Inside PENN’s costly quest to turn flashy partnerships into market dominance as it ends ESPN deal

Inside PENN’s Quest for Market Dominance

PENN Entertainment, formerly known as Penn National Gaming, evolved from a regional racetrack operator into one of the largest casino and racing companies in the United States. Over the years, it expanded by acquiring numerous properties—sometimes strategically, other times opportunistically.

Beyond acquisitions, PENN pursued ambitious partnerships to boost its market presence. Its most recent collaboration was with ESPN Bet, which was terminated on November 6, 2025. While some partnerships briefly flourished, others struggled due to high costs, lofty expectations, and shifting market conditions, making PENN’s growth journey uncertain and dynamic.

Major Deals and Strategic Shifts

“PENN was tired of being known as the plucky regional operator and was ready to audition for a national spotlight.”

Following these efforts, PENN redirected its focus toward strengthening its casino portfolio and adopting a more sustainable business strategy, moving away from risky media partnerships.

Summary

PENN’s rapid expansion through acquisitions and partnerships faced many challenges, leading to a renewed emphasis on core casino operations and sustainable growth.

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ReadWrite ReadWrite — 2025-11-06