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As the clock ticks down on President Donald Trump’s latest wave of sweeping tariffs, his usual allies — the podcasters, billionaires, and online firebrands who helped propel him to a second term — are beginning to show signs of unease.
This time, it's not Democrats or Wall Street critics sounding the alarm. It’s Joe Rogan, Dave Portnoy, Ben Shapiro, Bill Ackman, and even Elon Musk — a constellation of Trump-friendly power players who have been fixtures in MAGA media and fundraising circles.
Now, they’re pushing back, publicly questioning the scope, strategy, and sanity of a policy Trump has declared essential to “leveling the global playing field.”
"This is economic nuclear war," hedge fund billionaire Bill Ackman wrote on X. "And it's self-inflicted."
For years, Trump has enjoyed unwavering support from a core of high-profile media and finance figures. Their influence has been instrumental in shaping public perception, funding super PACs, and fueling the culture of loyalty that defines Trumpism.
But in the days leading up to the activation of tariffs that could touch everything from European cars to Canadian dairy, that circle is showing visible cracks.
Even those still backing Trump’s re-election are drawing lines around the policy.
Ben Shapiro, the conservative commentator and Daily Wire founder who once supported Ron DeSantis but now backs Trump, was blunt about the rollout.
“I think that the way that the tariff plan was rolled out is about as bad a rollout as you could do,” he said on the “All-In” podcast over the weekend.
In a separate YouTube video posted Monday — to his 7 million+ subscribers — Shapiro went further, calling the entire concept “really problematic.”
“The idea that this is inherently good and makes the American economy strong is wrongheaded,” Shapiro said. “It’s untrue. The idea that it will result in massive reshoring of manufacturing is also untrue.”
Coming from one of the right’s most articulate voices, it wasn’t just disagreement — it was economic heresy in MAGA terms.
Barstool Sports founder Dave Portnoy, long a loud and loyal Trump backer, said his “Orange Monday” livestream was meant to be non-political. But when the market tanked, so did his portfolio — to the tune of $20 million, or roughly 15% of his net worth.
"I think they’re smarter than me when it comes to these tariffs. I also think he’s playing a high-stakes game here," Portnoy said. “I’m gonna roll with him for a couple days, a couple weeks, see how this pans out.”
His tone was uncertain — more day trader on damage control than political firebrand. And for someone who’s interviewed Trump in the White House, that shift matters.
Joe Rogan, one of the most influential voices in the country with a podcast audience larger than most cable news networks, has voiced multiple criticisms of Trump’s recent direction — and the tariffs didn’t escape his scrutiny.
“This feud with Canada is stupid,” he said, referencing recent tariff-driven tension that led to booing of American athletes in Canadian arenas.
Rogan, who once gave Trump a nearly three-hour platform days before the 2024 election, also recently called wide-scale deportations “horrific” — signaling a slow but notable distance forming between the host and the president.
He hasn’t renounced Trump — but he’s definitely not repeating him.
Bill Ackman, the hedge fund king and occasional economic oracle of the political right, issued an unusually sharp rebuke of Trump’s trade strategy.
“We are heading for a self-induced, economic nuclear winter,” Ackman posted Sunday on X. He later apologized for part of his commentary — notably accusing Commerce Secretary Howard Lutnick of profiting from the collapse — but doubled down on the core message.
“This is a major policy error,” he wrote. “I’m just frustrated watching what I believe to be massive progress wiped out by this move.”
Ackman, who has raised and donated millions in pro-Trump circles, isn’t abandoning the campaign. But he’s clearly signaling that faith has its limits — especially when portfolios are bleeding.
Even Elon Musk, now a key player in Trump’s shadow cabinet for government overhaul, has found the tariff talk hard to swallow.
“I hope it is agreed that both Europe and the United States should move ideally... to a zero-tariff situation,” Musk said in a video conference with Italian officials. He floated the idea of a US–EU free trade zone, calling it “ideal.”
That didn’t sit well with Trump trade adviser Peter Navarro, who told Fox News that Musk “doesn’t understand” the complexity of tariffs.
Musk’s response?
"Navarro is truly a moron. Dumber than a sack of bricks," Musk posted on X — shattering any illusion of unity between Trump’s closest billionaire backer and the administration’s economic brain trust.
What’s unfolding is more than just criticism — it’s a cultural clash within the MAGA machine. For years, the movement has sold itself as pro-business, pro-growth, and anti-regulation. Now, its most famous allies in business and media are being forced to square that identity with a policy they believe is doing real economic damage.
And some are realizing — in public — that they can’t square it at all.
“When people who backed Trump from the jump start questioning the math, that tells you it’s not just political noise — it’s actual damage,” said one GOP strategist privately. “This isn’t a think tank war. It’s their money, their companies, their followers. And it’s at risk.”
For now, most of Trump’s influential supporters are staying in the tent, hoping the tariffs either pay off or quietly fade from focus. But behind the scenes, pressure is mounting — and more voices are joining the skepticism.
Some see this as a test of how far loyalty will stretch, especially as elections near, and the economy wobbles.
“A lot of these guys — Portnoy, Ackman, even Musk — they’re gamblers, risk-takers. But even gamblers like to know the odds,” the strategist added. “And right now, the odds look bad.”
Trump may still control the party. He may still dominate the headlines. But he no longer controls the narrative — not entirely.
The same media machines and megaphones that once echoed every rally cry are now asking real questions, and the answers from Trumpworld — when they come — sound defensive, rushed, and increasingly hollow.
