Dave Portnoy Scores the 'Biggest Win' of His Life on UConn March Madness Bet

It seems as though no one was as hyped about UConn's epic win against the Purdue Boilermakers in Monday night's NCAA men’s basketball national championship game as Barstool Sports founder Dave Portnoy. The 47-year-old revealed that he had placed and won the bet of his life on the Huskies, walking away with a cool $2.7 million.

"The greatest bet of my life. Thank you UConn," Portnoy wrote on X late Monday night. "Destroyed everybody and everything in their path. They'd win the tournament 100 out of 100 times. The biggest win of my life by a mile."

In the accompanying screenshot Portnoy shared, he had placed the wager for $600,000 last month on March 20. And despite the fact that UConn were favored to win, he still scored a $2,760,000 payout. Of course, this adds to Portnoy's already impressive net worth, which is estimated to be at least $100 million.

This also marks the second big win for Portnoy this year, who won $1 million after coming out of gambling "retirement" back in January to place a bet on his alma mater Michigan in the Rose Bowl championship. He had previously given up the habit in 2023 after a "string of monster losses."

But the win is likewise a major one for UConn, which defeated Purdue 75–60 to clinch the team's second straight men's national championship and sixth overall.

"I think it's up there in terms of the greatest two-year runs that a program maybe has ever had," said head coach Dan Hurley after the game. "I just think it's the best two-year run I think in a very, very long time just because of everything we lost from last year's team. To lose that much, and again, to do what we did again, it's got to be as impressive a two-year run as a program's had since prior to whoever did it before Duke."

"To me, it's more impressive than what Florida and Duke did because they brought back their entire teams. We lost some major players," he added.