The gambling problem for this A list celebrity is out of control.

He keeps chasing the big win and is losing insane amounts of money.

Dave Portnoy
David Scott Portnoy is an American businessman and social media personality. He is the founder and owner of sports and popular culture company Barstool Sports.

Dave Portnoy, the Barstool Sports founder, is on an incredible betting hot streak, with a $150,000 wager placed on the Edmonton Oilers to win the Stanley Cup at +700 odds.

If successful, he stands to win $1.2 million.

This bet is part of his overall impressive winnings in 2024, totaling $5.4 million so far, with potential additional earnings of $2.5 million if the NHL and NBA championships go his way.

Portnoy also has a $1.6 million stake in the Boston Celtics winning the NBA Finals.

His recent successes include wins from various sporting events, such as the Michigan Wolverines’ victory on New Year’s Day, the Kansas City Chiefs’ Super Bowl win, and UConn’s national championship.

Portnoy’s betting prowess has seen him rake in millions despite past bankruptcy filings due to gambling losses. Currently, the Oilers are at +115 to win the series, while the Celtics are strong favorites to win the NBA title.