Industry Shocker: Penn and ESPN End Partnership
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Bookmakers Review
- November 7, 2025
In a stunning turn of events, the partnership between Penn Entertainment and ESPN, which formed sports betting operator ESPN Bet, will be terminated as of December 1st.
Tearing the Sheets
Marriages always begin blissfully, but sometimes things go awry that will cause the wedded parties to tear the sheets and sign divorce papers. That is essentially what happened between Penn Entertainment and sports media giant ESPN when the product of their union, ESPN Bet, did not pan out as planned.
PENN Entertainment President and CEO Jay Snowden released a statement that said, in part, “When we first announced our partnership with ESPN, both sides made it clear that we expected to compete for a podium position in the space. Although we made significant progress in improving our product offering and building a cohesive ecosystem with ESPN, we have mutually and amicably agreed to wind down our collaboration. We plan to refocus our digital strategy on our growing iCasino business, while continuing to capitalize on our omnichannel advantage as the nation’s leading regional retail casino operator.”
ESPN chairman Jimmy Pitaro released his own statement, saying, “Together, ESPN and PENN created a truly unique offering with unparalleled integrations across our various media assets. ESPN drove over 2.9 million new users into the PENN ecosystem, with a strong uptick in first-time bettors this fall. We appreciate the collaboration we had with PENN and are now pursuing other media and marketing opportunities within this space.”
Road to Ruin
Penn Entertainment had initially partnered with Barstool Sports to brand its mobile sports betting entity as Barstool Sportsbook, a bro-cultured audience cultivated by the charismatic, to some, loathsome to others, Dave Portnoy, also known as El Presidente. The price tag was a cool $650 million, but only months after completing the deal, word got out that ESPN’s call letters were available to the highest bidder.
The ESPN Bet Deal and Barstool Divestment
Although most CEOs who just shelled out hundreds of millions of dollars for a new company would have abstained from any further negotiations with another entity, CEO Jay Snowden was undeterred. Snowden struck a deal with ESPN to form ESPN Bet for what amounted to $2 billion over 10 years in August 2023 to essentially lease the four letters and gain digital access to ESPN’s website.
But the kicker was that Disney-owned ESPN demanded that Penn divest itself of the Barstool Sports media empire and, by default, the sportsbook, due to its controversial reputation. Snowden had to act fast or lose the deal, so he sold Barstool Sports, sans the sportsbook, to its founder, Dave Portnoy, for $1 and the rights to 50% of the proceeds should Portnoy decide to sell at some point in the future. Portnoy has vowed never to sell.
That was the beginning of a tumultuous era of Penn’s stock plummeting from a high of $136.47 on March 15, 2021, to where it now stands at $14.96 per share. The executive board had grown restless, which prompted HG Vora, a Manhattan-based financial firm and one of Penn Entertainment’s major investors, to demand that the company vote in three of its hand-picked directors to the board.
Legal Tensions and Strategic Shift
Penn complied somewhat by voting for two of the three, which has triggered a legal battle. But while this was happening, rumors began to swirl that the parties may bail out of their agreement at the earliest contractually stipulated deadline.
That time has apparently come, and Penn will now be shifting its online sportsbook to theScore Bet, which it operates in Ontario, Canada, on December 1, 2025, to coincide with its ESPN Bet departure.
