Late-Night Rekindling: Kimmel and O’Donnell’s On-Air Trump Takedown Ignites Presidential Fury and Mar-a-Lago Mayhem

By James Poniewozik and Michael M. Grynbaum Washington — Nov. 26, 2025

WASHINGTON — The embers of one of President Donald J. Trump’s most enduring celebrity grudges burst into flames Tuesday night on “Jimmy Kimmel Live!,” as host Jimmy Kimmel welcomed Rosie O’Donnell for a raucous reunion that skewered the president over his handling of the Jeffrey Epstein files and long-buried personal barbs. The segment, a whirlwind of biting satire and unfiltered reminiscence, left the El Capitan Theatre audience in stitches — and Mr. Trump in a midnight rage on Truth Social, with shock waves rippling to his Mar-a-Lago club where donors recoiled from the spectacle.

Ms. O’Donnell, the comedian and former “The View” co-host whose 2006 spat with Mr. Trump — sparked by her calling him a “snake-oil salesman” and his retort labeling her a “real loser” — has defined two decades of mutual vitriol, joined Mr. Kimmel to promote her new memoir, “Rosie’s Revenge: Laughing Through the Fire.” What started as a nostalgic nod to their shared history devolved into a full-throated assault on Mr. Trump’s recent reluctance to fully declassify Epstein documents, which Ms. O’Donnell tied directly to the president’s past social ties with the financier. “Jimmy, Don and I go way back — he sued me, I prayed for his cell in Rikers, and now he’s hiding files that could finally air out the dirty laundry,” Ms. O’Donnell said, brandishing a prop Rolodex card emblazoned with “Trump: ‘Terrific guy who likes ’em young.’” The studio exploded in laughter and cheers as Mr. Kimmel deadpanned, “Rosie, you’ve got more dirt on him than the EPA has on Flint — but at least they release their reports.”

The takedown escalated when Ms. O’Donnell recounted her January relocation to Ireland, a move she attributed to Mr. Trump’s reelection and threats of media crackdowns — a decision echoed by celebrities like Ellen DeGeneres and, more recently, Mr. Kimmel’s own acquisition of Italian citizenship as a “backup plan.” “I left because I couldn’t breathe the same air as a guy who’d deport his own bad hair day,” she quipped, prompting Mr. Kimmel to unveil a split-screen of archival footage: Mr. Trump’s 2016 inauguration alongside Ms. O’Donnell’s iconic “The View” impression of him as a blustery buffoon. “See? Even then, we knew — it’s all bluster, no backbone,” Mr. Kimmel added, as the crowd chanted “Rosie! Rosie!”

Aired at 11:40 p.m. Eastern, the eight-minute bit amassed 3.1 million YouTube views by 1 a.m., surging to the top of X trends under #RosieRoastsTrump and #KimmelODonnellRevenge. Posts flooded the platform: One from a progressive activist read, “Rosie just dropped the mic on Mar-a-Lago — Trump’s face must be redder than his ties!” while a MAGA counterpunch fumed, “Two has-beens peddling 20-year-old grudges. FCC, time to yank ABC for good.” Prediction markets on Polymarket spiked the odds of renewed FCC scrutiny on ABC to 22 percent, invoking the shadow of Mr. Kimmel’s September suspension over a monologue mocking the assassination of conservative activist Charlie Kirk.

Mr. Trump’s eruption was predictably volcanic. At 12:58 a.m. — mere minutes after the West Coast feed wrapped — he unleashed a 17-post Truth Social fusillade. “Slob Rosie O’Donnell, the fat, ugly disaster who BEGGED me for forgiveness (she didn’t get it!), crashes LOSER Kimmel’s DYING show to spew LIES about Epstein! I threw that creep out of my club — unlike Rosie, who throws tantrums! Kimmel’s a no-talent hack, ratings in the toilet. FCC, REVOKE ABC NOW — or I will!” The barrage, viewed 12.4 million times by morning, recycled slurs from their 2006 feud — when Mr. Trump threatened lawsuits and Mr. Kimmel, then an emerging host, stayed neutral — but laced them with fresh demands for regulatory reprisal, echoing his July prediction that late-night shows like Mr. Kimmel’s were “next to go.”

The pandemonium spread to Mar-a-Lago by 1:15 a.m., where Mr. Trump was presiding over a high-dollar donor mixer themed “Transparency Thanksgiving.” Club members, including real estate tycoons and tech investors, had tuned into the segment on communal iPads — a misguided bid by event planners to “lean into the buzz.” The room fractured instantly. “It was like a grenade went off: Laughter from the never-Trumpers, stunned silence from the loyalists,” said one guest, a Palm Beach financier who spoke anonymously to preserve access. Two major contributors, sources confirm, slipped out mid-toast, firing off emails to aides about “recalibrating support” amid the “circus optics.” By 2 a.m., Mr. Trump, according to witnesses, hurled a crystal tumbler — ketchup optional — while dialing FCC Chair Brendan Carr, the suspension’s architect, to vent: “These witches are killing us — make it hurt!”

This clash revives the Kimmel-Trump war, a saga spanning Oscars read-alongs of mean tweets in 2024 and Mr. Trump’s aborted 2015 “Jimmy Kimmel Live!” appearance. Ms. O’Donnell’s role amplifies the stakes; her signature on the September open letter from 400 entertainers — protesting the Kimmel blackout alongside Ben Stiller and Mark Ruffalo — had already irked the White House. Now exiled in Ireland, she framed the appearance as “exile edition payback,” telling Mr. Kimmel off-air: “From Dublin with disdain — free speech isn’t a suggestion; it’s a superpower.” The Epstein angle, meanwhile, dovetails with bipartisan pressure for unredacted releases, a bill Mr. Trump signed Monday under duress, prompting Ms. O’Donnell’s on-air zinger: “He’s all for draining swamps — except when his golf buddies are the alligators.”

Conservative media pounced at dawn. Fox News’s Sean Hannity labeled the segment a “Hollywood hex,” urging boycotts of Ms. O’Donnell’s book and speculating on ABC’s license woes. On X, Trump allies amplified the posts, with one thread claiming the reunion was “deep state scripted” to sabotage holiday fundraising. Democrats, by contrast, crowed: House Minority Leader Hakeem Jeffries retweeted a clip with, “Rosie and Jimmy: The dynamic duo democracy needs. Trump’s tantrum? Just more deflection.”

Critics discern a pattern in Mr. Trump’s celebrity skirmishes, from Alec Baldwin to Stephen Colbert. “He thrives on the fight — it’s his brand — but this one bleeds donors and boosts ratings for Kimmel,” said Bill Carter, author of “The Late Shift.” ABC reported a 28 percent viewership spike Wednesday, its strongest since the suspension lift. Polling from Emerson College shows Mr. Trump’s “media handling” approval at 39 percent among independents, with Epstein transparency cited as a drag.

For Ms. O’Donnell, 63, the night was cathartic closure to a feud that birthed memes and merchandise. “I won’t sue for peace — I’ll roast till he’s well-done,” she told backstage reporters, hugging Mr. Kimmel. He signed off with a nod to their shared exile vibes: “Rosie, if Italy calls, save me a villa. Until then, to Don: Keep tweeting; we’ll keep laughing.”

At Mar-a-Lago, the mixer dissolved into awkward small talk over pie, with one donor quipping, “We paid for prime rib, got prime time drama.” As Mr. Trump motored to the links at sunrise, waving off questions with “Fake fight, real winners — us!,” the episode encapsulated his second term’s tightrope: Unyielding base adoration clashing with a cultural backlash that no executive order can mute. In the arena of outrage, where a grudge from 2006 fuels 2025 headlines, comedy proves the ultimate unassailable foe — and the grudge, eternally evergreen.