Dave Portnoy is looking to bounce back from his recent financial woes in tonight’s March Madness final between the Florida Gators and Houston Cougars.
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 as if that wasn’t bad enough, Duke’s stunning collapse in their Final Four showdown with Houston cost him a $200k parlay at the weekend.
Despite his bad luck over the past week, Portnoy hasn’t lost any faith as he lines up another bet on the men’s championship game between the Cougars and the Gators on Monday night.
Houston guard Emmanuel Sharp has the power to turn his fortunes around, with the tycoon backing him to score 12 points or more in San Antonio, Texas.
As part of a special DraftKings parlay, which also includes bets on Monday’s MLB game between the Boston Red Sox and the Toronto Blue Jays, he will also tick off a section of his parlay if either team fights back from five points down to win.
Dave Portnoy is seeking financial redemption in tonight’s March Madness showpiece
The Barstool founder has lost nearly $20m and counting due to Donald Trump’s tariff plans
It is unclear how much he has wagered on the four-leg parlay, but Portnoy is desperate to land ‘one more winner before this thing goes “boom” on me’ amid his stocks troubles.
‘I’ve got nothing to say, I’m still kind of reeling,’ he admitted. ‘But that’s what I’ve got.’
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 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.
Portnoy says Trump’s tariffs have caused his fortune to slump by a significant amount
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.’
For those March Madness fans wanting to get on board with tonight’s action, the Gators are -118 favorites with FanDuel.
