As President Donald Trump’s tariffs send shockwaves through global financial markets, a surprising number of prominent conservatives and influential supporters from the media, tech, and finance worlds are beginning to question his approach despite having previously backed his agenda. With the new tariffs now in effect, the backlash is growing louder, even among Trump allies.
Conservative commentator Ben Shapiro, who supported Florida Gov. Ron DeSantis in the GOP primaries before aligning with Trump, didn’t hold back during a recent appearance on the “All-In” podcast. He criticized the chaotic rollout of the tariff plan, saying it felt “contradictory” and poorly executed. Shapiro doubled down on his YouTube channel, telling his seven million subscribers that the idea tariffs would strengthen the U.S. economy was “really problematic” and “untrue.” He also dismissed the notion that the tariffs would lead to a large-scale return of American manufacturing.
Barstool Sports founder Dave Portnoy, known for his unapologetic support of Trump, appeared shaken by the market fallout. “Welcome to Orange Monday,” he joked on his financial livestream earlier this week, referencing Trump as he reviewed his own losses initially estimating he was down $7 million, later updating that figure to closer to $20 million. Despite the hit to his portfolio, Portnoy said he’s still backing Trump for now. “I’m gonna roll with him for a couple days, a couple weeks, see how this pans out,” he said, while also acknowledging that Trump is playing a “high-stakes game.”
Joe Rogan, a podcast giant who has been influential among younger and independent voters, criticized Trump’s recent clash with Canada. Calling the trade tensions “stupid,” Rogan said Canadian fans even booed Americans during sporting events in protest of the tariffs. He has also voiced opposition to Trump’s aggressive deportation policies, calling them “horrific.”
Even longtime Trump booster and hedge fund manager Bill Ackman expressed alarm. On social media, Ackman warned of a “self-induced, economic nuclear winter” if the tariffs continue unchecked. While he walked back some of his harsh words about Commerce Secretary Howard Lutnick, whom he accused of being indifferent to the market collapse, Ackman reiterated that he believes Trump’s policies could derail the economic progress made in recent months.
Elon Musk, perhaps Trump’s most powerful ally in reshaping the federal government, also criticized the tariff strategy. Musk warned that the import taxes would raise costs for American consumers and for Tesla, his electric vehicle company. He proposed a bold alternative: zero tariffs between the U.S. and Europe to create a North Atlantic free trade zone. Musk’s suggestion drew a dismissive response from White House trade adviser Peter Navarro, who claimed the billionaire “doesn’t understand” trade policy.
Musk fired back sharply, calling Navarro “truly a moron” and “dumber than a sack of bricks.”
This wave of dissent among Trump’s supporters especially those with significant influence over public opinion and financial markets signals a growing concern that the president’s aggressive trade policies could backfire economically and politically. With Wall Street rattled and key allies expressing skepticism, questions are emerging about whether Trump’s tariff gamble will deliver results or spark deeper trouble ahead.