The Dictatorship
Trump tried to make an example of Rosie O’Donnell. It backfired.
ByI dig Shroff
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 showwhich 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-madeand was in no position to lecture anyone about morality. At the time, the landlord-turned-game show host was furiousbut 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.
Which is what makes his threat last summer worth remembering: “Because of the fact that Rosie O’Donnell is not in the best interests of our Great Country, I am giving serious consideration to taking away her Citizenship.” It wasn’t a serious legal proposal – the president cannot revoke a native-born American’s citizenship – as much as it was a MAGA theory of belonging. In threatening O’Donnell, Trump threatened to make citizenship a privilege he extends and can revoke (based on mere speech, no less). It was a warning to any critic whose passport is the only thing standing between them and a very different life and who doesn’t have O’Donnell’s resources or profile.
In the context of a twenty-year battle with the now-most-powerful man in the world, a regrouping abroad is not surrender.
Of course, there is an obvious objection to holding Rosie up as any kind of resistance example: she left. Staying carries real moral weight. Many people who have absorbed this past decade of Trump’s politics did not have an Irish grandmotheror the means to build a life somewhere else. There is something a little uncomfortable about resistance broadcast from another country, particularly when only some can afford it. But in the context of a twenty-year battle with the now-most-powerful man in the world, a regrouping abroad is not surrender.
And the impetus for her decision is crucial: “I knew, after reading Project 2025, that if Trump got in, it was time for me and my non-binary child to leave the country,” she told CNN last year. After years of being Trump’s favorite target, O’Donnell had better reason than almost anyone alive to know his obsession with settling scores and having things his way. Indeed, she knew better than much of institutional Washington, which was still reassuring itself about guardrails, norms, and adults in the room. Many institutions folded alarmingly quickly this time around: the museums, the law firms, the universities. O’Donnell did not wait for them to capitulate.
Yet she did not disappear. Now she is telling her story on her own terms, projecting Trump’s own words onto a theater wall for audiences that laugh at them instead of with them. While on Friday, the president described a broken woman pleading across the Atlantic, the actual Rosie was onstage a short train ride away, turning his words into part of her act. Twenty years after he decided she would be the punchline, she is still standing.
That is why Trump keeps coming back to O’Donnell. His campaign against her only worked if it ended with her gone or begging him for forgiveness. Personal intimidation is never only about the person being targeted. It is a warning to others: cross me and you will regret it. Too many institutions accepted that bargain. Rosie O’Donnell never did. In trying to make an example of her, Trump only made a point – and not the one he intended.
I dig 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.