Joe Rogan and Dave Portnoy

President Donald Trump’s aggressive tariff policies have long been a cornerstone of his economic agenda. But as new tariffs take effect, sparking market turmoil and international tension, even some of his most loyal supporters are raising eyebrows. High-profile figures like podcast giant Joe Rogan, Barstool Sports founder Dave Portnoy, and conservative commentator Ben Shapiro—all once vocal Trump allies—are now openly questioning the strategy. Here’s why these influential voices are pushing back and what it means for Trump’s political momentum.  

1. Joe Rogan: “The Feud With Canada Is Stupid”

Joe Rogan, whose endorsement of Trump ahead of the 2024 election shocked many, has not held back his criticism. In March, Rogan slammed Trump’s tariff-driven feud with Canada as “stupid,” especially after Canadian fans booed U.S. teams at sporting events over the policy. “It’s embarrassing,” Rogan said, highlighting how the tariffs have strained diplomatic relations .  


But tariffs aren’t the only issue where Rogan has broken ranks. He recently called Trump’s mass deportation operations “horrific,” signaling a broader rift on immigration policy. Despite this, Rogan’s three-hour pre-election interview with Trump helped solidify the president’s hypermasculine, anti-establishment image—a move that now feels at odds with his current critiques .  

2. Dave Portnoy’s $20 Million Lesson

Dave Portnoy, the brash Barstool Sports mogul and longtime Trump supporter, is feeling the tariff pain in his wallet. On his “Davey Day Trader” livestream, Portnoy dubbed the market chaos “Orange Monday” as stocks and crypto plummeted. He revealed losses of up to $20 million—roughly 15% of his net worth—blaming the tariffs for spooking investors .  


Yet, Portnoy isn’t abandoning Trump. “He’s a smart guy playing a high-stakes game,” Portnoy said, vowing to “roll with him for a couple weeks” to see if the strategy pays off. His loyalty stems from years of support, including a 2020 White House interview with Trump. But his financial bruises show how the tariffs are hitting even die-hard backers where it hurts .  

3. Ben Shapiro: “Tariffs Don’t Make Us Rich

Conservative commentator Ben Shapiro, who initially backed Ron DeSantis in the GOP primary, called Trump’s tariff rollout “about as bad as you could do.” On his podcast and YouTube channel (with 7 million subscribers), Shapiro argued that tariffs are “really problematic” and won’t revive U.S. manufacturing as promised. “The idea that this makes the economy strong is wrongheaded… It’s untrue,” he said .  


Shapiro’s critique focuses on contradictions in Trump’s messaging. While he still supports the president, his warnings reflect growing anxiety among conservatives that the tariffs could backfire economically. 

4. Elon Musk vs. the White House: A “Moron” Fight

Elon Musk, a Trump advisor, has clashed publicly with the administration over tariffs. Musk warned that tariffs would raise costs for Tesla and urged a “zero-tariff” free trade zone with Europe. When White House trade adviser Peter Navarro claimed Musk “doesn’t understand” the issue, Musk fired back on X, calling Navarro “truly a moron” and “dumber than a sack of bricks” .  


The White House dismissed the feud as “boys will be boys,” but the spat underscores deeper tensions. Musk’s push for free trade contrasts sharply with Trump’s protectionist agenda, putting the billionaire at odds with key advisors .  

5. Bill Ackman’s “Economic Nuclear Winter” Warning

Hedge fund manager Bill Ackman, another Trump ally, issued dire predictions on social media. He likened the tariffs to “economic nuclear war” and warned of a “self-induced nuclear winter” if Trump doesn’t rethink the policy. Ackman also blasted Commerce Secretary Howard Lutnick as “indifferent” to the market crash, though he later apologized for the remark .  


Despite his frustration, Ackman acknowledged Trump’s past economic successes. “We were making huge progress… now it’s at risk,” he wrote, capturing the conflicted stance of many Trump backers .  

Why This Matters

Trump’s tariffs aim to boost U.S. manufacturing and pressure trading partners, but the backlash from his own camp reveals three key issues:  

1. Economic Uncertainty: Portnoy’s losses and Ackman’s warnings show tariffs are rattling markets.  

2. Diplomatic Strains: Rogan’s criticism of the Canada feud highlights damaged international relations.  

3. Ideological Splits: Shapiro and Musk represent a growing divide between free-market conservatives and Trump’s protectionism.  

The Bigger Picture: Loyalty vs. Policy

What’s striking is that none of these figures have abandoned Trump entirely. Portnoy insists Trump is “smarter than me,” while Rogan’s podcast interview helped galvanize the president’s base. Even Shapiro and Musk couch their critiques with lingering support. This balancing act shows Trump’s hold on his coalition—but also its fragility if economic pain deepens .  

Conclusion

Trump’s tariffs are more than a policy debate—they’re a stress test for his alliance with populist influencers. As Joe Rogan, Dave Portnoy, and others voice doubts, the president faces a tricky choice: double down on tariffs or adjust course to keep his base intact. For now, these critics are sticking with Trump… but their patience isn’t unlimited.