Donald Trump vs. Rosie O'Donnell: A History of Their Public Beef

Donald Trump in 2016
Win McNamee/Getty Images

Republican presidential nominee Donald Trump speaks during the Presidential Debate at Hofstra University on Sept. 26, 2016 in Hempstead, N.Y.

A sure way to get under Republican presidential candidate Donald Trump's skin is to accuse him of not treating women properly (or ask about his taxes) -- which is exactly what Democratic candidate Hillary Clinton did at the end of Monday night's contentious first presidential debate.

When Clinton read off a list of insults Trump has made about women over the years, including unkind remarks about comedian Rosie O'Donnell, a frustrated Trump shot back, "Rosie O'Donnell -- I said very tough things to her, and I think everybody would agree that she deserves it and nobody feels sorry for her."

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That slam drew a strong reaction from the crowd in the room at Hofstra University and an even bigger response from the Twitterverse, including one pointed tweet from Family Guy creator and crude humor champion Seth MacFarlane.

But seriously, what's the deal with these two, who pick on each other and name-call like a pair of grade-school bullies? Why can't they stop sniping? It all began back in December 2006, when O'Donnell slammed Trump for his decision not to fire Miss USA Tara Conner after stories emerged of drug and underage alcohol use by the beauty queen. "I've always been a believer in second chances," Trump said on Dec. 19 of that year. O'Donnell, then a co-host of The View, was not impressed, saying the next day on the show that Trump is not a "self-made man" but rather a "snake-oil salesman on Little House on the Prairie."

She doubled down with the insult that seems to have really stuck in his craw: "[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." That's when the gloves came off and Donald let loose, never turning back, calling O'Donnell a "real loser" in People magazine and threatening to sue her for claiming he'd gone bankrupt several times. "Rosie's a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie," he said.

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Thus began a strange good cop/bad cop scenario in which Trump would alternately insult O'Donnell and come to her defense. He did the latter in May 2007 when Rosie left The View eight months after joining following a fight with co-host Elisabeth Hasselbeck over the conservative's support of the Iraq war. "On this one I think Rosie should win, but Rosie is not much herself," he told Extra, according to CNN. Trump went on to call Hasselbeck "not a very smart person, she's one of the dumber people in television."

Things were quiet for a few years, but they heated up again in December 2011, when Trump lashed out at O'Donnell following the announcement of her engagement to now-ex-wife Michelle Rounds. "I feel sorry for Rosie's new partner in love whose parents are devastated at the thought of their daughter being with @Rosie -- a true loser."

Rosie's response? "Wow u r an ass."

Trump wasn't done, denigrating O'Donnell's then-new show on Oprah's OWN network as a "complete and total disaster, lumping her in with another frequent punching bag, MSNBC host Lawrence O'Donnell.

"It's really amazing," he said. "When I don't like somebody their shows do really badly."

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He was back at it in May 2012, after Cher fired shots at then-GOP presidential candidate Mitt Romney, once again dubbing Rosie a "total loser."

Donald returned in August 2012, after O'Donnell suffered a heart attack and he wished her a speedy recovery, adding, "I'm starting to miss you!" O'Donnell appreciated the kind words, saying she was shocked and wondering if he was secretly "trying to kill" her.

Unable to keep his powder dry, Trump struck out at Rosie again in May 2014 after she discussed her 50-pound weight loss following surgery several months earlier. "Rosie O'Donnell just said she felt 'shame' at being fat -- not politically correct!" he tweeted. "She killed Star Jones for weight loss surgery, just had it!" That time, Rosie told him to just "go away."

Things heated up again in July of that year when O'Donnell announced her upcoming return to The View. While he called it a "good move" on ABC's part, his joy quickly turned sour as he said it was proof of how "desperate" the network was before unleashing both barrels on Rosie.

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That thing about sticks, stones and words? It's true. When O'Donnell made it back on air at The View she said the venom from Trump was the "most bullying I ever experienced in my life, including as a child." Trump's response? "Good luck on your new show, but remember, you started it!"

O'Donnell was back out at The View by February 2015, saying the stress was too much after her heart attack. Trump didn't miss the chance to pounce. "Well, it's very sad what's happened to 'The View' and I predicted that with Rosie O'Donnell it would fail," he said. I guess the prediction is correct, but, I mean she's a total train wreck, 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."

Things got especially nasty in August 2015, when Trump was asked by GOP debate moderator and Fox News host Megyn Kelly about his history of referring to women as "fat pigs," "dogs" and "slobs." His response? "Only Rosie O'Donnell." Rosie, a mother of four, was devastated by the renewed attack on national TV.

Trump gloated about his latest diss the next day, telling Fox & Friends that the line got "tremendous applause" in the room.

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After Monday night's debate comments, O'Donnell responded with her own string of tweets, in which she referred to Trump as an "orange anus" and mocked him for not being able to get over the comments that started it all.

And that wasn't all she had to say.

Her old pal Madonna also came to Rosie's defense.

And, in a sign that he's not done yet, on Tuesday morning (Sept. 27) Trump called in to Fox & Friends, congratulating himself for holding his fire against Clinton the previous evening. "She hit me at the end with the women,” Trump said of Clinton's characterization of his misogynistic attitude toward O'Donnell and other women. "I was going to hit her with her husband’s women, and I decided I shouldn’t do it. I didn’t feel comfortable doing it with [the Clintons’ daughter] Chelsea in the room. I think Chelsea’s a fine young lady."


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