Ask Rosie OâDonnell if thereâs anyone she hates more than Donald Trump and she doesnât hesitate: âNo.â To her, heâs not just a political opponent. Heâs a liar, a fraud, and a man New Yorkers have known for decades as all branding, no backbone. And thanks to Jimmy Kimmel, that truth has been broadcast to millionsâover and overâon live TV.

The feud began long before Trump ever stepped into the White House. December 20, 2006: Trump holds a cringey press conference about Miss USA Tara Conner, lecturing the country about âsecond chancesâ and moral values. Rosie, sitting at The View table, watched this serial adulterer lecture a 20-year-old about morality and snapped.
âHe left his first wife, had an affair, left the second wife, had an affair, had kids both times,â she said. âAnd heâs the moral compass for 20-year-olds in America? Donald, sit and spin, my friend.â
Then she messed with the one thing Trump cares about most: his image. She pushed her hair over her forehead to mimic his combover, called him a snake-oil salesman who inherited daddyâs money, and shredded his self-made myth in under a minute. The audience roared. Trump lost it.
He called People magazine and promised Rosie would ârue the words she said,â sneered about her weight, and bragged about wanting to âtake money out of her fat little pockets.â From that moment, it stopped being a joke. For nearly 20 years, Trump turned Rosie into a personal obsessionâmocking her at conferences, on TV, and even during the 2015 GOP primary debate, where he responded to a question about insults toward women with a smirking âOnly Rosie OâDonnell.â
Rosie later said his attacks were the worst bullying sheâd ever experienced in her lifeâworse than anything from childhoodâbecause it was national, constant, and âsanctioned by society.â Crowds laughed, media replayed it, and the most powerful man in the world made her his favorite punchline.

Then Jimmy Kimmel joined the fight.
Kimmelâs been torching Trump for years, but as Trumpâs power and paranoia grew, so did the stakes. When Trump ranted about Kimmelâs Oscars hostingâcalling him talentless and begging ABC to âget the bum off the airââKimmel read the post live, thanked âPresident Trumpâ for watching, and asked, âIsnât it past your jail time?â It was savage, and Trump clearly watched every second.
As Trumpâs scandals piled upâEpstein files, pardoned drug kingpins, war-crime allegations over Venezuelan âdrug boatâ strikesâKimmel went from late-night clowning to full-blown public cross-examination. He hammered Trumpâs obsession with approval ratings, mocked his âperfectâ cognitive tests, and pointed out the absurdity of a president with lower favorability than diarrhea and P. Diddy combined.
Meanwhile, Trumpâs fixation on Rosie got darker. In March 2025, at an event with Irelandâs prime minister, a MAGA reporter joked that Rosie would âlower Irelandâs happiness.â Trump grinned and agreed. In July, he crossed a frightening line: posting that he was âseriously consideringâ stripping Rosie of her U.S. citizenship because she was ânot in the best interest of our countryâ and should stay in Ireland.
It was impossible, unconstitutionalâand chilling. Constitutional experts slammed it. Rosie answered with a photo of Trump and Jeffrey Epstein and a caption that cut straight through the bluster: he hates that she sees him exactly as he is.
By then, Rosie had already left. On January 15, 2025, just days before Trumpâs second inauguration, she moved to Ireland with her daughter and service dog, saying sheâd only return when it was safe for all citizens to have equal rights. âHe is a dangerous, soulless man with dementia who lacks empathy, compassion, and basic humanity,â she said bluntly.
Kimmel is now planning his own escape hatch. In August 2025, he revealed heâd secured Italian citizenship and admitted Trumpâs America was âso much worseâ than even his darkest expectations.
And when Trumpâs regime tried to silence Kimmel? That just proved their point.
After Kimmel joked about Trumpâs reaction to the Charlie Kirk assassination, FCC chair Brendan Carr used mob-style language to threaten ABCâs license. Nexstar and Sinclair pulled Jimmy Kimmel Live. Disney suspended him. Trump cheered online.

But the backlash was immediate. Free-speech advocates erupted. Ted Cruzâyes, that Ted Cruzâcompared the FCCâs language to a mob shakedown from Goodfellas. Under pressure, Disney brought Kimmel back. His return episode shattered ratings records. The attempt to muzzle him had turned him into a symbol of resistance.
Now youâve got Rosie in Ireland, Kimmel with an Italian passport, both still hammering Trump from opposite sides of the Atlantic. Rosie calls him a âcriminal con manâ whose cruelty knows no bounds. Kimmel calls out his hypocrisy, his obsession with revenge, and his terror of the Epstein files.
Trump wanted to destroy them. Instead, he made them bigger, sharper, and harder to ignore.
Because hereâs what he never understood: you can threaten licenses, rant on social media, and fantasize about revoking citizenshipâbut you canât bully comedy into silence. You canât sue away the fact that millions of people have now watched you be exposed, mocked, and stripped of your myth in real time.
And nothing is more dangerous to a man like Donald Trump than a world thatâs finally laughing at him, not with him.
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