In a whirlwind of market chaos and political pivots, Barstool Sports founder Dave Portnoy has made headlines with a stunning about-face, seemingly abandoning his long-standing loyalist support for President Donald Trump.
The catalyst?
A stock market nosedive triggered by Trump’s aggressive tariff policies, which Portnoy claims cost him millions.
In a candid interview with CNN’s Dana Bash on Inside Politics last week, the outspoken media mogul signaled he’s ready to swim for calmer waters, even hinting at a potential vote for Democrats if the economic turbulence persists.
This was later overshadowed by Portnoy’s use, or lack thereof, of a hammer trying to nail a 1×1 with a roofing nail into a fence, but failing.
Portnoy, once a vocal Trump ally who attended the president’s inauguration and championed his campaigns since 2016, appeared rattled by the financial fallout of Trump’s trade war.
“I’m down millions,” Portnoy told Bash, estimating losses as high as $20 million—roughly 15 to 20 percent of his net worth—due to the market’s reaction to tariffs imposed on April 2.
Labeling the downturn “Orange Monday” on his Davey Day Trader livestream, he didn’t mince words about the economic gamble.
“If the stock market keeps tanking, we’re headed for an economic meltdown,” he warned, a far cry from his usual bravado.
The CNN sit-down marked a stark departure from Portnoy’s typical MAGA-friendly rhetoric. While he insisted he’s “not some crazy MAGA guy,” his frustration was palpable as he criticized Trump for golfing in Florida amid the market’s freefall.
“I voted for Trump, I support him, but I look at each candidate,” Portnoy said, emphasizing his independence.
When Bash pressed him on whether he’d consider backing Democrats in the 2026 midterms, he didn’t hesitate: “Absolutely.” For a man who once called Democrats “arrogant” and morally superior, this was no small leap.
Portnoy’s pivot isn’t just personal—it’s a potential bellwether. Known for commanding the elusive 18- to 35-year-old male demographic, his influence stretches far beyond Barstool’s “bro culture” empire. He told Bash his audience isn’t “jumping ship” on Trump yet, but their loyalty hinges on economic stability.
“The left is far more intolerant of me,” he noted, yet his willingness to entertain a Democratic vote suggests a crack in the Trump coalition’s armor.
The timing of Portnoy’s CNN appearance, just before Trump announced a 90-day tariff pause that sparked a market rebound, only adds to the drama. Portnoy reportedly recouped $8.2 million in investments after the pause, but his public hand-wringing had already set the internet ablaze. Social media lit up with reactions, from MAGA diehards calling him a traitor to liberals gleefully amplifying his critique.
“Dave Portnoy knows you can’t play poker with the economy,” one X user quipped, echoing a sentiment Portnoy himself voiced.
This isn’t Portnoy’s first brush with Trump criticism—he previously slammed the administration over a leaked Signal chat exposing war plans, calling it a “f***-up of epic proportions.”
But his latest move feels different: less a fleeting rant, more a calculated step toward political flexibility.
“I think he’s playing a high-stakes game,” Portnoy said of Trump, still hedging his bets. Yet his flirtation with CNN’s safer harbor signals he’s not afraid to jump ship if the waters get too rough.
As the midterms loom and markets remain volatile, all eyes are on Portnoy. Will he stay adrift, or fully dock with a new political crew? For now, one thing’s clear: the Barstool boss isn’t afraid to make waves.