Rosie O’Donnell, the comedian and television personality who has feuded publicly with President Donald Trump since 2006, opened her second night guest-hosting “Jimmy Kimmel Live!” on Tuesday, August 18, 2026, by mocking the president’s widely ridiculed escape from Air Force One inside a catering cart — and making clear she knew he was watching every minute.
The episode marked another high-profile chapter in a years-long rivalry that has grown sharper since Trump’s return to the White House. O’Donnell, 64, wasted little time going after the 80-year-old president, welcoming the audience before crediting him, with dripping sarcasm, for her renewed visibility. “I’m back in the spotlight, all thanks to President Oompa J. Loompa, who is watching us this evening from inside a catering cart,” she said. She capped the moment by telling the audience, “You know, I couldn’t have done it without you, sweetie. You brought me back, just like you did with fascism and the measles.”
The Catering Cart Incident That Became a Punchline
The catering cart reference landed because the underlying story had already become a national embarrassment for the administration. In July 2026, President Trump attended a NATO summit with other world leaders in Turkey, and on his departure, the Secret Service arranged for him to slip away from Air Force One concealed inside a catering vehicle — the type typically used to load food and supplies onto aircraft. He then switched to a different plane before heading home. The operation was prompted by an alleged Iranian plot to target the aircraft. Although the maneuver succeeded and the administration kept it quiet for weeks, the story eventually broke and has been mocked ever since.
O’Donnell’s willingness to mine the episode for material on only her second night behind Kimmel’s desk underscored why late-night television had been anticipating her run. Late-night host Jimmy Kimmel had announced on his June 18 broadcast, that O’Donnell would join his summer rotation of stand-in hosts. Kimmel framed the pick as a “special treat for our commander-in-chief,” a description that left little ambiguity about his intentions.
A Feud Two Decades in the Making
The bad blood between O’Donnell and Trump stretches back to 2006, when she was a co-host on the daytime talk program “The View.” What began as a public spat has since calcified into one of the more durable grudge matches in American celebrity politics. Trump has continued to insult O’Donnell at public events and has posted demeaning AI-generated videos of her on his Truth Social platform. In July 2025, he escalated further, posting a heavily edited photograph of her and threatening to strip her of her American citizenship. O’Donnell fired back on Instagram, telling him that 18 years later, she still lived rent-free in what she called his “collapsing brain.”
Those exchanges formed the backdrop for her debut on the Kimmel stage, and O’Donnell leaned into them — but with a disciplined twist. Her first monologue focused almost entirely on her decision to relocate to Ireland after Trump’s 2024 election victory, and she made it through the entire segment without saying the president’s name once. O’Donnell said she had read Project 2025 and concluded she needed to leave the country, then described Ireland as “a place where people are driven to drink regardless of who’s running their country.” She also recalled how her child had explained the move to classmates, saying the family was being “forced to move to another country because the president of the United States hates my mother.” The monologue closed with a pointed aside: “You know, right now he’s in the White House crying because I haven’t mentioned him.”
A Surprising Invitation and Critical Notice
The booking itself was notable given the history between O’Donnell and Kimmel, who had themselves been adversarial at an earlier point in their careers. O’Donnell told Variety she had been caught off guard when the offer came through, recounting that her first reaction was to point out she had never even appeared on the show as a regular guest. She said she ultimately committed on the condition that Kimmel genuinely wanted her there. In a separate interview with journalist Kara Swisher, O’Donnell said she planned to honor Kimmel’s writers and his legacy by treating the assignment seriously.
Critics noticed. The Hollywood Reporter described O’Donnell’s approach during her monologues as deliberately avoiding the trap of seeming consumed by her fixation on the president — calling that restraint refreshing. Rather than leading with grievance, she led with her own story: the year and a half living quietly in Ireland, largely outside the American media cycle, before this high-profile return to network television pulled her back into it. The irony — that Trump’s relentless attention to O’Donnell had ultimately handed her a prime-time platform — was not lost on her or her audience.
A Four-Night Run, Now Concluded
O’Donnell was booked for four nights, the week of August 17, with musician Jelly Roll taking over the desk on August 21. Her debut monologue drew attention for its tonal control; her second-night opening, built around the catering cart imagery, showed a willingness to escalate when the news cycle handed her material she could not ignore. Through her first two nights she never once said the president’s name — a restraint that was, by her own design, the joke.
