A Short History of Donald Trump's Feud With Rosie O'Donnell

An unusual and perfect opportunity to mess with Donald Trump has presented itself.

Saturday Night Live has been doing a terrific job getting Trump’s goat, but it was last weekend’s White House press secretary/communications director Sean Spicer sketch that may have revealed Trump’s weakness because the White House is rattled, and it isn’t just because SNL is punching up pretty hard. It’s because Melissa McCarthy (a woman!) portrayed Sean Spicer. This White House is the leakiest in a long time, with secret sources depicting Trump as a clueless child who is easily distracted, and inside sources have also said why the McCarthy sketch got under Trump’s skin: “It was Spicer’s portrayal by a woman that was most problematic in the president’s eyes.”

Trump is a misogynist, a fraud, and a bully, and that’s never been clearer than in his behavior towards Rosie O’Donnell. O’Donnell has seen him for who he truly is for decades—and what could be more embarrassing for Trump than having his number one enemy, Rosie O’Donnell, play the real president, Steve Bannon?

A short history of Trump’s feud with O’Donnell: 

December 2006

Here’s where it all began, and O’Donnell agrees: O’Donnell criticizes Trump on The View for saying he’ll give Miss USA Tara O’Connor “a second chance” after allegations that O’Connor was abusing drugs, drinking while underage, and sneaking men into her temporary Trump Place apartment. O’Donnell mocks Trump’s combover and his position as some kind of “moral authority,” says that he’s not a self-made man because he inherited all his wealth from his father, and calls him a snake-oil salesman. And that’s about it. That’s all you have to say about Trump for him to launch a decades-long vendetta against you.

Trump responds in a statement to People: “You can’t make false statements. Rosie will rue the words she said. 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 sue.)

Trump responds again to Entertainment Tonight, saying, “Rosie O’Donnell is disgusting—both inside and out. If you take a look at her, she’s a slob. How does she even get on television?… If I were running The View, I’d fire Rosie. I’d look her right in that fat, ugly face of hers and say, ‘Rosie, you’re fired.’ We’re all a little chubby but Rosie’s just worse than most of us. But it’s not the chubbiness—Rosie is a very unattractive person, both inside and out. Rosie’s a person that’s very lucky to have her girlfriend and better be careful or I’ll send one of my friends over to pick up her girlfriend. Why would she stay with Rosie if she had another choice?”

December 2011

O’Donnell announces that she is engaged. Trump tweets this:


August 2012

O’Donnell suffers a heart attack. Trump troll-tweets this:


April 2014

Trump troll-tweets at O’Donnell about her weight-loss surgery:


September 2014

O’Donnell says that the bullying she received from Trump was the worst in her life: “Probably the Trump stuff was the most bullying I ever experienced in my life, including as a child. It was national, and it was sanctioned societally. Whether I deserved it is up to your own interpretation.” Trump reminds her that she “started it.”


February 2015

O’Donnell leaves The View. Trump responds, “Well, it’s very sad what’s happened to The View and I predicted that with Rosie O’Donnell it would fail. I guess the prediction is correct, but, I mean she’s a total trainwreck, so let’s see what happens and I hope it works out well. … I like the show a lot, but let’s face it, Rosie is a loser.”


August 2015

During the first Republican presidential primary debate, Megyn Kelly prefaces a question about “the War on Women,” by citing examples of Trump using language like “fat pigs,” “dogs,” and “slobs” to describe women he doesn’t like. Trump responds, “Only Rosie O’Donnell.”


September 2016

During a presidential debate, after a jab from Hillary Clinton about his treatment of women, Trump brings up O’Donnell to concede that “I said very tough things to her, and I think everybody would agree that she deserves it and nobody feels sorry for her.”

O’Donnell is the perfect person for this mission because (at least in Trump’s imagination) she was the first to call him out for being a charlatan, and because she is a woman that he does not find attractive. It’s easy to imagine Trump scratching his head and wondering aloud, as he did to Entertainment Tonight in 2006, why O’Donnell is even on television if he doesn’t find her sexually desireable. Trump is (literally) heavily invested in heteronormative beauty standards—the Miss USA pageant was owned by Trump from 1996–2015, he wants the women who work for him to “dress like women,” and his obsession with his daughter Ivanka’s looks is more than disturbing—and that strikes right to the heart of his fear of O’Donnell and women like her. Trump does not understand why anyone would like or listen to a woman he does not find attractive. And that’s why O’Donnell has the power to devastate him.

Anyone could make fun of Trump and it’d bother him because he has the thinnest skin of all time and is a bully who can dish it but can’t take it, but O’Donnell has a rare power to fire an arrow straight into his troll heart. If O’Donnell takes on Bannon, not only is a woman making Trump look weak and powerless, but a woman whom he bullied for years is overpowering him through comedy—and everyone will be watching.

This inspired casting suggestion has been floating around the internet since last weekend, and don’t think O’Donnell doesn’t know about it. She tweeted: “I am here to serve. I would need a few days to prepare—so if called—I will be ready.” And last night she changed her Twitter profile photo to a pretty great looking rendition of herself as Bannon.


February 2017

O’Donnell utterly devastates the Trump empire with her portrayal of Steve Bannon? Make it so, SNL writers!


by Dahlia Balcazar
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Dahlia Balcazar was a senior editor at Bitch Media, the co-host of the podcast Backtalk, and the host of the live show Feminist Snack Break. She’s passionate about horror films, ’90s music, girl gangs, and Shirley Jackson. You can follow her on Instagram and Twitter.

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