President Donald Trump’s recent actions—refusing to bring back a Maryland man wrongly deported to El Salvador, expressing interest in deporting U.S. citizens, and cracking down on free speech at universities and media outlets—prompted comedian Jon Stewart to compare him to some of the world’s most infamous authoritarian leaders.
In Monday night’s episode of The Daily Show, Stewart launched into a satirical segment called “How Authoritarian Are We?” where he examined Trump’s behavior and persona through an authoritarian lens.
From the lavish and gaudy décor of the Oval Office to his loyal, praise-singing cabinet and questionable medical reports, Stewart ranked Trump alongside names like Vladimir Putin, Xi Jinping, and even fashion mogul Anna Wintour.
Though Stewart has previously called out liberals for overusing the term “fascist” when describing Trump, he admitted his stance may be shifting in light of Trump’s growing hostility toward the press, judges, lawyers, and other critics.
In one clip, a reporter asked Trump if he would consider deporting U.S. citizens. Trump responded, “If it’s a homegrown criminal, I have no problem… I’m talking about really bad people.
Really bad people.” Stewart reacted, saying, “He’s going to do that to U.S. citizens? I think the hosts of The View are about to get administratively error’d.”
“I didn’t think we’d get this authoritarian this fast,” Stewart continued. “Who could’ve predicted it? Maybe if someone had yelled at me on Bluesky in all caps, I’d have known.”
He also showed video clips of top Trump officials like Secretary of the Interior Doug Burgum, Homeland Security Secretary Kristi Noem, and Secretary of State Marco Rubio heaping exaggerated praise on the president.
But Stewart pointed out that true authoritarian leaders don’t just demand respect—they demand uncomfortable and often humiliating displays of loyalty.
To illustrate this, he rolled footage of Trump’s cabinet laughing awkwardly at one of his jokes, emphasizing the eerie forced laughter common under autocratic regimes.
Stewart wrapped up the segment by summarizing, “Trump checks all the authoritarian boxes: the image, the behavior, the nonstop assault on dissent.”
But he added that what Trump lacks is the cold, effective execution typical of more competent strongmen. Referencing Trump’s economic missteps, the chaos caused by tariffs, a spike in measles cases, and the erratic actions of the Department of Government Efficiency (DOGE), Stewart remarked, “He still hasn’t sealed the deal with ruthless competence.”