• Jimmy Kimmel compared Trump’s Iran negotiation style to bad sex during his Wednesday night monologue
• Kimmel also mocked Trump’s bizarre Oval Office remarks to children about transgender athletes
• The feud with the White House is escalating — both Donald and Melania Trump are publicly calling for Kimmel’s firing
• The FCC has ordered a review of ABC’s station licenses amid pressure from the Trump administration
• Constitutional law experts say any legal threats against Kimmel are “utterly frivolous” and protected by the First Amendment

Jimmy Kimmel had a lot to work with this week — and he used every bit of it.

In his Wednesday night monologue on Jimmy Kimmel Live!, the late-night host unloaded on President Donald Trump’s ongoing negotiations with Iran, delivering what may be his most memorable line of the year. “For him, a negotiation, it’s like sex,” Kimmel said. “He’s bad at it. It mostly consists of flailing around. And he can only do it for a short amount of time before he starts yelling that he’s finished.”

He opened the bit with a pointed question about the Strait of Hormuz — “I wonder which will open first, the Strait of Hormuz or his ballroom?” — before settling into a full takedown of the White House’s handling of the Iran conflict. Kimmel mocked reports that a deal could be imminent, noting that the details were “still very much in flux. As in, what the flux are we doing over there?”

He also drew a pointed comparison to the Obama-era nuclear deal — the one Trump spent years calling the worst deal in history — noting that the proposed new agreement would reportedly include a uranium enrichment moratorium of more than 10 years, shorter than the Obama deal’s 15-year restrictions. “And now he’s going to top it by making an even worse worst deal in history,” Kimmel said. “It’s called ‘The Art of the Deal.’ Folks, you should read the book.”

Kimmel also took aim at the administration’s ever-shifting vocabulary around the conflict. “One of the most ridiculous things about this war is that half the time they talk about it, they don’t call it a war because you’re supposed to get approval from Congress to go to war, which Trump did not do,” he said. After playing a clip of Trump describing the situation, Kimmel tracked the linguistic evolution in real time: “First it was an excursion, then it was a mini war. And now it’s a skirmish. Next month it’ll be a tiff. It’ll be a $200 billion tiff.”

“This Man Is Insane”

The Iran riff came a night after Kimmel was equally floored by Trump’s Tuesday Oval Office event — a ceremony to reinstate the Presidential Physical Fitness Award, which quickly went somewhere else entirely.

Surrounded by grade-school children and administration officials, Trump riffed on Iran, why he deserved a Nobel Peace Prize, the planned UFC fight on the White House lawn, and then — pivoting sharply — “transgender mutilization.” He caught himself mid-rant, told the kids “don’t listen to this,” and then kept going anyway.

“This man is insane, OK?” Kimmel said flatly. “He made up a word, ‘mutilization,’ and he’s telling children about it. Next thing you know, he’ll be telling them his favorite story, the tale of the lady weightlifter.”

Sure enough, in the next clip, Trump was doing exactly that — repeating a story from his campaign trail days about a transgender weightlifter, directing it at a preteen boy. “You’ll never compete against women in powerlifting,” Trump told the child. “Do you think you can take me in a fight?”

Kimmel’s response was pure deadpan: “Very, very normal. Just a totally lucid, very rational, clear-minded, level-headed person sharing his thoughts on gender reassignment with a group of young kids. That’s our guy.”

Kimmel also flagged a moment where Trump appeared to suggest a young girl in attendance — a volleyball player — was too short for the sport and should try soccer instead. The host’s reaction was, again, withering sarcasm.

The Feud That Won’t Quit

All of this is unfolding against the backdrop of the most intense stretch of the long-running Kimmel-Trump feud. It started in earnest on April 23, when Kimmel joked during a “pretend roast” segment that Melania Trump had “a glow like an expectant widow” — a line he later said was “a very light roast joke about the fact that he’s almost 80 and she’s younger than I am.” Two days later, a gunman was charged with attempting to assassinate the president at the White House Correspondents’ Dinner.

Melania issued a rare public statement, calling Kimmel’s rhetoric “hateful and violent” and demanding action from ABC. “People like Kimmel shouldn’t have the opportunity to enter our homes each evening to spread hate,” she wrote. “A coward, Kimmel hides behind ABC because he knows the network will keep running cover to protect him.”

Trump, for his part, called Kimmel “a lowlife, whether he apologized or not” during an appearance on Newsmax. White House communications director Steven Cheung called for Kimmel to be fired “immediately” and “shunned for the rest of his life.” A White House spokesperson told The Daily Beast this week that “nobody in their right mind wants to watch or listen to Jimmy Kimmel, who is a talentless hack with failing ratings.”

The pressure hasn’t been just rhetorical. The FCC last week ordered a review of ABC’s station licenses, with the Trump-aligned agency citing possible violations of federal law — a move widely seen as connected to the administration’s campaign against the network. Disney, ABC’s parent company, is facing mounting pressure on multiple fronts.

Kimmel has not backed down. On Monday, he poked fun at an uncaptioned photo Trump posted on Truth Social showing Melania smiling. “At 11:04, he posted this even more unbelievable picture of Melania smiling,” Kimmel said. “I don’t know the last time we saw that.” He also riffed on Trump’s claim — made at a Florida retirement community — that Melania “hates” when he dances to “Y.M.C.A.” at rallies. “What a buzzkill,” Kimmel said. “Why would she hate that? It’s so much fun. He’s just trying to have fun.”

On Wednesday, he also mocked Secretary of State Marco Rubio’s upcoming meeting with Pope Leo XIV, noting that the pope had publicly rebuked Trump’s stance on nuclear weapons. “Marco Rubio plans to sit down with Pope Leo to discuss the attacks from our president, the war on Iran, and on a personal level: why God didn’t answer his prayers for smaller ears,” Kimmel joked. He then showed viewers a close-up of Rubio wearing oversized Florsheim shoes — reportedly a gift from Trump that Rubio was too afraid to decline — and said incredulously, “This is the guy who’s going to confront the pope.”

As for the legal threats swirling around him, constitutional law scholar Robert McWhirter, author of Fixing the Framers’ Failure, is unambiguous about where Kimmel stands. “From the very founding of the American republic, ridiculing public officials hasn’t merely been tolerated, it’s been explicitly protected by the First Amendment,” McWhirter said. “These lawsuits are pure theater. It’s a show of claimed offense designed to deter speech.”

Kimmel, for his part, seems to have figured that out. When asked recently about his apparent knack for making jokes that land him in hot water, he offered his own explanation: “Every day in the morning, I wake up, I make coffee, and then I look into the future to see which events have yet to occur and then we write jokes we know are going to make trouble.”

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