Barstool Sports founder Dave Portnoy says he lost $20 million in just three days due to President Donald Trump's new tariffs—but despite his fury, he insists he doesn't regret voting for the president.

Portnoy, once a vocal supporter of Trump, backed him through previous controversies and policy decisions. But tensions boiled over this week after Trump announced sweeping new tariffs aimed at boosting U.S. manufacturing—what he dubbed "Liberation Day" tariffs, Mediaite reported.

Portnoy, who has a reported net worth of over $100 million, has frequently live-streamed his market commentary and high-stakes bets, blending business with bombast.

On April 7—what Portnoy dubbed "Orange Monday"—the S&P 500 opened with a 4% plunge, capping a staggering three-day slide of 13%, the worst since 2008. During a Monday morning livestream on X, Portnoy revealed he'd lost roughly 20% of his net worth, blaming the president directly for the chaos.

"This is a decision that one guy made that crashed the whole stock market," he ranted, mocking Trump for golfing during the downturn. He also detailed the ripple effects on his company, saying advertiser pullbacks could force layoffs at Barstool.

Despite his anger, Portnoy made it clear he did not regret voting for Trump.

"That's the game." he said. "Do I like it? No. Am I crying, 'Woah is me, I wish I voted for Kamala?' No. Do I wish this didn't go down like this? Yes."

Though markets have since shown slight recovery, with the Dow down about 1.9% by midday Monday, fears of a deeper recession persist. Meanwhile, Trump's administration insists the tariffs will ultimately revitalize U.S. industry.

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Dave Portnoy, Donald trump