The Real Reason Trump Has Hated Rosie O'Donnell for 19 Years

Yahoo

a day ago

If President Donald Trump, like Richard Nixon, kept an enemies list, one seemingly unlikely name would be right at the top — not a lawmaker or one of his predecessors, but the funny lady who tossed Koosh balls into the audience, and who speaks in frank and unadorned language about her disdain for him.
Trump's latest salvo against Rosie O'Donnell, who hosted an eponymous daytime talk show from 1996 to 2002 and did two yearlong stints on 'The View,' was his strangest yet. '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,' Trump posted on his social network, Truth Social, on Saturday. O'Donnell moved to Ireland following Trump's election and told Variety, in a recent interview about her role on 'And Just Like That,' that she does not plan to return to the U.S. 'until this administration is completely finished and hopefully held accountable for their crimes against the nation.' Trump cannot revoke the citizenship of someone born in the U.S., no matter how much he may dislike her.
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At this point in the national convulsions Trump has brought on, it should come as no surprise that Trump can hold a grudge and is quick to offend. But there may be no single person who has the capacity to drive him to ire as much as O'Donnell. Perhaps that's because, unlike many politicians, who must continue to work with the President, and unlike most other celebrities, who are willing to back down in order to preserve their images, she gives as good as she gets. She also speaks his language of insult as fluently as anyone in the public eye.
Trump's hatred of O'Donnell can be traced to a 2006 incident on 'The View'; O'Donnell mocked Trump, then the owner of the Miss USA brand, for publicly declaring that a pageant winner would be allowed to retain her title despite a scandal around her substance use. O'Donnell sarcastically declared 'He's the moral authority!' while listing off Trump's past infidelities and business struggles, concluding with 'Sit and spin, my friend!' Perhaps most gallingly to an image-obsessed butt of the joke, she pulled her shoulder-length hair across her head to create a mocking version of the Trumpian pompadour.
Then as now, Trump was obsessed with gaining favor in the world of popular culture. (What is his second-term takeover of the Kennedy Center but a deferred expression of his early ambition to produce on Broadway?) And so O'Donnell's mockery must have cut deep. Not merely was it coming from a widely-loved talk show host (who was, oddly enough, a guest at his second wedding), it happened on a show whose creator, Barbara Walters, had spent years cultivating him. O'Donnell's on-air claim that Trump had personally declared bankruptcy later became a bone of contention, as Trump's businesses had gone bankrupt but the man himself had not, making the show vulnerable to a lawsuit; Walters, when she next appeared on the show, issued a careful statement that Trump had never personally gone bankrupt.
By this point, though, the feud between Trump and O'Donnell had exploded in the press, and Walters' statement also included the claim that she'd never criticized O'Donnell to Trump. He'd been having a Trumpian field day listing off all the things he claimed Walters had told him about O'Donnell's presence on the show. O'Donnell had been a marquee hire for 'The View' just months before; the Trump feud helped precipitate her quitting before the end of the season. O'Donnell's willingness to burn a bridge with Walters, the woman she'd called her TV mentor, indicates just how committed she is to her sense of what's right; little wonder she is the celebrity avatar for not backing down from Trump.
In the years to follow, Trump would pick up and drop the subject of O'Donnell as the spirit moved him. In the first debate of the 2016 GOP primary cycle, Megyn Kelly — who would, years later, come to be one of Trump's most ardent defenders — began asking a challenging question about the way Trump speaks about women, calling them 'fat pigs, dogs, slobs, and disgusting animals.' Trump cut Kelly off to declare 'only Rosie O'Donnell.' This wasn't true, but it didn't matter — the crowd erupted. Surely Trump knows that among the dynamics in his constantly counterpunching a somewhat butch lesbian who has publicly struggled with her weight is that it plays to his base.
But she's also always there under the surface: Asked a tough question? Bring up Rosie. Base demanding you fire your attorney general? Bring up Rosie. (As the New York Times' report on the O'Donnell post states, Trump's current seething comes at a particularly apt time for a distraction: Trump changed the conversation, however briefly, from a series of scandals including a feud over files related to Jeffrey Epstein that is dividing the MAGA base.) Trump's seething at an enemy from the world of culture often has a clear antecedent: Meryl Streep is 'one of the most overrated actresses in Hollywood,' he posted, immediately after her Golden Globes lifetime-achievement acceptance speech lambasting him. O'Donnell hadn't done anything in particular against Trump in recent memory other than continue to live her best expat life.
But nineteen years ago, she went on the air and blasted him the way he blasts others. Streep's critique of Trump landed, but it was veiled and allusive — she never used the man's name. And so Trump doesn't still bring up hating 'Sophie's Choice.' He's found a way towards a weird sort of detente with various political opponents, alternating a sort of kayfabe mockery of them with moments of strange grasps toward friendship (asking Barack Obama to golf with him; telling Joe Biden that 'in another life,' they'd be, yes, golfing buddies). O'Donnell doesn't get that treatment, because Trump cannot brook being spoken to the way he speaks to others. Her Long Island attitude matches his outer-borough one; her willingness to outright declare distaste matches his; her eye for the telling detail and the way to twist it into a way to exact maximum damage. If anyone else had Trump's hairstyle, he'd make fun of it just the way O'Donnell did.
Indeed, O'Donnell has had — for now, until the next eruption that is surely but hours away — the last word. '[Y]ou are everything that is wrong with america — and I'm everything you hate about what's still right with it,' O'Donnell wrote on Instagram, calling Trump 'king joffrey with a tangerine spray tan.' The president threatening legal consequences for O'Donnell's speech is, obviously, scary, and an indication of just how untrammelled his view of power, in his second term, has become. It's also a sign that he's lost some sense of himself amidst the swirl of resentments that surround him. O'Donnell is driving him crazy; that's nothing new. But, beyond empty threats, he now cannot think of anything to say in response.
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