Jimmy Kimmel Roasts Trump’s White House Demolition: ‘We Should Have Made Him Put Down a Security Deposit’ | Video

“Is it possible that he’s planning to sell the White House?” the late night host asks

Jimmy Kimmel hosting the Oct. 27, 2025 edition of "Jimmy Kimmel Live!" (Credit: ABC)
Jimmy Kimmel hosting the Oct. 27, 2025 edition of "Jimmy Kimmel Live!" (Credit: ABC)

In his first episode back from break, Jimmy Kimmel told viewers he has returned to America just as confused about the current state of the country as those he met during his vacation overseas.

“In case you’re wondering what other countries think about what’s going on here in our country, I’ll tell you, they’re worried about us,” Kimmel announced, after briefly recapping his family’s trip to Ireland. “They’re worried about us in the same way you worry about a nephew who maybe you haven’t seen for a few years who shows up at Thanksgiving missing all his front teeth.”

“They had a lot of questions I couldn’t answer, like, ‘Why is he knocking down the White House?’” Kimmel explained, referencing President Trump’s recent demolition of the White House’s East Wing to make room for his new ballroom. “I don’t know. Nobody knows. I don’t think he even knows.” The “Jimmy Kimmel Live!” host revealed that his family just so happened to visit Ireland the week of its presidential election.

After Catherine Connolly beat Heather Humphreys in the election, Kimmel noted that Humphreys wished her opponent “the very, very best” as president. “No caps, no whining about the election being rigged,” Kimmel observed, before joking, “Makes you wonder what’s wrong with these people.” He then teed up footage of “unrest” in Portland, only to reveal that the clips were actually of the White House’s Trump-sanctioned partial destruction.

“Oh, that’s what Trump did on purpose without permission to the White House,” Kimmel realized. “I told you we should have made him put down a security deposit.” You can watch Monday’s full “Jimmy Kimmel Live!” monologue yourself in the video below.

Kimmel noted that Trump has spent an awful lot of time since he took office again in January redecorating and redesigning parts of the White House and its grounds. “Trump is behaving less like a president and more like a Property Brother,” the “Jimmy Kimmel Live!” host remarked. “Is it possible that he’s planning to sell the White House? He’s going to fix it up and flip it on us.”

Later, Kimmel rolled a clip of Trump telling reporters that Texas congresswoman Jasmine Crockett and New York congresswoman Alexandria Ocasio-Cortez would never be able to pass the cognitive test he reportedly took during a recent, presidential health exam. “There’s only one way to find out,” Kimmel said in response. “Let’s do it on TV. Let’s put together the biggest and greatest IQ test of all time. Donald Trump versus Jasmine Crockett. Crockett versus Tubs and AOC.”

“Let’s make this happen,” Kimmel offered. “I’m willing to do whatever. I’ll host it. I’ll produce the whole thing. I’ll pay for it. ‘Grandpa Don’s Dementia Bowl,’ folks. Maybe we could make it the undercard before that UFC fight they’re having on the White House lawn. All proceeds go to fund the government.”

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