Dave Portnoy has been left with the bitter taste of regret in his mouth after the NCCA men’s championship game.
Back in March, the sports media personality predicted that he would regret not betting on one particular team. On Monday night, that premonition came true.
Florida won its third March Madness title Monday, defeating the Houston Cougars 65-63 in San Antonio.
And all the fans Portnoy urged to wager on a Gators’ victory will be cashing in in the aftermath. All except Portnoy himself, that is.
The Barstool Sports founder has had a rough time of late after losing nearly $20million and counting thanks to Donald Trump’s controversial new tariff plan, which crashed the stock markets last week.
And if that wasn’t bad enough, he had a chance to win some of it back. He just failed to take it.
Dave Portnoy has been left ‘haunted’ by his March Madness wagers after Monday’s final
Final Four Most Outstanding Player Walter Clayton Jr. lifts Florida’s national title trophy
‘I’m gonna regret not betting Florida to win the title at 16-1 when I was telling everybody and their grandmother to bet them to win the title for the rest of my life if they win the title,’ Portnoy said in an X post on March 16.
And, following this week’s result, Portnoy was once again left kicking himself.
‘Officially haunted,’ Portnoy quoted-tweeted the original post after the final result.
It continued a crushing March Madness for Portnoy, who lost a brutal parlay wager Saturday night thanks to Houston’s comeback win.
Duke’s stunning collapse in their Final Four showdown with Houston cost him a $200k parlay at the weekend amid his plummeting stock woes.
Portnoy fumed about his stocks and crypto losses during a Monday morning live stream he manned for nearly an hour on X, as markets opened to general unrest.
The stream quickly devolved into an anti-Trump rant, when he revealed he had suffered some $20m in losses since the trade obstacles were announced last week.
‘This is a decision that one guy made that crashed the whole stock market,’ he raged about the president. ‘That’s why we’re calling it Orange Monday.’
The Barstool chief correctly predicted in March that he would regret not backing Florida
The Barstool founder has lost nearly $20m and counting due to Donald Trump’s tariff plans
‘The stock market is getting crushed. I’ve lost 20 percent of my net worth,’ he continued, before bringing up how Trump over the weekend bragged about being ‘a very low handicap’ at a senior-aged golf tournament in Jupiter, Florida, Sunday.
‘And you’re out on the golf course,’ Portnoy, who has a reported net worth of more than $100million, added.
The Barstool chief has turned on Trump just months after throwing his support behind him in the presidential election.
However, he insists his fury with the 78-year-old is not solely based on his own financial woes.
‘You think if I’m losing money, if the stock market is tanking that only affects rich people?’ he continued. ‘We’re probably affected the least.
‘Yeah I’m losing $20 million, but I still have plenty of money… it all shakes down.
‘Look at Barstool Sports, alright? This economy tanks. Our advertisers, who do business overseas and sell products and advertise with us. They sell less products. It gets more expensive. What’s the first thing they cut? Ad budgets. Ad budgets that we get.
‘Suddenly we’re not getting as much money,’ he went on, juxtaposing the two business models to make his point. ‘Suddenly I have to fire Nate [a Barstool staffer] and lay people off.’
