Podcast Summary: "Making Trump Pay with E. Jean Carroll and Roberta Kaplan"

Podcast Information:

• Title: On with Kara Swisher
• Host: Kara Swisher, Vox Media
• Guests: E. Jean Carroll (Writer and Former Advice Columnist) and Robby Kaplan (Attorney)
• Episode Release Date: July 17, 2025

1. Introduction and Background

In this compelling episode of On with Kara Swisher, host Kara Swisher engages in a deep and candid conversation with E. Jean Carroll and her attorney, Robby Kaplan. The discussion centers around Carroll's new memoir, Not My Type: One Woman Versus a President, which chronicles her legal battles against former President Donald Trump. Carroll, a renowned writer and former advice columnist, accuses Trump of sexually assaulting her in a Bergdorf Goodman dressing room in 1996. The memoir not only delves into the harrowing legal struggles but also highlights the resilience and strategic prowess of Carroll and Kaplan in taking on a powerful figure like Trump.

2. Overview of Not My Type and the Trials

E. Jean Carroll's memoir serves as both a personal narrative and a legal exposé. She recounts her experiences preparing for and enduring two high-stakes trials against Donald Trump—one for sexual abuse and defamation, and the other for defamation leading to harassment and threats. Carroll describes the trials as "high comedy," blending humor with the gravity of the situation, a testament to her unique writing style.

"I was surrounded with a group of characters straight out of Jonathan Swift. It was as a journalist, at the end of every night trial, I'd go back and I would put notes into my phone. I was flabbergasted. Thank God. I got those details down and it just turned out to be funny."
—E. Jean Carroll [06:28]

3. Details from the Trials

a. E. Jean Carroll's Courtroom Experience

Carroll vividly describes the courtroom dynamics, highlighting Trump's unorthodox and contemptuous behavior. She contrasts this with Robby Kaplan's composed and methodical approach, which was pivotal in swaying the jury.

"She is a sensation. And just this tiny woman. And she drove Donald Trump so insane, Kara, that in her final argument in the trial, when Trump was sitting, listening, final argument, he stood up, turning vermilion with like steam coming out his nostrils and his ears, like his hair had swelled to twice its size because of the fire in his brain, and walked out of court."
—E. Jean Carroll [08:11]

b. Robby Kaplan's Legal Strategy

Kaplan discusses the balance between allowing Carroll to remain authentic on the stand while ensuring the jury perceives her credibility. He likens their teamwork to classic comedy duos, where Carroll remains herself, and he serves as the "straight guy" to reinforce legal arguments.

"I think Eugene and I make a pretty good Mutt and Jeff that way, or Abbott and Costello, whoever you want to say."
—Robby Kaplan [09:48]

4. Evidence and Legal Hurdles

a. Avoided Evidence and Epstein Issues

Carroll and Kaplan faced challenges in introducing certain pieces of evidence, including connections to Jeffrey Epstein. Kaplan explains that the evidence was deemed inadmissible due to hearsay and reliability concerns, leading them to focus on other strong evidence that ultimately secured their victory.

"He was on a tape recording. He had hundreds of hours of Jeffrey Epstein on tape. Robbie was so calm here. At the time, she was Jeffrey Epstein, in 1996..."
—E. Jean Carroll [29:40]

"I mean, the main reason is I don't think Judge Kaplan would ever have let it in. And we need, you know, one of the most important things when you're court is having credibility with the court and not making arguments that he's gonna be disdainful of."
—Robby Kaplan [28:52]

5. Trump's Appeal and Public Perception

The discussion delves into why Donald Trump continues to garner support despite his controversial actions and statements. Both Carroll and Kaplan analyze Trump's adeptness at social media and his ability to tap into societal resentments.

"He is a genius at social media and he only thinks of himself and every therefore, everybody around him only think of him."
—E. Jean Carroll [40:37]

"What'S always been most astounding to me about Jeffrey Epstein is that it happened in plain sight. Right. He wasn't hiding in some upstate cabin..."
—Robby Kaplan [30:48]

6. Support Systems and Funding

Kaplan highlights the crucial support from billionaire Reid Hoffman, whose pro bono contributions were instrumental in funding Carroll's legal battles. This support underscores the importance of having powerful allies in challenging high-profile litigations.

"Reid Hoffman made that possible."
—E. Jean Carroll [51:23]

7. Future Legal Steps and Appeals

With victories in both trials, Carroll and Kaplan discuss the potential path forward, including the possibility of taking the case to the Supreme Court. Kaplan expresses confidence that the Supreme Court is unlikely to grant presidential immunity to Trump in this context.

"I think if you're the justices, you have to be thinking... is this really the best use of the factual scenario where we want to deal with presidential immunity again?"
—Robby Kaplan [45:35]

"They’re trying to wear you down, presumably. But can you explain to where things stand in the appeals process?"
—Kara Swisher [40:38]

8. Personal Impact and Life Changes

Carroll shares the personal toll the trials have taken, including threats and a transformed lifestyle. Despite the challenges, she remains steadfast and determined to use her experiences to advocate for women's rights and societal change.

"I don't care if they shoot me. I don't care. I'd like to get shot in the arm. I like to get shot."
—E. Jean Carroll [54:51]

"We have to stop being despondent and look at each other. It's called praxis. We organize. When we organize, we can change laws."
—E. Jean Carroll [59:11]

9. Conclusion and Calls to Action

The episode concludes with a passionate call to action from Carroll and Kaplan, urging listeners to mobilize and advocate for change. Their unwavering commitment underscores the broader implications of their legal victories beyond personal vindication.

"This fucking guy."
—Kara Swisher [59:54]

"Let's get this going. Okay."
—E. Jean Carroll [59:58]

Notable Quotes:

1. "I was surrounded with a group of characters straight out of Jonathan Swift."
   —E. Jean Carroll [06:28]

2. "We just have to let Eugene be E. Jean, we're not turning Eugene into a yes, no witness."
   —Robby Kaplan [09:48]

3. "He is a genius at social media and he only thinks of himself and every therefore, everybody around him only think of him."
   —E. Jean Carroll [40:37]

4. "We have to stop being despondent and look at each other. It's called praxis."
   —E. Jean Carroll [59:11]

5. "This fucking guy."
   —Kara Swisher [59:54]

Conclusion

This episode of On with Kara Swisher offers an intimate look into the formidable legal battle between E. Jean Carroll, Robby Kaplan, and Donald Trump. Through incisive discussion and poignant anecdotes, listeners gain insight into the complexities of taking on a powerful adversary, the strategic maneuvers within the courtroom, and the personal resilience required to persevere against overwhelming odds. Carroll's memoir not only serves as a testament to her courage but also as a rallying cry for justice and accountability.