E. Jean Carroll Hopes Her Explosive Telluride Doc Will ‘Finish Off’ Donald Trump – and That Potential Buyers Won’t Fear President’s Wrath

The sitting room of E. Jean Carroll’s modest hotel suite in Telluride is washed in muted mountain tones: beige carpets, pine fixtures and an ancient fireplace. Don’t worry, the decades-long advice columnist brings the color with her.

Carroll enters the room with her signature blonde bob and a shock-orange jumpsuit, brandished in logos reserved for Naval recruits. It’s apt, as the vaunted magazine writer has been doing battle with Donald Trump since 2019 – when she accused the president of sexual assault sometime between 1995 and 1996 in New York City.

She joins two other women in accusing Trump of that crime over the years, though two separate cases brought by Carroll (one for defamation, the other for sexual assault) were the only to be tried in court. Her journey through the accusations and eventual victory – totaling close to $90 million in damages awarded by a jury – are the subject of “Ask E Jean,” an official selection of the Telluride Film Festival, directed by Ive Meeropol. Trump appealed both Carroll cases, and the process is still ongoing. Meeropol is the granddaughter of Julius and Ethel Rosenberg, uniquely positioning her to have examined one of the architects of Trump’s rise to power — Roy Cohn — in her previous work.

Variety sat for a candid conversation with director and subject to discuss the film, one that offers unprecedented access to the process behind the Carroll-Trump fight. The doc includes never-before-seen footage of Carroll’s harrowing deposition led by Alina Habba, Trump’s attorney who is now Acting U.S. Attorney and Special Assistant to the United States Attorney General. It also serves up a fascinating history of Carroll’s legacy as a pioneering female gonzo journalist, a syndicated TV host (on a show greenlit and run by Roger Ailes) and an advice guru whose direction for women did not age as well as she’d hoped.

One of the most fascinating parts of this film is you admitting you didn’t like any of the advice you gave to women for decades. You told them to “suck it up and get on with it.” 

E. Jean Carroll: Fifty percent of my answers were bad. I thought I knew everything at the time, particularly about women in the workplace. If you want to get ahead, use your looks. And, of course, that is good advice. But if a man calls you honey bunch and gives you a pat on the rear? Just move right on. Don’t make a fuss, or you won’t get the promotion. Now – that advice is exactly wrong.  

You say that professional adults today have no idea what it was like for a woman in workplace in the ‘90s. 

EJC: If I had said, “Stand up and scream” the minute [any abuse happened], there might have been a bit of a revolution. My advice was wrong.

Ivy Meeropol: But if you look at something like E. Jean’s syndicated TV show, she was empowering women. She’s telling them, “You don’t have to be married to be a full person.” “You should go to college.” “You should have passion in your life.” “You should work.” It’s a complicated thing, because she was talking about empowerment. 

I saw some of those old show clips. Do you think the women at the time were waiting for permission, to live full lives and not be defined by men or motherhood?

EJC: That is a deep question. What were women waiting for? What are we waiting for now? What are men waiting for? 

Some could say there’s a feeling of suspension in the current political climate. No one is being as outspoken as they were during Trump’s first term. Does that feel true?

EJC: I hate to say this, but yeah. We’re waiting because we’re fearful and anxious and worried, but we do have one weapon — Ivy and all documentary filmmakers. They show you how to step up and speak up. And if an 81-year-old woman can beat Donald Trump? Twice? Anybody can. In the larger picture. I think money is the answer. When the [powers that be] get hit in the pocket book by Trump, that’s going to be it. That moment hasn’t come yet. 

There’s been speculation that your documentary is going to have trouble finding a buyer, given the fears media companies have that Trump will retaliate. Look at what happened last year with “The Apprentice.” What do you think? 

IM: I feel like we’re in a different place. 

EJC: We are flying [in terms of buyer interest]. 

IM: We thought about this – what if we had premiered in January at a festival I will not name? We would have been lost in the show of [Trump’s] inauguration. No one was ready to even think about this, it was a shock for even his supporters. But we’re in a different place today because he’s been doing so much damage on so many levels. People are looking for something to feel that there’s a way out of the madness. 

A sure sign of authoritarianism is repression of women and censorship and abuse of power. The timing of this film is absolutely important. And people will get to know E. Jean’s entire story. That was always my intent. I did not make this to focus purely on the assault. I wanted to tell E. Jean’s whole story, which helps people understand how this could have happened – as opposed to people writing it off. Surprisingly, there are many progressives who don’t actually believe what happened. 

Do you think that includes potential distributors for the film?

EJC: I’m not worried at all. Remember, Ivy is the woman who studied Trump and what made him – and that was her film “Bully. Coward. Victim. The Story of Roy Cohn.” [This film is] a natural progression to finish Trump off.

Many women in situations like yours, E. Jean, are subject to harassment and death threats – especially involving someone like Trump. Is that still happening today? 

EJC: I have a sludge of garbage coming in everywhere, every minute. But that’s just fine. If that’s the price, I’m willing to pay it. Also, I don’t care if somebody shoots me. You can’t be in documentary films or the arts and think life is going to be easy. If you’re an artist, then you do what you must do. Nothing stopped Ivy. Well, they tried to stop Ivy. Did you know that? 

No, say more.

EJC: [My lawyer] Robbie Kaplan, the world’s greatest attorney, told Ivy to stop filming several times.

IM: There was a time I was showing up, out of money, with my little iPhone in the pouring rain, just to get footage of E. Jean and Robbie doing a presser on the steps of the courthouse. Basically, You can’t shoot a documentary during a trial because the footage can be used as evidence.

EJC: Another important part of this film is the video of E. Jean’s depositions with Trump’s lawyer. No one has seen those before. 

Those were difficult to watch. How many hours were you deposed? 

EJC: Seven, for the first one. Most people don’t know that you have to go to a trial before you go to trial. Yeah. That’s going to be new and interesting for the audience, to watch how they torture you before you go to trial. Alina Habba is a magnificent woman, effervescent and super smart. Didn’t know diddly squat about the law. She’s the one who handled the depositions, but she was brutal. She was making the case that you would make in the 1700s. [Habba’s office did not immediately respond to Variety‘s calls for comment].

Were you charged with witchcraft? 

EJC: Basically. Alina is the one who started asking me if I screamed [during the assault] or not —  over and over. Ivy caught things that were even more brutal than what went on during the trial. Women will be astounded [when they see the film].

IM: I’ve always felt the trial took precedent over any film I was making. I wanted to do this right. I didn’t even know that the video depositions could be signed over to me. It was an incredible amount of trust they gave me. But [that blackout period] helped me spend time interviewing E. Jean about her incredible life, work and adventures. 

E. Jean, the film mentions briefly that your syndicated show in the ‘90s was made with Roger Ailes. It never comes up again. What was your experience working with him, in light of how is career ended?

EJC: He’s a great broadcaster. He was a great boss. He could run a network … he was one of my best friends. I adored Roger. So did Katie Couric. Knowing him personally, he was wonderful. We had no idea that underneath all of this was a cesspool. It’s astonishing. This film is trying to alert the nation that it’s still going on, right in front of them. 

Is the Trump administration currently trying to intervene with this documentary, or targeting you in any other way?

EJC: Not a peep. And that’s with my New York Times bestseller [“Not My Type”] out there right now. 

Why do you think that is? 

EJC: We haven’t heard from him because he’s before a United States Court of Appeals Second Circuit. Yeah, and he’s going to have to pay me $100 million if he doesn’t behave [The combined settlements from two cases brought against Trump by Carroll awarded her close to $89 million]. And even if he does behave, he’s going to have to pay me. He thinks that he could win if he just shuts up, yeah, but there is no way. Too late.  [The White House did not immediately return Variety‘s request for comment].

What’s your relationship to writing right now? What are you working on? 

EJC: Oh, horrible. I’m in the horrible stage of not knowing what I want to do next. I may write about Telluride! 

These past few years have observably been an ordeal for you. Where do you find joy? 

EJC: Joy? I grab that motherfucker whenever it comes up.