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Dave Portnoy, the Barstool Sports founder, is seeking to recoup recent financial losses by placing a significant wager on tonight’s March Madness championship game featuring the Florida Gators and Houston Cougars. This high-stakes sports betting move comes as Portnoy grapples with substantial financial setbacks linked to Donald Trump’s tariff plan, which has negatively impacted the stock market. His attempt to recover losses is focused on the college basketball championship.
Portnoy Bets on March Madness Final Amidst Financial Downturn
The Barstool Sports head has reportedly experienced a challenging period recently, with losses nearing $20 million due to the market instability triggered by former President Trump’s newly proposed tariff policies. These policies are cited as the primary cause for the recent stock market decline.
Duke’s Defeat Adds to Portnoy’s Betting Woes
Adding to his financial strain, the unexpected defeat of Duke University in their Final Four matchup against Houston resulted in a $200,000 parlay loss for Portnoy over the weekend. This unsuccessful wager further compounded his recent monetary challenges.
Undaunted, Portnoy Places New Bet on Cougars vs. Gators
Despite the previous week’s misfortunes, Portnoy remains confident, venturing another substantial bet on the men’s championship game between the Houston Cougars and the Florida Gators on Monday evening. He aims to reverse his current losing streak with this latest wager.

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Betting on Emmanuel Sharp to Lead Houston
Portnoy’s hopes for a turnaround are partially pinned on Houston guard Emmanuel Sharp. The media personality is betting on Sharp to score at least 12 points in the game held in San Antonio, Texas. This player-specific bet forms a key part of his overall parlay.
Multi-faceted Parlay Includes MLB Game and Comeback Condition
As part of a DraftKings parlay, Portnoy’s wager extends beyond the March Madness final. It also includes bets on Monday’s Major League Baseball game between the Boston Red Sox and the Toronto Blue Jays. Additionally, a leg of his parlay hinges on whether either team in the basketball final can overcome a five-point deficit to secure victory.
Dave Portnoy is aiming for financial recovery in tonight’s March Madness final.
The Barstool Sports founder has reportedly lost nearly $20 million due to Donald Trump’s tariff proposals.
“One More Winner” Needed Amidst Stock Concerns
The exact amount wagered on this four-leg parlay remains undisclosed. However, Portnoy expressed a strong desire to secure “one more winner before this thing goes ‘boom’ on me,” indicating anxiety regarding his ongoing stock market difficulties.
“Still Reeling” from Financial Hits, Says Portnoy
“I’ve got nothing to say, I’m still kind of reeling,” Portnoy admitted, conveying his shock and disappointment. “But that’s what I’ve got,” he added, referring to his new betting strategy.
Portnoy’s Anti-Trump Rant and Stock Market Losses
Portnoy voiced his frustration regarding his stock and cryptocurrency losses during a live stream on X, lasting nearly an hour on Monday morning as markets opened amid widespread unease. His commentary quickly shifted to criticism of Donald Trump.
$20 Million Loss Attributed to Trump’s Trade Policy
During the stream, Portnoy revealed that he had incurred approximately $20 million in losses since the announcement of the trade barriers the previous week. He directly blamed the former president’s policies for his financial downturn.
“Orange Monday” and Criticism of Trump’s Golf Outing
“This is a decision that one person made that crashed the whole stock market,” Portnoy asserted, referring to President Trump. “That’s why we’re calling it Orange Monday,” he stated, highlighting the market’s negative reaction. He further elaborated, “The stock market is getting crushed. I’ve lost 20 percent of my net worth,” and criticized Trump for reportedly boasting about his golf skills at a senior tournament in Florida over the weekend, while the market was in turmoil.
Net Worth Impact and Golf Course Criticism
“And you’re out on the golf course,” Portnoy, whose estimated net worth exceeds $100 million, remarked, expressing his disapproval of Trump’s leisure activities during the financial crisis he believes Trump instigated.
Shift in Political Stance: Portnoy Criticizes Trump
The Barstool Sports leader’s recent outburst marks a notable shift in his political alignment. Portnoy has now publicly criticized Trump just months after apparently offering his endorsement in the presidential race. This criticism is primarily driven by the financial repercussions of Trump’s policies on Portnoy’s investments.
Portnoy contends that Trump’s tariffs have caused a significant decline in his wealth.
Economic Impact Beyond the Wealthy, Portnoy Argues
However, Portnoy maintains that his discontent with the 78-year-old politician is not solely motivated by his personal financial woes. He insists that the trade policies impact a wider spectrum of individuals and businesses.
Broader Economic Repercussions of Tariff Policies
“You think if I’m losing money, if the stock market is tanking that only affects rich people?” he questioned. “We’re probably affected the least.”
Trickle-Down Effect on Businesses Like Barstool Sports
“Yeah I’m losing $20 million, but I still have plenty of money… it all shakes down,” he acknowledged, before explaining the broader economic impact. “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.”
Job Security Concerns and Advertising Budget Cuts
“Suddenly we’re not getting as much money,” he continued, drawing a parallel between the macro-economic impact and his business operations. “Suddenly I have to fire Nate [a Barstool staffer] and lay people off,” he concluded, highlighting potential job losses due to the broader economic downturn spurred by the tariffs.
FanDuel Odds for March Madness Final
For those interested in participating in tonight’s March Madness action, the Florida Gators are currently favored at -118 with FanDuel, indicating their slightly higher probability of winning according to current betting odds. This provides context for those considering wagering on the championship game.