Dave Portnoy Lost Out On $1 Million Through Oilers Bet But Is Trying To Win It Back With A World Series Gamble

Dave Portnoy, the founder of Barstool Sports, is known for betting large sums of money in sporting events.

What Happened: Despite a recent hot streak, including winning nearly $1.5 million when the Boston Celtics won the NBA finals, Portnoy’s luck seemed to run out when he lost a $150,000 bet that would have netted him more than $1 million on the Edmonton Oilers to win the Stanley Cup.

Portnoy seemed undeterred by the loss. He shared a DraftKings Inc DKNG bet slip showing that he placed $200,000 on the Philadelphia Phillies to win the 2024 World Series at +600 odds. That means he would win $1.2 million if the Phillies end up taking home the championship.

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Basically: Barstool, one of the leading sports media companies in the country, partnered with DraftKings after Penn Entertainment PENN sold Barstool back to Portnoy for $1. Penn, which previously ran the Barstool Sports book, now operates the ESPN Bet sports book. 

Past Wins: Portnoy has also netted money by betting on top golfer Scottie Scheffler.

Portnoy had a two-leg parlay of Scheffler winning the RBC Heritage in April and the Celtics to win the NBA Championship.

Scheffler's odds of winning the tournament were more than +500, while the Celtics' odds at the time were around +150. Both legs were victorious and the bet paid out more than $1.5 million in winnings on a $100,000 bet.

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