Rosie O’Donnell isn’t the only celebrity to <a href="https://www.dailywire.com/news/exit-stage-left-celebrities-fleeing-trump-and-x">defect from the United States</a> after Donald Trump was re-elected president. But out of all the famous faces who have turned their back on America because of a political leader they don’t like, O’Donnell does have the longest-running public feud with the current commander-in-chief.
As Trump and O’Donnell trade barbs back and forth even now, it’s helpful to go back in time and figure out how their beef began.
Their first public altercation happened close to two decades ago in 2006 when Trump, as co-owner of the Miss USA pageant, decided not to fire Miss USA Tara Conner after it was discovered that she had a history of drug use, underage drinking, and sexual activities, which violated the rules of the competition. 
At the time, O’Donnell was a panelist on “The View” and made comments about the decision, and then took aim at Trump personally. The comedian said Trump went bankrupt and was not a “self made man.” She described him as a “snake oil salesman on ‘Little House on the Prairie.’”
&#8220;He annoys me on a multitude of levels,” O’Donnell said on the show. “[He] left the first wife, had an affair, left the second wife, had an affair, had kids both times, but he&#8217;s the moral compass for 20-year-olds in America,&#8221; she said. &#8220;Donald, sit and spin, my friend. I don&#8217;t enjoy him.&#8221;
Trump fired back, telling <a href="https://people.com/all-about-rosie-odonnell-donald-trump-feud-11702390">People</a> at the time, “You can’t make false statements. Rosie will rue the words she said,” specifically targeting claims that he went personally bankrupt, as Trump only ever declared corporate bankruptcy. “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.”
O’Donnell left “The View” the following year after having a conflict with fellow panelist Elisabeth Hasselbeck — a conflict in which Trump actually took her side. However, the two of them continued their feud mostly on social media for years after their first major spat.
When the “A League of Their Own” actress announced her engagement to Michelle Rounds in 2011, Trump again made his thoughts known. 
“I feel sorry for Rosie &#8216;s new partner in love whose parents are devastated at the thought of their daughter being with @Rosie — a true loser,” he <a href="https://x.com/realDonaldTrump/status/146994336670822400">wrote</a> at the time. 
O’Donnell responded by calling Trump an “a**.”
Two years later, he <a href="https://metro.co.uk/2025/03/25/rosie-odonnells-brutal-takedown-donald-trump-led-a-vicious-20-year-feud-22790469/">said</a> in a reply to another person on X that their feud “will never end.”
In 2014, Trump tweeted, “Rosie is crude, rude, obnoxious and dumb – other than that I like her very much!”
The pair sparred back and forth several times on X over the years. But it wasn’t all bitterness. In 2012 after O’Donnell suffered a heart attack, Trump tweeted, “Rosie, get better fast. I’m starting to miss you!”
She replied by saying, “well thank u donald &#8211; i must admit ur post was a bit of a shock … r u trying to kill me ?”
The comedian discussed their ongoing feud during a 2014 <a href="https://people.com/health/rosie-odonnell-on-weight-loss-surgery-the-view-cohost-talks-losing-50-lbs/">interview</a> with People, saying, “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,” she added. “Whether I deserved it is up to your own interpretation.” This referenced how many social media users pointed out how O’Donnell started the back-and-forth with the comments she made on “The View.” 
Any hopes of the two reaching a truce ended when Trump ran for president in 2015. The presidential candidate kept mentioning O&#8217;Donnell during his campaign, like during the first Republican presidential primary debate in August 2015 when former Fox News host Megyn Kelly asked him about some of the more colorful language he uses to describe people.
“Only Rosie O’Donnell,” Trump retorted.
Trump mentioned his nemesis again during a debate against his Democratic opponent, Hillary Clinton. &#8220;Somebody who has been very vicious to me, 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,&#8221; he said.
O&#8217;Donnell responded in a post on X which she later deleted, calling Trump an &#8220;orange anus.&#8221;  In September 2016, she tweeted, “HE WILL NEVER BE PRESIDENT.”
The comedian lamented Trump winning the presidency during a 2017 <a href="https://www.wmagazine.com/story/rosie-odonnell-smilf-showtime-new-donald-trump-interview">interview</a> with W Magazine.
“It has taken me a full year to integrate the reality of him being a president in a way that I don’t come across as either so full of rage that no one can hear my words, or so sad that I can’t articulate the level of pain,&#8221; she O’Donnell told the outlet. &#8220;It’s taken a year for me to get my equilibrium back, to come back up to the surface.”
She continued, “I seriously worry whether I personally will be able to live through [his presidency] and whether the nation will be able to live through it and survive. It’s a terrifying concept, on the brink of nuclear war with a madman in charge.”
At another point in the interview, O’Donnell complained that no one spoke up in her defense during the years-long feud.
“Unbeknownst to me, for reasons I can’t really still figure out, he was allowed with impunity to brutally assault me and my character for a decade,” she told the outlet. “No one – not the National Organization For Women, not Gloria Steinem, no one – stood up and said, ‘What the hell are you doing?’ It was laughed about.”
She continued, “When it was only me in that arena, it was a very lonely, isolated and depressing place to be. Even though [people say], ‘Oh you started it,’ well I actually told the truth about him on a show where my job was to talk about pop culture.”
Fast forward to almost a decade later and O’Donnell is once again forced to live in a world where Trump was elected president. Only this time, she decided to flee the country and apply to become a citizen of Ireland. 
The 63-year-old TV personality said part of the reason she defected to Europe after Trump’s big comeback was because she has a “non-binary” child who needs to be protected.
O’Donnell also <a href="https://www.dailywire.com/news/rosie-odonnell-discusses-move-to-ireland-with-nonbinary-child-will-return-when-it-is-safe">talked about</a> being on her way to getting her Irish citizenship thanks to having Irish grandparents.
During a nine minute TikTok posted earlier this month, the celebrity mentioned how “proud and impressed” she is of her daughter Clay adjusting to their move. O’Donnell said, “It’s not easy to move to another country, and we really felt as a family this was the safest and best thing for us to do.”
“It looks like sadly we were correct for what’s happening in the United States is overwhelmingly depressing, unconstitutional, illegal, criminal, and so, so very sad,” she added. “Let’s hope that the world and the nation rallies against the current administration and their horrific ideas for what will make America great again. And it’s not racism. And it’s not homophobia. And it’s equality for all. That’s what we’re promised as American citizens.”
“I feel healthier, I’m sleeping better without the stress and anxiety over what was happening politically in the country,” she said of the United States.
Next, O’Donnell addressed the “feud.” 
“I knew that it would really tax me emotionally to have to do that,” she said of continuing to live in the country while Trump was president. “So I’m very happy that we made the decision that we made.”
The comedian has previously spoken about how her youngest child is a “nonbinary, beautiful human.”
Irish Taoiseach [Prime Minister] Micheál Martin visited the White House in March. A reporter asked him, “Ireland is known for very happy, fun-loving people. Why in the world would you let Rosie O’Donnell move to Ireland? I think she is going to lower your happiness.”
Before Martin could answer, President Trump chimed in saying, “That’s true, I like that question. Do you know you have Rosie O’Donnell? Do you know who she is? You’re better off not knowing.”

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Art Of The Feud: Donald Trump And Rosie O’Donnell’s Beef Goes Way Back