Barstool founder Dave Portnoy will look to keep riding high following some big-time wins, placing a major bet on the Philadelphia Phillies to win the World Series.
Placed with DraftKings Sportsbook at +600, Portnoy’s $200,000 bet would pay out a whopping $1.4 million if Bryce Harper and his squad can lead the City of Brotherly Love to the top of the baseball mountain.
— Barstool Gambling (@stoolgambling) June 25, 2024
At 52-27, the Phillies currently sit atop the National League East and are tied for the Major League Baseball lead in wins with the New York Yankees.
Portnoy, meanwhile, will look to carry the momentum he's gained over the past several weeks with several big betting wins.
Earlier this month, Portnoy cashed in winnings just shy of $1.6 million following the Celtics 4-1 series win over the Dallas Mavericks, thanks to a two-leg parlay that included Scottie Scheffler to win the RBC Heritage Classic.
His big bets on Scheffler don’t end there, however. He also cashed in with a $504,000 payout on the PGA star this past week after his playoff win over Tom Kim at the Travelers Championship. Those two wins added to Portnoy’s major winnings on the 28-year-old, as a $300,000 Masters bet turned into a remarkable $1.65 million for Portnoy at +450, amid concerns Scheffler would withdraw from the tournament.
Guys I don't think people realize what we are witnessing. To come into #themasters as the world's #1 and the hottest gambler on the planet. To have a bullseye on your forehead and still win with ease? We may never see a 4 month stretch like this again. #eprestheallknowing pic.twitter.com/Pq7jkq87FE
— Dave Portnoy (@stoolpresidente) April 14, 2024
Interestingly, Portnoy’s last few months of success haven’t come without blemishes.
At the beginning of the Stanley Cup Playoffs, Portnoy boldly proclaimed Connor McDavid and the Edmonton Oilers would hoist Lord Stanley’s Mug come June. While the City of Champions came within a single goal in Game 7, it was ultimately the Florida Panthers ultimately walked away victorious as Stanley Cup Champions this past Monday.
Portnoy bringing in big wins
Even amidst his incredible hot streak, it’s easy to argue Portnoy's biggest recent win has come away from the books.
In 2020, Penn Entertainment acquired 36% of Barstool Sports for $163 million, then later acquired the rest of Portnoy’s media empire for $388 million in February 2023. But in a bizarre turn of events, Penn sold Barstool Sports back to Portnoy a few months later for just $1 — a consequence of Penn's partnership at the time with ESPN and eventual founding of ESPN Bet.
A notable clause in the Penn-Portnoy deal states Penn receives 50% of the purchase price should the Massachusetts native choose to sell; however, the 47-year-old has claimed he plans to keep the company “till I die.”
As for Portnoy’s current betting destination, a multi-year deal between Barstool Sports and DraftKings secured the book in February as the former's official sports betting partner.
“We’re back to our roots,” Portnoy said at the time. “DK is once again the exclusive sports betting partner of Barstool Sports. The more things change, the more things stay the same.”
