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Joanna Coles
Welcome back to our second episode of our new podcast, Inside Trump's Head. I'm Joanna Coles.
Michael Wolff
I'm Michael Wolff.
Joanna Coles
What are we going to be talking about today, Michael?
Michael Wolff
Sex, money, sex, social climbing and royalty.
Joanna Coles
The British royal family.
Michael Wolff
There is only the British royal family.
Joanna Coles
Not true. This is the Belgian royal family. The Swedish royal family, if you point them out.
Michael Wolff
Otherwise, I think they go under the radar.
Joanna Coles
All right.
Michael Wolff
In America, let's put a fine point on this. There's only British royalty.
Joanna Coles
All right, so what we're talking about specifically, sex, money, social climbing. Prince Andrew, let's be specific. And of course, his friends Donald Trump and Jeffrey Epstein.
Michael Wolff
Is there anything else?
Joanna Coles
Let's get into it. I'm Joanna Coles.
Michael Wolff
I'm Michael Wolff.
Joanna Coles
And I think nobody has a more original insight into why Donald Trump operates the way he does than Michael Wolff, who's written not one, not two, but four biographies. I don't know how you managed him as a subject for 10 years. Did you not think you were going crazy?
Michael Wolff
Well, no. I mean, in his defense, you know, if you're a writer, he's kind of a gift. I mean, and he keeps giving.
Joanna Coles
He does keep giving.
Michael Wolff
He is a larger than life character. He is a character that Defies expectations. He is.
Joanna Coles
Every day, he defies expectations.
Michael Wolff
And he is often, maybe constantly inexplicable. So if you're a writer, this is a great character. If you're a citizen, that would be another story.
Joanna Coles
Well, and almost if you're a citizen of anywhere in the world. Right. You are untouched by. By Donald Trump. I mean, it's hard to think of anybody who's had global impact as a leader as much as Donald Trump has in the last few years. In living memory.
Michael Wolff
Yeah. No, I mean, yeah. I mean, you can make comparisons, but you're not going to find somebody to compare him to in the modern age.
Joanna Coles
And it's also the unpredictability of it. I mean, part of your period writing about him and your last book, all or Nothing, was about the fallow years when in fact, he disappeared to some extent from public view. Mar. A la.
Michael Wolff
I mean, I wouldn't for a couple of months. I mean, that was one of. I mean, he should have been disappeared forever. And as all people who have, who have all former presidents, what happens to them? They basically disappear. He disappeared, you know, I mean, really for an incredibly brief period of time and had no intention of going away. So it was just. His wilderness was a very short. Was like a park. His wilderness.
Joanna Coles
His wilderness was a short little piece of lawn, actually, I think. But. But also, it's almost as if we've forgotten the intervening Biden years. It just feels like the 10 years, the last 10 years have been utterly dominated by Donald Trump and that. The Biden years, I can't even remember them.
Michael Wolff
No, I mean, again. And I think whatever you have to say about this guy, I mean, whatever your, your, your views are. We know our views. He's been an incredible success.
Joanna Coles
So one of the things I wanted to talk about again today was this new book that's come out about Prince Andrew, which is rocking the Royal family, It's rocking Britain. It is page after page of really remarkable stories. Thai orgies, deep corruption, financial corruption that the Queen somehow colluded with. I mean, it even begins with a startling first line which says that Prince Philip had an affair with Fergie's mum. And I'm talking about the book entitled the Rise and Fall of the House of York.
Michael Wolff
We always think you Brits have had affairs with several people in the same family. Yes. And in the Royal family.
Thumbtack
Yes.
Joanna Coles
Actually, someone who knows Prince Andrew told me that, and this isn't in the book, actually, that because he had sex with a lot of different women, he was also the one Thing he was very careful about was always wearing a condom and always taking the condom with him because it contained royal sperm and he wasn't allowed to leave it anywhere. And I suppose this is true of all celebrities, actually, but he didn't want to leave it somewhere because obviously, what, a hostage to fortune, Someone could take it, grab a turkey baster and suddenly.
Michael Wolff
Have a. I'm not going to have this discussion. I'm going to let you know.
Joanna Coles
Anyway, we're talking about Andrew Lowney's book entitled the Rise and Fall of the House of York. And what's particularly interesting about it is it comes out in a week where Donald Trump is paddling like crazy under the surface to move the narrative on from Jeffrey Epstein. We know that he and Jeffrey Epstein were best friends. You've written about this, you interviewed Epstein at length after he invited you in to write a biography of him. But this book puts Epstein right back central with Donald Trump and with no.
Michael Wolff
And Andrew is this. You know, they were kind of three musketeers, you know, and it's important to understand that both Epstein and Trump had a thing of, about the royal family. And it was actually perfectly natural, these two, Epstein and Trump, among everything else, they were, they were also inveterate social climbers. That's what they understood. They understood the power. Power comes from who you know. And not only power comes from who you know, but money comes from who you know. I mean, these guys, Epstein and Trump, are not exactly AAA businessmen.
Joanna Coles
Right.
Michael Wolff
And so the question is, how do you get, how do you, how do you get money? How do you raise capital? How do you get, how do you raise, how do you get loans when you are not debt worthy?
Joanna Coles
Well, and to be fair, in fact, almost all of New York life is like this, Right? It's an entire social climb. Everybody in New York pretty much all the time is social climbing.
Michael Wolff
Yes.
Joanna Coles
No, it's a very transactional city.
Michael Wolff
Absolutely. But these two guys were consummate players in this. In New York as a transactional place, but also in the grift. I mean, you know, I mean, a lot of people are social climbing and, you know, in a very establishment fashion. These guys are not. These guys are outside of the establishment. They are both outsiders. Epstein is from Brooklyn, Trump is from Queens. There is nothing fundamentally respectable about either one of them.
Joanna Coles
And neither of them, I mean, Jeffrey Epstein taught at Dalton, a very, you know, expensive elite private school in the city, but he didn't have a degree.
Michael Wolff
Yeah, well, that was part of his, his grift. I mean, And I think that's how he began to see this, see the possibilities of New York life by teaching at the Dalton School. And Epstein was quite charming. People liked being with him. He had a gift for appealing to men who were older than he was. And I think he met a whole set of parents of his students at Dalton and began to see the possibilities.
Joanna Coles
Well, and it was a parent at Dalton who got him his job at Bear Stearns, his first job in the financial market.
Michael Wolff
Yes. No. And he became friends, which is not. Not widely known, with the publisher of the New York Times. His daughter was one of Epstein's students.
Joanna Coles
Was that Arthur Saltzberger?
Michael Wolff
Well, they're all named Arthur, so it's. But this is Punch Salzburger.
Joanna Coles
I did not know that. So Jeffrey Epstein was friendly with the publisher of the New York Times?
Michael Wolff
Yes. No, no. I mean, you know, very close, very taken into that. To that. I mean, he was the daughter. Punch Salzberger's daughter was one of Epstein's students. And Epstein was very appealing. I mean, this is the kind of thing which I think people are going to object to anyone saying, how could he be appealing, this monster? But in fact, what is the reason all of these men of power and influence became his friends or frequented his table? It's because he was appealing. And this is important in the context of the social climbing world. How do you rise up? How do you meet people who can help you? And you got to offer something. And it's partly, it's partly because you are amenable, you are appealing to people, you are a good conversationalist. And in addition to the fact that, you know, people who other, you know, this is a complicated. This is a complicated transaction with both Trump and Epstein came to understand what, that Prince Andrew was a currency in this transaction.
Joanna Coles
Right. And actually, Stacey Williams, who was a. Was briefly a girlfriend of Epstein in the 90s when she was a huge model and she was, you know, on the front of the Sports Illustrated calendar, she did Coca Cola, she did huge campaigns. She dated him. And she said, the thing that people don't like to hear is when I first met him, he was incredibly appealing. He would have long conversations about politics, about current affairs. He was very dynamic. And then she began to realize that actually he had a very dark side to him, which she, you know, she had an incident where he took her to visit Donald Trump. Donald Trump then allegedly groped her. And Jeffrey did nothing. Did nothing as his girlfriend was being groped in front of him. And then when they got in the elevator in Trump Tower down to the ground floor. He yelled at her for allowing Trump to do that. And she realized there was something weird. She left him and she hasn't looked back. But she did say, the thing that people don't understand about Jeffrey Epstein is he was incredibly appealing the first few times you met him.
Michael Wolff
Yeah, or more than a few times. I mean, many people spent a long time with him and, you know, there's an explanation that he was blackmailing them and he was offering them girls. But I know that there were many people around him who were not there, who were, who were there for none of those reasons and there because they enjoyed his company and also enjoyed the flow of information. And the flow of information was, was partly a byproduct of being a social climber. How do you meet people who can supply you with information and supply you with introductions to people who can supply you with more information or supply you with the wherewithal to get money to move into essentially financial circles? Well, one of the reasons or one of the ways is make friends with Prince Andrew, who is, you know, the Royal family has always been a, you know, one of the great social climbing vectors.
Joanna Coles
Well, and what's so fascinating is seeing it through a British perspective, is that Prince Andrew always felt like the most washed up of the princes. First of all, he was the third of Queen Elizabeth's children. He was never going to be heir to the throne. He was third in line to the throne. So first you have Prince Charles, now King Charles, Princess Anne, and then you have Andrew. And he always seemed different from his.
Michael Wolff
Siblings, but of course, that made him more accessible for somebody like Jeffrey Epstein and Donald Trump and no less of interest to people who were interested in the Royal Family.
Joanna Coles
Of course, he comes to America and he's immediately fated. Everybody wants to hold a dinner for him. Everybody wants to attend the dinner. I want you to talk about his relationship with Donald Trump and Jeffrey Epstein.
Michael Wolff
Yeah, well, you know, both of these guys, you know, and Epstein and Trump functioned as a duo. They were, you know, you know, grifter buddies, basically. I mean, they had the same interest in women and also in money. How do you get money? How do you do these two guys who don't work for major corporations, don't have relationships with major banks, or don't have good relationships.
Joanna Coles
And the other person who needed money in this triangle was Prince Andrew.
Michael Wolff
Yes, exactly. And so Prince Andrew could get. I mean, they perceived that Prince Andrew had two weaknesses, women who apparently he had an utterly insatiable appetite for.
Joanna Coles
Well, one of the astonishing things in the book. Michael, hold on. We're just going to take a break.
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Alltrails
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Joanna Coles
We love our advertisers, but we're back to talking about what else Donald Trump and Jeffrey Epps. One of the astonishing things in the book is that Jeffrey Epstein says, I'm a pervert, but you are the king of kink. Yeah, it's just oh my goodness. Jeffrey Epstein the apostle.
Michael Wolff
I hadn't heard that line, but that is a line. Certainly that sounds like Jeffrey Epstein.
Joanna Coles
Well, I mean, so here we have. I mean, in Britain he was always known as Randy Andy. The tabloid newspapers would always have some story of his latest hapless exploit and he would be called Randy Andy. We didn't understand until this book came out with all of Andrew Loney's exclusive reporting quite how Randy he was. There's a description of a Thai orgy in which 40 women get ferried in and out of a hotel suite over a weekend. And then he passes some of these women that prostitutes onto an Arab prince friend. But to come back to your point, what did they have in common? A lust for women and sex and money. And Andrew in particular needed money.
Michael Wolff
And what he. What he gave in return was this social climbing currency. And again, it's both Epstein and Trump. This is their grift. I mean, among the many grifts that they had, this is the royal family grift. And you know, there was a point in which they had a competition. Trump and Epstein, who would be the one who would. The first one to sleep with Princess Diana. You know, this was. And it was about the royal. I mean, they just understood. What could you get from these people? Both Trump and Epstein? What can you get from somebody? Is the question you would always ask about anybody.
Joanna Coles
Okay, so I just want to highlight that ring fence that Jeffrey Epstein and Donald Trump both wanted to sleep with Diana. And they were both sort of.
Michael Wolff
It was a competition. Yes. Whether it was a. I knew Donald.
Joanna Coles
Trump had reached out to Diana because I think she wrote about that in one of her diaries. I didn't know Jeffrey Epstein had.
Michael Wolff
Yeah, no. And Epstein got. I don't know if this is an official position that when Diana would go to a function, charitable function, whatever, she could not be. There could not be an empty chair next to her. So Epstein had the job of when whoever was sitting, formally sitting next to Diana got up to go to the bathroom or whatever, then Epstein would be the guy who would then warm the chair.
Joanna Coles
He was a chair warmer. Jeffrey Epstein was a chair warmer for Diana. I did not know that. Like one of those people that followed fills a seat filler at the Oscars. So there cannot be an empty seat when they sweep across the Oscar audience. I did not know that. Do we know what Diana thought of Jeffrey Epstein?
Michael Wolff
We do not.
Joanna Coles
Maybe, you know, I don't know because I haven't heard that before. I knew that Donald Trump had pursued her and I think she Found it amusing. And he sent her flowers. I know he sent her a lot of flowers.
Michael Wolff
No, I mean, this was, you know, this was part of this. That the Royal Family amused them or it amused them that they had access. They had broken the code there. And they had broken the code. Also. Ghislaine is the important connection here. How did they initially get to the Royal Family? Through Ghislaine Maxwell, who was deeply connected throughout British society.
Joanna Coles
One of the revelations in the book also is that Ghislaine was sleeping on and off with Andrew and sleeping on and off with Epstein. And Epstein got a great thrill from this. Yeah.
Michael Wolff
I mean, I can't among. I never had that conversation with. With Epstein, but I did have the conversation about the girlfriend that he did share with Trump and that clearly amused him. And I seemed to amuse Trump also, that they. At the same time, and this is 92, 93, they shared a girlfriend together. I mean, openly and without a parent friction.
Joanna Coles
So let's bring this back to Donald Trump, which is why we're interested in this.
Michael Wolff
Yeah. And I think it brings it back. The Donald Trump. The Donald Trump of it all. And I think it's important to realize the life he lived, who this guy is, and he has really spent a lot of time editing that life out. I mean, he somehow has managed to become an icon of the evangelical set, while for so long living a life absolutely antithetical to people who live in a. Live in the context of church and religion. This is Donald Trump. It's extraordinary. But then also the fact that he was as close as he was to Jeffrey Epstein. Again, this is another detail which I think must come as quite a shock to the MAGA people who thought that everyone else in power was going to be implicated in their Jeffrey Epstein relationships when it is Donald Trump again.
Joanna Coles
And the MAGA God. At one point, Elon Musk also pointed this out to them when he was having his fit of pique with Trump after he'd left Doge, he tweeted out, Trump is in the Epstein file, but it is.
Michael Wolff
And that among the connections, Prince Andrew is a key connection to Donald Trump. They were. And essentially these two guys are conspiring. How do we get Prince Andrew to do what we want him to do, which is basically introduce us to people who will be of further help to us. And the plan is women and money.
Joanna Coles
And let's just take a break for these messages.
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Joanna Coles
And we're back talking about Donald Trump with Michael Wolff. And one of the things that, of course, Donald Trump is doing now is denying that he really had any relationship with Prince Andrew. And yet, as Andrew Lowney, the author, points out, there is endless photographic evidence. They're playing golf together, they're hanging out together.
Michael Wolff
Yeah. No, no, no. I mean, and he is doing the same, of course, with Epstein. The issue on Andrew and why he has to deny that is that it ties him further to Epstein. So this is this, at this moment again in the Trump presidency, this is the Epstein moment. Will he get out from under this or will more and more connections tie him to Epstein and the life they live together?
Joanna Coles
Well, and I was very interested to see a report this week that Ghislaine Maxwell had approached the Biden administration with dirt on Donald Trump and they hadn't taken her up on it.
Michael Wolff
And that would have been, from the Biden standpoint, honorable. Of course, if someone, if someone, a convicted sex offender, approaches us with with, with, with information. You would, if you were a reasonable, decent person, reject that.
Joanna Coles
Well, they may also have known that Democrats were also frequent visitors to Jeffrey Epstein's private club.
Michael Wolff
Well, I don't, I actually don't think we should, we should go there because that's not, that's not what, what she was saying. I can give you dirt on Donald Trump, which would have been, if you're Joe Biden or the Democrats in the White House, you would have thought, man, yes, dirt on Donald Trump. Let's take that. Except if you gave it some amount of, if you're a decent person, you say no. This is first thing, how could we ever trust this? And secondly, we have no truck with convicted criminals.
Joanna Coles
Well, we know they're not releasing the grand jury files from the Ghislaine Maxwell case. And now she's sitting in a much more comfortable jail in Texas where she has a family member, unlike Florida, where she was before. And I guess she's hoping that she can. That the information she obviously gave to Todd Blanche, number two in the.
Michael Wolff
Who's the family member? I hadn't heard.
Joanna Coles
Sister. She has a sister who lives in Texas.
Michael Wolff
Curious. And we should come back to that because once I was almost in business with the Maxwell sisters.
Joanna Coles
Well, you may have dodged a bullet. Or they may have dodged a bullet. Either way, thank you for guiding us inside Trump's head. How do you think Trump's head is gearing up for his conversation with Putin tomorrow?
Michael Wolff
Well, as I remember, when before his last one on one was in Helsinki and he refused to do any preparation for that.
Joanna Coles
So no preparation for a sit down with Vladimir Putin on how to resolve the war in Ukraine.
Michael Wolff
Yes. And even then, I remember Steve Bannon pointing out that, that certainly at that point in time, Trump would not have been able to locate Ukraine on the map.
Joanna Coles
I'm very mindful of your conversation with people in the White House, which you talked about on the podcast earlier this week, where you said that they think he is so desperate to move the narrative on from Jeffrey Epstein that he will insist that parts of Ukraine are given up to Russia.
Michael Wolff
Yeah. No, I mean, I think, I mean, Friday, the conversation that he is going to have with Putin in Alaska tomorrow is. It's frightening because basically they will divvy up Ukraine.
Joanna Coles
What a week. What a week. Michael, thank you very much. How did we find our second episode?
Michael Wolff
We're rolling right along, Joanna.
Joanna Coles
We're rolling right along. There's so many strange little caverns and potholes in Trump's head. I feel very confident we're going to need grappling hooks.
Michael Wolff
And who knew that Prince Andrew occupied a space in Donald Trump's head, A privileged space.
Joanna Coles
We'll be back with two more podcasts, Inside Trump's Head, next week where we'll unpack whatever happens in Alaska. Don't forget to subscribe. Leave us a comment, share it with your friends. Sign up and subscribe wherever you get your podcast on Spotify, Audible, Apple for Inside Trump's Head. And leave us your questions too. We're going to have several episodes where we talk about questions, conspiracy theories, theories and your comments. So do you want to thank our producers?
Michael Wolff
Thank you producers.
Joanna Coles
That's Devon Rogerino and Anna Von Erssen and our editor, Jesse Millwood.
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Inside Trump's Head – Episode Summary: "Why Trump and Epstein Competed to Bed Princess Di"
Release Date: August 15, 2025
Hosts: Michael Wolff and Joanna Coles
Published by: The Daily Beast
In the second episode of Inside Trump's Head, Michael Wolff and Joanna Coles delve into the intricate and scandalous relationships between Donald Trump, Jeffrey Epstein, and Prince Andrew. Titled "Why Trump and Epstein Competed to Bed Princess Di," the episode explores the convergence of power, sex, and social climbing within elite circles, shedding light on lesser-known connections that have significant global implications.
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Michael Wolff and Joanna Coles provide a comprehensive analysis of the tangled relationships that underscore the dark intersections of politics, royalty, and illicit activities. The episode underscores how the entanglement of Trump, Epstein, and Prince Andrew not only shapes their personal legacies but also has profound implications for global political dynamics.
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"Why Trump and Epstein Competed to Bed Princess Di" offers a provocative exploration into the hidden dynamics of power, influence, and scandal. Through detailed discussions and exclusive insights, Wolff and Coles peel back the layers of one of the most contentious alliances of the 21st century.
For those interested in the intricate workings of power and influence at the highest levels, this episode of Inside Trump's Head provides a compelling and eye-opening narrative that is both informative and engaging.