Will Trump’s Deportation Plan Be Done With a ‘Fine Tooth Comb?’ Questions Jon Stewart

On Monday night’s episode of The Daily Show, comedian Jon Stewart took sharp aim at Donald Trump’s proposed deportation plan, urging viewers to consider whether it would be carried out with any sense of precision. Stewart’s critique centered around Trump’s ambitious pledge to “launch the largest deportation program in American history,” a plan that left Stewart questioning its feasibility.

Stewart opened his monologue by poking fun at The Washington Post‘s sudden decision to stop endorsing presidential candidates. “Normally, I just vote for who the Washington Post endorses,” he quipped. “But I’m not an Amazon Prime member, so…” The comedian then targeted the Kamala Harris campaign’s recent rally, where pop icon Beyoncé made an appearance — but surprisingly, did not perform.

“No singing?” Stewart asked in disbelief. “Just a heartfelt statement on the importance of the election? F– it, I’m voting for Trump.” Transitioning to Trump’s deportation plan, Stewart expressed skepticism over its scale and lack of clear strategy. He poked fun at the idea that Trump’s first day would involve anything so enormous.

“Day one? Have a snack, and meet the staff! Day one, we typically just read the syllabus!” Stewart joked. He then showed a clip of Trump citing the 1798 Alien Enemies Act as the legal foundation for his deportation efforts, adding, “Who the f— told Donald Trump about the Alien Enemies Act of 1798? Because I’m going to bet you something. He did not come to the meeting and go, ‘Hey, why don’t we use the 1798 Alien Enemies Act?’”

Stewart also mocked Trump’s imprecision, sharing a clip where Trump struggled to provide a clear estimate of undocumented immigrants, throwing out numbers from 2 million to 21 million. Stewart remarked sarcastically, “But listen! They’re all bad! They’ve all committed terrible crimes! And we’ve cataloged — without due process — the terrible things they’ve done, yes?”

Stewart then played a clip where Trump repeated a baseless conspiracy theory that Haitian immigrants in Springfield, Ohio, are abducting and eating people’s pets. He followed this with a series of Trump’s claims that he would deport not just undocumented immigrants, but even Special Counsel Jack Smith, who is prosecuting an election subversion case against him.

Taking his argument further, Stewart highlighted Trump’s repeated mix-ups in the past, like when he confused former San Francisco Mayor Willie Brown with Los Angeles councilman Nate Holden and misidentified a photo of E. Jean Carroll — his accuser in a sexual assault case — as his ex-wife, Marla Maples. Stewart jabbed, “You know what I just realized? Donald Trump doesn’t have affairs — he just thinks everyone is his wife.”

In a final critique, Stewart questioned the logic of entrusting such a massive deportation effort to someone with Trump’s track record. “If Trump can’t identify his second wife in a photo, what makes Americans think he cares about who gets deported?” he asked.