Rosie O’Donnell and Donald Trump’s Longstanding Feud Explained

While the two used to be friends — O’Donnell has even claimed to have attended Trump’s 1993 wedding to his ex-wife

in 2006 spiraled into a nasty war of words that carries over to the present day.

The feud has occasionally been reignited during Trump’s decade in politics, including the president warning O’Donnell that he could

Keep scrolling for a rundown of some major moments in the epic O’Donnell vs. Trump feud.

The drama started after Trump held a press conference to announce that he would not strip then-reigning Miss USA

of her crown when accusations of recreational drug use and drinking came to light. (Trump owned the Miss USA pageant at the time and required Conner to enter rehab to keep her title.)

Rosie O'Donnell and Daughter Chelsea O'Donnell's Relationship Ups and Downs

Rosie O’Donnell hasn’t shied away from publicly discussing the challenges her daughter Chelsea O’Donnell has faced over the years. After Chelsea was arrested in November 2024 for the third time in as many months, Rosie took to Instagram to address her daughter’s legal troubles. “So yes this is true – after being bailed out by […]

, O’Donnell accused Trump’s press conference of being self-serving and mockingly compared him to the “snake-oil salesman on

.” O’Donnell further claimed that Trump cheated on his ex-wives and had previously gone bankrupt — both of which Trump has denied.

“He’s the moral compass for 20-year-olds in America. Donald, sit and spin, my friend,” she joked.

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

to be released from her contract when Hasselbeck refused to condemn media pundits for equating O’Donnell’s anti-war criticism to comparing U.S. troops to terrorists.

: “On this one, I think Rosie should win, but Rosie is not much herself. I think anybody that’s against the war in Iraq is the winner of the fight, because to justify the war in Iraq — only an imbecile could do that.”

Trump seemingly buried the hatchet with O’Donnell following her heart attack in 2012,

via Twitter (now known as X): “Rosie, get better fast. I’m starting to miss you.”

Nobody seemed more surprised than O’Donnell, who replied: “Well thank u donald – i must admit ur post was a bit of a shock … r u trying to kill me?”

Trump initially responded favorably to ABC’s announcement that O’Donnell was returning to

that fall after a seven-year absence. He credited ABC with making a “good move” by rehiring O’Donnell but he wasn’t supportive for very long.

which tells you how desperate they must be. It is the standard short term fix and long term disaster,” he later

Rosie O'Donnell Compares Old Neighbor Diddy to Harvey Weinstein

Rosie O’Donnell revealed that she and Sean “Diddy” Combs were formerly neighbors — while comparing him to Harvey Weinstein. “Although I only met him once, he did invite me to his New Year’s Eve party, which I believe everybody was wearing white, but we didn’t know,” O’Donnell, 62, said in a recent TikTok video. “We […]

The feud took center stage once again during one of Trump’s Republican presidential debates, after moderator

asked if he regretted referring to women as “fat pigs,” “disgusting animals” and “dogs” in the past.

“Only Rosie O’Donnell,” Trump replied, eliciting gasps of shock from the debate crowd.

O’Donnell reacted to Trump’s debate insult by tweeting: “Try explaining that 2 ur kids.”

A few months prior to the 2016 election, O’Donnell derisively referred to Trump as an

reboot. (Baldwin is also known for his longstanding dispute with Trump over

O’Donnell led a protest against then-President Trump outside the White House in Washington D.C., according to

host delivered a fiery speech calling on Trump’s political opponents to resist his administration’s policies.

“Let the president know, in no uncertain terms, that we are alive, awake and we are woke,” she told a cheering crowd.

in the days before Trump’s second presidential inauguration.

“[I’m] in the process of getting my Irish citizenship, as I have Irish grandparents,” she explained via Instagram. “And that’s what’s going on, and that’s where I’ve been and what I’ve been doing. And although I was never someone who thought I would move to another country, that’s what I decided would be the best for myself and my 12-year-old child. And here we are.”

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as payback for her continuous criticism. Political scholars dispute that a president has the power to strip a U.S. citizen of their legal status.

“Because of the fact that Rosie O’Donnell is not in the best interests of our Great Country, I am giving serious consideration to taking away her Citizenship,” Trump nevertheless warned via Truth Social. “She is a Threat to Humanity, and should remain in the wonderful Country of Ireland, if they want her. GOD BLESS AMERICA!”

O’Donnell replied via Instagram, “The president of the USA has always hated the fact that I see him for who he is — a criminal con man sexual abusing liar out to harm our nation to serve himself. This is why I moved to Ireland.” (Trump has denied all allegations of sexual misconduct.)

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