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Donald Trump Calls Rosie O'Donnell A 'Nasty Woman' And 'Total Slob' Through His Rep After She Replaces Jimmy Kimmel On 'Live': 'Trump Derangement Syndrome'

August 23, 2026 by Abigail Connolly
shefinds | Celebrity
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A new development has occurred in the feud between Rosie O’Donnell and President Donald Trump, and one of his reps did not hold back when recently insulting her.

The president and comedian’s decades-long feud has been reignited after she used her brief stint as guest host of Jimmy Kimmel Live! to repeatedly take aim at the president. After several nights of jokes targeted at the 80-year-old, the White House fired back on Thursday, with a spokesperson releasing a series of insults at the 64-year-old actress. This opens another chapter in one of the entertainment industry’s most infamous celebrity wars, which dates back to 2006. Read more about the situation below.

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"Donald Trump and Rosie O'Donnell feud"

Rosie O'Donnell Took Aim At Donald Trump Throughout Her Jimmy Kimmel Live! Guest-Hosting Gig

The former View co-host stepped behind the desk on the popular late-night show on Monday, August 17th, while Jimmy Kimmel was away on his summer break. She received a standing ovation when she made her debut and quickly made it clear that her version of the late-night show would include plenty of comments about the president. During her opening monologue, she mentioned her decision to move to Ireland following Trump getting re-elected and warned viewers to "buckle up" if they thought Trump already disliked Kimmel's show.

 

"If you thought the president hated Jimmy Kimmel Live when it was hosted by Jimmy Kimmel, buckle up, people," she joked during her opening monologue, eventually telling the president directly, "Hi, I know you're watching."

 

Rosie continued her jokes throughout the week, giving the president a series of mocking nicknames from "Mango Mussolini" to "Oompa J. Loompa." On Wednesday, August 19th, she also took a jab at White House aide Natalie Harp, telling Trump it was time to "hang up your wig and let Natalie tuck you in."

A Rep For President Trump Responds To Rosie's On-Air Comments

Given that her episodes of the famous late-night talk show had gone viral and were viewed by millions of people through social media and more, it didn't take long for the Trump administration to respond, specifically, a representative for him. The latest exchange between the two popular figures is hardly the first time they've gone after one another.

 

Their feud began around 2006 when O'Donnell criticized Trump on The View and questioned Trump's authority to act as a "moral compass" in relation to the Miss USA pageant and mocked his business history, prompting Trump to respond with his own insults. Since then, their feud, which primarily takes place online, has only intensified as he entered politics and became president twice.

 

Now, after nearly two decades of public back-and-forth, the White House has responded to the comedian's latest round of jokes on television. As reported by Entertainment Weekly, on Thursday, August 20th, spokesperson Davis Ingle responded, "Rosie O'Donnell is a nasty woman and a total slob whose brain has been completely destroyed by Trump Derangement Syndrome."

 

The statement came just one day before Rosie's final show on Jimmy Kimmel Live!, so she clapped back with a parody song about the president, set to the tune of the classic ballad, "Danny Boy."

 

"Oh Donny boy, it's Rosie, Rosie calling," she sang. "From Hollywood, the Jimmy Kimmel show. Drop that Big Mac that we all know you're holding, because, my dear, I worry for you so. Poor Donny boy, your polls, your polls are falling. Your reflecting pool is green as Mountain Dew. Your wig's a mess, your ballroom is appalling, and with Iran you bit off more than you can chew."

Author:

Editorial Assistant

Abigail is a journalist based in Brooklyn, New York. As an Editorial Assistant for SheFinds, she covers topics ranging from celebrity news and fashion to wellness. She has written for other publications, including Chip Chick, Bandsintown, BroadwayWorld, and more. When she isn't writing, Abigail loves spending time in the city with her friends, being a 'dog mom' to her Chihuahua, and singing along to some of her favorite music.

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