Oshana humorously showcased before-and-after photos of celebrities he claimed were afflicted by "Trump Derangement Syndrome," a term coined by supporters of President Donald Trump to describe what they see as irrational and extreme reactions to the President, particularly among celebrities and political figures.
The discussion on the show took a turn when radio host Brian Shapiro engaged in a debate with Michael Knowles from the Daily Wire regarding Rosie O'Donnell's recent insinuation that billionaire Elon Musk had somehow manipulated the 2024 election in favor of Trump. According to the Daily Caller, Oshana responded by displaying a photo of O'Donnell from before Trump's presidency, commenting on her appearance before flipping to a more recent image, which prompted laughter from Morgan, Knowles, and other guests. Oshana quipped, "This is Rosie O’Donnell before Trump, right? Nice, good. Look what happens, Piers, with Trump Derangement Syndrome, alright? Rachel Maddow! Look at how hot Rachel Maddow was. Then look, Trump Derangement Syndrome," further adding, "She looks like Stephen Colbert."
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Oshana continued his comedic critique by referencing Kathy Griffin, suggesting that the syndrome had transformed her appearance dramatically. "Then look, Kathy Griffin, someone that I might have hooked up with if I was drunk. They turned her into Carrot Top, OK? That’s what it does to you people, OK? You guys have lost your freaking mind," he remarked.
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The conversation also touched on O'Donnell's recent move to Ireland, which she announced on TikTok, citing the current political climate as a motivating factor. Oshana, undeterred by Shapiro's attempts to interject, continued his commentary, drawing parallels between O'Donnell's criticisms of Trump and allegations against other political figures. He stated, "Piers, in that interview, she’s like, ‘I can’t believe, you know, the sexual assault, because when Conor McGregor came there,’ she supported Bill Clinton. How many sexual assault, rape allegations? Biden did the same thing. Biden sniffing kids live on camera all the time," and further alleged, "His freaking daughter writes in her diary that her father showered with her at inappropriate ages."
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O'Donnell has been a vocal critic of Trump since his first term, even going so far as to accuse him of rape by sharing a tweet with the words "child rapist" overlaid. Meanwhile, during Joe Biden's 2020 presidential campaign, he faced accusations from multiple women of inappropriate touching, and former Senate aide Tara Reade alleged he sexually assaulted her in 1993.
Oshana expressed skepticism about O'Donnell's decision to relocate, questioning her understanding of Ireland's social and political issues. "She [O’Donnell] left to freaking Ireland. Do you know what’s happening in Ireland, Rosie? Freedom of speech, migration, all the freaking rise in crime. It’s unbelievable," he said. He further criticized her departure, suggesting she should make way for others who wish to immigrate to the United States, stating, "Here’s my thing, Piers. There’s people waiting in line and fighting and dying to come to this country. She wants to leave. To hell with her. Let her give up her spot for somebody else. I have family members that are waiting to come here, Piers. Let them come in and to hell with her."
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In a separate interview on March 12, President Trump, when asked about O'Donnell's move, told Irish Prime Minister Micheál Martin that he’s “better off not knowing” who O’Donnell is, underscoring the ongoing tension between the celebrity and the President.
