He Said, She Said: Donald Trump Vs. Rosie O’Donnell

When Donald Trump insulted TV host Rosie O’Donnell last night, it was the latest insult in a decade’s worth of sniping. What lies behind their beef?

Donald Trump offered up a cornucopia of asinine remarks last night during the first GOP debate that even Bill Clinton could not have dreamed up when he urged the man whose most endearing characteristic is his horribly coiffed comb-over to run for the highest office in our country.

But perhaps one of the foulest and most unprofessional strings of words to leave his lips was a quick jab at comedian Rosie O’Donnell.

Fox News anchor Megyn Kelly rightly pointed out that The Donald has a history of calling women abominable names—such as “fat pigs, dogs, slobs, disgusting animals,” which should make any person who respects women immediately exclude him as a presidential contender.

“Only Rosie O’Donnell,” Trump said to quickly interrupt Kelly—another manifestation of his respect for women, or more appropriately, lack thereof.

Hours later, he tweeted that Kelly was a “bimbo” for daring to question him on his sexism.

It’s almost as if Trump doesn’t realize that people with vaginas also have the right to vote.

While the audience disturbingly lapped up Trump’s O’Donnell jab, the former talk-show host responded with restraint and ambiguity. Thus far, she’s only tweeted “try explaining that 2 ur kids.”

The latest flare-up is a relatively small ripple in the river of bad blood between her and Trump.

The two staples of early 21st-century network television have been going toe-to-toe for nearly a decade.

In 2006, O’Donnell criticized Trump for failing to fire that year’s Miss USA, Tara Conner.

Reports of her drunkenness, drug abuse, and hard partying were New York tabloid gold at the time, but have mostly faded in the gilded trash.

At the time, though, the New York Post charmingly referred to the then-21-year-old pageant queen as “drug-snorting” and “man-eating.”

Get The Beast In Your Inbox!

Daily Digest

Start and finish your day with the top stories from The Daily Beast.

Cheat Sheet

A speedy, smart summary of all the news you need to know (and nothing you don't).

By clicking “Subscribe,” you agree to have read the Terms of Use and Privacy Policy
Thank You!
You are now subscribed to the Daily Digest and Cheat Sheet. We will not share your email with anyone for any reason.

O’Donnell compared Trump to the "snake-oil salesman on Little House On The Prairie.”

She also skewered his past, calling him out because he “left the first wife—had an affair. [He] had kids both times, but he’s the moral compass for 20-year-olds in America. Donald, sit and spin, my friend.”

For a hothead fool like Trump, those words were like waving red at a bull in a china shop.

“Rosie will rue the words she said. I’ll most likely sue her for making those false statements—and it’ll be fun,” he told People. “Rosie’s a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie.”

Trump took things a step further when O’Donnell refused to back down.

The fame-monger milked the feud for all it was worth, calling O’Donnell a “very, very unattractive woman,” a “slob,” and insinuating that her ire toward Miss USA was a result of unrequited love for Conner.

“Maybe she wanted to put the crown back on Miss USA’s head. I think she’s very attracted to Miss USA so she probably wanted to put the crown on her head herself,” Trump told Good Day L.A.

Trump’s insults at O’Donnell were beyond repugnant. They’re more than lightly tinged with homophobia and sexism.

O’Donnell is hardly a softie. It’s worth noting that O’Donnell has racked up nearly as many enemies as Trump. She had countless spats with nearly every woman she worked with on The View, and appeared to pick a fight with Kelly Ripa.

In 2006, O’Donnell accused Ripa of being homophobic when Clay Aiken (who had not yet come out publicly) put his hand over her mouth and she said “Oh, that’s a no-no. I don’t know where that hand’s been, honey!”

And then came her big blow-up with the right wing Elisabeth Hasselbeck over the Iraq War, which led to O’Donnell leaving The View, and remains one of the daytime’s show most memorable moments.

Trump’s comments appear to have left a lasting mark on the bombastic comedienne.

When O’Donnell spoke in 2014 about her noticeable weight loss, she brought up how hurt she was by Trump’s attacks. “Probably the Trump stuff was the most bullying I ever experienced in my life, including as a child,” O’Donnell told People. “It was national, and it was sanctioned societally. Whether I deserved it is up to your own interpretation.”

In response to O’Donnell’s open discussion of the spat, Trump so maturely tweeted in July 2014: “Rosie is crude, rude, obnoxious and dumb—other than that I like her very much!”

He followed up a few months later in September by tweeting a Daily Mail article recapping their spat with the text, “No offense, and good luck on the new show, but remember, you started it!”

To be fair to Trump, not all of his comments to O’Donnell have been negative. He even tweeted at her in 2012 to “get better fast. I’m starting to miss you!” after she suffered a heart attack.

O’Donnell hasn’t exactly remained silent during these Twitter flair-ups, either. She has no problem calling him “an ass… in every way” on Twitter, while linking to a Time.com article that catalogued his financial failures.

Neither Trump nor O’Donnell looks like anything more than a petulant child with too much social media swagger when all is said and done.

Still, looking back at the war of words and Trump’s disgusting display last night, one can’t help but wish the White House contender had taken O’Donnell’s advice at least once in May 2014 when she simply tweeted: “Donald—go away.”