Jimmy Kimmel knows exactly how to leave a parting gift.
As the late night host signed off for his annual summer break on Thursday, he delivered what he called “a special treat for our commander-in-chief.” The punchline? Rosie O’Donnell will be filling in as a guest host while he’s gone. You know, the woman Trump has called everything from a “loser” to someone he once threatened—illegally, it bears noting—to strip of citizenship.
“You’re welcome,” Kimmel said. “And all I ask in return, Mr. President, is that you don’t do anything stupid while I’m gone.”
That’s classic Kimmel. A little joke, a little bite, and a whole lot of “I know exactly what I’m doing.”
O’Donnell has been Trump’s adversary since way before his political career ever started. The two have been trading insults for decades, and if anything, the animosity has only intensified. Earlier this month, outside the Tony Awards, she called him an “asshole and a liar” and a “psychopath.” That’s not subtle. That’s not coded. That’s exactly the kind of rhetoric that gets under Trump’s skin.
And let’s be clear about the citizenship thing, because it deserves to be repeated: Trump once suggested he could take her citizenship away. He can’t. She was born in the United States. That’s not how any of this works. But the threat itself says something about how he views opponents—as people who can be wielded, punished, dismissed.
Kimmel has taken summer breaks since 2020, when COVID had him broadcasting from home. Guests have filled the gap ever since, and he’s curated a rotating list that usually leans comedic but occasionally lands somewhere more pointed. This year’s lineup includes Tiffany Haddish, Ike Barinholtz, Colman Domingo, Anthony Anderson, and Jelly Roll. It’s a mix designed to keep ratings up and audiences engaged.
But the O’Donnell booking feels different. It’s not just about filling a seat. It’s a statement. It says, “I’m going on vacation, but the reminders aren’t stopping.”
There’s something almost poetic about it. A billionaire reality TV star turned president vs. a comedian who’s never backed down. Their feud predates Twitter, predates MAGA hats, predates every thing we now associate with this era of American politics. And yet here we are in 2026, still watching the same old script play out, just with different sets and bigger stakes.
Kimmel asked Trump not to do anything stupid while he’s away. That’s either genuine concern or a dare. Probably both.
The show goes into repeats next week, then guest hosts take over starting July 6. By the time Kimmel returns, Trump will have endured weeks of Rosie O’Donnell on national television, saying exactly what she thinks, the way she’s always done.
Some things, it seems, never change.
