Kellyanne Conway lit up Fox News’ The Five during its December 30 broadcast, unloading on longtime Trump critic Rosie O’Donnell and telling the comedian she ought to “get a husband” and “find somebody who loves her.” It was the latest chapter in a rivalry that has now stretched across two decades, multiple elections, and both of Donald Trump’s presidencies.
Conway, now a senior adviser to President Trump in his 2026 administration, didn’t hesitate to hit back after O’Donnell posted a TikTok urging Americans to remove Trump from office before the November elections.
“Don’t you have anybody who loves you?” Conway asked the camera, shaking her head as the co-hosts looked on. “You need a hug, or a husband, or a hobby, or a dog. Something. Anything.”
Conway’s jab came after O’Donnell claimed on TikTok that Trump was preparing to “start a war” and suspend the election, calling him “hardly even a human.” The video went viral on left-wing feeds, drawing instant pushback from conservative commentators.
Conway fired right back on air:
“She moved to Ireland, but she never moved on,” she said. “This is Trump Derangement Syndrome at its most toxic. It’s chaotic, it’s hysterical, and frankly—it’s sad.”
The Trump-O’Donnell rivalry began in 2006, long before either imagined a second Trump presidency.
O’Donnell arrived on The View and immediately tore into Trump’s character, accusing him of hypocrisy and womanizing. Trump fired back with classic Trump bombast, calling her “vicious,” “a slob,” and “a disaster.” The feud became one of the earliest pop-culture markers of Trump’s political rise.
By the time Trump won in 2016, the hostility had become personal. O’Donnell famously vowed to leave the country—and kept her word after Trump’s 2017 inauguration, moving to Ireland with her son Clay. She has continued positioning herself as one of the entertainment industry’s most outspoken anti-Trump voices.
“It’s been heartbreaking to see what’s happening politically,” O’Donnell said in a past interview when explaining the move. “Clay and I felt we needed to take care of ourselves and follow through.”
Conway, who returned to the White House in 2025 with Trump’s reelection, said she’s “not surprised” O’Donnell is back to attacking the president now that he’s deep into his second term.
“Rosie has made a career out of hating Donald Trump,” Conway said. “But this idea that she’s some political truth-teller? Please. She thinks screaming into a phone in Ireland is activism.”
A Fox insider tells us Conway’s remarks were “only the beginning,” hinting that more back-and-forth between the two women is almost inevitable as Trump’s reelection campaign machine ramps up ahead of the midterms.
O’Donnell, who came out as a lesbian in 2002, shares four children with ex-wife Kelli Carpenter and one with the late Michelle Rounds. She has described her political commentary as “deeply personal,” saying Trump’s rise affected her “spiritually, emotionally, and mentally.”
Trump, however, has never been shy about returning fire. Just this past fall, he wrote on Truth Social:
“She is not a Great American and is, in my opinion, incapable of being so.”
With Trump now firmly back in the Oval Office in 2026, old tensions have resurfaced—and Conway appears ready to lead the charge on cable news.
“Rosie’s been ranting about Donald Trump for twenty years,” she said on The Five. “At some point, you have to ask: is this about politics, or is she just lonely?”
Conway ended the segment with one more parting shot:
“Maybe instead of obsessing over President Trump from across the Atlantic, she should try finding some joy in her own life. Start small. Adopt a dog.”
In Trump-era politics, some feuds fade.
This one clearly never will.
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Rosie can\’t keep her mouth SHUT!!
Sound advice for Rosie who has a very severe case of TDS. She really should seek some serious mental health.