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Jimmy Kimmel Channels Trump, Promises $5,000 to Every Audience Member If Guillermo Wins ‘DWTS’

September 29, 2026
in News
Jimmy Kimmel Channels Trump, Promises $5,000 to Every Audience Member If Guillermo Wins ‘DWTS’

Jimmy Kimmel appeared to pull a Donald Trump on Monday evening in an attempt to keep Guillermo Rodriguez on “Dancing With the Stars.” Specifically, Kimmel promised $5,000 to every audience member at the Brooklyn taping if his sidekick wins the competition.

During Monday’s monologue for “Jimmy Kimmel Live!,” which is taping in Brooklyn for a week of shows, the late-night host explained that his longtime sidekick wasn’t able to join him Monday because he’s still competing on “Dancing With the Stars.”

“I do have some bad news. Our friend Guillermo is not with us tonight. He had to stay back home because he’s been dancing up a storm back home,” he told his studio audience. “I hope you’ve been watching, ’cause he’s been going mirrored balls to the wall on ‘Dancing with the Stars’ – in what many critics are saying is the funniest thing to ever happen.”

He continued: “Guillermo has survived two eliminations despite getting the lowest score both weeks. You know how Mr. Magoo would kind of blindly walk through a construction site and come out unscathed? That’s Guillermo every week now on ‘Dancing with the Stars.’”

Kimmel then cut to a video call with Rodriguez, who shared an update on his progress on the show.

“I’m learning faster. It’s good. I like it,” Rodriguez shared. Per Kimmel, Rodriguez will be dancing the foxtrot to Rupert Holmes’ “Escape (The Piña Colada Song)” on Tuesday.

“I don’t know if you know how popular you are right now, but yesterday after they beat the Bengals, the Steelers, the Pittsburgh Steelers posted this picture of you to celebrate their win,” Kimmel said. “I don’t know what you have to do with the Steelers. You’re a Cowboys fan. But this is a real Cinderella story. Nobody thought Guillermo could succeed. He’s been the lowest scorer every week. And yet, somehow, he has made it to week three like a human Air Bud. We’re all behind him.”

Here’s where Kimmel issued his rallying call to his audience.

“We don’t want to get too comfortable. We need votes to keep this going,” Kimmel said. “Every vote counts. So vote for Guillermo. And this is my promise. If Guillermo wins ‘Dancing with the Stars,’ I will give every American in this theater a check for $5,000.”

However, it remains unclear how serious Kimmel was with his promise, as a transcription of his monologue noted that the late night host added this after the declaration: “Signed by Donald Trump.”

Yet, the crowd’s cheering and clapping was so loud it was hard to hear what exactly Kimmel said after that big cash vow. He notably also quipped: “You hear how stupid that sounds?”

Kimmel was clearly referencing the promise Trump made during his midterm convention speech earlier this month, where he vowed to payout a $5,000 “Trump Dividend” if Republicans retained control of Congress. This promise sparked quite a bit of controversy, with many blasting it as a bribe to voters.

“So, Guillermo, we’ll be watching you tomorrow,” Kimmel said as the crowd settled down. “We will be voting for you tomorrow. Break a leg, but try not to break a leg.”

Watch Kimmel’s full monologue, which featured cameos from Matt Damon and Jon Hamm, above.

“Jimmy Kimmel Live!” airs weeknights at 11:35 p.m. ET on ABC.

The post Jimmy Kimmel Channels Trump, Promises $5,000 to Every Audience Member If Guillermo Wins ‘DWTS’ appeared first on TheWrap.

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