During the make-up White House Correspondents’ Dinner last Friday, the President of the United States tried to take a swipe at an old foe. “Even Rosie O’Donnell reached out from Ireland,” he told the room. “She was desperate to come back to the United States and pay her respects to Donald J. Trump. But that didn’t work out, unfortunately, because nobody wanted her to come back.”
The joke wasn’t merely unfunny, it was also inaccurate. O’Donnell already came back to the country. Two nights before Trump’s speech, she opened her new comedy show, which centers on her life and feud with Trump, at Manhattan’s Daryl Roth Theatre. On Thursday, she appeared on “Late Night with Seth Meyers.” And next month, she will guest host “Jimmy Kimmel Live!”
Two decades and two presidential inaugurations later, Trump still hasn’t let it go – and O’Donnell hasn’t backed down.
After the 2024 presidential election, O’Donnell actually did what many Americans threatened to do – leave the country. But now she is back, and that matters – because the story was never just about O’Donnell herself. It was also about the rest of us, the people watching Trump attack her.
While co-hosting a 2006 episode of “The View,” then one of the biggest daytime platforms in America, O’Donnell said that Trump was not self-made and was in no position to lecture anyone about morality. At the time, the landlord-turned-game show host was furious, but the feud was tabloid fodder rather than national news.
Two decades and two presidential inaugurations later, Trump still hasn’t let it go – and O’Donnell hasn’t backed down. There were years of insults, including the 2015 primary debate where moderator Megyn Kelly asked Trump about women he’d called pigs and slobs and he cut her off with three words: “only Rosie O’Donnell.” He brought her up again in his first debate with Hillary Clinton. And on Friday, in a ballroom filled with media elite who have yet to call him out as bluntly and forcefully as O’Donnell has, Trump called her a “a sick young woman. Sick older woman, I guess now I have to say.”
The two-time president of the United States, in other words, has spent twenty years returning to the same woman. She was among the first with a national platform to publicly refuse the premise his whole life is built on, and he has never been able to get over it.
Kaivan Shroff
Kaivan Shroff is a senior advisor to the Institute for Education and a political commentator. He previously served on the advisory board for Dream for America, a progressive Gen Z-led non-profit. He is an alumnus of the Hillary for America digital team, holds a joint degree from Harvard Law School and Harvard Kennedy School, an MBA from the Yale School of Management and a BA in Political Science from Brown University.
