term growth strategy and value creation initiatives. • Strategic Planning / M&A: Gained over the course of his professional career as an investment banker, followed by decades as a public and private executive across multiple industries, including global enterprise software, cloud-based SaaS solutions, business process outsourcing, wireline, and wireless communications. As President and CEO of Convergys Corporation, Mr. Fox led the company through a multi-year strategic and operational transformation from a multi-line business services supplier into a well-capitalized market leader in the customer management business. As Chairman, Mr. Fox oversaw the $2.4 billion acquisition by SYNNEX Corporation (NYSE: SNX). Prior to Convergys, Mr. Fox was Co-President at Alltel Corporation, where he was part of the leadership team that executed the company’s $27 billion acquisition by TPG Capital and Goldman Sachs. • Financial (Capital Markets, Accounting & Tax): Developed over 30+ years as a public and private executive, including his role as COO of Alltel Corporation, then the fifth largest wireless provider in the United States. In this role, he was responsible for more than $10 billion in annual revenue and approximately $3.5 billion in EBITDA, overseeing large scale P&Ls, capital investment decisions and operating performance. In addition, as CEO of Endurance International Group and Convergys Corporation, Mr. Fox led the improvement in operating results, simplified strategic portfolios and prioritized the return of capital to shareholders. • Technology / Digital: Acquired through executive leadership roles at technology and technology-enabled businesses, including as CEO of Endurance International Group, a leading provider of technology platform solutions designed to help small and medium-sized businesses successfully execute digital transformation strategies. As CEO, Mr. Fox led the transformation of Endurance International Group’s multi brand portfolio into a successful organic growth platform, culminating in the company’s successful $3 billion sale to Clearlake Capital Group in 2021. EXPERIENCE: Circumference Group – An investment firm • CEO and Founder (2009-2010; since 2021) Endurance International Group Holding Inc. – A leading provider of cloud-based platform solutions for small and medium sized businesses (former Nasdaq: EIGI) • President and CEO (2017-2021) Convergys Corporation – A market-leading customer management company (former NYSE: CVG) • Chairman of the Board (2013-2018) • Executive Chairman (2012-2013) • President and CEO (2010-2012) Alltel Corporation – A major U.S. telecommunications provider (former NYSE: AT) • COO (2007-2009) • Group President, Shared Services (2003-2007) • Group President, Alltel Information Services (1996-2003) | | Jeffrey Fox | | | Class II Director (Independent) Age: 64 Director Since: 2026 Public Board Directorships: • Westrock Coffee Company (NASDAQ: WEST) (2020-Present) • Resources Connection, Inc. (NASDAQ: RGP) (2025-Present) Education: • Duke University: BA, Economics | |

  26. Introduction

    | 22 | PROXY STATEMENT - 2026 |

  27. Introduction

    | | KEY SKILLS AND EXPERTISE: Mr. Hartnett contributes extensive experience scaling and guiding online sports betting, entertainment and gaming businesses to achieve sustained long-term growth. His expertise working with globally reaching brands, along with history of delivering enhanced shareholder value, bolsters the Board’s oversight of the Company’s growth initiatives. • Strategic Planning / M&A: Acquired over a 20-year tenure in various leadership roles at an entertainment company, where he oversaw several successful strategic M&A initiatives, including the $770 million acquisition of FanDuel. • Technology / Digital: As CEO of a Blackstone-backed betting and gaming business, Mr. Hartnett was responsible for implementing innovative, digitally-focused growth initiatives. • Risk Management: Mr. Hartnett brings extensive gaming and entertainment company risk management expertise developed from his career leading operational teams in the highly regulated industry. EXPERIENCE: Superbet Group – Blackstone-backed betting and gaming company • Chief Executive Officer (2019-2024) Paddy Power Betfair – Dublin-based gambling company, part of Flutter Entertainment (NYSE: FLUT) • Chief Development Officer (2018-2019) • Managing Director, International (2016-2019), Online (2015-2016) • Chief Operating Officer (2014-2016), Sportsbet Australia, a Paddy Power affiliate company | | Johnny Hartnett | | | Class II Director (Independent) Age: 50 Director Since: 2025 Committees: • Compliance Education: • University College Dublin: Economics Degree | |

  28. Introduction

    | PROXY STATEMENT - 2026 | 23 |

  29. Introduction

    | | KEY SKILLS AND EXPERTISE: Mr. Ruisanchez is a proven, experienced executive with a long track record of leading strategic capital allocation decisions and growth initiatives. As the former President and CFO of Pinnacle Entertainment (which was purchased by PENN Entertainment), co-founder and partner of a family office focused on real estate development, a successful career in investment banking, as well as nearly a decade as a board member of public companies, Mr. Ruisanchez bolsters the Board’s oversight of capital structure management, risk mitigation and growth strategies. • Finance: Developed over his investment banking experience and service as President and CFO of a public company in the gaming industry, where he oversaw financial and administrative operations and all M&A activities. • Industry Experience: Mr. Ruisanchez brings deep expertise in the casino industry. At Pinnacle Entertainment, he led key expansion initiatives, including the acquisition of a leading multi-jurisdiction gaming operator, the development of several new casinos in various jurisdictions and the sale of Pinnacle to PENN Entertainment in 2018. Prior to that, he spent over a decade as an investment banker at Bear Stearns, advising corporate clients in the gaming, lodging and leisure industries. • Strategic Planning / M&A: As President and CFO of a public company in the gaming sector, his tenure focused on operational improvements, effective capital deployment and mergers & acquisitions. Mr. Ruisanchez was instrumental in driving shareholder value through transformative initiatives, including the acquisition of Ameristar and the sale-leaseback transactions with GLPI. EXPERIENCE: Sorelle Capital – A family office focused on real estate development, primarily in the multifamily and hospitality sectors • Founding Partner (since 2018) Pinnacle Entertainment – Leading gaming entertainment company (acquired by PENN in 2018) • President, CFO (2013-2018), CFO (2011-2013) • EVP, Strategic Planning and Development (2008-2011) Bear Stearns & Co. – Investment banking firm • Roles of increasing responsibility, including Senior Managing Director (1997-2008) | | Carlos Ruisanchez | | | Class II Director (Independent) Age: 55 Director Since: 2025 Committees: • Compliance Public Board Directorships: • Southwest Gas Holdings (NYSE: SWX) (since 2022) • Cedar Fair Entertainment Company (NYSE: FUN) (2019-2024) • Pinnacle Entertainment, Inc. (NASDAQ: PNK) (2016-2018) Education: • University of Connecticut School of Business: BS, Finance • University of California, Berkeley, Haas School of Business: MBA | |

  30. Introduction

    | 24 | PROXY STATEMENT - 2026 |

  31. Compensation Committee

    | • | Recommending director compensation to the Board; and |

  32. Review and Approval of Transactions with Related Persons

    | DIRECTOR COMPENSATION |

  33. Non-Employee Director Compensation

    Non-Employee Director Compensation The Company pays fees to each director who is not an employee of the Company. During the year ended December 31, 2025, the annual compensation for each non-employee director consisted of an annual retainer of $70,000, plus an additional $10,000 for service on each of the Audit Committee, the Compensation Committee and the Compliance Committee, as applicable, and $5,000 for service on the Nominating and Corporate Governance Committee. The Chair of the Audit Committee receives an additional $15,000 annual retainer, and the Chairs of the Compensation Committee and the Nominating and Corporate Governance Committee each receive a supplemental $10,000 annual retainer. For 2025, each non-employee director had the opportunity to elect to receive his or her annual retainer in the form of either cash or shares of restricted stock, with forfeiture restrictions for restricted stock lapsing on the first anniversary of the date of grant. In 2025, each non-employee director other than the Board Chair received a grant of cash settled restricted stock units or restricted stock at his or her election with a grant value of $250,000, and the Board Chair received a grant of restricted stock with a grant value of $375,000. Each award of cash settled restricted stock units or shares of restricted stock vests on the first anniversary of the date of grant. Beginning in 2026, the Board and Compensation Committee determined that the annual equity grant made to all non-employee directors will be comprised solely of shares of restricted stock, as opposed to the historical practice of allowing directors to elect to receive either shares of restricted stock or cash-settled restricted stock units. Director Stock Ownership Guidelines. We believe that equity ownership supports the alignment of director interests with those of the Company’s shareholders. To this end, the Compensation Committee has established stock ownership guidelines which provide that each non-employee director should own shares with a value equal to at least five times the current annual cash retainer amount, within five years from the date they joined the Board. All of our non-employee directors either currently meet our director stock ownership guidelines or we expect that they will meet the guidelines within five years of becoming a director. The Company’s Chief Legal Officer monitors compliance with these guidelines on an annual basis and apprises the Compensation Committee no less than annually regarding the same.

  34. 2025 Director Compensation Table

    2025 Director Compensation Table The following table sets forth information with respect to all compensation awarded to the Company’s non-employee directors for 2025.

  35. 2025 Director Compensation Table

    | NAME | FEES EARNED OR PAID IN CASH ($)(1) | STOCK AWARDS ($)(2) (3) | TOTAL ($) | | Vimla Black-Gupta | 90,425 | 250,005 | 340,430 | | Anuj Dhanda | 81,890 | 250,005 | 331,895 | | David Handler | 80,849 | 375,007 | 455,856 | | Johnny Hartnett(4) | 43,397 | 249,993 | 293,390 | | Marla Kaplowitz | 100,425 | 250,005 | 350,430 | | Barbara Shattuck Kohn(5) | 100,000 | 250,005 | 350,005 | | Ronald Naples(6) | 85,000 | 250,005 | 335,005 | | Saul Reibstein(5) | 90,000 | 250,005 | 340,005 | | Carlos Ruisanchez(4) | 43,397 | 249,993 | 293,390 | | Jane Scaccetti | 110,425 | 250,005 | 360,430 |

  36. 2025 Director Compensation Table

    | (1) In 2025, each non-employee director could elect to receive his or her retainer fees in cash or shares of restricted stock, which vest on the first anniversary of the date of grant. This column reflects director compensation eligible to be paid in cash, which consists of the annual Board retainer and any applicable fees for committee members and committee chairs. None of the directors elected to receive restricted stock in lieu of such amounts eligible to be paid in cash. |

  37. 2025 Director Compensation Table

    | (2) As of December 31, 2025, the following stock awards were outstanding: (i) for Ms. Black-Gupta 12,994 cash settled restricted stock units; (ii) for Mr. Dhanda 12,994 cash settled restricted stock units; (iii) for Mr. Handler, 19,491 shares of restricted stock; (iv) for Mr. Hartnett, 14,775 cash settled restricted stock units; (v) for Ms. Kaplowitz, 12,994 cash settled restricted stock units; (vi) for Ms. Shattuck Kohn, 12,994 cash settled restricted stock units; (vii) for Mr. Naples, 12,994 cash settled restricted stock units; (viii) for Mr. Reibstein, 12,994 cash settled restricted stock units; (ix) for Mr. Ruisanchez, 14,775 shares of restricted stock; and (x) for Ms. Scaccetti 12,994 shares of restricted stock. |

  38. 2025 Director Compensation Table

    | (3) Reflects the aggregate grant date fair value of stock awards granted in 2025. The listed amounts were determined using the closing price of PENN's common stock on the day prior to the grant date, calculated in accordance with FASB ASC Topic 718. |

  39. 2025 Director Compensation Table

    | (4) Messrs. Hartnett and Ruisanchez were appointed to the Board in June 2025, and therefore their retainer fees were pro-rated. |

  40. 2025 Director Compensation Table

    | (5) Ms. Shattuck Kohn and Mr. Reibstein did not stand for re-election at the 2025 Annual Meeting. The Board determined to pay Ms. Shattuck Kohn and Mr. Reibstein their respective 2025 cash retainers through December 31, 2025 in consideration of their service as directors emeriti through January 3, 2026. |

  41. 2025 Director Compensation Table

    | (6) Mr. Naples resigned from the Board in April 2025 and the Board determined to pay Mr. Naples his 2025 cash retainer through December 31, 2025 in consideration of his service as director emeritus through January 3, 2026. |

  42. 2025 Director Compensation Table

    | 44 | PROXY STATEMENT - 2026 |

  43. 2025 Director Compensation Table

    | EXECUTIVE OFFICERS |

  44. 2025 Director Compensation Table

    Set forth below is certain information regarding each of our executive officers, other than Mr. Snowden, whose biographical information is presented under “Proposal 1: Election of Class III Directors—Continuing Directors.”

  45. 2025 Director Compensation Table

    | NAME | AGE(1) | POSITION | | Jay Snowden | 50 | Chief Executive Officer, President and Director | | Felicia Hendrix | 57 | Executive Vice President, Chief Financial Officer | | Chris Rogers | 50 | Executive Vice President, Chief Strategy and Legal Officer and Secretary | | Todd George | 56 | Executive Vice President, Operations |

  46. 2025 Director Compensation Table

    | (1) Ages as of our 2026 Annual Meeting. |

  47. 2025 Director Compensation Table

    Felicia Hendrix has served as our Chief Financial Officer and Executive Vice President since March 2021, and Principal Accounting Officer since February 25, 2024. Ms. Hendrix oversees Accounting, Finance, Internal Audit, and Procurement. Prior to joining PENN, Ms. Hendrix spent 25 years on Wall Street and was most recently a Managing Director and Equity Research Analyst at Barclays, covering the gaming, lodging and leisure industries. Before joining Barclays, Ms. Hendrix was a Managing Director at Lehman Brothers. Ms. Hendrix holds a bachelor's degree from the University of Virginia and an MBA from the Darden School of Business at the University of Virginia. Chris Rogers has served as our Executive Vice President, Chief Strategy Officer since January 2020 and Executive Vice President, Chief Strategy and Legal Officer and Secretary since June 2024. In his capacity as Chief Strategy and Legal Officer, Mr. Rogers leads the team responsible for developing and pursuing PENN's strategic growth initiatives and oversees the Company’s legal department. Over his past ten years with PENN, Mr. Rogers also served as Senior Vice President, Corporate Development, and Vice President, Deputy General Counsel. Prior to joining PENN, Mr. Rogers was a corporate attorney at the Dallas-based law firm Vinson & Elkins and the Boston-based law firm Ropes & Gray, as well as a CPA for PricewaterhouseCoopers and Arthur Andersen. Mr. Rogers holds a Bachelor of Business Administration from the University of Oklahoma's Price College of Business and a J.D. from Harvard Law School. Todd George served as our Executive Vice President, Operations from January 2020 until January 5, 2026 and thereafter served in an advisory capacity from January 5 to February 28, 2026. In his former role, Mr. George oversaw PENN's Regional Operations, Interactive, Marketing and Information Technology, as well as Design and Construction. In 2025, Mr. George served a critical role in the execution of our omnichannel strategy, including our efforts to use our expanded digital database to drive increased visitation to our casinos. Prior to his role as EVP, Operations, Mr. George served as Vice President and General Manager of Hollywood Casino in Lawrenceburg, Indiana, and Hollywood Casino St. Louis. In 2017, Mr. George was promoted to Senior Vice President, Regional Operations, overseeing nine properties in PENN's Midwest Region. Prior to PENN, Mr. George spent 12 years in various management positions at Pinnacle Entertainment, including leading the development and launch of Pinnacle's two St. Louis properties, River City Casino and Lumiere Place. Mr. George holds a bachelor's degree from LeMoyne College and an MBA from Villanova University.

  48. 2025 Director Compensation Table

    | PROXY STATEMENT - 2026 | 45 |

  49. 2025 Director Compensation Table

    The following table sets forth certain information regarding the beneficial ownership of the Company’s common stock, as of the Record Date of this proxy statement. This table lists: (i) each person known to us to beneficially own more than 5% of any class of the outstanding voting securities of the Company, (ii) each of our directors, (iii) each of our named executive officers listed in the table entitled “2025 Summary Compensation Table” below, and (iv) all of our current directors and executive officers as a group. Beneficial ownership of shares is determined under rules of the SEC and generally includes any shares over which a person exercises sole or shared voting or investment power. Except as noted by footnote, and subject to community property laws where applicable, we believe based on the information provided to us that the persons and entities named in the table below have sole voting and investment power with respect to all shares of our common stock shown as beneficially owned by them. Unless otherwise noted below, the address of the persons listed in the table is c/o PENN Entertainment, Inc., 825 Berkshire Blvd., Suite 200, Wyomissing, PA 19610. The percentages shown in this table are calculated based on 133,705,284 shares of our common stock outstanding as of the Record Date of this proxy statement.

  50. 2025 Director Compensation Table

    | 5% SHAREHOLDERS, OFFICERS AND DIRECTORS | NUMBER OF SHARES BENEFICIALLY OWNED | PERCENTAGE OF COMMON STOCK (%) | | Beneficial Owners of 5% or more of our common stock: | | | | BlackRock, Inc.(1) | 17,659,980 | 13.2 | | The Vanguard Group, Inc.(2) | 16,496,265 | 12.3 | | Named Executive Officers and Directors: | | | | Heather Ace | 17,077 | 0.01 | | Vimla Black-Gupta | 41,835 | 0.03 | | Anuj Dhanda | 48,358 | 0.04 | | Jeffrey Fox | 17,077 | 0.01 | | David Handler(3) | 408,194 | 0.31 | | Johnny Hartnett | 16,835 | 0.01 | | Marla Kaplowitz | 43,038 | 0.03 | | Carlos Ruisanchez(4) | 34,760 | 0.03 | | Jane Scaccetti | 109,153 | 0.08 | | Fabio Schiavolin | 17,077 | 0.01 | | Jay Snowden(6) | 2,873,931 | 2.15 | | Felicia Hendrix(6) | 359,533 | 0.27 | | Todd George(5),(6) | 414,661 | 0.31 | | Chris Rogers(6) | 343,069 | 0.26 | | All current executive officers and directors as a group (13 persons) | 4,329,937 | 3.24 |

  51. 2025 Director Compensation Table

    | (1) Based on its Schedule 13G/A filed with the SEC on October 18, 2024, the number of shares in the table includes shares beneficially owned as of September 30, 2024, by BlackRock, Inc. and its listed affiliates. BlackRock, Inc. has sole voting power over 17,102,228 shares, shared voting power over 0 shares, sole dispositive power over 17,659,980 shares and shared dispositive power over 0 shares. The address of BlackRock, Inc. is 50 Hudson Yards, New York, New York 10001. |

  52. 2025 Director Compensation Table

    | (2) Based on its Schedule 13G/A filed with the SEC on July 10, 2024, the number of shares in the table includes shares beneficially owned as of June 28, 2024, by The Vanguard Group, Inc. and its listed affiliates. As of June 28, 2024, The Vanguard Group, Inc. had sole voting power over 0 shares, shared voting power over 48,331 shares, sole dispositive power over 16,301,637 shares and shared dispositive power over 194,628 shares. According to the most recent Schedule 13G/A filed by The Vanguard Group, Inc. with the SEC on March 27, 2026, The Vanguard Group, Inc. beneficially owns 0.0% as of March 13, 2026, following an internal reorganization pursuant to which The Vanguard Group, Inc.’s beneficial ownership has been disaggregated. The address of Vanguard Group, Inc. is 100 Vanguard Blvd., Malvern, Pennsylvania 19355. |

  53. 2025 Director Compensation Table

    | (3) The number of shares reported includes 20,000 shares held by a charitable foundation for which Mr. Handler has discretionary control. |

  54. 2025 Director Compensation Table

    | (4) The number of shares reported includes 1,950 shares indirectly held by Mr. Ruisanchez in a trust. |

  55. 2025 Director Compensation Table

    | (5) The number of shares reported for Mr. George is as of February 27, 2026. |

  56. 2025 Director Compensation Table

    | (6) The number of shares in the table includes shares that may be acquired upon the exercise of outstanding options or options that may be exercised within 60 days from the Record Date, as follows: (i) Mr. Snowden: 1,925,401; (ii) Ms. Hendrix, 177,177; (iii) Mr. George: 319,089; (iv) Mr. Rogers: 193,635; and (v) all current executive officers and directors as a group: 2,615,302 shares. |

  57. 2025 Director Compensation Table

    | 46 | PROXY STATEMENT - 2026 |

  58. Positioned for Long-Term Value Creation

    Positioned for Long-Term Value Creation The achieved gains in return on invested capital, cash flow and margin quality in 2025 resulted from disciplined execution against our strategic priorities. We bolstered our Interactive positioning through brand unification and operational improvements, while our Retail portfolio continued to deliver resilient performance and meaningful growth from recent capital investments. To sustain this momentum, in early 2026 we implemented a new corporate structure aligned with our refreshed strategic priorities, allowing us to be a leaner and flatter organization while enabling business leaders to be more empowered to drive greater productivity and more effective execution across the enterprise. As we enter 2026, we remain focused on:

  59. Positioned for Long-Term Value Creation

    | • | Driving free cash flow growth; |

  60. Positioned for Long-Term Value Creation

    | • | Maximizing the value of our extensive retail footprint; |

  61. Positioned for Long-Term Value Creation

    | • | Executing on our realigned digital strategy, including accelerating our iCasino growth; |

  62. Positioned for Long-Term Value Creation

    | • | Strategically expanding our digital product capabilities; and |

  63. Positioned for Long-Term Value Creation

    | • | Creating long-term value for our shareholders, inclusive of disciplined capital allocation decisions across our business |

  64. Positioned for Long-Term Value Creation

    In connection with this strategic realignment and following the 2025 ‘Say-on-Pay’ vote outcome, we also conducted an in-depth, rigorous review of our executive compensation program, as further described in this Compensation Discussion and Analysis section. The changes that resulted from this review are designed to ensure that our incentive structure appropriately rewards strategic progress and optimizes alignment between pay and performance, one of the key messages we heard from our shareholders throughout both our in-season and off-season engagement discussions. We believe the actions taken in 2025 and into 2026 have enhanced our competitive positioning and organizational alignment, establishing a stronger foundation for sustainable earnings growth and long-term shareholder value creation.

  65. Positioned for Long-Term Value Creation

    | PROXY STATEMENT - 2026 | 55 |

  66. 2025 Key Executive Compensation Actions

    | Enhanced 2025 Long-Term Incentive Plan (LTIP) Design | The 2025 LTIP reflects a significant evolution of our incentive plan design to more closely align with market practice and shareholder feedback: • Maintained the three-year cumulative performance period initially implemented with the 2024 PSU program, which replaced the prior annual goal-setting framework, to better align with shareholder expectations for enhanced long-term performance focus. • Increased weighting of financial performance metrics to 80% from 70%, enhancing accountability for long-term financial results. The remaining 20% focused on strategic operational metrics designed to advance our omnichannel growth strategy and expand our customer database. • Aligned equity compensation mix with peer practices by incorporating restricted stock units (“RSUs”) into the LTIP structure. Consistent with peer group practices, and in response to feedback from several of our shareholders, the Committee allocated 25% of the long-term incentives for our CEO and other NEOs to RSUs, 50% to PSUs and 25% to stock options. The Committee believes this equity incentive structure continues to maintain a substantial at-risk, performance-based component and supports stronger alignment of the equity mix with shareholder priorities. | | Strengthened Governance and Responsiveness to Our Shareholders | Following the 2025 ‘Say-on-Pay’ vote outcome, and in direct response to shareholder feedback, the Board and Committee implemented several actions to bring fresh perspectives to its deliberations and enhanced oversight of the compensation program: • Refreshed the Committee leadership and composition by appointing a new Compensation Committee Chair and evolved membership to introduce additional viewpoints and strengthen independent oversight of the executive compensation program design. • Engaged a new independent compensation consultant, Semler Brossy Consulting Group, LLC (“Semler Brossy”), to provide fresh external perspectives and expertise on leading compensation governance practices, support a rigorous review of the executive compensation program and assist in the development of responsive actions to fully address shareholder feedback. | | Responded to our Shareholder Feedback Through Changes to 2026 Compensation Program | Since most decisions related to the 2025 compensation program were made before the 2025 Annual Meeting and associated off-season shareholder engagement, the Committee incorporated investor feedback into a series of responsiveness actions approved for the 2026 compensation program, including: • Refreshed the 2026 compensation peer group by removing five digital and entertainment companies and adding six additional casino, gaming and/or hospitality companies to more closely reflect the Company’s relative size and the realignment of our strategic focus. • Lowered the target grant value of the CEO’s 2026 equity awards by $7.87 million, equivalent to a 41% reduction in LTIP opportunity and 31% reduction in total target direct compensation compared to 2025, effectively resetting total target CEO pay to 2023 levels. This decision followed the peer group update and strategic digital realignment described above and was made with the support and agreement of CEO Jay Snowden and in consultation with the Committee’s independent compensation consultant. The CEO’s base salary and STIP opportunity have remained unchanged since 2021. In addition, in light of the refreshed 2026 peer group changes, which positioned NEO target pay above the peer group median, and the Company’s 2025 performance results, the Committee affirmed that there will be no target pay increases for the other NEOs for fiscal 2026. • Committed to not adjust in-progress 2024 and 2025 performance metrics or targets: In connection with the digital strategy realignment, the Committee has determined that no adjustments will be made to in-progress 2024 and 2025 PSUs, including the ESPN BET market share metric, to ensure pay outcomes align with shareholder experience and Company performance. • Re-evaluated and updated LTIP design to better reflect our realigned digital strategy and streamline performance measures by eliminating duplicative metrics: Beginning with the 2026-2028 performance cycle, the PSU grant will be tied to the achievement of a cash flow from operations goal, with a relative TSR payout modifier (±20% ) measured against the Russell 3000 Casino and Gambling Index. This incentive structure is designed to drive cash generation across our retail and digital operations, support disciplined capital allocation and better align our long-term financial performance with shareholder interests. These LTIP changes also address our shareholders’ preference for diversified metrics across short- and long-term incentive plans. |

  67. Paying for Performance

    Paying for Performance Annual and long-term incentive payouts aligned with shareholder experience. We believe our 2025 short- and long-term incentive payouts of ~66.3% and 74.75% of target, respectively, are directly aligned with our financial and operational performance results and reflect shareholder experience over the same period, underscoring the rigor of the performance hurdles built into our incentive plans and reinforcing our commitment to robust management accountability. The substantial majority of CEO and NEO executive compensation, 93% and 85%, respectively, is performance-based and at-risk, with actual outcomes based on pre-set financial and strategic objectives.

  68. Paying for Performance

    | * Payout percentage does not include the first tranche earned for the 2023 performance period, following the transition of the PSUs program to a three-year performance cycle. As disclosed in last year’s proxy statement, in connection with the transition to a full three-year long-term performance cycle beginning with the 2024 PSU awards, the Compensation Committee approved a cumulative two-year performance period for the unvested portion of the 2023 PSUs. |

  69. Paying for Performance

    | * Realizable pay: Calculated as a sum of actual cash paid, value of vested equity as of applicable vesting date and value of unvested equity awards valued at $14.77 stock price as of April 1, 2026, with unvested PSU awards valued at target payout level. Target pay: Calculated as a sum of base salary, target annual short-term incentive opportunity and all long-term incentive awards issued during 2021-2025, with PSUs valued at target. |

  70. November 2025 – February 2026: Off-Season Shareholder Engagement (cont.)

    | WHAT WE HEARD | HOW WE RESPONDED | | Peer Group Relevance Many shareholders focused on the Company’s go-forward strategy and alignment of the compensation program with strategic outcomes | Updated the compensation peer group for the 2026 compensation cycle • As a foundational component of the executive compensation program, conducted a comprehensive review of the compensation peer group: As part of its in-depth assessment of the executive compensation program following the Company’s strategic digital realignment, the Committee, with the support of its new independent compensation consultant, oversaw a significant update to the Company’s compensation peer group. The new peer group was developed using a refreshed selection framework that reflects the Company’s realigned business focus and growth priorities, current size and market dynamics. Finalized in the fourth quarter of 2025, in part in response to the 2025 “Say-on-Pay” vote outcome, the updated compensation peer group informed the Committee’s compensation decisions for 2026. Additional details on the compensation peer group changes can be found on page 63 of this proxy statement. • Shifted peer group composition toward more relevant industry peers: The 2026 compensation peer group places a greater emphasis on casino, gaming and hospitality companies in replacement of digital and entertainment companies to better reflect PENN’s new strategic focus areas. The compensation peer group changes more closely align PENN with its closest similarly-sized competitors with comparable geographic footprints, reinforcing alignment with performance and go-forward strategy. | | CEO Target Pay Level Many shareholders expressed concern about year-over-year increases in the CEO target pay approved for 2024 and continued in 2025, which was perceived as misaligned with recent performance | Substantially reduced 2026 CEO target pay • Lowered the target grant value of the CEO’s 2026 equity awards by $7.87 million, equivalent to a 41% reduction in LTIP opportunity and 31% reduction in total target direct compensation compared to 2025, effectively resetting total target CEO pay to 2023 levels: This decision followed the peer group update and strategic digital realignment described above and was made with the support and agreement of CEO Jay Snowden and in consultation with the Committee’s independent compensation consultant. The CEO’s base salary and STIP opportunity have remained unchanged since 2021. • CEO annualized realizable pay represented 42.5% of target annual pay: Over the past five years, Mr. Snowden’s realizable pay on an annualized basis represented only 42.5% of his reported pay. Nevertheless, the Committee determined to reduce Mr. Snowden’s LTIP opportunity for 2026 as described above. |

  71. November 2025 – February 2026: Off-Season Shareholder Engagement (cont.)

    | WHAT WE HEARD | HOW WE RESPONDED | | Pay and Performance Alignment Many shareholders emphasized the importance of aligning pay opportunities and incentive outcomes with strategic direction and long-term value creation | Ensured 2025 incentive plan payouts aligned with shareholder experience • Delivered performance-aligned incentive payouts: 2025 STIP payouts and the remaining portion of the 2023 PSUs associated with the 2024-2025 performance cycle paid out at ~66.3% and 74.75% of target, respectively, reflecting rigorous performance goals and clear accountability for results. The cumulative payout under the 2023 PSUs (for the 2023 – 2025 period) resulted in 85.85% achievement of the target performance level. This included the first tranche earned for the 2023 performance period, with earned shares that remained subject to continued service vesting through the end of the full 2023–2025 performance cycle, and the final tranche earned based on performance over the 2024–2025 performance period. The payout represented 39.56% of the initial target grant value on the vest day after considering the change in market value of the Company’s common stock since the grant date. • Committed to not adjust in-progress 2024 and 2025 performance metrics or targets: In connection with the digital strategy realignment, the Committee has determined that no adjustments will be made to in-progress 2024 and 2025 PSUs, including the ESPN BET market share metric, which will be measured at 0% achievement, to ensure pay outcomes align with shareholder experience and Company performance. • All stock options issued over the last five-year period remain underwater: All stock options granted to our executives since 2020 are underwater as of the Record Date, underscoring the performance-based nature of our program and strong alignment with shareholder returns. Shareholder-aligned 2026 compensation levels • No 2026 target compensation increases for NEOs: In light of the 2026 peer group changes, which resulted in NEO target pay above the new peer group median, and the Company’s 2025 performance, the Committee affirmed that there will be no target pay increases for the other NEOs for fiscal 2026. | | Performance Metrics Selection and Rigor Several shareholders expressed a preference for differentiated performance metrics across the STIP and LTIP, with a preference for financial metrics, along with a better explanation of performance metric selection and rigor with strategic outcomes | Redesigned 2026 PSU program to reflect realigned strategic priorities and enhanced disclosures on performance metric selection and rigor • Streamlined performance measures by eliminating duplicative metrics: Beginning with the 2026-2028 performance cycle, PSUs will be tied to the achievement of a cash flow from operations goal, with a relative TSR payout modifier (±20% ) measured against the Russell 3000 Casino and Gambling Index. This incentive structure is designed to drive cash generation across our retail and digital operations, support disciplined capital allocation and ensure long-term financial performance is aligned with shareholder interests. We believe this is directly responsive to shareholder preferences for stronger performance-alignment in our pay program and diversified performance metrics across STIP and LTIP programs. This revised LTIP structure also incorporates a downside safeguard, such that no upward TSR modifier will apply if three-year absolute TSR is negative. • Enhanced transparency around performance metrics selection and rigor: The Committee expanded disclosure regarding its process for setting rigorous incentive goals, with additional detail provided on page 61 of this proxy statement. |

  72. Compensation Framework

    Compensation Framework The primary components of our executive compensation program are base salary, short-term incentive compensation (cash bonus plan) and long-term equity incentive compensation (RSUs, PSUs and stock options). The components of our 2025 executive compensation program are described in more detail below.

  73. Compensation Framework

    | | COMPONENT | CEO* | OTHER NEOS* | KEY CHARACTERISTICS | 2025 PERFORMANCE METRICS | | FIXED PAY | Base Salary | | | • Fixed cash compensation designed to provide executives with market-competitive pay for their day-to-day responsibilities, based on their role, individual performance, experience, expertise and qualifications | N/A | | VARIABLE PAY | SHORT-TERM INCENTIVE PROGRAM (“STIP”) | | | | | | | STIP | | | • Cash compensation tied to the achievement of a rigorous pre-set quantitative performance goal • Intended to drive near-term results that are aligned with our long-term growth strategy | Adjusted EBITDAR (100%) (consolidated results from the Company’s Retail and Interactive segments and Other (including Corporate Overhead) | | | LONG-TERM INCENTIVE PROGRAM (“LTIP”) | | | | | | | PSUs 50% of Total LTIP | | | • Equity incentive designed to motivate achievement of robust pre-determined performance goals over a three-year performance period and drive long-term shareholder value • Performance metrics reflect key drivers of our long-term growth, including both financial and operational objectives related to the advancement of our omnichannel growth strategy • Promote an ownership mentality, and motivate long-term shareholder value creation | Financial Metrics (80%) • Retail Adj. EBITDAR (60%) • Interactive Adj. EBITDA (20%) Operational Metrics (20%) • Database growth (10%) • Omnichannel play (10%) | | | RSUs 25% of Total LTIP | | | • Vest ratably over a three-year period to encourage long-term retention, reflect peer group practices and strengthen the resiliency of our compensation program | RSUs are subject to continued employment through the applicable vesting date to promote retention | | | Stock Options 25% of Total LTIP | | | • Equity incentives motivate executives to build long-term shareholder value • Vest ratably over a three-year period to encourage long-term retention | Stock options only deliver value to executives to the degree our stock price appreciates after the grant date, fostering a strong alignment with shareholder value creation and motivating sustained, long-term outperformance |

  74. Executive Compensation Peer Group

    Executive Compensation Peer Group

  75. 2025 Compensation Peer Group

    2025 Compensation Peer Group To ensure total direct compensation for our executives remains competitive, the Committee annually reviews benchmark data for our compensation peer group, with companies selected based on data analysis prepared by the Committee’s independent compensation consultant. Consistent with the objectives of our executive compensation program, the Committee compares NEO compensation to the median compensation opportunities within the compensation peer group to support our ability to attract and retain highly qualified executive talent. With the assistance of its independent consultant, the Committee also evaluates the compensation peer group each year to determine whether updates are warranted. At the end of 2024, the Committee reviewed the input of its independent compensation consultant, Exequity, and approved the compensation peer group of 12 companies as listed in the table below. The compensation peer group remained unchanged from the prior year and was used to set target compensation levels for our NEOs for 2025.

  76. 2025 Compensation Peer Group

    | 2025 COMPENSATION PEER GROUP | | | Boyd Gaming Corporation | Live Nation Entertainment, Inc. | | Caesars Entertainment, Inc. | MGM Resorts International | | DraftKings, Inc. | Red Rock Resorts, Inc. | | Electronic Arts, Inc. | Roku, Inc. | | Las Vegas Sands Corp. | Sirius XM Holdings, Inc. | | Lions Gate Entertainment Corporation | Wynn Resorts, Ltd. |

  77. 2025 Compensation Peer Group

    This compensation peer group encompassed gaming, online and digital entertainment companies, reflecting PENN’s operational complexity and growth strategy at the time of the peer group review and approval. These peer companies were selected based on similarity of their business models, market capitalization and annual revenues, and their relevance as competitors for executive talent. When the Committee reviewed the compensation peer group in October 2024, the Company ranked at the 44th percentile of this peer set based on annual revenue.

  78. 2026 Compensation Peer Group

    2026 Compensation Peer Group As part of its in-depth assessment of the executive compensation program following the Company’s strategic realignment, the Committee, with the support of its new independent compensation consultant, oversaw a significant update to the Company’s compensation peer group. This action also considered shareholder feedback received following the 2025 ‘Say-on-Pay’ vote outcome. For fiscal 2026, the Committee approved several changes to the compensation peer group composition, including the removal of five digital and entertainment companies and the addition of six casino, gaming and/or hospitality peers. These adjustments reflect a deliberate shift toward companies whose business models, revenue mix and competitive dynamics more closely mirror the Company’s go-forward strategic direction. The Committee believes the revised compensation peer group better reflects the Company’s realigned strategic focus areas, improves the relevance of competitive benchmarking and provides a more accurate representation of the Company’s closest operational and talent competitors.

  79. 2026 Compensation Peer Group

    | FISCAL 2026 COMPENSATION PEER GROUP | | | | | | | | REMOVED | Digital and Entertainment Companies Removed | | ADDED | Casinos, Gaming and/or Hospitality Companies Added | | Electronic Arts, Inc. Lions Gate Entertainment Corporation Live Nation Entertainment, Inc. Roku, Inc. Sirius XM Holdings, Inc. | | | Churchill Downs, Inc. Hilton Worldwide Holdings, Inc. Hyatt Hotels Corporation Light & Wonder, Inc. Norwegian Cruise Line Holdings Ltd. Royal Caribbean Cruises Ltd. | | |

  80. 2026 Compensation Peer Group

    | 64 | PROXY STATEMENT - 2026 |

  81. Base Salary

    | • | The median salaries of similarly situated, comparable executives in our compensation peer group; and |

  82. Annual Short-Term Incentive Plan

    Annual Short-Term Incentive Plan Our NEOs are eligible to participate in the STIP, which is designed to motivate achievement of near-term performance objectives that support the Company’s long-term success and ability to create sustained shareholder value. The STIP payout opportunities are based on performance against pre-established corporate performance objective(s), with actual STIP bonuses earned based on the achievement of such performance objective(s) each fiscal year. The Committee sets the range of the STIP opportunity payable to each executive as a percentage of annual base salary, consistent with compensation peer group practices, with reference to the compensation peer group median target bonus levels. If actual performance falls between threshold and target, or between target and maximum, payouts are determined by linear interpolation between threshold and target or target and maximum level of achievement, as applicable.

  83. 2025 STIP Awards

    2025 STIP Awards For 2025, the Committee maintained all target STIP opportunities for NEOs from 2024, with no increases. Our CEO’s annual STIP opportunity has remained the same since 2021. The Committee approved Adjusted EBITDAR as the performance metric for the 2025 STIP, defined as the consolidated results for the Company’s Retail, Interactive and Other (including Corporate Overhead). The Committee determined that Adjusted EBITDAR is an objective and quantifiable measurement of the Company’s financial performance, balancing a forward-looking approach to executing on our strategic initiatives with a disciplined approach to supporting our long-term growth priorities. To ensure the Adjusted EBITDAR goal for the 2025 STIP reflected appropriate rigor, the Committee conducted a comprehensive review of both internal and external considerations. Specifically, the Committee evaluated the Company’s 2025 operating plan, projected market conditions, expected progress against our long-term growth strategy, and perspectives gathered from analysts and shareholders. This review was designed to ensure that the Adjusted EBITDAR goal established for the year was both grounded in the Company’s financial outlook and aligned with shareholder expectations for disciplined target setting. Following this analysis, the Committee approved the threshold, target, and maximum performance levels for Adjusted EBITDAR. The target goal was set 12% above the prior year’s target and 26% above the actual result achieved in 2024, reflecting the Company’s approved operating plan and public financial guidance for the year. Threshold and maximum performance levels were informed by sensitivity analyses around the Company’s operating plan, which was approved by the Committee and the Board. The threshold level reflected performance at the lower end of the anticipated range, while the maximum level required a significant degree of outperformance relative to the operating plan and public financial guidance. The Committee believes the maximum goal appropriately represented stretch performance that would require exceptional execution by the management team to achieve.

  84. 2025 STIP Awards

    | 2025 STIP PERFORMANCE METRIC | THRESHOLD 50% OF TARGET PAYOUT | TARGET 100% OF TARGET PAYOUT | MAXIMUM 200% OF TARGET PAYOUT | ACHIEVEMENT ($) | ACHIEVEMENT (% of Target) | PAYOUT (% of Target) | | Adjusted EBITDAR | $1,382M | $1,626M | $1,869M | $1,461.8M | 89.9% | ~66.3% |

  85. 2025 STIP Awards

    | 66 | PROXY STATEMENT - 2026 |

  86. 2025 STIP Awards (cont.)

    2025 STIP Awards (cont.) During the first quarter of 2026, the Committee certified the Adjusted EBITDAR achievement level and associated STIP payouts for 2025, and the Board approved the CEO’s STIP award following the Committee’s recommendation, as set forth below:

  87. 2025 STIP Awards (cont.)

    | NAMED EXECUTIVE OFFICER | BASE SALARY | 2025 ANNUAL INCENTIVE OPPORTUNITY (% of Base Salary) | TARGET STIP OPPORTUNITY | PAYOUT (% of Target) | ACTUAL 2025 ANNUAL INCENTIVE PAYOUT | | Jay Snowden | $1,800,000 | 250% | $4,500,000 | 66.3% | $2,984,400 | | Felicia Hendrix | $927,000 | 125% | $1,158,750 | 66.3% | $768,638 | | Chris Rogers | $824,000 | 125% | $1,030,000 | 66.3% | $683,233 | | Todd George | $1,030,000 | 125% | $1,287,500 | 66.3% | $854,042 |

  88. Long-Term Incentive Program

    Long-Term Incentive Program We maintain the LTIP for our executives to encourage an ownership mindset and incentivize long-term shareholder value creation. The LTIP is delivered through a combination of performance- and time- based equity awards, designed to drive progress toward our strategic and operational priorities, which are critical for the Company’s ability to create long-term shareholder value. Both performance- and time-based awards vest over a three-year period to incentivize executives to generate sustained value creation by successfully executing a range of financial and strategic initiatives that advance our long-term growth priorities.

  89. 2025 LTIP Awards

    2025 LTIP Awards For 2025, the Committee approved an LTIP mix for our NEOs consisting of 50% PSUs, 25% stock options, and 25% RSUs. The Committee determined that the addition of RSUs strengthens the overall balance of the LTIP design, aligns it with peer practices, and reflects the preference of some shareholders to incorporate service-based awards into the LTIP to support the resiliency of the incentive structure. Under the 2025 LTIP, target opportunities for our NEOs remained predominantly performance-based, with 50% allocated to PSUs that vest only upon achievement of rigorous performance goals, and 25% allocated to stock options that deliver value only if our stock price appreciates from the grant date. We believe this performance-based mix reinforces alignment with shareholder interests and supports the Company’s long-term value-creation strategy.

  90. 2025 LTIP Awards

    | NAMED EXECUTIVE OFFICER | 2025 TARGET LTIP AWARD VALUE | PSUs (TARGET VALUE) | STOCK OPTIONS | RSUs | | Jay Snowden | $19,000,000 | $9,500,000 | $4,750,000 | $4,750,000 | | Felicia Hendrix | $3,708,000 | $1,854,000 | $927,000 | $927,000 | | Chris Rogers | $3,296,000 | $1,648,000 | $824,000 | $824,000 | | Todd George | $5,150,000 | $2,575,000 | $1,287,500 | $1,287,500 |

  91. 2025 LTIP Awards

    | PROXY STATEMENT - 2026 | 67 |

  92. 2025 Performance Stock Units

    2025 Performance Stock Units To further reinforce accountability for long-term financial performance and reflect shareholder preferences, the Committee maintained a three-year cumulative performance period for the 2025 PSU awards. The Committee also increased the weighting of the financial metric to 80% (up from 70% in 2024), with the remaining 20% allocated to two strategic operational metrics (reduced from three in 2024). The Committee believes this structure places greater emphasis on financial outcomes while maintaining focus on key operational priorities. Performance for the 2025 PSUs will be assessed at the end of the full three-year period (December 31, 2027), without interim PSU vesting opportunities. The actual number of shares earned may range between 0% to 200% of target, based on the Company’s performance from 2025 - 2027 against the goals set forth below, subject to continued employment through the applicable vesting date. If performance falls between threshold and target or between target and maximum, the number of PSUs earned will be determined using linear interpolation. Under the 2025 LTIP, 80% of the PSU target value is tied to financial performance metrics allocated as follows:

  93. 2025 Performance Stock Units

    | • | Cumulative Retail Adjusted EBITDAR (60%) |

  94. 2025 Performance Stock Units

    | • | Cumulative Interactive Adjusted EBITDA (20%) |

  95. 2025 Performance Stock Units

    The 2025 PSU financial metrics were selected to emphasize long-term profitability in the Company’s Retail and Interactive segments. The Committee established rigorous three-year cumulative performance goals that reflect the Company’s long-term growth plan, market expectations, the likelihood of achieving various performance levels, and broader industry trends. The Committee determined that these targets require a significant level of effort to achieve. The Committee selected Adjusted EBITDAR for the STIP and Retail Adjusted EBITDAR and Interactive Adjusted EBITDA for the LTIP because we view these measures as providing the most meaningful insight into the Company’s underlying operating performance and its ability to generate profitable growth. Although both plans incorporate EBITDAR or EBITDA-based metrics, they assess distinct time horizons: the STIP evaluates one-year operational execution, while the three-year LTIP metrics measure management’s ability to deliver durable, resilient growth across the Company’s strategic investments. Additionally, the LTIP places greater weight on Retail Adjusted EBITDAR, reinforcing the strategic importance of the Retail segment to the Company’s long-term value-creation priorities. The remaining 20% of the target 2025 PSU opportunity is tied to operational metrics designed to incentivize growth in our customer database and the increase of omnichannel players who engage with the Company across both retail and digital channels—key drivers of our omnichannel strategy and long-term profitability. The Committee set rigorous targets aligned with internal projections and the Company’s annual plan for user acquisition and cross-channel engagement, requiring significant growth to achieve.

  96. 2025 Performance Stock Units

    | 68 | PROXY STATEMENT - 2026 |

  97. 2025 Performance Stock Units (cont.)

    2025 Performance Stock Units (cont.)

  98. 2025 Performance Stock Units (cont.)

    | 2025 PSUs Performance Metrics for 2025-2027 | | WEIGHTING | LINK TO STRATEGY | | FINANCIAL METRICS (80%) | Retail Adjusted EBITDAR | | 3-Year cumulative Retail Adjusted EBITDAR. This metric incentivizes effective operation of our Retail Segment, including revenue growth and cost efficiencies. | | | Interactive Adjusted EBITDA | | 3-Year cumulative Interactive Adjusted EBITDA. This metric focuses on initiatives designed to drive profitable growth and responsible scaling of our Interactive Segment. | | OPERATIONAL METRICS (20%) | Database Growth | | 3-Year cumulative PENN Play database growth. This metric focuses on expanding our customer ecosystem to increase cross-sell opportunities. | | | Omnichannel Play | | 3-Year cumulative growth in the number of customers playing with PENN across multiple channels (e.g., retail, OSB, iCasino). This metric focuses on the effectiveness of our cross-sell strategies. |

  99. 2025 Performance Stock Units (cont.)

    The 2025 PSU financial goals were set using the Company’s internal three-year forecast, with the first-year performance being equal to the Company’s publicly announced guidance for such year, to ensure the rigor of targets is in alignment with internal projections. The Committee follows a rigorous goal-setting process to ensure that PSU targets are appropriately calibrated. In setting threshold, target, and maximum goals, the Committee considers a broad range of factors, including the Company’s multi-year strategic and financial plans, peer and industry benchmarks, expected market conditions, competitive positioning, and alignment with shareholder interests. As a result, the performance goals represent ambitious targets that require meaningful financial execution and progress on key strategic priorities to achieve. The Committee does not disclose forward-looking PSU performance goals because these goals contain sensitive information tied to the Company’s long-term strategic assumptions and releasing them could pose harm by placing the Company at a competitive disadvantage. To maintain transparency for shareholders, the Committee discloses the full details of PSU goals after the completion of each applicable performance period, enabling investors to evaluate the rigor of the program and the alignment between realized compensation and long-term value creation. The Committee believes this balanced approach protects the Company’s competitive position while providing shareholders with meaningful insight into the effectiveness, rigor and integrity of the LTIP.

  100. 2025 Performance Stock Units (cont.)

    | PROXY STATEMENT - 2026 | 69 |

  101. Stock Options

    Stock Options Stock options represented 25% of the annual LTIP opportunity awarded in 2025 to our NEOs. The fair value of stock options on the grant date is based on the Black-Scholes option-pricing model, consistent with the stock option valuation model used to determine amounts reported in the Company’s Annual Report on Form 10-K. Stock options vest ratably over three years, subject to continued employment through the applicable vesting date (except as otherwise provided in the participant’s employment agreement in specific instances, such as terminations “without cause” or for “good reason” including following a “change in control,” each term as defined in the Second Amendment to our 2022 Long-Term Incentive Compensation Plan (the “2022 Plan”)). Stock options are issued with an exercise price equal to the closing price of PENN common stock on the trading day immediately preceding the grant date and have a maximum term of 10 years.

  102. RSUs

    RSUs Restricted stock units represented 25% of the annual long-term incentive opportunity awarded in 2025 to our NEOs. RSUs vest ratably over three years, subject to continued employment (except as otherwise provided in the participant’s employment agreement in specific instances, such as terminations “without cause” or for “good reason” including following a “change in control,” as defined in our 2022 Long-Term Incentive Compensation Plan, as amended).

  103. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period)

    Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) In connection with the transition to a three-year long-term performance cycle beginning with the 2024 PSU awards, the Committee approved a cumulative two-year performance period for the unvested portion of the 2023 PSUs tied to the 2024–2025 performance years. As disclosed in last year’s proxy statement, the Committee applied a 70% weighting to financial performance measures and 30% to strategic operational metrics for these unvested 2023 PSUs, replacing the legacy approach under which PSUs were measured solely against operational goals established at the start of each annual performance period. This updated PSU design was adopted in response to shareholder feedback to strengthen the alignment of the unvested and go-forward PSUs with the Company’s long-term incentive philosophy and enhance accountability for long-term financial performance results. The performance hurdles applicable to the 2023 PSUs were intended to be rigorous and required strong execution to achieve target performance levels. The Retail Adjusted EBITDAR and Interactive Adjusted EBITDA targets were consistent with our publicly disclosed financial guidance in the year the goals were set. Based on the performance results achieved during the 2024-2025 performance period, the last tranche of the 2023 PSUs performance period was earned at 74.75% of target. The cumulative payout under the 2023 PSUs (2023 – 2025 period) resulted in 85.85% cumulative achievement of the target performance level. This included the first tranche earned for the 2023 performance period at 108.05% of target, with earned shares that remained subject to continued service vesting through the end of the full 2023–2025 performance cycle, and the final tranche earned based on performance over the 2024–2025 performance period. The payout represented 39.56% of the initial target grant value on the vest day after considering the change in market value of the Company’s common stock since the grant date.

  104. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period)

    | 70 | PROXY STATEMENT - 2026 |

  105. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.)

    Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.)

  106. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.)

    | PROXY STATEMENT - 2026 | 71 |

  107. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.)

    Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.) The following table shows the PSU achievement for the final performance period of the 2023 PSUs covering fiscal 2024 and 2025.

  108. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.)

    | NAME | TARGET 2023 PSUs Associated with 2024-2025 Performance Period (# of PSUs) | 2024-2025 Performance Period PAYOUT (% of Target)(1) | EARNED 2023 PSUs – 2nd & 3rd Tranches Associated with 2024-2025 Performance Period (# of PSUs) | | Jay Snowden | 124,372 | 74.75% | 92,968 | | Felicia Hendrix | 32,946 | 74.75% | 24,627 | | Chris Rogers | 19,270 | 74.75% | 14,404 | | Todd George | 36,822 | 74.75% | 27,524 |

  109. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.)

    The following table shows the cumulative payout under the 2023 PSUs, including the first tranche earned for the 2023 performance period, with earned shares that remained subject to continued service vesting through the end of the full 2023–2025 performance cycle, and the final tranche earned based on performance over the 2024–2025 performance period, resulting in 85.85% cumulative achievement of the target performance level.

  110. Vesting of 2023 PSU Awards (2024 – 2025 Performance Period) (cont.)

    | AWARD | 2023 Performance Period 1/3 of 2023 PSUs (% of target earned) | 2024-2025 Performance Period 2/3 of 2023 PSUs (% of target earned) | TOTAL PAYOUT (% of target earned) | | 2023 PSUs | 108.05% | 74.75% | 85.85% |

  111. Evolution of the 2026 Compensation Structure

    | 2026 Compensation Peer Group Update | Refreshed the 2026 compensation peer group composition to more closely reflect PENN’s relative size, provide a more accurate representation of the Company’s closest operational and talent competitors and better reflect focus areas following the Company’s realigned digital strategy. The 2026 peer group removed 5 digital and entertainment companies and added 6 casinos, gaming and/or hospitality companies, as follows: | | | | | | | Fiscal 2026 Compensation Peer Group – Digital and Entertainment Companies Removed • Electronic Arts, Inc. • Lions Gate Entertainment Corporation • Live Nation Entertainment, Inc. • Roku, Inc. • Sirius XM Holdings, Inc. | | Fiscal 2026 Compensation Peer Group – Casinos, Gaming and/or Hospitality Companies Added • Churchill Downs, Inc. • Hilton Worldwide Holdings, Inc. • Hyatt Hotels Corporation • Light & Wonder, Inc. • Norwegian Cruise Line Holdings Ltd. • Royal Caribbean Cruises Ltd. | | | Additional details on compensation peer group changes can be found on page 63 of this proxy statement. | | | |

  112. Evolution of the 2026 Compensation Structure (cont.)

    | 2026 CEO and NEO Target Pay Opportunities | In the fourth quarter of 2025, with the support and agreement of Mr. Snowden and in consultation with its independent compensation consultant, the Committee lowered the target grant value of the CEO’s 2026 equity awards by $7.87 million, equivalent to a 41% reduction in LTIP opportunity and 31% reduction in total target direct compensation compared to 2025, effectively reducing Mr. Snowden’s total target pay to 2023 levels. The Committee concluded that this reduction appropriately reflects updated benchmarks of our refreshed peer group, which provide a better presentation of the Company’s realigned focus areas. We believe this demonstrates the Board’s thoughtful and measured approach to executive compensation as part of a multi-year effort to rebuild shareholder support for the program. In addition, in light of the 2026 compensation peer group changes, which resulted in NEO target pay above the new peer group median, and the Company’s 2025 performance, the Committee affirmed that there will be no target pay increases for the other NEOs for fiscal 2026. |

  113. Evolution of the 2026 Compensation Structure (cont.)

    | NAMED EXECUTIVE OFFICER | 2026 BASE SALARY | 2026 TARGET STIP | 2026 TARGET LTIP | 2026 TOTAL TARGET COMPENSATION | 2025 TOTAL TARGET COMPENSATION | % Change Total Target Compensation 2025 to 2026 | | Jay Snowden | $1,800,000 | $4,500,000 | $11,129,940 | $17,429,940 | $25,300,000 | -31% | | Felicia Hendrix | $927,000 | $1,158,750 | $3,708,000 | $5,793,750 | $5,793,750 | 0% | | Chris Rogers | $824,000 | $1,030,000 | $3,296,000 | $5,150,000 | $5,150,000 | 0% |

  114. Evolution of the 2026 Compensation Structure (cont.)

    | Annual Incentive Plan Metrics | Adjusted EBITDAR (100%) | | | 2026-2028 Long-Term Incentive Program | PSUs (50%) • Financial Metrics • NEW FOR 2026: Cash Flow from Operations (100%) • NEW FOR 2026: Relative TSR modifier (±20%) measured against the Russell 3000 Casino and Gambling Index RSUs (25%) Stock Options (25%) | Following the Company’s realigned digital strategy and in response to shareholder feedback encouraging a closer alignment between performance metrics and strategic outcomes and a clearer differentiation between STIP and LTIP measures, the Committee conducted a robust review of the performance metrics. The vesting of 2026 PSUs covering the 2026-2028 performance period will be tied to the achievement of a cash flow from operations goal, with a relative TSR modifier measured against the Russell 3000 Casino and Gambling Index (±20%). This revised LTIP program also incorporates a downside safeguard, such that no upward TSR modifier will apply if absolute TSR is negative. To reflect the updated peer group benchmarks, the Committee approved the maximum LTIP payout opportunity at 200% of target before the impact of the relative TSR modifier. | | In-Progress PSUs | 2024-2026 PSUs 2025-2027 PSUs | In connection with the digital strategy realignment in November 2025, the Committee has determined that no adjustments will be made to in-progress 2024 and 2025 PSUs, including the ESPN BET market share metric, to ensure pay outcomes align with shareholder experience and Company performance. |

  115. Other Compensation Program Elements and Policies

    Other Compensation Program Elements and Policies Deferred Compensation. The Company does not maintain any defined benefit pension programs for its executives. The Company maintains an elective non-qualified deferred compensation plan (the “Deferred Compensation Plan”) for tax planning and retirement purposes for our executives. In 2025, the minimum annual deferrable amount was $3,000 and the maximum was 90% of the executive’s base annual salary and/or bonus. Deferral elections must be made before the beginning of the year in which compensation will be earned. The Company’s contributions under the plan in 2025 were equal to 50% of the participant’s deferral for the first 10% of the salary and/or bonus deferred, subject to a maximum annual Company contribution equal to 5% of the participant’s salary and/or bonus. All amounts credited to an executive’s account are invested, as directed by the executive, in commonly available mutual funds, and the Company does not guarantee any minimum returns. The Deferred Compensation Plan is unfunded, and benefits are paid from the Company’s general assets; however, the Company currently contributes funds into a grantor trust on a monthly basis in respect of these deferred compensation obligations. Separately, the Company generally sets aside the amounts deferred by the executives and the matching contributions thereon and, to protect against excess liabilities, invests such amounts in the mutual funds notionally selected by each executive. This program is described in more detail beginning on page 79. The Compensation Committee believes that the Deferred Compensation Plan is necessary to attract and retain our executives and is consistent with competitive and industry practices. Benefits and Perquisites. We offer a set of benefits to all our employees, including medical, dental and vision insurance, group life insurance, short- and long-term disability and a 401(k) with certain contributions matched. We believe that executives should be offered benefits and perquisites that are reasonable relative to the benefits provided to all employees and that are consistent with competitive and industry practices among the Company’s compensation peer group. Consistent with these objectives, the Company also provides certain executive officers with selected supplemental benefits and perquisites, including matching contributions under the Company’s Deferred Compensation Plan and financial and tax planning services. In addition, our CEO is entitled to life insurance in the amount of three times his base salary. He is also entitled to use of Company aircraft, which is important in ensuring safe and efficient travel to our gaming facilities located across a wide geographic area without regular commercial flight alternatives, and which is generally consistent with evolving personal security landscape and our gaming peer group practices that permit their chief executive officers to use the company’s aircrafts for personal use and commuting. In determining the supplemental benefits and perquisites that our executive officers are entitled to receive, the Compensation Committee evaluates the benefits and perquisites provided by companies in the Company’s core gaming peer group. The description and value of such supplemental benefits and perquisites in 2025 can be found in the “All Other Compensation” column of the Summary Compensation Table in this proxy statement. Hedging and Pledging Policy. We maintain policies prohibiting each of the Company’s directors and employees (including executive officers) from engaging in hedging transactions (such as short sales, puts and calls and other derivatives), and pledging Company shares as collateral for a loan or holding shares in a margin account. Compensation Clawback Policy. As a highly regulated, multi-jurisdictional gaming operator, the Company has maintained a long-standing commitment to ensure that its executive officers adhere to the highest professional and ethical standards. The Company adopted its first Executive Incentive Compensation Recoupment Policy (“Clawback Policy”) on April 25, 2014, which was then subsequently amended on November 9, 2022, and further amended on September 19, 2023, with the latter amendment designed to meet compliance requirements of Section 10D of the Exchange Act and Nasdaq Rules. To further align the policy with the market leading practices, on March 12, 2025, the Board again amended the Clawback Policy by expanding the policy to cover time-based incentives, in addition to the performance-based incentives. The Clawback Policy is administered by the Committee and requires the Company to recover from specified current and former executive officers, certain incentive-based compensation received during the three years immediately preceding an accounting restatement. Such recovery will be made without regard to any individual knowledge or responsibility related to the accounting. Without limiting the foregoing, the Clawback Policy also permits, at the discretion of the Board, the recovery of time-based incentives in the event of an accounting restatement. Stock Ownership Guidelines for Senior Management. We believe that equity ownership fosters an atmosphere where directors and officers “think like owners” and are motivated to increase the long-term value of the Company by aligning their interests with

  116. Other Compensation Program Elements and Policies (cont.)

    As with the director stock ownership guidelines, the value of a NEO’s stock ownership at any time will be based on the aggregate value of common stock, restricted stock and stock-settled RSUs held by such NEO. Each NEO is required to achieve compliance with these guidelines within five years of assuming his or her current position. Once in compliance with the stock ownership guidelines associated with his or her position, each NEO will remain in compliance with these guidelines regardless of decreases in the trading price of our shares or changes to base salary until attainment of a position requiring a higher threshold, in which case the five-year compliance period starts again. All NEOs comply with these guidelines. Timing of Equity-Based Awards. The Company’s Equity Based Award Policy dictates that the grant date for regular annual stock option awards to executive officers will be the second trading day of the calendar year. Performance-based awards are typically made during the first quarter of each year when the Committee approves the performance goals for the year. From time to time, annual grants may be made on a later date in the year as a result of the timing of the determination of the awards and terms or other factors, such as performance metrics for a given year. In 2025, the annual performance awards with three-year metrics were approved by the Committee on April 7, 2025 for our NEOs (other than the CEO) and by the Board on April 9, 2025 for our CEO. New hire equity-based awards granted outside of the regular annual pay program are made on the first trading day of the quarter following the award approval, and ad hoc equity-based awards are generally granted on the fifth business day following the date upon which the CEO approves such awards. All equity-based grants, whether granted on the second trading day of the calendar year or later in the year, are priced in accordance with the terms of the applicable equity compensation plans or performance-based equity programs, which require, among other things, that the exercise price of all stock options be established by reference to the closing price on the trading day immediately prior to the date of grant. The Committee does not grant equity awards in anticipation of the release of material nonpublic information and the timing of filings of material nonpublic information is not based on equity award grant dates.

  117. Risk Assessment (cont.)

    Risk Assessment (cont.) PSUs, RSUs and stock options, which we believe are important to help further align executives’ interests with those of our shareholders. PSUs are tied to objective financial and operational goals aligned with our long-term growth priorities. Equity incentive awards are subject to long-term vesting schedules, and the annual bonus and performance-based equity awards are subject to maximum payout limits. We believe that the focus on annual short-term incentive pay is balanced by our long-term incentive awards, which incentivize long-term performance results and align interest of our executives with the Company’s ability to create sustained value in alignment with shareholder interests. These cash and equity incentive awards, especially when combined with our Clawback Policy described on page 73 of this Proxy Statement, appropriately balance payment for performance and alignment of executive compensation with shareholder interests, without encouraging imprudent conduct or excessive risk-taking. Additionally, we have stock ownership guidelines, as described on page 73 of this Proxy Statement, that require our NEOs to own a given multiple of their base salary in the form of our common stock, restricted stock or stock-settled RSUs (ranging from six times base salary for our CEO to three times base salary for other NEOs) to help ensure that the majority of executive compensation always has significant value tied to long-term stock price performance. Based on the foregoing, we believe that our compensation policies and practices do not create risks that are reasonably likely to have a material adverse effect on the Company. We also believe that our incentive compensation arrangements do not encourage risk-taking beyond the Company’s ability to effectively identify and manage significant risks, are compatible with effective internal controls and are supported by the oversight of the Committee.

  118. 2025 Summary Compensation Table

    2025 Summary Compensation Table This Summary Compensation Table summarizes the total compensation paid or earned by each of our named executive officers for the years ended December 31, 2025, 2024 and 2023, respectively.

  119. 2025 Summary Compensation Table

    | EXECUTIVE NAME AND PRINCIPAL POSITION | YEAR | SALARY ($) | BONUS ($) | STOCK AWARDS ($) (a) | OPTION AWARDS ($) (a) | NON-EQUITY INCENTIVE PLAN COMPENSATION ($) (b) | ALL OTHER COMPENSATION ($) (c) | TOTAL ($) | | Jay Snowden Chief Executive Officer and President | 2025 | 1,800,000 | — | 14,249,989 | 4,750,004 | 2,984,400 | 342,258 | 24,126,651 | | | 2024 | 1,800,000 | — | 16,877,840 | 4,750,003 | 2,835,000 | 413,457 | 26,676,300 | | | 2023 | 1,800,000 | — | 3,388,480 | 5,564,999 | 4,365,000 | 423,826 | 15,542,305 | | Felicia Hendrix Executive Vice President, Chief Financial Officer | 2025 | 925,754 | — | 2,781,001 | 926,998 | 768,638 | 104,475 | 5,506,866 | | | 2024 | 898,077 | — | 2,450,090 | 1,800,008 | 708,750 | 106,829 | 5,963,754 | | | 2023 | 844,808 | — | 751,055 | 1,487,504 | 824,500 | 100,150 | 4,008,017 | | Chris Rogers Executive Vice President, Chief Strategy & Legal Officer and Secretary | 2025 | 822,892 | — | 2,471,985 | 824,002 | 683,233 | 95,395 | 4,897,507 | | | 2024 | 797,115 | — | 2,016,108 | 1,600,007 | 630,000 | 95,918 | 5,139,148 | | | 2023 | 723,079 | — | 526,479 | 869,992 | 703,250 | 91,979 | 2,914,779 | | Todd George Executive Vice President, Operations | 2025 | 1,028,615 | — | 3,862,503 | 1,287,495 | 854,042 | 99,556 | 7,132,211 | | | 2024 | 998,077 | — | 2,726,742 | 1,999,992 | 787,500 | 103,275 | 6,615,586 | | | 2023 | 948,077 | — | 839,580 | 1,662,504 | 929,417 | 100,196 | 4,479,774 |

  120. 2025 Summary Compensation Table

    | (a) Amounts set forth in the Stock Awards and Option Awards columns represent the aggregate grant date fair value of awards granted in each year as computed in accordance with ASC 718, disregarding estimates of forfeitures related to service- based vesting conditions. Performance Award values are based upon their probable outcome of the performance condition as of the grant date. For compensation purposes, Performance Awards are not considered granted until such time that the performance goals are established. For additional information about the assumptions used in these calculations, [see (i) footnote (a) in the Grants of Plan Based Awards Table below, and (ii) Notes 2 and 15 to our audited consolidated financial statements included in our 2025 Annual Report. Higher stock award values reported for 2024 reflect in part a shift from a one-year to a full three-year performance period starting with 2024 performance-based restricted stock unit awards. Stock award values reported for 2024 include the full three-year target grant date fair value of 2024 performance-based restricted stock units, in addition to 2023 performance-based restricted stock units associated with the two-year 2024-2025 performance period and 2022 performance-based restricted stock units associated with the one-year 2024 performance period, for which performance goals were set in 2024. In accordance with SEC disclosure rules, portions of these previously issued 2022 and 2023 performance-based restricted stock units, covering the 2024 and 2025 performance periods, could not be included in the executive compensation tables until all applicable performance targets were approved. At the time of grant, the performance targets for the 2022 and 2023 performance-based awards were set annually for 33% of each year’s overall targeted award, so only the 33% portion of each year’s overall targeted PSU awards could be included in the proxy tables for the year in which the goals were established.] |

  121. 2025 Summary Compensation Table

    | The amounts presented in the Stock Awards column for each named executive officer during 2025 include the grant date fair value of their awards as follows: |

  122. 2025 Summary Compensation Table

    Mr. Snowden: (i) the 2025 time-based restricted stock unit award ($4,749,990); and (ii) the 2025 performance-based restricted stock unit award at target ($9,499,999) and at stretch ($18,999,998). Ms. Hendrix: (i) the 2025 time-based restricted stock unit award ($927,002); and (ii) the 2025 performance-based restricted stock unit award at target ($1,853,999) and at stretch ($3,707,998). Mr. Rogers: (i) the 2025 time-based restricted stock unit award ($823,991); and (ii) the 2025 performance-based restricted stock unit award at target ($1,647,994) and at stretch ($3,295,988). Mr. George: (i) the 2025 time-based restricted stock unit award ($1,287,502); and (ii) the 2025 performance-based restricted stock unit award at target ($2,575,001) and at stretch ($5,150,002).

  123. 2025 Summary Compensation Table

    | (b) The amounts reflect cash payments for 2025 pursuant to the Company’s annual short-term incentive plan, which provided for the payment of incentive compensation upon the Company’s achievement of pre-established performance goals. A discussion of our annual short-term incentive plan may be found in our CD&A under “Annual Short-Term Incentive Plan." |

  124. 2025 Summary Compensation Table

    | (c) For Mr. Snowden, All Other Compensation in 2025 consisted of: (i) $231,750 in Company matching contributions under the Company’s Deferred Compensation Plan (“DCP”); (ii) $8,551 in Company paid insurance premiums; (iii) $28,551 in tax and financial planning; (iv) $8,750 in matching 401(k) contributions; and (v) $64,656 representing aggregate incremental cost for use of the Company’s aircraft which is based on variable costs of operating the aircraft including fuel costs, landing costs and repairs and maintenance. |

  125. 2025 Summary Compensation Table

    For Ms. Hendrix, All Other Compensation in 2025 consisted of: (i) $81,725 in Company matching contributions under the DCP; (ii) $14,000 in tax and financial planning; and (iii) $8,750 in matching 401(k) contributions. For Mr. Rogers, All Other Compensation in 2025 consisted of: (i) $72,645 in Company matching contributions under the DCP; (ii) $14,000 in tax and financial planning; and (iii) $8,750 in matching 401(k) contributions. For Mr. George, All Other Compensation in 2025 consisted of: (i) $90,806 in Company matching contributions under the DCP; and (ii) $8,750 in matching 401(k) contributions.

  126. 2025 Summary Compensation Table

    | PROXY STATEMENT - 2026 | 77 |

  127. 2025 Grants of Plan Based Awards

    2025 Grants of Plan Based Awards

  128. 2025 Grants of Plan Based Awards

    | Name | Grant Date(a) | ESTIMATED FUTURE PAYOUTS UNDER NON-EQUITY INCENTIVE PLAN AWARDS ($) | | | ESTIMATED FUTURE PAYOUTS UNDER EQUITY INCENTIVE PLAN AWARDS (#) | | | ALL OTHER STOCK AWARDS (#) | ALL OTHER OPTION AWARDS (#) (b) | EXERCISE PRICE OF OPTION AWARDS ($/SHARE) | GRANT DATE FAIR VALUE OF STOCK AND OPTION AWARDS ($) (c) | | | | THRESHOLD ($) | TARGET ($) | MAXIMUM ($) | THRESHOLD ($) | TARGET ($) | MAXIMUM ($) | | | | | | Jay Snowden | — | 2,250,000 | 4,500,000 | 9,000,000 | — | — | — | — | — | — | — | | | 1/3/2025 | — | — | — | — | — | — | — | 372,269 | 19.24 | 4,750,004 | | | 1/3/2025 | — | — | — | — | — | — | 246,881 | — | — | 4,749,990 | | | 4/9/2025 | — | — | — | 345,455 | 690,909 | 1,381,818 | — | — | — | 9,499,999 | | Felicia Hendrix | — | 579,375 | 1,158,750 | 2,317,500 | — | — | — | — | — | — | — | | | 1/3/2025 | — | — | — | — | — | — | — | 72,651 | 19.24 | 926,998 | | | 1/3/2025 | — | — | — | — | — | — | 48,181 | — | — | 927,002 | | | 4/7/2025 | — | — | — | 64,871 | 129,741 | 259,482 | — | — | — | 1,853,999 | | Chris Rogers | — | 515,000 | 1,030,000 | 2,060,000 | — | — | — | — | — | — | — | | | 1/3/2025 | — | — | — | — | — | — | — | 64,579 | 19.24 | 824,002 | | | 1/3/2025 | — | — | — | — | — | — | 42,827 | — | — | 823,991 | | | 4/7/2025 | — | — | — | 57,663 | 115,325 | 230,650 | — | — | — | 1,647,994 | | Todd George | — | 643,750 | 1,287,500 | 2,575,000 | — | — | — | — | — | — | — | | | 1/3/2025 | — | — | — | — | — | — | — | 100,904 | 19.24 | 1,287,495 | | | 1/3/2025 | — | — | — | — | — | — | 66,918 | — | — | 1,287,502 | | | 4/7/2025 | — | — | — | 90,098 | 180,196 | 360,392 | — | — | — | 2,575,001 |

  129. 2025 Grants of Plan Based Awards

    | (a) The grant date shown in the table was determined pursuant to ASC 718, which is the date our Compensation Committee (or our Board for the CEO) established the performance criteria and awarded the target number of the 2025 Performance Awards. |

  130. 2025 Grants of Plan Based Awards

    | (b) Option awards represent stock options granted to the executives as part of their annual equity incentive compensation. The option awards vest over three years, 33.33% on the first anniversary of the date of grant and 33.33% on each succeeding anniversary. |

  131. 2025 Grants of Plan Based Awards

    | (c) Represents the full grant date fair value of awards under ASC 718. Generally, the full grant date fair value is the amount the Company expenses in its financial statements over the award’s vesting period. Assumptions used in the calculation of the amounts for stock option awards and performance awards are included in Notes 2 and 15 to the Company’s audited financial statements in our 2025 Annual Report. |

  132. 2025 Grants of Plan Based Awards

    | 78 | PROXY STATEMENT - 2026 |

  133. Outstanding Equity Awards at Fiscal Year End

    Outstanding Equity Awards at Fiscal Year End

  134. Outstanding Equity Awards at Fiscal Year End

    | NAME | OPTION AWARDS | | | | STOCK AWARDS(a) | | | | | | NUMBER OF SECURITIES UNDERLYING UNEXERCISED OPTIONS: | | OPTION EXERCISE PRICE ($) | OPTION EXPIRATION DATE | NUMBER OF SHARES OR UNITS HELD THAT HAVE NOT VESTED (#) | MARKET VALUE OF SHARES OR UNITS HELD THAT HAVE NOT VESTED ($) | EQUITY INCENTIVE PLAN AWARDS: NUMBER OF UNEARNED SHARES, UNITS OR OTHER RIGHTS THAT HAVE NOT VESTED (#) | EQUITY INCENTIVE PLAN AWARDS: MARKET OR PAYOUT VALUE OF UNEARNED SHARES, UNITS OR OTHER RIGHTS THAT HAVE NOT VESTED ($) | | | EXERCISABLE (#) | UNEXERCISABLE (#) | | | | | | | | Jay Snowden | 156,203 | — | 19.45 | 1/3/2029 | 246,881(e) | 3,641,495 | — | — | | | 1,032,706 | — | 18.81 | 8/6/2029 | 62,185(f) | 917,229 | 124,372(f) | 1,834,487 | | | 89,639 | — | 80.89 | 1/5/2031 | — | — | 882,900(g) | 13,022,775 | | | 119,556 | 39,852(b) | 50.64 | 1/4/2032 | — | — | 690,909(h) | 10,190,908 | | | 148,283 | 148,283(c) | 29.27 | 1/4/2033 | — | — | — | — | | | 70,466 | 211,398(d) | 25.95 | 1/3/2034 | — | — | — | — | | | — | 372,269(d) | 19.24 | 1/3/2035 | — | — | — | — | | Felicia Hendrix | 11,697 | — | 117.82 | 2/23/2031 | 48,181(e) | 710,670 | — | — | | | 21,303 | 7,102(b) | 50.64 | 1/4/2032 | 16,473(f) | 242,977 | 32,946(f) | 485,954 | | | 39,635 | 39,636(c) | 29.27 | 1/4/2033 | — | — | 107,784(g) | 1,589,814 | | | 26,703 | 80,109(d) | 25.95 | 1/3/2034 | — | — | 129,741(h) | 1,913,680 | | | — | 72,651(d) | 19.24 | 1/3/2035 | — | — | — | — | | Chris Rogers | 24,290 | — | 19.45 | 1/3/2029 | 42,827(e) | 631,698 | — | — | | | 23,485 | — | 26.14 | 1/3/2030 | 9,634(f) | 142,102 | 19,270(f) | 284,233 | | | 15,272 | — | 80.89 | 1/5/2031 | — | — | 95,808(g) | 1,413,168 | | | 20,113 | 6,705(b) | 50.64 | 1/4/2032 | — | — | 115,325 (h) | 1,701,044 | | | 23,181 | 23,182(c) | 29.27 | 1/4/2033 | — | — | — | — | | | 23,736 | 71,208(d) | 25.95 | 1/3/2034 | — | — | — | — | | | — | 64,579(d) | 19.24 | 1/3/2035 | — | — | — | — | | Todd George | 25,404 | — | 19.45 | 1/3/2029 | 66,918(e) | 987,041 | — | — | | | 61,061 | — | 26.14 | 1/3/2030 | 18,411(f) | 271,562 | 36,822(f) | 543,125 | | | 19,256 | — | 80.89 | 1/5/2031 | — | — | 119,760(g) | 1,766,460 | | | 23,848 | 7,950(b) | 50.64 | 1/4/2032 | — | — | 180,196(h) | 2,657,891 | | | 44,298 | 44,299(c) | 29.27 | 1/4/2033 | — | — | — | — | | | 29,669 | 89,010(d) | 25.95 | 1/3/2034 | — | — | — | — | | | — | 100,904(d) | 19.24 | 1/3/2035 | — | — | — | — |

  135. Outstanding Equity Awards at Fiscal Year End

    | (a) Consists of time based and performance based restricted stock units granted under the 2022 Long Term Incentive Compensation Plan with a market value calculated based on the Company’s closing stock price on December 31, 2025 of $14.75 |

  136. Outstanding Equity Awards at Fiscal Year End

    | (b) Vesting date: January 4, 2026. |

  137. Outstanding Equity Awards at Fiscal Year End

    | (c) Vesting dates: January 4, 2026 and January 4, 2027. |

  138. Outstanding Equity Awards at Fiscal Year End

    | (d) Vesting dates: January 3, 2026, January 3, 2027, and January 3, 2028. |

  139. Outstanding Equity Awards at Fiscal Year End

    | (e) Time-based restricted stock units are scheduled to vest on January 3, 2026, January 3, 2027, and January 3, 2028. |

  140. Outstanding Equity Awards at Fiscal Year End

    | (f) The vesting date shall be in the first quarter of 2026 following the certification of performance by the Compensation Committee or the Board of Directors, as applicable. Per instructions to Item 402(f)(2), since performance goals exceed the threshold, the disclosure reports the next higher performance measure. |

  141. Outstanding Equity Awards at Fiscal Year End

    | (g) The vesting date shall be in the first quarter of 2027 following the certification of performance by the Compensation Committee or the Board of Directors, as applicable. Per instructions to Item 402(f)(2), since performance goals exceed the threshold, the disclosure reports the next higher performance measure. |

  142. Outstanding Equity Awards at Fiscal Year End

    | (h) The vesting date shall be in the first quarter of 2028 following the certification of performance by the Compensation Committee or the Board of Directors, as applicable. Per instructions to Item 402(f)(2), since performance goals exceed the threshold, the disclosure reports the next higher performance measure. |

  143. Outstanding Equity Awards at Fiscal Year End

    | PROXY STATEMENT - 2026 | 79 |

  144. 2025 Option Exercises and Stock Vested

    2025 Option Exercises and Stock Vested

  145. 2025 Option Exercises and Stock Vested

    | | OPTION AWARDS | | STOCK AWARDS | | | NAME | NUMBER OF SHARES ACQUIRED ON EXERCISE (#) | VALUE REALIZED ON EXERCISE ($) | NUMBER OF SHARES ACQUIRED ON VESTING (#) | 2025 VALUE REALIZED ON VESTING ($) (a) | | Jay Snowden | — | — | 111,695 | 1,890,996 | | Felicia Hendrix | — | — | 17,381 | 366,218 | | Chris Rogers | — | — | 16,409 | 345,738 | | Todd George | — | — | 19,457 | 409,959 |

  146. 2025 Option Exercises and Stock Vested

    | (a) Value realized represents fair value, per share, as of the trading day immediately prior to the vesting date. |

  147. 2025 Nonqualified Deferred Compensation

    2025 Nonqualified Deferred Compensation

  148. 2025 Nonqualified Deferred Compensation

    | NAME | EXECUTIVE CONTRIBUTIONS IN LAST FISCAL YEAR ($) (a) | COMPANY CONTRIBUTIONS IN LAST FISCAL YEAR ($) (b) | AGGREGATE EARNINGS IN LAST FISCAL YEAR ($) (c) | AGGREGATE WITHDRAWALS/ DISTRIBUTIONS ($) (d) | AGGREGATE BALANCE AT LAST FISCAL YEAR END ($) (e) | | Jay Snowden | 463,500 | 231,750 | 1,170,562 | 5,608 | 9,647,600 | | Felicia Hendrix | 163,450 | 81,725 | 231,717 | 3,176 | 1,547,087 | | Chris Rogers | 217,934 | 72,645 | 274,848 | 1,754 | 2,343,778 | | Todd George | 363,223 | 90,806 | 941,454 | 2,192 | 7,024,074 |

  149. 2025 Nonqualified Deferred Compensation

    | (a) Each executive’s contribution is included in the executive’s Salary column for 2025, as reported in the Summary Compensation Table. |

  150. 2025 Nonqualified Deferred Compensation

    | (b) For each executive, the Company’s contribution is included in the executive’s All Other Compensation column for 2025 as reported in the Summary Compensation Table. |

  151. 2025 Nonqualified Deferred Compensation

    | (c) Amounts reflect the change in account value during fiscal year 2025. No amounts are reported in the Summary Compensation Table because the earnings were not above market or preferential. |

  152. 2025 Nonqualified Deferred Compensation

    | (d) Reduction in account balance due to FICA tax owed on 2025 vested company match. |

  153. 2025 Nonqualified Deferred Compensation

    | (e) The amount of each executive’s aggregate balance at fiscal year-end that was reported as compensation in the Summary Compensation Table for previous years is as follows: (i) Jay Snowden: $2,072,676; (ii) Felicia Hendrix: $356,579; (iii) Chris Rogers: $295,727; and Todd George: $414,020. |

  154. Potential Payments Upon Termination or Change in Control

    Potential Payments Upon Termination or Change in Control The following tables describe and quantify the compensation that would become payable in the event of a termination of a named executive officer’s employment under several different circumstances or a change in control. The amounts shown are estimates of amounts that would be paid to the named executive officers assuming that such termination or change in control was effective as of December 31, 2025, and include amounts earned through such time and are based (where applicable) on the closing price of the Company’s common stock on such date, which was $14.75 per share. Therefore, the tables below are merely illustrative examples of the impact of a hypothetical termination of employment or change in control. The actual amounts to be paid can only be determined at the time of such named executive officer’s separation from the Company and/or change in control. For a description of the severance and change in control provisions giving rise to the payments set forth below in the Company’s plans and individual agreements, see the summary of executive employment agreement provisions following the post-employment payments tables. In establishing the appropriate payment and benefit levels, the Company evaluates the practices and levels set by companies in its compensation peer group.

  155. Potential Payments Upon Termination or Change in Control

    | PROXY STATEMENT - 2026 | 81 |

  156. CEO Pay Ratio

    CEO Pay Ratio Pursuant to SEC rules, we are required to disclose in this Proxy Statement the ratio of the annual total compensation of Mr. Snowden, our Chief Executive Officer and President, to the median of the annual total compensation of all of our employees (excluding Mr. Snowden). For purposes of calculating the CEO pay ratio, we used the annual total compensation for our CEO as reported for 2025 in the Summary Compensation Table ($24,126,651), and the median of the 2025 annual total compensation of all of our employees, excluding Mr. Snowden ($43,833), with the ratio of these amounts being 550:1. The Company believes that the foregoing ratio is a reasonable estimate determined in accordance with SEC rules. Under the SEC rules, companies may identify the median annual total compensation using a wide variety of methods including reasonable assumptions and estimations. It is therefore difficult to compare our ratio to the ratio of other companies. We identified our median employee using payroll compensation consistent with what is reported on each employee’s W-2, Box 1 or equivalent taxable wages as of October 31, 2025 for all individuals, excluding our Chief Executive Officer and President, who were employed by us on such date. We measured total annual compensation based on all pay periods between November 1, 2024 and October 31, 2025. We did not make any assumptions or estimates with respect to total annual compensation. As of October 31, 2025, we had a total of 23,066 employees, excluding our Chief Executive Officer. We did not exclude any of our non-U.S. employees from this determination. We selected the median employee from that group for purposes of preparing the ratio of Chief Executive Officer pay to median employee pay. We then calculated the compensation for our median employee based upon the same components of compensation used to determine Mr. Snowden’s pay for purposes of Summary Compensation Table disclosure.

  157. CEO Pay Ratio

    | 86 | PROXY STATEMENT - 2026 |

  158. Pay Versus Performance

    Pay Versus Performance As required by Section 953(a) of the Dodd-Frank Wall Street Reform and Consumer Protection Act, and Item 402(v) of Regulation S-K, we are providing the following information about the relationship between executive compensation actually paid and certain financial performance of the Company. For further information concerning the Company’s variable pay-for-performance philosophy and how the Company aligns executive compensation with the Company’s performance, refer to “Executive Compensation—Compensation Discussion and Analysis” on page 53.

  159. Pay Versus Performance

    | | | | | | VALUE OF INITIAL $100 INVESTMENT BASED ON: | | | | | FISCAL YEAR | SUMMARY COMPENSATION TABLE TOTAL FOR PEO(1) | COMPENSATION ACTUALLY PAID TO PEO(2) | AVERAGE SUMMARY COMPENSATION TABLE TOTAL FOR NON-PEO NEOS(3) | AVERAGE COMPENSATION ACTUALLY PAID TO NON-PEO NEOS(4) | PENN TOTAL SHAREHOLDER RETURN(5) | PEER GROUP TOTAL SHAREHOLDER RETURN(6) | NET INCOME ($M)(7) | ADJUSTED EBITDAR ($ IN MILLIONS)(8) | | 2025 | $24,126,651 | $10,375,989 | $5,845,528 | $3,063,710 | $17.08 | $85.84 | ($845.30) | $1,461.8 | | 2024 | $26,676,300 | $13,213,672 | $5,906,163 | $3,034,477 | $22.95 | $89.32 | ($313.30) | $1,292.3 | | 2023 | $15,542,305 | $10,187,197 | $3,800,856 | $3,866,865 | $30.13 | $92.81 | ($491.40) | $1,512.6 | | 2022 | $14,075,614 | ($10,073,072) | $3,105,185 | $1,412,413 | $34.39 | $73.75 | $221.70 | $1,939.4 | | 2021 | $65,887,214 | $7,961,396 | $3,440,477 | $2,027,447 | $60.03 | $98.54 | $420.50 | $1,994.4 |

  160. Pay Versus Performance

    | 1 | The dollar amounts reported are the amounts of total compensation reported for Mr. Snowden (our Principal Executive Officer) for each corresponding year in the “Total” column of the Summary Compensation Table. Refer to “Executive Compensation—Compensation Tables and Arrangements—2025 Summary Compensation Table.” |

  161. Pay Versus Performance

    | 2 | The dollar amounts reported represent the amount of “compensation actually paid” to Mr. Snowden, as computed in accordance with Item 402(v) of Regulation S-K. The dollar amounts do not reflect the actual amount of compensation earned by or paid to Mr. Snowden during the applicable year. In accordance with the requirements of Item 402(v) of Regulation S-K, the below “Compensation Actually Paid Calculation” table displays the adjustments made to Mr. Snowden’s total compensation for each year to determine the compensation actually paid. |

  162. Pay Versus Performance

    | 3 | The dollar amounts reported represent the average of the amounts reported for the Company’s named executive officers (NEOs) as a group (excluding Mr. Snowden) in the “Total” column of the Summary Compensation Table in each applicable year. The names of each of the NEOs (excluding Mr. Snowden) included for purposes of calculating the average amounts in each applicable year are as follows: (i) for 2022, 2023 and 2024, Felicia Hendrix, Todd George and Chris Rogers; and (ii) for 2021, Felicia Hendrix, Todd George and Harper Ko. |

  163. Pay Versus Performance

    | 4 | The dollar amounts reported represent the average amount of “compensation actually paid” to the NEOs as a group (excluding Mr. Snowden), as computed in accordance with Item 402(v) of Regulation S-K. The dollar amounts do not reflect the actual average amount of compensation earned by or paid to the NEOs as a group (excluding Mr. Snowden) during the applicable year. In accordance with the requirements of Item 402(v) of Regulation S-K, the below “Compensation Actually Paid Calculation” table displays the adjustments made to average total compensation for the NEOs as a group (excluding Mr. Snowden) for each year to determine the average compensation actually paid to the NEOs as a group (excluding Mr. Snowden). |

  164. Pay Versus Performance

    | 5 | Cumulative TSR is calculated by dividing the sum of the cumulative amount of dividends for the measurement period, assuming dividend reinvestment, and the difference between the Company’s share price at the end and the beginning of the measurement period by the Company’s share price at the beginning of the measurement period. |

  165. Pay Versus Performance

    | 6 | Represents the weighted peer group TSR, weighted according to the respective companies’ stock market capitalization at the beginning of each period for which a return is indicated. The peer group used for this purpose is the following published industry index: Russell 3000 Casino and Gambling Index. |

  166. Pay Versus Performance

    | 7 | The dollar amounts reported represent the amount of net income (loss) reflected in the Company’s audited financial statements for the applicable year. |

  167. Pay Versus Performance

    | 8 | The Company believes Adjusted EBITDAR is the financial performance measure most closely linked to the calculation of compensation actually paid. Adjusted EBITDAR is a non-GAAP financial measure. For a definition and reconciliation of this non-GAAP financial measure to the most directly comparable GAAP measure, see Appendix B to this Proxy Statement entitled “Reconciliation of GAAP to Non-GAAP Financial Measures.” |

  168. Pay Versus Performance

    | PROXY STATEMENT - 2026 | 87 |

  169. Compensation Actually Paid Calculation

    Compensation Actually Paid Calculation

  170. Compensation Actually Paid Calculation

    | | PEO | | | | | NEO AVERAGE | | | | | | | 2025 | 2024 | 2023 | 2022 | 2021 | 2025 | 2024 | 2023 | 2022 | 2021 | | Summary Compensation Table Total | $24,126,651 | $26,676,300 | $15,542,305 | $14,075,614 | $65,887,214 | $5,845,528 | $5,906,163 | $3,800,856 | $3,105,185 | $3,440,477 | | Less: Reported Fair Value of Equity Awards(a) | $18,999,993 | $21,627,843 | $8,953,479 | $6,961,325 | $57,104,584 | $4,051,328 | $4,197,649 | $2,045,705 | $1,470,912 | $1,645,208 | | Add: Year End Fair Value of Equity Awards(b) | $12,399,543 | $15,717,740 | $9,604,572 | $5,919,253 | $22,335,085 | $2,591,162 | $2,577,342 | $2,302,218 | $1,016,402 | $1,231,271 | | Add: Change in Fair Value of Outstanding and Unvested Equity Awards(b) | ($7,351,186) | ($7,005,536) | ($4,077,352) | ($18,419,902) | ($20,839,582) | ($1,337,465) | ($1,133,519) | ($271,763) | ($1,066,153) | ($1,020,003) | | Add: Fair Value as of Vesting Date of Equity Awards Granted and Vested in the Year(b) | — | — | — | — | — | — | — | — | — | — | | Add: Change in Fair Value of Equity Awards Granted in Prior Years that Vested in the Year(b) | $200,974 | ($546,988) | ($1,928,849) | ($4,686,713) | ($2,316,737) | $15,812 | ($117,859) | $81,259 | ($172,109) | $20,909 | | Less: Fair Value at the End of the Prior Year of Equity Awards that Failed to Meet Vesting Conditions in the Year(b) | — | — | — | — | — | — | — | — | — | — | | Add: Value of Dividends or other Earnings Paid on Stock or Option Awards not Otherwise Reflected in Fair Value or Total Compensation(b) | — | — | — | — | — | — | — | — | — | — | | Compensation Actually Paid(c) | $10,375,989 | $13,213,672 | $10,187,197 | ($10,073,072) | $7,961,396 | $3,063,710 | $3,034,477 | $3,866,865 | $1,412,413 | $2,027,447 |

  171. Compensation Actually Paid Calculation

    | (a) The grant date fair value of equity awards represents the total of the amounts reported in the “Stock Awards” and “Option Awards” columns in the Summary Compensation Table for the applicable year. |

  172. Compensation Actually Paid Calculation

    | (b) The equity award adjustments for each applicable year include the addition (or subtraction, as applicable) of the following: (i) the year-end fair value of any equity awards granted in the applicable year that are outstanding and unvested as of the end of the year; (ii) the amount of change as of the end of the applicable year (from the end of the prior fiscal year) in fair value of any awards granted in prior years that are outstanding and unvested as of the end of the applicable year; (iii) for awards that are granted and vest in the same applicable year, the fair value as of the vesting date; (iv) for awards granted in prior years that vest in the applicable year, the amount equal to the change as of the vesting date (from the end of the prior fiscal year) in fair value; and (v) for awards granted in prior years that are determined to fail to meet the applicable vesting conditions during the applicable year, a deduction for the amount equal to the fair value at the end of the prior fiscal year. The valuation assumptions used to calculate fair values did not materially differ from those disclosed at the time of grant. |

  173. Compensation Actually Paid Calculation

    | (c) The Company does not maintain any defined benefit pension programs for its executives. |

  174. Compensation Actually Paid Calculation

    | 88 | PROXY STATEMENT - 2026 |

  175. Analysis of the Information Presented in the Pay versus Performance Table

    Analysis of the Information Presented in the Pay versus Performance Table While the Company utilizes several non-financial performance measures to align executive compensation with Company performance, all of those Company measures are not presented in the Pay versus Performance table. Moreover, the Company generally seeks to incentivize long-term performance and therefore does not specifically align the Company’s performance measures with compensation that is actually paid (as computed in accordance with Item 402(v) of Regulation S-K) for a particular year. In accordance with Item 402(v) of Regulation S-K, the Company is providing the following descriptions of the relationships between information presented in the Pay versus Performance table.

  176. Analysis of the Information Presented in the Pay versus Performance Table

    | PROXY STATEMENT - 2026 | 89 |

  177. Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Company TSR

    Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Company TSR The following chart sets forth the relationship between Compensation Actually Paid to our PEO, the average of Compensation Actually Paid to our Non-PEO NEOs, and cumulative TSR of the Company and the peer group (the Russell 3000 Casino & Gambling Index) over the five most recently completed fiscal years.

  178. Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Company TSR

    | 90 | PROXY STATEMENT - 2026 |

  179. Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Net Income

    Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Net Income The following chart sets forth the relationship between Compensation Actually Paid (CAP) to our PEO, the average of Compensation Actually Paid to our Non-PEO NEOs, and our Net Income during the five most recently completed fiscal years. While the Company does not use net income as a performance measure in the overall executive compensation program, the measure of net income is correlated with the measure Adjusted EBITDAR, which the Company does use when setting goals in the Company’s STIP and LTIP.

  180. Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Net Income

    | PROXY STATEMENT - 2026 | 91 |

  181. Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Adjusted EBITDAR

    Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Adjusted EBITDAR The following chart sets forth the relationship between Compensation Actually Paid (CAP) to our PEO, the average of Compensation Actually Paid to our non-PEO NEOs, and our Adjusted EBITDAR during the five most recently completed fiscal years. While the Company uses numerous measures, both financial and non-financial, for the purpose of evaluating performance for the Company’s compensation programs, the Company has determined that Adjusted EBITDAR is the most important financial performance measure used to link the Company’s financial performance to compensation actually paid to the Company’s NEOs for the most recently completed fiscal year.

  182. Description of Relationship Between PEO and Average Non-PEO NEO Compensation Actually Paid and Adjusted EBITDAR

    | 92 | PROXY STATEMENT - 2026 |

  183. Equity Awards Outstanding as of April 15, 2026

    | * The outstanding equity awards reflected in this table include awards granted under the Company’s 2018 Long Term Incentive Compensation Plan and Score Media and Gaming Second Amended and Restated Stock Option and Restricted Stock Unit Plan (the “Legacy Plans”). No new awards may be granted under the Legacy Plans; however, outstanding awards under the Legacy Plans remain in effect in accordance with their original terms. |

  184. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS Unite Here (the “proponent”), which was the beneficial owner of 469 shares of the Company’s common stock as of December 29, 2025, has notified the Company that it intends to present the following proposal for consideration at the Annual Meeting. The proponent has presented the proposal and supporting statements set forth below, and we are presenting the proposals and the supporting statements as they were submitted to us. Although we do not support certain of the statements contained in the proposal and the supporting statements, we have limited our response to the most important points and have not attempted to address all the statements with which we disagree. The address and stock ownership of the proponent will be furnished by the Company’s Secretary to any person, orally or in writing as requested, promptly upon receipt of any oral or written request. RESOLVED: Shareholders of PENN Entertainment, Inc. (the "Company") request that the Board of Directors take all necessary steps, promptly and in accordance with Pennsylvania law, the Company's governing documents, and all applicable gaming regulatory requirements, to eliminate the classification of the Board of Directors and transition to the annual election of all directors, with each director elected to a one-year term. The declassification should be implemented in a manner that does not affect the unexpired terms of directors elected prior to the effectiveness of such action. WHEREAS: The annual election of all directors is widely recognized as a leading corporate governance practice that enhances director accountability and aligns the board more closely with shareholders' long-term interests. Annual elections are the prevailing standard of good corporate governance across the majority of companies in the S&P 500 and the Russell 3000. Our Company currently maintains a classified board in which directors serve staggered three-year terms. While historically common, classified boards are increasingly viewed as limiting shareholders' ability to provide timely feedback on board performance and composition. Academic research has suggested that classified boards are associated with lower firm value, reduced market discipline, and increased entrenchment risk (Faleye, 2007). In the 2025 proxy season, proposals in favor of declassification of boards of directors had an average support of 77.9% (The Harvard Law School Forum on Corporate Governance, 2025). A transition to annual elections is both overdue and essential. For more than a decade, the Company's board has chosen to maintain a classified structure in contradiction to shareholders' 2010 majority vote in favor of declassification. Corporate governance standards and investor expectations have since shifted in greater favor of annual elections, and renewed shareholder action is appropriate as our Company continues to face a dynamic competitive landscape and ongoing technological change in the industry. Annual elections would strengthen board accountability and improve the Board's responsiveness to these challenges.

  185. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | 108 | PROXY STATEMENT - 2026 |

  186. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    A transition to annual elections would:

  187. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | • | Improve accountability, ensuring each director is evaluated by shareholders every year |

  188. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | • | Promote Long-term value creation by ensuring the board remains adaptable and responsive |

  189. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | • | Enhance oversight during periods of strategic transition or operational underperformance |

  190. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | • | Reduce entrenchment risk and align our Company with governance norms embraced by leading gaming peers, including MGM Resorts International and Caesars Entertainment |

  191. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | • | Improve shareholder confidence, supporting long-term value creation |

  192. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    This proposal is precatory only, and does not mandate that the Board take any particular action with respect to its subject matter. Rather, we envision (and expect) that the Board will exercise its discretion to adopt changes approved by the majority of shareholders because doing so supports sound governance and confidence in Board leadership. Nothing in this proposal conflicts with the Company's obligations under gaming laws, its gaming licenses, or the authority of any gaming regulator. The Board retains full discretion to sequence any implementation in a manner consistent with applicable suitability requirements while ensuring shareholders receive the annual accountability that is now standard market practice. We urge shareholders to vote FOR this proposal.

  193. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | PROXY STATEMENT - 2026 | 109 |

  194. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | Board Recommendation | | OUR BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE “AGAINST” THIS SHAREHOLDER PROPOSAL. |

  195. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    | The Board recommends shareholders vote AGAINST this proposal. We believe the classified Board structure is in the best interests of PENN and its shareholders for the following reasons: • PENN operates in a highly regulated industry, and, given our extensive regional footprint, some jurisdictions restrict Board members from voting until they are fully licensed – a process that has historically taken a year or longer • Our rapidly changing industry requires a deep understanding of our business and a long-term strategic focus • Six of our eleven directors have been on the Board for less than four years, underscoring our commitment to Board refreshment • PENN maintains a comprehensive shareholder engagement program with a robust track record of responsiveness |

  196. SHAREHOLDER PROPOSAL REQUESTING ANNUAL ELECTION OF DIRECTORS

    The Board considered this proposal and has determined that it would not serve the best interests of the Company or its shareholders. The Board continues to believe that maintaining a classified Board structure is appropriate for the reasons set forth below. The Board periodically reviews the Company’s governance framework and believes that the existing structure appropriately balances director accountability to shareholders with the stability required to effectively mitigate potential risks in the context of our highly regulated operating environment and long-term strategic priorities. PENN operates in a highly regulated industry and, given our extensive regional footprint, some jurisdictions restrict Board members from voting until they are fully licensed – a process that has historically taken a year or longer PENN has the largest regional footprint in the industry and operates in multiple jurisdictions that require extensive regulatory review and licensing of directors. These processes are highly comprehensive and involve detailed background investigations into all aspects of the director’s financial and personal matters. The licensing requirements, which are unique to the gaming industry, can hinder our ability to attract talented director candidates. Our current structure helps mitigate the significant time commitment required for licensure by providing for an initial term of three years. More significantly, certain of our jurisdictions, each of which is important to our operations, require directors to obtain licensure before they are permitted to vote on Board matters. The licensing process is extremely time intensive and historically has taken a year or longer to complete. In a scenario in which a majority of new directors are added to the Board in a single year, these new directors would be unable to vote for an extended period of time due to licensing restrictions, creating a significant risk that Board and committee functions could be seriously impaired by failure to achieve necessary quorums required for Board and/or committee actions. The Board believes that the Company’s current classified structure effectively mitigates these risks by supporting continuity in Board composition while newly elected directors complete required licensing processes.