Wait a second. Do you hear that noise? That’s the sound of comedienne Rosie O’Donnell and President Donald Trump getting into it once again. The archenemies have been going at it for decades, hurling insults back and forth like their lives depended on it. Their feud has experienced brief moments of peace — for example, when O’Donnell suffered a devastating health crisis and Trump reached out to her in a sign of solidarity, but that friendly banter didn’t last long. These two have been squabbling with each other for so long, most people aren’t even sure why they dislike one another in the first place…until now.
We’ve traced this dirt all the way back to the ’90s, and you won’t believe how petty things have gotten between them over the years. From Trump mocking O’Donnell’s weight to the then-presidential candidate making the comedienne a topic of discussion during a debate, we finally understand Rosie O’Donnell’s feud with Donald Trump. Here are all the juicy details.
It all started at his 1993 wedding
Believe it or not, there was once a time when Donald Trump and Rosie O’Donnell were cordial with one another. In fact, O’Donnell was chummy with Trump’s second wife, Marla Maples (pictured, left), and she even snagged an invite to the couple’s 1993 wedding at Trump’s Plaza Hotel. It was during that festive occasion that O’Donnell got up close and personal with The Donald, and she apparently wasn’t pleased with what she encountered.
In an interview with Vanity Fair, the television personality called Trump « the most absurdly transparent con man, » and she didn’t stop there. « He’s dumb, » she said. « His parents didn’t like him; they sent him away to New York Military Academy. » Wowzer. O’Donnell even talked about how horrible a parent Trump allegedly was to his kids, although she admitted she had never spoken to his children. « I’m friendly with Marla, which is how I was at his wedding, » O’Donnell said. « I know the s**t that he did. »
Trump and Maples divorced in 1999, according to the New York Post. While that love story had obviously cooled, O’Donnell’s feud with Trump was just heating up.
She ripped him apart for his support of Miss USA
In 2006, the rumor mill was boiling over with stories pertaining to Miss USA Tara Conner (pictured, second from left) testing positive for cocaine, partying too hard, and putting her crown in jeopardy, according to the New York Daily News (via TMZ). At a press conference (via People), Donald Trump, the then-owner of the pageant, decided it was best to give Conner a second chance and announced she would enter rehab. That really ticked off Rosie O’Donnell.
As a co-host on The View, O’Donnell had access to a nationwide platform to air her grievances, and she didn’t hold back. According to People magazine, O’Donnell « impersonated Trump by deepening her voice and flipping her hair to one side, » mocked reports that Trump cheated on his first wife, and quipped: « But he’s the moral compass for 20-year-olds in America. Donald, sit and spin, my friend. » O’Donnell then reportedly « discussed Trump’s finances — saying he went bankrupt, which Trump denies — and likened him to the ‘snake-oil salesman on Little House On The Prairie. »
When Trump heard about O’Donnell bashing him on her talk show, he told People, « 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 called her a ‘true loser’ following her engagement
After Rosie O’Donnell took the opportunity to bash Donald Trump following his wedding to Marla Maples, he returned the favor in 2011. While hosting The Rosie Show, O’Donnell announced to the audience that she had proposed to her then-partner, Michelle Rounds (pictured, left), and People reported that Rounds said yes! When the news hit the press, Trump sounded off on social media. « 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, » he tweeted. So rude. So savage. O’Donnell fired back with: « wow u r an a*s. »
O’Donnell and Rounds tied the knot in 2012 and adopted a daughter named Dakota O’Donnell. According to Us Weekly, they divorced in 2015. « It’s done. We’ve settled, » Rosie said, but one thing that wasn’t over was her scorching hot feud with Trump.
Cher and a moment of peace
Ahead of the 2012 presidential elections, iconic singer Cher began freaking out over the possibility of Republican candidate Mitt Romney being elected president of the United States. « If ROMNEY gets elected I don’t know if i can breathe same air as Him & his Right Wing Racist Homophobic Women Hating Tea Bagger Masters, » she wrote in a since-deleted tweet (via the New York Daily News). Even after Cher apologized for her comments, Donald Trump felt the need to clap back on Romney’s behalf, but he added an interesting twist to his statement. « @Cher attacked @MittRomney. She is an average talent who is out of touch with reality. Like @Rosie O’Donnell, a total loser! » he tweeted.
Three months later, O’Donnell suffered a near-fatal heart attack, ABC News reported. In the wake of the health scare, O’Donnell received an outpouring of support and well-wishes. Even Trump set their feud aside for a moment: « @Rosie, get better fast. I’m starting to miss you! » he tweeted. Was he being sincere or condescending? O’Donnell wasn’t even sure. She responded: « Well thank u donald — I must admit ur post was a bit of a shock…r u trying to kill me? »
He hurled more insults upon her return to The View
Remember that aforementioned episode of The View – the one where Rosie O’Donnell dragged Donald Trump for not firing Miss USA Tara Conner? The show’s creator and fellow co-host Barbara Walters was on vacation when all that went down, but when she heard that Trump was threatening to sue, she reportedly attempted to smooth things over with him. According to Vanity Fair, O’Donnell said she felt « shocked and hurt » and « very betrayed about [Walters] going behind my back and speaking to Donald Trump in Trumpian language. » O’Donnell left the show in 2007.
But in 2014, O’Donnell returned to the hit show. Trump, of course, had a thing or two to say about it, tweeting that the show must be « desperate » if it wanted O’Donnell back. He added: « Rosie is crude, rude, obnoxious and dumb — other than that I like her very much! » (What in the nice-nasty is going on here?)
His comments are the ‘worst bullying’ she’s ever endured
Rosie O’Donnell made some changes after suffering a heart attack in 2012. She underwent vertical gastric sleeve surgery in 2013 and revealed that she’d shed nearly 50 pounds by April 2014. Not only was O’Donnell hopeful that the surgery could help save her life, but she also hoped it would lessen the bullying and fat-shaming she had endured for most of her life. « Probably the Trump stuff was the most bullying I ever experienced in my life, including as a child, » she 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 statements, Trump tweeted: « No offense, and good luck on the new show, but remember, you started it! » Did that message mean Trump was on a mission to « finish » it? You betcha…
He made her a focal point at a presidential debate
At a GOP presidential debate in 2015, Fox News moderator Megyn Kelly hit Donald Trump with some tough questions. « You’ve called women you don’t like fat pigs, dogs, slobs and disgusting animals, » Kelly said before Trump interrupted her. « Only Rosie O’Donnell, » he quipped (via USA Today).
O’Donnell, who was probably just as surprised as we were that she was suddenly at the center of a presidential debate, tweeted: « Try explaining that 2 ur kids. »
That wouldn’t be the last time O’Donnell became the focal point of a debate for the nation’s highest office. In 2016, while battling it out against Democratic candidate Hillary Clinton (via NPR), Trump’s insults against O’Donnell came up again as Clinton accused him of being sexist. Trump responded that he says things for the sake of « entertainment. » He also added that O’Donnell has « been very vicious to me … 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 brought Trump’s son into it
Just when you thought this feud couldn’t get any worse, the battle took an exceedingly ugly turn in 2016. A YouTuber posted a video of Donald Trump’s youngest son, Barron Trump, that implied that the boy was autistic, reported TMZ. O’Donnell took it upon herself to retweet the video along with a caption that read: « Barron Trump Autistic? »
Trump’s wife and Barron’s mom, Melania Trump, sprung into action and got her lawyer involved. Attorney Charles J. Harder demanded the video be deleted from YouTube’s platform and requested that the creator of the video issue a public apology. « The video allegedly seeks to ‘stop the bullying’ of Barron Trump. Not true, » Hader said in a statement. « …The video did instigate further bullying by Rosie O’Donnell and others. »
O’Donnell issued a public apology in a since-deleted tweet (via Us Weekly), that said: « I apologize to @melaniatrump — I was insensitive in my RT — I am sorry for the pain I caused — it was not my intent — I am truly sorry. »
She’s an anti-Trump artist
Rosie O’Donnell took a different approach to venting about Donald Trump in 2018. Taking her cues from fellow comedian Jim Carrey — an avid anti-Trump artist — O’Donnell channeled her own her detest in the form of homemade artwork. Sold in her Etsy shop, O’Donnell’s anti-Trump images were so popular that the first round of autographed digital prints sold out, according to USA Today.
On her Etsy profile, the comedienne wrote that she started « doodling » images of Trump and « his regime » on her iPhone. The artwork became a way for her to express her « sadness rage disappointment. » O’Donnell also declared, « All money collected with be matched by me and donated to ANTI TRUMP CANDIDATES AND CAUSES. » While she initially planned to keep making art until Trump left office, O’Donnell’s Etsy shop is on hiatus as of this writing.
She’s an anti-Trump poet, too
Rosie O’Donnell continues to utilize different approaches to express her disdain toward Donald Trump. Of course, she’s as vocal as ever on Twitter, calling for America to « impeach the b*****d » in a June 2019 tweet, but she also appears to be trying her hand at poetry on the platform.
In a February 2019 tweet, Trump addressed the topic of border security by writing: « I want to thank all Republicans for the work you have done in dealing with the Radical Left on Border Security. Not an easy task, but the Wall is being built and will be a great achievement and contribution toward life and safety within our Country! »
Fellow comedian Tony Posnanski responded by tweeting: « I just like how you get no funding for a vanity wall and you pretend it’s being built and people who buy MAGA hats believe it … Amazing. » O’Donnell then posted what appeared to be a poem as a response to Posnanski’s tweet. She called Trump a « cowardly fraud » and concluded her message with: « i saw thru u always/that got to u/ a woman with no fear/a con man – he/a bad one. »
Ladies and gentlemen, this is the feud that never ends. Yes, it goes on and on my friends.