PoliticsWhy Donald Trump’s White House Keeps Turning Late-Night Jokes Into Bigger Stories
Rosie O’Donnell mocked Donald Trump and Natalie Harp during her ‘Jimmy Kimmel Live!’ guest-hosting stint.
Aug. 25 2026, Published 7:14 a.m. ET
The Trump White House keeps proving late-night hosts’ favorite point: it cannot resist taking the bait.
Rosie O’Donnell, guest-hosting Jimmy Kimmel Live!, opened her August 19 monologue with a “special hello” to Washington and a joke about President Donald Trump’s aide Natalie Harp.
“That’s all I’m gonna say about you tonight, sweetheart,” O’Donnell said, before adding, “You gotta realize it’s time to hang up your wig and let Natalie tuck you in.”
The White House fired back at Rosie O’Donnell after her late-night jokes about the president.
The White House answered with a statement from spokesperson Davis Ingle: “Rosie O’Donnell is a nasty woman and a total slob whose brain has been completely destroyed by Trump Derangement Syndrome.”
The Joke Gets a Second Life
Rosie O’Donnell continued with her Donald Trump jokes throughout her guest-hosting week.
O’Donnell’s Kimmel stint has leaned into her long-running feud with Trump. On Monday, August 17, she waved to the president and called him “Mango Mussolini.” On Tuesday, she joked that Trump had helped put her “back in the spotlight” and called him “Oompa J. Loompa.”
The White House response arrived as O’Donnell was drawing strong numbers for the show. LateNighter reported that her Monday episode brought in 1.87 million total viewers, citing preliminary Nielsen Live+Same Day figures, making it the biggest audience for any Kimmel guest host this summer so far, with those numbers expected to grow as delayed viewing is added in the following days. Her opening monologue has also passed 2.8 million YouTube views as of August 21.
- Joe Scarborough Says White House Turned Natalie Harp Into a National Meme by Overreacting to Scrutiny: 'They Blew This Up Into a Massive Story'
- CNN Panel Accuses Scott Jennings of Double Standard in Heated Jon Ossoff Debate: 'You Have No Idea How Dishonest You Are'
- Megyn Kelly Lashes Out at Jimmy Kimmel Over 'Widow' Remark: 'He's Desperate'
Want OK! each day? Sign up here!
When Outrage Becomes Oxygen
Her Donald Trump jokes gained renewed attention after the White House responded publicly.
“Generally speaking I think most of the response to comedians is unwise,” said Samantha Karlin, CEO of Empower Global.
“The latter are exercising freedom of speech and utilizing satire to highlight salient political issues, and serving to the public often incredibly dark news, and the only way the public can digest it is by laughing at the incredulity of it,” she explained.
“When the admin reacts it just shows that they don’t know how to laugh at themselves and are allergic to free speech,” she added.
The Natalie Harp Lesson
Joe Scarborough said that the administration’s reaction helped make the Natalie Harp story bigger.
The same dynamic has played out around Harp, Trump’s executive assistant. After Sen. Jon Ossoff said in a speech that Trump would rather “build his ballroom and travel with Natalie” than do his job, the White House blasted CNN’s Kristen Holmes for asking about the comment, and coverage snowballed from there.
On Morning Joe, host Joe Scarborough argued the administration’s reaction to the “throwaway” line made Harp into a bigger story.
“For the White House to freak out like that, to melt down like that, they made this story, well, into something it would not have been,” he said. “Just a classic miscalculation inside the White House from a White House that’s been doing that to everybody else for a decade now.”
