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"Hi, I Know You're Watching!": Rosie O'Donnell Waves at Trump in Explosive Kimmel Guest-Hosting Debut

Rosie O'Donnell sat behind a late-night desk Monday for the first time in decades, and she used it to reignite one of America's longest-running celebrity feuds. Guest hosting "Jimmy Kimmel Live!" while Jimmy Kimmel vacations, the comedian aimed her opening monologue squarely at President Donald Trump, explained why she fled to Ireland two years ago, and finished by smiling into the camera with a message for the man himself: "Hi, I know you're watching!"

EntertainmentBy J. Mendez2h ago4 min read

Last updated: August 19, 2026, 11:15 AM

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"Hi, I Know You're Watching!": Rosie O'Donnell Waves at Trump in Explosive Kimmel Guest-Hosting Debut

"Buckle Up, People!"

O'Donnell opened with a warning to the audience, then got straight to work. Reflecting on her run hosting "The Rosie O'Donnell Show" from 1996 to 2002, she noted she had not sat behind a TV desk in more than 30 years and marveled, sarcastically, at how much has changed.

"Well back then, there was a war in the Middle East, climate change was ravaging our planet, we had a president who was embroiled in scandals," she deadpanned. "But today, everything is so chill."

"Mango Mussolini" and the Move to Ireland

The monologue's centerpiece was the story of her 2024 exit from the United States.

"I've been living in Ireland for the past two years because of Mango Mussolini," O'Donnell said. "I read that Project 2025 and said, 'Gotta get myself out of here.' And I decided to go to Ireland, a place where people are driven to drink regardless of who's running their country."

She took her then-11-year-old child Clay along, with strict instructions to keep the move quiet to avoid press and paparazzi. Clay proceeded to tell the entire class.

O'Donnell impersonated the farewell: "I'm very sorry, I won't be able to graduate sixth grade with you. I'm being forced to move to another country because the president of the United States hates my mother. But in all fairness, I believe my mother hates him more."

Then came the wave at the camera, and the line of the night, directed at the White House.

No Fear of the FCC

The monologue landed at a tense moment for ABC, and O'Donnell walked into it unbothered. Earlier this month, asked on the "On with Kara Swisher" podcast whether she worried about FCC Chairman Brendan Carr or censorship during her hosting week, she shrugged the question off.

"What are they gonna say, that you can't say that?" she said. "I don't listen to them. I don't pay any heed to them."

The Lawsuit That Followed Hours Later

The timing proved almost cinematic. Just hours after O'Donnell's monologue aired, ABC filed a lawsuit Tuesday against the FCC, claiming the agency's investigations and regulatory actions are part of a Trump administration "retaliatory campaign" to curb the network's free speech.

A guest host taunting the president on ABC's airwaves, followed within hours by the network suing his administration's regulators, made for one of the most combative 24-hour stretches in the network's recent history.

What Comes Next

O'Donnell has the "Jimmy Kimmel Live!" desk for the rest of the week, and Monday made clear she intends to use it. The bigger fight now runs on two tracks: her nightly monologues, and ABC's First Amendment case against the FCC winding into court. Trump, whose feud with O'Donnell stretches back nearly two decades, has not yet responded. Few expect that to last.

Frequently Asked Questions

Why is Rosie O'Donnell hosting "Jimmy Kimmel Live!"?
She is guest hosting this week while Jimmy Kimmel is on vacation, her first time behind a TV desk since her own talk show ended in 2002.
What did she say about Trump?
She called him "Mango Mussolini," said she moved to Ireland because of him and Project 2025, and told the camera: "Hi, I know you're watching!"
Why did she move to Ireland?
She said reading Project 2025 convinced her to leave the US two years ago, taking her child Clay with her.
Is she worried about FCC censorship?
No. "I don't listen to them. I don't pay any heed to them," she said of the FCC and Chairman Brendan Carr.
What lawsuit did ABC file?
Hours after her monologue, ABC sued the FCC, calling its investigations part of a Trump administration "retaliatory campaign" against the network's free speech.
JM
J. Mendez

Writer

J. Mendez is a writer with a decade of experience covering the full spectrum from politics to entertainment. Holding a degree in political science, Mendez brings analytical depth to reporting on government, policy, and public affairs while also delivering sharp, engaging coverage of film, television, music, and celebrity culture. Over ten years in the field, their work has spanned hard news, cultural analysis, and feature writing, consistently connecting the political and the popular for a broad audience.

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