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Barstool founder Dave Portnoy once had to file bankruptcy for gambling losses.
Now, he appears to be the hottest gambler in the United States.
Portnoy claims he has won $5.4 million on sports betting in 2024 and stands to win an additional $1.6 million if the Celtics win the NBA Finals.
Portnoy wagered $100,000 on a two-leg parlay featuring Scottie Scheffler wining the Masters (+550) and the Celtics winning the NBA Finals (+145) that will pay him $1,592,500.
Boston — after rolling through a depleted Eastern Conference — is now a -225 favorite on DraftKings to win the NBA Finals, as they match up with the No. 4 seed Dallas Mavericks.
“Guys, I hate to be that guy but I have the Celtics for 1.1 million and the Oilers for another million,” Portnoy said on X.
Portnoy’s initial post on his Celtics bet showed that he would net approximately $1.5 million, so it’s possible that he hedged some of his potential Celtics winnings off on a Mavericks series bet.
“If both those teams win I will be up 7.5 million in 2024 and have won every big event this year. This run should be taught in history books,” Portnoy continued.
The media mogul is in an excellent spot while holding these two tickets that could add roughly $2.5 million to his portfolio, on top of his previous wins.
Portnoy previously cashed huge amounts on Michigan and Washington winning in the CFP semifinals, the Chiefs winning the Super Bowl, UConn winning the national title ($2.2 million) and Scheffler winning the Masters ($1.35 million).
DraftKings, the company with which he has been exclusively betting and partnered up up with his Barstool Sports, is the one paying these bets out.
Guys I hate to be that guy but I have the Celtics for 1.1 million and the Oilers for another million. If both those teams win I will be up 7.5 million in 2024 and have won every big event this year. This run should be taught in history books. https://t.co/c1r8zmncCh— Dave Portnoy (@stoolpresidente) June 3, 2024
DraftKings is likely to keep the publicity going with his wild bets and even this parlay, but it’s fair to say that even the sportsbook wasn’t expecting this level of heater just a few months into their content deal.
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There were previously some questions being raised about why Portnoy was allowed to bet on PENN’s app, formerly Barstool Sportsbook, which has since been rebranded ESPN BET.
Many thought that Portnoy’s massive action was going to skew market share numbers and misrepresent the company’s true betting figures.
For now, Portnoy is on a blazing sports betting heater, burning a hole in DraftKings’ pockets.
