Jimmy Kimmel’s Savage Monologue on Don Jr. Sparks Eruption From Trump Scion, Igniting Family Feud and Online Frenzy

By Sarah Ellison The New York Times November 23, 2025

LOS ANGELES — Donald Trump Jr., the president’s eldest son and a vocal architect of the MAGA movement, unleashed a torrent of fury on social media Friday after Jimmy Kimmel devoted a segment of “Jimmy Kimmel Live!” to what the host called the “dirty secrets” of Don Jr.’s business dealings and personal life — a blistering 9-minute roast that left the studio audience in hysterics and prompted rumors of a full-blown Trump family meltdown.

The monologue, aired Thursday night and viewed by 4.8 million — a 12 percent uptick from the prior week — zeroed in on Don Jr.’s recent ventures, including a $75 million cryptocurrency fund tied to his father’s memecoin and a memoir sequel reportedly ghostwritten amid plagiarism allegations. Mr. Kimmel, leaning into the camera with his trademark wry grin, opened with a clip from Don Jr.’s latest Fox News appearance, where he defended the family’s Saudi investments as “smart business, not grift.” “Smart business?” Mr. Kimmel echoed, flashing a graphic of the fund’s logo superimposed on a cartoon pig — a nod to his father’s “Quiet, piggy!” retort to a reporter last week. “Don Jr.’s out here hawking crypto to MAGA grandmas while his dad dines with MBS. It’s less ‘Triggered’ — his book title — and more ‘Rigged’ for the Saudis.”

The audience howled, many doubling over as Mr. Kimmel escalated. He replayed a 2024 audio leak from Don Jr.’s podcast, where the 47-year-old boasted of “closing deals in Dubai that make Hunter Biden look like a choir boy,” juxtaposed with emails from a House Oversight probe alleging the fund funneled $12 million from foreign donors to Trump-aligned PACs. “These are the receipts, Don: Your ‘smart business’ is just family grift with a blockchain bow,” Mr. Kimmel said, holding up a prop folder labeled “Don Jr.’s Little Black Ledger.” The line detonated the room — cheers, whistles and a spontaneous chant of “Re-leasel Re-leasel” referencing the Epstein files — forcing the house band to improvise a transition as confetti cannons fired.

Mr. Kimmel didn’t spare the personal. He mocked Don Jr.’s 2018 Moscow trip — the infamous Trump Tower meeting with Russian operatives — as “the family’s speed-dating disaster with Putin,” and quipped about his ex-wife Vanessa’s 2018 divorce filing: “Divorce papers hit harder than Kimmel’s ratings. Sorry, Don — even your prenup couldn’t save you from alimony Armageddon.” The savage delivery, laced with clips from Don Jr.’s hunting trips and a 2023 tabloid exposé on his alleged affair, drew uneasy laughter from some, but the crowd’s ovation lasted 40 seconds, spilling into the aisles.

By 1:02 a.m. Friday, Don Jr. erupted on X, posting a 300-word thread: “Crooked Jimmy Kimmel, ratings in the toilet, digs up ancient smears to attack me and my family because he can’t handle TRUTH. My business is transparent — unlike Hunter’s laptop! This is deep-state desperation. ABC, get the bum off air NOW! #MAGA #Triggered2.” The thread, viewed 7.5 million times by midday, included a video of Don Jr. pacing in what appeared to be his Florida home, face flushed, gesturing wildly: “Kimmel’s a fraud — I’ll sue him into oblivion!” It drew cheers from MAGA influencers like Charlie Kirk, who retweeted: “Don Jr. fighting back — Kimmel’s done!” But it also sparked infighting: Steve Bannon, on his podcast, accused Don Jr. of “going soft” by not naming Soros explicitly, while Eric Trump liked a post calling the response “weak sauce.”

At Mar-a-Lago, where the president was hosting a donor brunch, the fallout was immediate. Two people familiar with the morning, speaking on condition of anonymity, described Mr. Trump watching the monologue on a side screen during breakfast, slamming his coffee cup down at the “grift” line. “Don Jr.’s a fighter — Kimmel’s a loser!” he reportedly bellowed, dictating a supportive Truth Social post at 1:47 a.m.: “Great son Don Jr. owns fake news clown Kimmel! Low-rated has-been exposes his jealousy. Full Epstein truth coming — Dems in PANIC! #MAGA.” Press secretary Karoline Leavitt amplified it, accusing Mr. Kimmel of “coordinated smears with House Dems,” but insiders say the family views the roast as a harbinger of Epstein scrutiny, with Don Jr.’s fund mentioned 17 times in preliminary files.

The segment’s viral reach — #DonJrDirtySecrets hit 8.3 million posts on X, with TikTok duets of the “prenup Armageddon” line racking up 20 million views — has shattered fragile GOP alliances. Moderates like Senator Susan Collins distanced themselves, tweeting: “Humor’s fair game, but let’s focus on policy, not personal attacks.” Democrats pounced: House Oversight Ranking Member Jamie Raskin demanded a probe into the fund, quipping on MSNBC: “Kimmel’s receipts hit harder than Don Jr.’s excuses.” A Cygnal poll released Friday shows Mr. Trump’s approval at 38 percent — a low — with independents citing family business ties as a top concern amid the shutdown.

For Don Jr., whose post-2024 pivot to crypto and books has netted $45 million but drawn ethics complaints, the takedown risks amplifying perceptions of nepotism. Allies like Brian Ballard defended him on Fox News: “Don’s building empires — Kimmel’s building jokes.” But even they worry it distracts from midterms.

Mr. Kimmel, whose contract expires in May, addressed the backlash in a post-credits clip: “If exposing grift is a crime, guilty. Don Jr., debate invite stands — bring the ledger.” ABC executives, bracing for FCC heat from Trump appointee Brendan Carr, demurred on comment, but sources say they’re prepping for affiliate pushback like September’s suspension.

In Trumpworld, where feuds fuel the fire, Mr. Kimmel’s roast wasn’t just savage — it was seismic. As clips flood feeds and the family scrambles, one insider summed it: “Don Jr.’s eruption? That’s the sound of the house of cards wobbling.” With Epstein files due next week, this late-night thunderbolt may herald a stormier horizon.