Barstool Owner Dave Portnoy Boasts That He Won $2.7 Million on UConn’s NCAA March Madness Victory: ‘Greatest Bet of My Life’

Dave Portnoy, owner of digital media outfit Barstool Sports, said he won $2.76 million on a $600,000 wager that the University of Connecticut men’s basketball team would prevail in the championship game over Purdue.

“The greatest bet of my life,” Portnoy posted on X after the game’s conclusion, alongside a screenshot showing his winning bet on DraftKings. “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.”

The UConn Huskies claimed the 2024 NCAA men’s basketball championship trophy — the team’s second straight title — with their decisive 75-60 win over the Purdue Boilermakers Monday night. This year, Americans were expected to legally bet more than $2.72 billion on the men’s and women’s collegiate national basketball tournaments, according to the American Gaming Association.

Last summer, Portnoy bought Barstool back from casino and online gambling operator Penn Entertainment for $1. That came just months after Penn Entertainment paid a total of about $550 million to acquire 100% control of Barstool, before deciding to part ways with Barstool. Penn’s fire sale of Barstool back to Portnoy came as Penn entered into a major deal with ESPN to rebrand the online sports-betting business from Barstool Sportsbook to ESPN Bet.

At the time of the deal to buy back Barstool Sports, which Portnoy had founded in 2003, he conceded that “we underestimated just how tough it is for myself and Barstool to operate in a regulated world.” According to Portnoy, “We got denied [gambling] licenses because of me. So the regulated industry [is] probably not the best place for Barstool Sports and the type of content we make.”

Portnoy is a graduate of the University of Michigan (which did not make the March Madness tournament this year) with a degree in education.