Dave Portnoy, the founder of Barstool Sports, is expressing frustration and announcing his departure from gambling once again. This marks the third time Portnoy has declared his exit from gambling, citing a significant loss on a “monster bet” on the Buffalo Bills and alleging that the NFL is “rigged.”
The Buffalo Bills faced the Philadelphia Eagles in a game that ended with a late comeback, resulting in a 37-34 overtime victory for the home team. Portnoy, in response to the loss, tweeted, “I quit gambling. F–k Buffalo.”
While Portnoy did not disclose the exact amount of his bet, the intensity of his reaction suggests a substantial wager, likely in the six-figure range or higher.
Recent questionable betting decisions by Portnoy include a $10,000 bet on Notre Dame quarterback Sam Hartman winning the Heisman Trophy, a prediction that is unlikely to materialize. Additionally, he has threatened the NFL with a lawsuit over allegations that the Cincinnati Bengals failed to disclose information about a pre-existing injury related to Joe Burrow, who is now out for the year.
Portnoy has a history of describing himself as a “degenerate gambler,” and his recent actions align with this characterization. In August of the same year, PENN Entertainment removed Barstool Sportsbook from its portfolio, collaborating with ESPN to launch ESPN Bet, a new sportsbook. As part of the deal, PENN paid $1.5 billion to ESPN to establish the platform. Portnoy subsequently reacquired 100% of Barstool from PENN for one dollar, with a 50% sell-on clause if he decides to sell Barstool in the future.
While Portnoy can absorb losses, significant wagers pose a potential financial risk, and his recurring decisions to quit gambling may indicate the challenges he faces in this arena.