Barstool Sports founder Dave Portnoy keeps his sports betting hot streak alive with a $1.35 million score on Scottie Scheffler’s Masters win.
On April 10, Dave Portnoy posted a screenshot of his $300,000 bet on Scottie Scheffler to win the Masters. In the comments, one poster called it a “sucker” bet, while another called it a “donation,” alluding to Scheffler’s potential withdrawal from the tournament.
Keep the momentum. For people who wanted me to hedge for is why I didn't. So I could take another shot at glory. #DKPartner #scotty pic.twitter.com/X9a0X8HOTZ
— Dave Portnoy (@stoolpresidente) April 10, 2024
Scheffler was a favorite at +450. But not all favorites are “sucker” bets. After all, Scheffler was the 2019-20 PGA Rookie of the Year and won the Masters in 2022. He’s been the No. 1 ranked golfer since March 2022.
As several posters noted, however, Scheffler had stated that he would withdraw from the tournament should his wife go into labor. Covers reporter, Geoff Zochodne, posted on the social media site “X” about the risk to bettors should that happen. But Scheffler’s wife held on – and so did he.
— Geoff Zochodne (@GeoffZochodne) April 15, 2024
Portnoy’s recent win is just one of many high-profile bets he’s cashed. For instance, his bet on Michigan in the Rose Bowl delivered a cool million. He scored $500,000 on Washington in the Sugar Bowl and another $500,000 on the Kansas City Chiefs for their Super Bowl victory. His biggest recent win was more than $2 million when the Connecticut Huskies won the NCAA Men’s Basketball Championship. All told, that’s more than $5 million in winnings for the Barstool Sports owner.
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
Portnoy’s Biggest Win – Buying Back His Own Company
Portnoy’s biggest score, however, wasn’t from a bet placed on DraftKings. It was arguably buying back his media company – and one time sportsbook – for exactly $1.
In 2020, Penn Entertainment acquired 36% of Barstool Sports for $163 million. In Feb. 2023, Penn bought the rest of Barstool for $388 million. Granted, Portnoy owned less than 50% of the company by then, although he still made a pretty penny on the deal. But somehow, the deal got even better – and weirder – six months later.
In Aug 2023, Penn sold Barstool Sports back to Portnoy for $1. There is a clause that says Penn will receive 50% of the purchase price if Portnoy later sells the company. Portnoy, however, has said that he’ll now keep the company “till I die.”
In Feb 2024, Portnoy signed a multi-year deal with DraftKings. When the deal was announced, Portnoy said, “We’re back to our roots. DK is once again the exclusive sports betting partner of Barstool Sports. The more things change, the more things stay the same.”
