Two decades ago, a simple TV segment about a beauty pageant winner sparked one of the most enduring celebrity feuds in modern history. When Rosie O’Donnell criticized Donald Trump on The View in 2006, neither probably imagined their war of words would still be making headlines in 2025. What started as a disagreement over Trump’s handling of Miss USA Tara Conner’s controversy has evolved into a personal vendetta that has now literally driven O’Donnell out of the country. The feud shows no signs of cooling down, with Trump recently threatening to revoke O’Donnell’s citizenship.
The View segment that started everything
The whole mess began in December 2006 when Trump owned the Miss USA pageant and decided not to strip winner Tara Conner of her crown despite accusations of underage drinking and drug use. Instead, he held a press conference announcing he would give her a second chance if she entered rehab. O’Donnell wasn’t having it, using her platform on The View to tear into Trump during the show’s Hot Topics segment.
She called him a “snake-oil salesman” and questioned his moral authority, pointing out his history of affairs and divorces. “He’s the moral compass for 20-year-olds in America. Donald, sit and spin, my friend,” O’Donnell said on air. Trump fired back through People magazine, calling her “a woman out of control” and threatening to sue her for what he claimed were false statements. He also made personal attacks about her weight, setting the tone for nearly two decades of nasty exchanges.
Trump’s surprising support during O’Donnell’s health crisis
In a rare moment of humanity, Trump seemed to put their feud aside when O’Donnell suffered a heart attack in August 2012. He posted on Twitter saying “Rosie, get better fast. I’m starting to miss you.” The gesture caught everyone off guard, including O’Donnell herself, who responded with surprise and even a hint of humor, asking if he was “trying to kill” her with kindness.
This brief ceasefire didn’t last long though. By 2014, when ABC announced O’Donnell would return to The View after a seven-year absence, Trump initially called it a “good move” before quickly changing his tune. He tweeted that her return showed how “desperate” the network was and predicted it would be a “short term fix and long term disaster.” The temporary truce proved that even during personal crises, their fundamental animosity remained just beneath the surface.
The presidential debate moment that shocked everyone
Trump’s 2015 presidential campaign brought their feud into the national spotlight in a way nobody expected. During a Republican primary debate, moderator Megyn Kelly asked Trump about his history of calling women “fat pigs,” “disgusting animals,” and “dogs.” Without missing a beat, Trump responded “Only Rosie O’Donnell,” drawing gasps from the audience and making headlines worldwide.
The comment revealed how deeply personal their conflict had become for Trump, who couldn’t resist bringing up O’Donnell even during one of the most important moments of his political career. O’Donnell responded on social media, telling Trump to “try explaining that to your kids.” The exchange showed millions of Americans just how petty and long-lasting their feud had become, with Trump using a presidential debate as another opportunity to attack his longtime nemesis.
O’Donnell’s creative insults and protest activities
Never one to back down from a fight, O’Donnell developed her own arsenal of creative insults over the years. She called Trump an “orange slug” during an appearance on Alec Baldwin’s Match Game reboot in 2016, and later referred to him as an “orange anus” on social media. These colorful descriptions became part of her regular vocabulary when discussing the future president, showing she could give as good as she got.
When Trump became president, O’Donnell took her opposition beyond just words. In August 2018, she led a protest outside the White House, delivering a fiery speech to a crowd of Trump opponents. “Let the president know, in no uncertain terms, that we are alive, awake and we are woke,” she told the gathering. Her willingness to take to the streets showed how their personal feud had evolved into something much larger for both of them.
The Iraq War comment that surprised everyone
In one of the few times Trump actually sided with O’Donnell, he weighed in on her 2007 departure from The View after a heated argument with cohost Elisabeth Hasselbeck about the Iraq War. O’Donnell had criticized the war and faced backlash when media pundits suggested she was comparing U.S. troops to terrorists. The controversy eventually led to her asking to be released from her contract.
Trump told Extra that while he didn’t think much of either woman, “On this one, I think Rosie should win.” He added that “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.” It was a rare moment of agreement between the two enemies, though it didn’t soften their overall relationship. The comment showed that even bitter rivals can occasionally find common ground on major issues.
Social media battles and personal attacks
As social media became more prominent, Trump and O’Donnell’s feud found new platforms for expression. Trump frequently used Twitter to attack O’Donnell, calling her a “loser” multiple times and making personal comments about her appearance and relationships. When O’Donnell announced her engagement to Michelle Rounds in 2011, Trump posted that he felt “sorry” for her fiancée’s parents.
The online attacks became so frequent and vicious that O’Donnell later told People magazine that Trump’s bullying was “the most bullying I ever experienced in my life, including as a child.” She described the attacks as “national” and “sanctioned societally,” highlighting how their personal conflict had become public entertainment. The social media warfare showed how modern technology had amplified their feud beyond anything previous generations of celebrities could have imagined.
O’Donnell’s fear during Trump’s first presidency
When Trump won the 2016 election, O’Donnell’s concerns went beyond typical political opposition. In a 2017 interview with W Magazine, she admitted she “seriously worried” whether she would be able to “live through” his presidency. She described needing a full year to find her equilibrium after his election, saying it took that long to process the reality without being consumed by rage or sadness.
Her fears weren’t entirely unfounded, as Trump continued to reference their feud even after becoming president. During his 2016 campaign, he told audiences that O’Donnell had been “very vicious” to him and that “she deserves it and nobody feels sorry for her.” The fact that a sitting president was still publicly feuding with a talk show host highlighted just how personal and enduring their conflict had become over the years.
The move to Ireland and citizenship threats
Trump’s return to the presidency in 2025 proved to be the final straw for O’Donnell. She moved to Ireland with her 12-year-old child Clay just days before Trump’s second inauguration, citing her Irish grandparents as the basis for seeking citizenship there. On social media, she explained that while she never thought she’d leave America, she decided it was “best for myself and my 12-year-old child.”
Trump’s response was swift and characteristically extreme. He posted on Truth Social that he was “giving serious consideration to taking away her citizenship,” calling her “a threat to humanity.” When the Irish Prime Minister visited the White House for St. Patrick’s Day, Trump even asked if he knew who O’Donnell was, quipping that the leader was “better off” not knowing. O’Donnell fired back on Instagram, calling him “King Joffrey with a tangerine spray tan” and daring him to try revoking her citizenship.
What began as a simple disagreement over a beauty pageant has become a defining example of how personal feuds can escalate in the age of social media and political polarization. Their 20-year battle has literally reshaped both their lives, with O’Donnell now living in exile and Trump still using presidential platforms to attack her. The feud shows no signs of ending anytime soon, making it one of the most enduring celebrity conflicts in modern history.
