Here's Why Donald Trump Hates Rosie O'Donnell

Images via AP.
Images via AP.

At last night’s presidential debate, Republican candidate Donald Trump engaged in a number of activities no rational person could have anticipated a presidential candidate might do, such as accusing an unnamed, hypothetical person “that weighs 400 pounds” of hacking the DNC, suggesting Clinton does not have the “stamina” to be president, interjecting that not paying federal taxes “makes me smart,” and sniffing with wild abandon throughout. He also brought up Rosie O’Donnell. Why does he keep doing that?


“Rosie O’Donnell, I said very tough things to her and I think everyone would agree that she deserves it and nobody feels sorry for her,” Trump said, for some reason, in response to the allegation that he says terrible things about women. This seemingly random feud, as we’ve been made continually aware, has been going on for a while.

In the ’90s and early ’00s, O’Donnell and Trump ran in occasionally converging showbiz circles. In 1993, O’Donnell, then a comedian and actress beginning to hit the big time with roles in A League of Their Own and Sleepless in Seattle, was one of 1,000 guests at Trump’s wedding to Marla Maples at the Plaza Hotel. Over the next decade, they would sometimes turn up in gossip columns together—when they both attended a New York Knicks game, for example, or when the director of Hale House, a respected Harlem charity supported by both Trump (once) and O’Donnell, was indicted on charges of grand larceny and forgery. In 2002, they both attended Liza Minnelli’s wedding to David Gest.

Although O’Donnell had been publicly critical of Trump for at least a year prior—on her blog, for example, where she continues publish Trump rants, alongside Joni Mitchell lyrics and free-verse poems about Stephen Collins’ history of sexual abuse—it’s generally accepted that their rivalry took root in 2006, when O’Donnell, then a cast member on The View, ripped into Trump for a press conference he’d just given about then-Miss USA Tara Conner, who’d been found to have used drugs and alcohol.

In the 5-minute segment, O’Donnell imitated Trump, even flipping her hair into a combover. “He annoys me on a multitude of levels,” she said. “He’s the moral authority! Left the first wife, had an affair, left the second wife, had an affair, had kids both times but he’s the moral compass for 20-year-olds in America.”


A decade ago, as NBC points out, O’Donnell helped to mainstream a now-popular line of attack against Trump—that he’s not self-made but a product of his father, that he repeatedly bankrupted himself to get out of paying what he owed, that he’s a “snake-oil salesman.”

Trump didn’t take this so well, and has since referred to O’Donnell as “a woman out of control,” a “true loser,” a “total train wreck,” “disgusting,” a “slob,” “fat, ugly”; he told Entertainment Tonight in 2006: “Probably I’ll sue her, it’ll be fun. I’d like to take some money out of her fat-ass pockets.” He made similar threats to People, saying “I’ll most likely sue her for making those false statements—and it’ll be fun. Rosie’s a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie.” (He did not.)


In a 2014 interview with People, O’Donnell called Trump’s attacks “the most bullying I ever experienced in my life, including as a child.”


“It was national, and it was sanctioned societally,” she said. “Whether I deserved it is up to your own interpretation.”

Unfortunately, Trump seems unlikely to stop bringing up Rosie O’Donnell. She is, in effect, his boogeyman. The particular digs she lobbed at him a decade ago, back when his defective personality was not a topic of lasting national interest, triggered him immensely; not only because they poked at the foundation of his brand, but because they were floated by a woman, and one he did not find attractive. The fact that anyone listened must have absolutely confounded him.


Ever since Trump began to seek our nation’s highest office, these criticisms have snowballed into something rather inescapable, as we finally witnessed in last night’s meltdown—and now, they are coming from another woman, one whose physical presence, or lack of “stamina,” also scans to Trump as a disqualifying factor.

It’s not much of a stretch to imagine that Trump might consider Rosie O’Donnell, rather than his own actions, to be the root of any criticism he receives today. If he can just bring her up enough, and remind us how gross and messy she is, we will discount the things she said about him and everything that’s been said since, and the universe will slip right back into tremendous normalcy.


Correction: This post previously misspelled Liza Minnelli’s name.

Ellie is a freelance writer and former senior writer at Jezebel. She is pursuing a master's degree in science journalism at Columbia University in the fall.


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