The E. Jean Carroll Rabbit Hole Goes Deeper Than You Think

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There’s an unhinged 82-year-old in the woods of upstate New York, and she’s set to get $83 million from the president. But we may have been bamboozled by this career advice columnist even before she took Donald Trump to the cleaners in court.

Now, the U.S. Department of Justice is reportedly opening a criminal investigation into whether E. Jean Carroll perjured herself during civil proceedings, while poking into the nonprofit that contributed funds to her cause. 

In 2019, Carroll gathered mainstream media behind her as she accused President Trump of a sexual assault that happened 25 years earlier at high-end retailer Bergdorf Goodman. Trump denied that the incident ever happened, but a jury found him liable for defamation and a “lesser degree of sexual abuse” (not assault), awarding $5 million to Carroll. After calling her “not my type” in a deposition, Trump continued making public statements claiming not to know her, adding that she was just trying to sell books. 

First asking for $24 million for Carroll’s “anguish and fear” in light of defamatory comments by Trump, Carroll’s attorney Roberta Kaplan later confirmed her request of the jury: “I said to them … ‘You need to give enough money to make him stop.’” The court granted Carroll $83.3 million. 

While the scales of justice may tilt ever in her favor, Carroll’s sojourn on this mortal coil is supremely unsympathetic.  

Styling herself as a would-be Audrey Hepburn in a bizarro “Breakfast at Bergdorf’s,” Carroll described her presence as “the most attractive woman in Bergdorf’s,” telling CNN’s Anderson Cooper that Trump called her “old” just before the incident. But a key part of her interview has since been edited out of the clip: the moment Carroll said, “Most people think of rape as being sexy. Think of the fantasies,” as Cooper fumbled to cut the live feed. 

We’ll never know what really went down in Bergie D’s that day, but E. Jean Carroll’s account may be cluttered by her thirst for a good story. 

Carroll kicked off her campaign against the then-45th president by posing for the cover of New York magazine in the same dress she was wearing the day she was allegedly attacked. It smacked of Jussie Smollett keeping his fake attacker’s rope looped around his neck for the cops to see, in his own busted hoax that happened several months before Carroll’s covergirl stunt. 

After being forensically tested, Carroll’s dress showed unidentified male DNA, none of which was “sperm” (she alleged penetration). Trump declined to provide DNA samples, and counsel for both sides dropped the DNA issue. Maybe the “unidentified male DNA” was from Trump — or maybe it was from a male assistant steaming the bejesus out of the wardrobe options on the garment rack. Just give her a hundred mil and a book deal. 

Carroll’s “riveting” recollection of her rape trial, “Not My Type: One Woman vs. a President,” became a “hilarious, hopeful” New York Times bestseller in 2025, six years after her “darkly humorous” “What Do We Need Men For? A Modest Proposal” hit the bestseller list in 2019, just a month after Carroll first published her Trump saga.

Carroll’s complete list of those she dubbed “Hideous Men” was also published in New York magazine, where she recounted six other alleged attacks that seemingly never saw the inside of a courtroom. Possibly the most prominent figure was CBS exec Leslie Moonves, whom she never sued. Explaining why, she told the court, “[Moonves] just denied it. He didn’t call me names and grind my face through the mud like Donald Trump did.”

In the same magazine, she alleged that Trump got what she called “grindy-grindy, grabby-grabby” with other women, too. She even offered a regular “Hideous Men” walking tour in New York City, beginning at the north entrance to Bergdorf Goodman. What victim wouldn’t want to retrace their alleged assaults by Bill Cosby, Matt Lauer, Roger Ailes, Bill O’Reilly, and Charlie Rose on the first and third Sunday of every month?

Carroll’s mid-’90s empty lingerie department narrative is riddled with questionable details. First, it’s notable that someone who professionally doled out relationship and sex advice for a living in “Ask E. Jean” waited decades (and most of his first term in office) to accuse Trump of misbehavior. Also, according to her, she was flirting with Trump on an entirely empty floor of Bergdorf Goodman. She says she joked that he should try on a mesh bodysuit she had suggested he buy as a gift. True victimhood aside, where did she think she was driving this bus?

A former cheerleader and beauty queen, Carroll could have gone semi-quietly into the night, if she weren’t still doing everything she could to feed off the spotlight. Two years before speaking out about Trump, she gave ELLE a tour of her “Grey Gardens”-esque cabin, where she lives by herself. Carroll declared, “I get up around noon, and I stagger outside … and I throw open my arms and I thank God I don’t have children!” 

She then recounted one advice-seeker who couldn’t get over an obsession with an ex after 22 years. “She and I have a lot in common,” Carroll said, before showing the cameras how she painted all the nearby trees blue.

Thrilled to tout her $83 million settlement in the media, Carroll’s warbly elder voice quivered as she recalled facing Trump in court for the first time in almost three decades. She told ABC, “I’d like to give the money to something Donald Trump hates … perhaps a fund for the women who have been sexually assaulted by Donald Trump.” 

Later, she told Katie Couric she would be donating to “women’s reproductive rights,” “voting rights,” and “immigrants in L.A. who are being dragged by the heels into, you know, I don’t know.” She also aspired toward “making sure women can become lawyers,” along with backing the ASPCA “because [Trump] doesn’t have a dog.”

Carroll also joked about other plans for the money. “You and I are gonna go shopping,” she excitedly told Rachel Maddow. “We’re gonna get completely new wardrobes, new shoes … Rachel, what do you want? [A] penthouse? It’s yours, Rachel!” 

Still, maybe Carroll’s intentions had more to do with Trump’s reelection campaign than any untoward Bergdorf’s encounters. “He’s gonna lose the election,” she told Fortune in early 2024. “He’s behaved like an a** for the last year. It’s not going to fool, uh, enough Americans who are really pretty smart.” 

She has yet to receive any of the money, but based on how Carroll glows when talking about Bergdorf’s, calling it “posh and cozy … I just love it,” perhaps her next New York Times bestseller should be about a Trump-funded shopping spree.