Barstool Sports founder Dave Portnoy on Monday pocketed a massive chunk of change thanks to what he called “the greatest bet of my life.”
Portnoy backed UConn in their quest for back-to-back titles, and his faith in the Huskies netted him a $2.76 million payout. UConn handily beat Purdue 75-60 to win the 2024 NCAA Tournament championship at State Farm Stadium in Glendale, Ariz.
Portnoy posted his betting slip on X showing that he had wagered $600,000 on UConn to win it all at +360 odds.

“The greatest bet of my life,” captioned Portnoy in his post. “Thank you #uconn Destroyed [sic] 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.”
The greatest bet of my life. Thank you #uconn 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. pic.twitter.com/9MfrUNspyN
— Dave Portnoy (@stoolpresidente) April 9, 2024
The intensity seen on Portnoy’s face was evident as he watched the game live alongside some of his Barstool Sports employees.
STEP ON THEIR THROATS! pic.twitter.com/56KWObVGzN
— Dave Portnoy (@stoolpresidente) April 9, 2024
The UConn-Purdue clash stayed close early with neither team going ahead by more than three points over the first 15 minutes of action. But the Huskies went feral in the second half and led by as many as 18 points to cruise to another title.
Portnoy’s million-dollar return is certainly a huge financial windfall, even for a wealthy man such as himself. But Portnoy arguably got an even bigger monetary win last year that had nothing to do with a massive sports bet.