Making Trump Pay with E. Jean Carroll and Roberta Kaplan

On with Kara Swisher

New York Magazine

News Commentary, News, Society & Culture

4.2 • 2.2K Ratings

🗓️ 17 July 2025

⏱️ 63 minutes

🔗️ Recording | iTunes | RSS

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Summary

“Not my type” is what President Donald Trump said about writer and former advice columnist E. Jean Carroll after she accused him of sexually assaulting her in a dressing room at Bergdorf Goodman. Despite his denials, in 2023, a jury found Trump liable for assault and defamation and awarded Carroll $5 million. After he continued to defame her — leading his supporters to launch an avalanche of threats against her — a second jury in 2024 awarded Carroll $83.3 million in damages. Kara talks to Carroll and her lead attorney, civil rights lawyer Roberta Kaplan, about the two civil lawsuits Carroll details in her new memoir, “Not My Type: One Woman vs. a President.” They discuss potential evidence left out of the trial, including connections to Jeffrey Epstein, where Trump’s appeals stand, what chance he might have of bringing the cases to the Supreme Court and what impact his attempts to silence lawyers could have on our legal system. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	Hi, Eugene. I don't think we've met.
0:02.1	Oh, you two are going to like each other.
0:03.3	I can't wait to hear the Adam Becker thing.
0:05.4	I plan on being very scared after I hear your podcast.
0:24.1	Hi, everyone, from New York Magazine and the Vox Media Podcast Network.
0:26.5	This is on with Kara Swisher, and I'm Kara Swisher.
0:34.6	My guests today are writer, former advice columnist, and renowned Donald Trump ass kicker, E. Jean Carroll, and her attorney, the formidable Robbie Kaplan.
0:38.3	They're here to talk about Carol's new memoir, Not My Type,
0:44.3	One Woman versus a President. As you may remember, Not My Type is what Donald Trump said about E. Jean Carroll after she accused him of sexually assaulting her in a dressing room at the New York
0:49.1	City Department Stewart Bergdorf Goodman in 1996. At the time, she was a well-known advice columnist for Elle
0:55.7	magazine with her own TV show, Ask E. Jean, and had written a couple of books, including a
1:00.6	biography of Hunter S. Thompson. She was something of a gonzo journalist herself. Carol told two friends,
1:06.8	but otherwise she didn't talk about what happened in that dressing room until 2019.
1:11.5	Then she hooked up with legendary attorney Kaplan, a legal powerhouse who defended U.S.
1:16.0	versus Windsor, the Supreme Court case that overturned the Defense of Marriage Act, and won a $26 million verdict against the violent neo-Nazis from the Unite the Right rally in Charlottesville in 2017. Together they took on Trump,
1:29.8	and in 2023, a jury found him liable for having sexually abused Carol and for defaming her. To be clear,
1:36.9	Not My Type was not even close to the worst thing he'd said. The jurors awarded her $5 million.
1:43.3	And then, Trump kept joking about it and calling her names,
1:47.7	and she got death threats from his acolytes. So she sued him again and won again. In 2024,
1:53.7	a different jury awarded her $83.3 million in damages. I want to talk to Carolyn Kaplan about the trials and tribulations in Carol's
2:02.4	memoir. I really thought it was a really interesting book. She's very honest about herself and her
2:07.5	mistakes. And at the same time, she's gone through a harrowing process that has resulted in victory.
	...

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