President Trump’s party suffered historic losses in the midterm elections Tuesday. But defeat at the polls isn’t the only problem he faces. There’s also the matter of a pending $83 million civil judgment against him.
Unless the U.S. Supreme Court intervenes in his favor, Trump will have to pay E. Jean Carroll the $83 million plus interest on top of an earlier judgment of $5 million plus interest that he ultimately paid after being found liable in a defamation and sexual abuse lawsuit filed by Carroll.
Who is the woman at the center of the case? The real person – not the caricature pushed by the president and his supporters – emerges in the Oscar-contending documentary Ask E. Jean, directed by Ivy Meeropol. The film screened Tuesday night as part of Deadline’s For the Love of Docs virtual event series.
“She’s so eccentric and so fascinating,” Meeropol said as she took part in a panel discussion after the screening. As the film explores, Carroll became a prominent advice columnist for Elle magazine as well as a television personality known for dispensing frank counsel on sex and relationships. In her 2019 book What Do We Need Men For?: A Modest Proposal, which was initially excerpted in New York magazine, Carroll recounted an incident in the mid-1990s in which she said the future president sexually assaulted her in a dressing room of a high-end department store in Manhattan.
“I read the article in June 2019,” Meeropol explained. “I… was just struck by her voice, how she told the story of the interaction and assault by Donald Trump at Bergdorf Goodman. And I wanted to know more about her immediately, and that’s how it began, but it took a while to get her to agree to even meet with me. She was not interested. There were, of course, other filmmakers interested in her story as well. She was rebuffing all of us. And she eventually, through a mutual friend, was urged to watch some of my films. And specifically, she watched a film I had made about Roy Cohn that had come out that same year. And she was really taken with it and that made her more open to at least talking to me.”
E. Jean Carroll (center) leaves the courthouse on September 6, 2024 in New York City. To her right is attorney Roberta Kaplan.
Alex Kent/Getty Images
After Carroll published her article and book, Trump called her a liar, which prompted the writer to sue. She won the $5 million suit, then Trump continued to bash her, resulting in the second lawsuit and Carroll’s second victory in court. Carroll was represented by attorney Roberta “Robbie” Kaplan, famed for winning the Supreme Court case that led to the legalization of same-sex marriage.
“Ivy really needed to be in close contact with [Carroll’s] legal team to make sure that we were not bumping up against anything that would impact the case or create problems later,” producer Annabelle Dunne commented. “So, much of the production was done secretly. It was a very small group of people that knew what was happening. It was just really our film team. And that seemed to serve the project well for a number of reasons, but it allowed us to do what we needed to do. It kept us out of [Carroll’s] hair, out of the legal hair.”
A dilemma for the filmmaking team was how to give a sense of the testimony in the civil case.
“Creatively, our big challenge was initially we only had the transcripts of the trial, of E. Jean’s trial, and how were we going to get the trial into the film?” producer Laura Bickford noted. “And we had the idea that we would ask an actress to recreate the scenes, reading the transcripts of the trial, because E. Jean certainly wasn’t going to read them again and go through all of that… We ended up getting her depositions from Robbie, which was a game changer for the film.”
Director Ivy Meeropol
Manoli Figetakis/Getty Images
“We had to get through Robbie Kaplan [to obtain the videotaped depositions], which is almost harder than getting E. Jean on board,” Meeropol noted. “But once we did, when she trusted us and saw what we were doing, she was quite keen to help us… No one would’ve ever seen this footage if not for the film and if not for them trusting us with this. Those depositions would’ve remained in a vault, never to be seen.”
“You see the film and you see her deposition and you just see how incredibly authentic and truthful she is,” Bickford said of Carroll. “And also, in addition to the depositions, how funny and joyful and interesting and… this incredible life [she’s lived] that we didn’t know about either. So, she’s made an incredibly great subject for a documentary.”
Ask E. Jean premiered at the Telluride Film Festival in 2025. It won Best Documentary Feature at the Key West Film Festival and recently earned a nomination for Best Political Documentary at the Critics Choice Documentary Awards (which will be presented Sunday).
“[Carroll] has a hard time considering herself a victim. It’s part of her upbringing. It’s part of her generation. It’s part of her story,” Bickford said. “So, she really can’t look at herself as a victim and doesn’t present as one, even though of course she is one. And that tension is part of the story.”
Watch the full conversation in the video above.
For The Love of Docs is produced with the long-time support of National Geographic Documentary Films. Films are presented free of charge to the audience and to the filmmakers. The series continues with weekly screenings, followed by conversations with filmmakers through December 1. Join us next week for Kikuyu Land, directed by Andrew H. Brown and Bea Wangondu, the story of the legacy of colonialism In Kenya and one man’s attempt to regain possession of family lands worth a fortune. To RSVP for the screening, click here.
