NEWSJimmy Kimmel’s Rosie O’Donnell Guest Host Pick Turns Into Trump-Era Flashpoint
Jimmy Kimmel announced Rosie O’Donnell as a summer guest host.
June 25 2026, Published 6:29 a.m. ET
Jimmy Kimmel is going on break this summer, but he found a way to leave President Donald Trump with one more late-night headache.
During the June 18 episode of Jimmy Kimmel Live!, Kimmel announced the guest hosts who will fill in while he takes a two-month break, including Tiffany Haddish, Colman Domingo, Ike Barinholtz, Anthony Anderson and Jelly Roll. Then came the name built to get a reaction.
The late-night host joked about Donald Trump while revealing the guest hosts.
“And, as a special treat for our commander-in-chief, I asked one of his all-time favorites, Rosie O'Donnell, to be here to keep the hits coming,” Kimmel said.
“You're welcome,” he added, as the audience laughed and applauded. “And all I ask in return, Mr. President, is that you don't do anything stupid while I'm gone. OK?”
Why Rosie O'Donnell Hits Differently
The hosting stint reignited Rosie O’Donnell’s long-running feud with Donald Trump.
O’Donnell’s booking is not just another guest-host slot. Her feud with Trump dates back to 2006, when as a co-host on The View she criticized his handling of the Miss USA controversy involving Tara Conner, who was accused of underage drinking and drug use. The conflict only intensified during Trump’s presidencies, with the two repeatedly attacking each other in public and online.
Kimmel has his own long-running Trump feud. Trump has called him a “lowlife” and “seriously unfunny” and has said Jimmy Kimmel Live! should be taken off the air.
The Provocation Is the Point
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Critics argued the selection was designed to provoke controversy.
“Jimmy Kimmel and ABC couldn’t have chosen a more antagonistic host as summer replacement, one that would spew even more anti-Trump rhetoric, if they’d thought about it even longer,” said forensic psychiatrist Dr. Carole Lieberman.
“Rosie O’Donnell hates Trump even more than Kimmel and will likely raise ratings, since people will be curious to see how much further she will dare to go,” she added.
Lieberman also framed the booking through her own proposed classification of “Trump Derangement Syndrome” (TDS).
“In my diagnostic classification of Trump Derangement Syndrome, that I will soon be presenting to the American Psychiatric Association for inclusion into the Diagnostic and Statistical Manual, I have placed Rosie in the Severe category,” she said. “She picked up and moved to Ireland when President Trump was inaugurated for a second term.”
Lieberman said she had previously considered Kimmel and his wife and co-head writer Molly McNearney, to have “Mild” cases of TDS, “but his continued TDS rants have earned him placement in at least Moderate, and inching towards Severe.”
A Guest Host With Built-In Drama
Rosie O’Donnell’s upcoming appearance generated immediate attention.
O’Donnell moved to Ireland with her child before Trump took office for a second term, and she has continued criticizing him from abroad, making her guest-hosting stint feel less like a vacation fill-in and more like a deliberate late-night event.
Kimmel may be away from the desk, but the Trump jokes are clearly not going on hiatus.
