The fact that Donald Trump has a long list of adversaries, including former close allies who have abandoned him, is well known. Actress and comedian Rosie O’Donnell is one popular figure who has been outspoken in her criticism of Trump, even though they were never friends.
O’Donnell really committed one last, dramatic act in her battle with Trump by moving to Ireland shortly after the former “Apprentice” host was elected to a second term as president. This move made her one of several celebrities who departed the nation after Trump’s victory.
Trump’s conflict with O’Donnell predates his tenure as president, demonstrating that not all of his adversaries are from the political sphere. In fact, you might be shocked to hear that Trump and O’Donnell have been at odds for more than 20 years if you’ve only been following the drama lately.
Everything began in December 2006, a full ten years before Trump’s first term in office. In an episode of “The View,” O’Donnell pushed back against Trump’s portrayal as a “self-made” guy, citing his father, Fred Trump, being a successful businessman, his alleged history of infidelity in his marriages, and his response to the Miss USA 2006 controversy.
In an interview with PEOPLE that same month, Trump retaliated by labeling O’Donnell a “loser,” making fun of her weight, and even threatening to sue her for her remarks about Fred. Trump also asserted that he didn’t inherit a significant amount of money from his father. He never did, however, follow through on his threats to file a lawsuit.
Rosie O’Donnell on Donald Trump: “Well he is a cruel, criminal and mentally unstable man. I think he’s the worst thing to ever happen to the United States. And his cruelty knows no bounds.” pic.twitter.com/4ev0cjgGen
— Marco Foster (@MarcoFoster_) August 9, 2025
Shortly after the first round of jabs between Rosie O’Donnell and Donald Trump in January 2007, a surprising third person entered the fray. Trump’s close friend, then-WWE head honcho Vince McMahon, reportedly organized a televised match between Trump and O’Donnell in an effort to profit from all the commotion. It goes without saying that the truth is that impersonators clearly played both public persons.
Rosie O’Donnell responds to Donald Trump’s threat to revoke her citizenship in a post on Instagram alongside a photo of him with his best friend Jeffrey Epstein: “hey donald – you’re rattled again? 18 years later and I still live rent-free in that collapsing brain of yours. you… pic.twitter.com/iKmeeqy6hY
— Marco Foster (@MarcoFoster_) July 12, 2025
Prominent pro-wrestling analyst Brian Zane of Wrestling With Wregret pointed out that a 2016 video documenting Trump’s intermittent relationship with WWE was obviously intended to present Trump in a far more positive light than O’Donnell, again making fun of the comedian’s weight. Additionally, he criticized the entire affair for being simply subpar.
The actual Trump and O’Donnell have been at odds ever since, and it doesn’t appear that they will ever be able to work things out. The fact that O’Donnell resides in Ireland and that Trump has threatened to revoke her U.S. citizenship due to her being a “threat to humanity” means that they are unlikely to ever need to meet again.
