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Don Lemon
Host, The Don Lemon Show; Political Commentator, The Don Lemon Show

LEMON DROP - The Woman Who Made Trump Pay: E. Jean Carroll's Stunning Story

📅 Oct 12, 2026 Don Lemon 19 MIN 16988 VIEWS 58 SEGMENTS · 5 SPEAKERS
Donald Trump is used to fighting his enemies. But E. Jean Carroll fought back and beat him in court. Twice In this powerful conversation, Don speaks speaks with acclaimed filmmaker Ivy Meeropol, director of Ask E. Jean, a new documentary about the woman who took on Donald Trump and won two landmark civil cases. In 2023, a jury found Trump liable for sexually abusing and defaming Carroll, awarding her $5 million. In 2024, another jury ordered him to pay $83.3 million in a separate defamation case. Meeropol takes us behind the headlines to explore Carroll's extraordinary fight for justice, the...

What Don Lemon said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Don Lemon interviewed filmmaker Ivy Meeropol about her documentary 'Ask E. Jean,' which chronicles E. Jean Carroll's legal battles against Donald Trump. Lemon discussed the two civil jury verdicts against Trump: $5 million for sexual abuse and defamation in 2023, and $83.3 million for defamation. Meeropol revealed that Carroll received $5.6 million from the first judgment including interest, and that Chubb Insurance Company underwrote the bond for the second verdict, not Trump himself. She noted the Department of Justice launched a baseless perjury investigation into Carroll. Lemon connected these events to broader concerns about the administration's tactics, citing the raid on Ilhan Omar's home and proposals to televise executions, drawing parallels to the McCarthy era. Meeropol emphasized Carroll's unapologetic nature and the documentary's release on October 15th across major platforms.

Key takeaways

  1. Carroll received $5.6 million from the first verdict, including interest.
  2. Chubb Insurance Company underwrote the bond for Carroll's $83.3 million verdict, not Trump.
  3. The Department of Justice opened a baseless perjury investigation into Carroll.
  4. The documentary 'Ask E. Jean' will be available on video on demand starting October 15th.
  5. The Justice Department's perjury investigation was opened two days after the film's theatrical run began.

Numbers and commitments

FigureWhat it refers toTypeAt
$5 million Damages awarded to Carroll in first civil verdict commitment 0:00
$83.3 million Damages awarded to Carroll in second civil verdict commitment 0:00
$91 million Bond posted by Trump for appeal commitment 8:21
$5.6 million Amount Carroll received from first verdict including interest metric 3:52
October 15th Release date for the documentary on VOD timeline 14:50

Chapters

  1. 0:00Introduction to E. Jean Carroll's legal battles
  2. 1:37Personal price Carroll paid
  3. 3:55Details on payments and appeals
  4. 4:29Film excerpts and Carroll's testimony
  5. 6:26Carroll's breakdown and trial preparation
  6. 8:21Trump's bond and Carroll's fame
  7. 11:00Advertisement for Lean supplement
  8. 12:01Raids on Ilhan Omar and administration tactics
  9. 14:50Film release details and closing remarks

Questions asked in this interview

2
  1. 3:59He will, you know, he's run out his appeals and he will likely be bringing that to the Supreme Court with the same question: Will they hear it?
  2. 13:03I mean, that's like right out of the dictator's playbook, right?
Don Lemon 0:00 ↗
What is the price of standing up to Donald Trump? Because E. Jean Carroll knows something about that price. She accused Donald Trump of sexually assaulting her. He denied it. He attacked her credibility, and she took him to court. And guess what? She won. In 2023, a jury found Trump liable for sexually abusing and defaming E. Jean Carroll, awarding her $5 million. Then came another jury, another verdict: $83.3 million in damages for defamation. So, let that sink in there. Two civil injuries here, or two civil juries, I should say, two verdicts against Donald Trump and his madness. All right.
And throughout it all, E. Jean Carroll faced public scrutiny, personal attacks, years of legal battles, and she is just to tell her story. She put it before a jury. She put it before two juries, and the juries believed her. And what fascinates me is what happens after you take on someone that powerful. What does it actually cost to fight back? Well, joining me now is a filmmaker, Ivy Meeropol, director of "Ask E. Jean," a documentary exploring Carroll's life and extraordinary legal battle with Donald Trump. But Ivy has a remarkable family history of her own that we should tell you about. She is the granddaughter, the granddaughter of Julius and Ethel Rosenberg, the husband and wife executed by the United States government in 1953 after being convicted of conspiracy to commit espionage. So Ivy knows what it means to grow up with the legacy of a family caught at the center of a deeply controversial American prosecution. Ivy, welcome to the show. Thank you so much for joining us.
Ivy Meeropol 1:28 ↗
Thank you for having me, Don.
Don Lemon 1:30 ↗
You spent time telling a story of a woman who stood up to Donald Trump. What did you discover about the personal price that she paid?
Ivy Meeropol 1:37 ↗
Oh, she paid an enormous price. From the minute the first lawsuit was filed, she was under attack from not only Donald Trump but from his followers and his most rabid, most dangerous followers, actually, who threatened her life. I mean, Trump himself tried to share where she lived on Truth Social. It was quite terrifying for E. Jean from the get-go. And then when she won the first lawsuit, it ramped up even more, and she had to have security. She had to, you know, she had to acquiesce, and she didn't want to. She's a fiercely independent woman and quite strong, and it was very upsetting to her to have to, you know, accept that she needed protection.
Don Lemon 2:30 ↗
Well, Ivy, even after that, he didn't want to send the money. He tried to appeal it all. He did all the things, and she had to relive this and relive this and be re-traumatized by it. And now the courts have ordered. He's still trying to fight it, right?
Ivy Meeropol 2:43 ↗
Yes.
Don Lemon 2:44 ↗
What do you think of that?
Ivy Meeropol 2:45 ↗
Well, I mean, you know, it's par for the course. Although, you know, we keep saying like we shouldn't be surprised. We shouldn't be surprised. I have to say I was personally quite surprised when our film first, the theatrical run began here in New York City at the IFC Center, and two days later is when the Department of Justice filed a criminal, they started a criminal investigation into E. Jean for perjury. It was a completely baseless claim meant to threaten. And so it just showed that he was like, there was no, even though the Supreme Court had decided they were not going to hear the case, it was, you know, later he still continued to try to stop the payment. He's tried to, you know, he appealed again to the Supreme Court in ways that nobody ever does. He's just trying everything to not, you know, have to pay her. But she did, we are happy to report, receive the first five million and change. Well, not just change, but from the interest, quite a bit of change.
Don Lemon 3:48 ↗
We get what you mean. We get what you mean. And you got the interest, right?
Ivy Meeropol 3:52 ↗
Yes. Exactly. 5.6 million.
Don Lemon 3:55 ↗
Good for you. Now, let's see the 83.3 million.
Ivy Meeropol 3:59 ↗
We'll see what happens with... Well, that's heading, you know, we assume heading to the Supreme Court. He will, you know, he's run out his appeals and he will likely be bringing that to the Supreme Court with the same question: Will they hear it? And that, you know, it'll be who knows what will happen with this one.
Don Lemon 4:16 ↗
Yeah. You saw it just a little bit ago, but for everyone, I want everyone to just to give everyone a glimpse of the documentary itself, to see what's in store for them if they watch it. Here it is. Take a look.
E. Jean Carroll 4:29 ↗
There's no such thing as destiny. Dear listener, we ourselves make our lives.
All the time I'm writing, writing, writing, and then I write this little quiz and Esquire buys it. I got one taste of New York and I thought, "Wow, I was as happy a being as ever existed." All my dreams were about becoming an advice columnist. And then Roger Ailes gave me my own TV show.
Interviewer 4:59 ↗
You don't really care who comments on anything because, I mean, you comment on everything.
If you were concerned about being dragged through the mud, why would you choose to sue Donald Trump?
E. Jean Carroll 5:12 ↗
Because he called me a liar and I couldn't let it stand.
Interviewer 5:15 ↗
I called you right after the attack.
E. Jean Carroll 5:19 ↗
I was very disappointed that you wouldn't report him.
Interviewer 5:22 ↗
They never would have believed me.
You were more famous than he was.
E. Jean Carroll 5:26 ↗
Here comes this huge attorney, Robbie Kaplan. She laid out the case. If women could see what kind of questions their fellow woman is asked when she brings charges against a powerful man,
Interviewer 5:40 ↗
Were you wearing underwear? Did you wear a bra? Are you taking any medications or drugs? Have you ever had acting classes?
E. Jean Carroll 5:45 ↗
No.
There was some darkness coming in.
We were prepping for the second trial. And Robbie said, "The man you have not seen in 30 years is going to be in that courtroom."

23 more exchanges in this transcript

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APA

Lemon, D. (2026, October 12). LEMON DROP - The Woman Who Made Trump Pay: E. Jean Carroll's Stunning Story [Interview transcript]. Don Lemon. CEOInterviews.AI. https://ceointerviews.ai/interview/3048760/

MLA

Don Lemon. "LEMON DROP - The Woman Who Made Trump Pay: E. Jean Carroll's Stunning Story." Don Lemon, 12 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3048760/.

BibTeX
@misc{lemon2026_3048760,
  author       = {Don Lemon},
  title        = {LEMON DROP - The Woman Who Made Trump Pay: E. Jean Carroll's Stunning Story},
  howpublished = {Interview transcript, Don Lemon. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3048760/},
  note         = {Speaker-attributed transcript with timestamps}
}