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ESPN’s Bad Bet

The company’s splashy move into the app-based gambling market faced stiff headwinds from the start. In fact, it likely never stood a chance.

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Jimmy Pitaro
When ESPN chairman Jimmy Pitaro and Penn C.E.O. Jay Snowden shook hands in 2023, DraftKings and FanDuel were already basically a duopoly, controlling about two-thirds of the market, according to Casino Reports. Photo: Kyle Grillot/Bloomberg/Getty Images
Julia Alexander
November 11, 2025

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Anyone who took the under on the ESPN–Penn Entertainment marriage can cash out now. Less than three years after the gambling company became the network’s official sportsbook partner, ESPN is ditching Penn for a new deal with DraftKings, a much larger rival. Shocker. Penn executives had the odds stacked against them from the start: When ESPN chairman Jimmy Pitaro and Penn C.E.O. Jay Snowden shook hands in 2023, DraftKings and FanDuel were already basically a duopoly, controlling about two-thirds of the market, according to Casino Reports. Alas, ESPN Bet was never able to move the needle in a competitive market, allowing Pitaro to walk away from the deal.

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