Barstool Founder Dave Portnoy just won the biggest bet of his life.
At the onset of March Madness, Portnoy wagered $600,000 on the UConn Huskies at +360 with the hope for a run that another championship run would culminate in a $2.16 million profit.
And he won big Monday night with UConn’s 75-60 win over Purdue.
“The greatest bet of my life,” Portnoy said in a post on X. “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.”
Portnoy also said he hadn’t “even considered that I could lose this bet.”
And he didn’t need to think about it much throughout a second-half rout, although he displayed some uneasiness after UConn’s Donovan Clingan picked up an early foul that half.
“Huge foul. Just huge. Game back on now. Ass clenched to infinity,” he posted.
But UConn was simply a freight train on its way to the winner’s circle.
Its dominant victory over Zach Edey and the Purdue Boilermakers was another cover.
This was likely bad news for most bookies, who had a significant liability on UConn’s future market, with Portnoy being the largest reported bet on DraftKings.
The Huskies rolled through their competition, hardly being threatened en route to their back-to-back national championships.
The phrase “good teams win but great teams cover” applies to the Huskies more than most.
The Huskies not only won all six games but also covered each one, with the 86-72 Final Four win over Alabama as 10-point favorites being their biggest threat not to cover.
In fact, UConn covered against the spread (ATS) in every game during their back-to-back title runs, going 12-0. Action Network’s Evan Abrams reported that UConn is the first team ever to accomplish that feat.
Assuming -110 odds for each spread, if a bettor had started with $100 and rolled over the winnings of all six bets, they would be up $4,841.27.
This is to say that if Portnoy wasn’t just confident in a UConn national championship win but also to do it in the dominant fashion that they did, he could’ve rolled over some of that $600,000 into an ATS spread system that would’ve paid a pretty penny.
If he had invested $100,000 of his $600,000 initial stake and rolled over every bet ATS, Portnoy would’ve won roughly $4.841 million.
But for now, Portnoy can sit back and watch DraftKings pay him a fat check on this sports betting victory, one of many that the sportsbook has been paying him in recent months.