zz 📢 BREAKING NEWS: Rosie O’Donnell reveals the 20-year Trump obsession that drove her to Ireland as Jimmy Kimmel destroys him on live TV🔥

Ask Rosie O’Donnell who she hates most on Earth and she doesn’t hesitate: Donald Trump.
Not because of a petty personal grudge—but because, as she’s said over and over, he’s a liar, a fraud, and a fake. And if you grew up in New York, you knew that long before he ever set foot in the White House.

This feud didn’t start in politics. It started with a beauty pageant and a billionaire who thought he was America’s moral compass.

December 20, 2006.
Rosie is on The View. Trump has just held a self-righteous press conference about Miss USA Tara Conner, who’d been caught drinking underage and allegedly using cocaine. Instead of firing her, Trump stepped up as “Mr. Second Chance,” preaching morality like a televangelist with a spray tan.

Rosie was done.

She ripped into him on live TV:
He left his first wife, had an affair. Left his second wife, had an affair. Had kids both times. But now he’s the moral compass for 20-year-olds? “Donald, sit and spin, my friend.”

Then she pushed her hair forward to mimic his infamous combover, called him a snake oil salesman, and exposed the myth of the “self-made” Trump—reminding viewers he was just a rich kid who inherited daddy’s money.

The audience howled.
Trump snapped.

Within hours he was on the phone with People magazine, spitting venom: Rosie would “rue the words,” he’d “most likely sue her,” and—of course—he went straight for her body, fantasizing about taking money from her “fat little pockets.” He bragged later that he “hit that big pig face,” and joked about whether she was “fat” in front of business audiences like this was normal presidential material.

Rosie told People years later that it was the worst bullying she’d ever experienced—even worse than her childhood. It wasn’t just insults. It was national. It was sanctioned. The crowd laughed, the media replayed it, and Trump realized something terrifying: cruelty paid.

Fast forward to August 2015, the first Republican primary debate. Moderator Megyn Kelly confronts Trump about calling women “fat pigs, dogs, slobs, disgusting animals.” He cuts her off with two words that bring the house down:
“Only Rosie O’Donnell.”

It wasn’t true. He’d said it about many women. But he knew her name was a trigger. Her humiliation was his applause line.

Rosie never backed down. She called him what psychiatrists in the book Duty to Warn later described in clinical language: a narcissistic, mentally unstable man unfit for office. She called him a cruel criminal, a con man, a racist buffoon. She even urged Melania—after a speech on “courage”—to divorce him, take their son, and run.

Trump never forgot it. He never forgave it. And once he had presidential power, he weaponized his obsession.

As president, he mocked her on the world stage. At one point, after Ireland’s prime minister was asked if Rosie might lower Ireland’s happiness level, Trump gleefully agreed. He celebrated her leaving the United States. He publicly cheered the fact that she lost work. Imagine a president of the United States celebrating an American losing her job. That’s not leadership. That’s revenge.

Meanwhile, Jimmy Kimmel was circling into the fight.

From his late-night desk, Kimmel repeatedly shredded Trump’s behavior: his low approval ratings, his lies about the economy, his refusal to release the Epstein files. He joked that Trump had a lower rating than “Diddy and diarrhea,” and suggested if Trump really wants to boost his numbers, he could start by unsealing those Epstein records.

Kimmel read out Trump’s long, bitter posts attacking him by name, then fired back with nuclear one-liners: “Thank you for watching. I’m surprised you’re still up. Isn’t it past your jail time?”

As Trump raged over late-night jokes, real lines were crossed. In July 2025, Trump posted that he was “seriously considering” stripping Rosie of her U.S. citizenship because she was “not in the best interest of our great country” and should stay in Ireland. That’s not a joke. That’s authoritarian thinking out loud.

Constitutional lawyers immediately pointed out: You can’t revoke citizenship because someone hurt your feelings on daytime TV. But the message was clear—criticize him, and he will come for you.

Rosie responded with a photo of Trump and Jeffrey Epstein and a caption that cut deeper than any punchline: the president has always hated that she sees him exactly as he is.

She moved to Ireland in January 2025, taking her daughter and their dog. She said she’d return to America when it was truly safe and equal for all citizens. Kimmel, for his part, quietly secured Italian citizenship—his own escape hatch in case the slide into authoritarianism continued.

Trump wanted to silence them.
Instead, he created two of his fiercest enemies:
Rosie, broadcasting from abroad—and Jimmy Kimmel, mocking him nightly, calling out his cruelty, his lies, and his fear of the Epstein truth.

Because here’s what Trump never learned:
You can bully, threaten, and rage—but you can’t sue your way out of who you really are when the whole world is watching.