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

LEMON DROP - Author Drops Bombshell About Trump's Private Life

📅 Oct 15, 2026 Don Lemon 27 MIN 8023 VIEWS 28 SEGMENTS · 3 SPEAKERS
Author and political commentator Kurt Andersen, who has known Donald Trump for more than 40 years, joins Don for a revealing conversation about the president's behavior, personality, and increasingly controversial public appearances. Andersen offers his perspective on the man behind the political persona, describing Trump as "sexually confused and tormented" while examining how decades of personal history may help explain his conduct today. From Trump's rhetoric and treatment of women to his unpredictable campaign appearances and obsession with public image, Andersen tells us what Americans...

What Don Lemon said

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

Kurt Andersen, co-founder of Spy magazine, joined Don Lemon to discuss the Trump administration. He downplayed the press secretary's credential scandal, calling it minor compared to the administration's broader incompetence. Andersen asserted Trump will not run for president in 2028 and will lose the House, predicting a 'blue wave' due to inflation and exhaustion. He described Trump as sexually disturbed and tortured, citing alleged past behavior and the twelve-plus assault allegations. Andersen dismissed Trump's cognitive test claims as dementia screening, not intelligence, and foresaw mental decline post-midterms, noting the 25th Amendment won't be invoked. He affirmed he never voted for Trump. Discussing his novel 'The Division', Andersen said the fictional civil war starting in 2036 is now 'much less distant'.

Key takeaways

  1. Trump will not run for president in 2028; there will be a different Republican candidate.
  2. Trump will lose the House in the upcoming midterms, becoming a lame duck regardless.
  3. Andersen believes Trump is 'sexually disturbed and tortured' and not fully heterosexual.
  4. Trump's cognitive test boast is a dementia screening, not an intelligence test.
  5. Andersen never voted for Trump and never will, under any circumstances.

Numbers and commitments

FigureWhat it refers toTypeAt
25, 26, 27, 28% Percentage of Americans in the 'solid cult' of Trump supporters metric 5:28
2036 Year civil war starts in Andersen's novel 'The Division' timeline 25:48
40 years Years Andersen has covered Trump's news metric 23:49
January 20, 2029 Date Trump's term ends timeline 23:49

Chapters

  1. 0:00Press secretary credential scandal
  2. 5:28Midterm election outlook
  3. 12:47Trump's sexual identity
  4. 19:43Cognitive test claims
  5. 23:49Post-midterm mental decline
  6. 25:48The Division novel and 2036

Questions asked in this interview

5
  1. 2:31Kennedy Jr., who don't leave, and they're hugely and greatly incompetent and influential in the same way she might be incompetent. But I'm sorry, who cares?
  2. 4:13And again, I'm not used to that, but there are only a limited number of seconds in the day to share, you know?
  3. 5:28Have you seen the inflation numbers?
  4. 10:03And who knew I would be dedicated to this for the past ten years?
  5. 19:43But I can. Do you know why?
Don Lemon 0:00 ↗
My next guest has been covering Trump's news for a long time, before his presidency. His name is Kurt Andersen. He co-founded Spy magazine — that magazine that was tearing down Trump's image when he was a real estate developer in New York trying to become famous nationally. Kurt, you know I know that because I'm from New York. I came back — I mean, I arrived in New York permanently in the nineties. I loved Spy magazine, and you guys were talking about Trump long before anyone else. So, there are two things I remember. I remember you, and I remember that interview with Barbara Walters where you confronted him about his bankruptcy and the real size of his wealth. But, welcome, Kurt. Thank you for joining us. First, give us your take on the press secretary issue, and then we'll talk about other things.
Kurt Andersen 0:50 ↗
>> Okay, as you know, I'm happy to hold her accountable, as everyone should hold his followers accountable — who no one holds accountable, let's say, Congress, for example. But I have to say, whether the press secretary lied about her legal license — which she actually did — or she had a license somewhere, or she was a lawyer in China, which she doesn't seem to be by any Chinese standards, all of this... Okay, first of all, I'll put it on the low end of things that astonish me about Donald Trump and his administration. So, I'm not defending her, but she's just a minor character among those who are completely incompetent and unqualified that he surrounds himself with because they're loyal to him. And as you say, they look a certain way. So, that's it. That's what I think.
Don Lemon 1:53 ↗
>> You're not minimizing that. But, let's set that aside, Kurt, because I know you're not the type to back down. I don't think you're the type to hesitate to land blows. When you say it's not important — she's the official spokesperson and the face, isn't she? When people look at her, is the bar so low that this is considered a minor thing? Because under any other president or any other administration, this person would be gone. I mean, look what happened to Anthony Scaramucci. Look, I mean, Sean Spicer lasted a little longer than Scaramucci, but look at what would have happened in any other administration if someone in this position lied — the official spokesperson, if not the face of the White House.
Kurt Andersen 2:31 ↗
>> Absolutely. And of course, in this administration, in the last two years, she's a woman, so she might leave — unlike the likes of Pete Hegseth or Robert F. Kennedy Jr., who don't leave, and they're hugely and greatly incompetent and influential in the same way she might be incompetent. But I'm sorry, who cares? Oh, where... yes, they will... but we can move on... we can say every hour of the day, imagine what would happen in the Biden administration.
Don Lemon 3:02 ↗
>> And we do that. >> About everything they do every day. So, as you know, what are you going to do? >> No, you're right. I mean, what are you going to do? I think people will find out on Tuesday, two weeks from now, right? Don't you think? >> I... I think so. I think so. Yes.
>> So, um... you're saying... why do we doubt it, did she lie? Because if she hadn't lied, they would have come out and said: "This is a lie. She did that. She didn't lie." Or they would have presented the evidence. Why do we doubt it? Because... no, look, Kurt, the Wall Street Journal is not a shy newspaper. It's not a run-of-the-mill liberal newspaper, right? It's not a liberal tabloid. Are they liberal tabloids? I don't know. >> They used to be. >> They used to be, but they're not anymore, right? Now, it's limited to the Daily Mail and the New York Post. And they're saying... I think the New York Post might be doubting, but when you have the Wall Street Journal, and the New York Times, and the Washington Post, and so many others saying we can't find a law license anywhere, there's no evidence. Then I have... and you... I'm talking to reliable lawyers and they're saying you can't do this if you're in China, there are things... so, it seems she lied. No, why do we doubt it?
Kurt Andersen 4:13 ↗
>> No, she... she's totally... she and Trump, of course, literally lied about her identity... and... yes, it seems that's correct and I'm sure it will become clearer and an indisputable fact. Now, as I said, should the press secretary be a lawyer? No. Should she not be blatantly lying about a fundamental part of her résumé? No, they shouldn't. That's true. But again, I mean... yes, the bar of expectations for this corrupt and bizarre administration is very low. So, this... this... this is my position. And again, I'm not used to that, but there are only a limited number of seconds in the day to share, you know?
Don Lemon 5:03 ↗
>> Okay, and that's also part of it, because as you know, you know Steve Bannon. You've heard of Steve Bannon, I'm sure you've heard of Steve Bannon. >> I actually appeared on Steve Bannon's show a few weeks ago. >> I'm joking with you. He said the strategy would be a constant barrage of nonsense every day, and that's what's happening. And so, a person might get used to it, and maybe the American people will get used to it, but that doesn't mean we should.

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APA

Lemon, D. (2026, October 15). LEMON DROP - Author Drops Bombshell About Trump's Private Life [Interview transcript]. Don Lemon. CEOInterviews.AI. https://ceointerviews.ai/interview/3067822/

MLA

Don Lemon. "LEMON DROP - Author Drops Bombshell About Trump's Private Life." Don Lemon, 15 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3067822/.

BibTeX
@misc{lemon2026_3067822,
  author       = {Don Lemon},
  title        = {LEMON DROP - Author Drops Bombshell About Trump's Private Life},
  howpublished = {Interview transcript, Don Lemon. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3067822/},
  note         = {Speaker-attributed transcript with timestamps}
}