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Entertainer Rosie O’Donnell has offered new insights into her two-decade conflict with President Donald Trump, attributing the ongoing feud to their common New York roots. Speaking to Variety, O’Donnell, who recently returned to the United States after relocating to Ireland following the 2024 presidential election, discussed the origins of their contentious relationship and what may fuel it.
While many comedians have publicly targeted Trump with criticism, O’Donnell suggested that her particular dynamic with him differs because of their shared regional and cultural heritage. She recalled that observers have occasionally noted similarities in their New York accents and demeanor—a comparison she finds objectionable.
O’Donnell theorized that her assertive personality may evoke painful memories from Trump’s youth. “I think I’m one of those tough girls from elementary school and junior high that said to him, ‘Shut the hell up! You’re not playing with us,'” she stated, suggesting her willingness to challenge him triggers what she called a “PTSD response of all his failures in his life as a kid.”
During an appearance on Sophia Bush’s “Work in Progress” podcast this week, O’Donnell elaborated on her theory, describing the type of young women Trump grew up around as “tough, probably gay Irish girls who didn’t take s— from no stupid rich boy wannabe.” She characterized his televised confrontations with her as stemming from shock at being directly challenged by someone unimpressed by his wealth.
Social media reactions to O’Donnell’s comments split sharply between critics and supporters. Detractors accused her of obsession, with one commenter writing, “Omg so deluded. Trump lives rent free in her head,” while another asserted, “She is obsessed and it is poisoning her soul.”
Her defenders celebrated her outspokenness and steadfastness. One supporter wrote, “I am so grateful for Rosie having such a strong spine and never falling back,” while another expressed they would choose her as their preferred ally in any scenario.
The animosity between the two figures originated in 2006 when O’Donnell criticized Trump on “The View” over his management of a Miss USA pageant contestant facing misconduct allegations. She branded him a “snake-oil salesman” and questioned his self-made entrepreneur status, prompting Trump to counter by calling her a “real loser” and “a woman out of control.”
Earlier in 2024, O’Donnell disclosed to The Washington Post that she struggles to avoid publicly discussing Trump. She revealed that after committing to her therapist she would refrain from posting about him for two days before Thanksgiving, the pledge lasted only several hours before she returned to the subject.
Friend Jennifer Kopetic encouraged O’Donnell to distance herself from the topic during a recent personal meeting. O’Donnell then promised her 1.2 million Instagram followers she would withhold Trump-related commentary for three days, but that commitment similarly failed to hold.
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