The Baltimore Ravens weren’t the only ones to kick off the NFL season on a sour note—Barstool Sports founder and notorious high-stakes gambler Dave Portnoy also took a major hit. Portnoy, known for his penchant for placing large wagers, lost a whopping $300,000 after betting on the Ravens to defeat the Kansas City Chiefs in their season opener.
The game’s dramatic finish left Portnoy devastated. In the final moments, it appeared that the Ravens had tied the game when tight end Isaiah Likely caught a potential game-tying touchdown pass from Lamar Jackson in the back of the end zone. Ravens head coach John Harbaugh had even signaled his intention to go for a two-point conversion, setting up what could have been a thrilling win.
However, heartbreak struck for both Ravens fans and Portnoy when officials reviewed the play and determined that Likely had stepped out of bounds by the smallest of margins, with the edge of his cleat just outside the line. The pass was ruled incomplete, sealing the Ravens’ 27-20 loss and leaving Portnoy out $300,000. With the Ravens at +130 odds, Portnoy stood to gain a massive $390,000 if Baltimore had pulled off the upset.
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This isn’t the first time Portnoy has placed such an enormous bet. The Barstool Sports boss is known for making headline-grabbing wagers across multiple sports. Just last month, he placed $100,000 on the Indiana Fever to win the WNBA championship. In the NBA, Portnoy bet $1.1 million on the Boston Celtics to win the championship, while also placing a $1 million bet on the Edmonton Oilers to win the Stanley Cup. The Celtics’ playoff success kept Portnoy afloat, but the Oilers’ early exit saw him lose big in the NHL.
Portnoy, who once filed for bankruptcy, has since found financial success through his media empire, allowing him to routinely gamble large sums on sports events. He’s a self-described sports fanatic, frequently placing bets on some of his favorites, including Iowa basketball star Caitlin Clark, golfer Scottie Scheffler, and, of course, his beloved Boston sports teams.
In a live stream of the Ravens game, Portnoy’s emotions were on full display. Initially, he celebrated when Likely appeared to score the game-tying touchdown, visibly excited as Harbaugh signaled the Ravens would attempt a two-point conversion for the win instead of settling for overtime. But the celebration was short-lived. When the play was overturned, Portnoy’s hopes—and his $300,000—vanished.
Despite the devastating loss, Portnoy’s penchant for high-stakes betting is unlikely to slow down. Known for his resilience and bravado, he’ll likely be back with another massive wager soon, chasing the thrill of the next big win.
