The Daily Beast Podcast - Why Trump and Epstein Competed to Bed Princess Di

Episode Date: August 15, 2025

What really connects Donald Trump, Jeffrey Epstein, and Prince Andrew? In this explosive episode of Inside Trump’s Head cohosts Joanna Coles and Trump biographer Michael Wolff dive deep into royal biographer Andrew Lownie’s explosive new book, 'Entitled: The Rise and Fall of the House of York'. They unpack the scandals, secrets, and political games linking Donald Trump, Jeffrey Epstein, and Prince Andrew. From private rivalries over Princess Diana to Epstein’s chilling social manipulations—and Trump’s quiet moves to rewrite his past—this is the untold story of how money, sex, and influence brought down a royal and shook the world. Hosted on Acast. See acast.com/privacy for more information. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome back to our second episode of our new podcast Inside Trump's Head. I'm Joanna Coles. I'm Michael Wolfe. What are we going to be talking about today, Michael? Sex. Money? Social climbing and royalty. The British royal family.

There is only the British royal family. Not true. It's the Belgian royal family, the Swedish royal family. If you point them out, otherwise, I think they go. under the radar. In America, let's put a fine point on this. There's only British royalty. 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. Is there anything else? Let's get into it. I'm Joanna Coles. I'm Michael Wolfe. And I think nobody has a more original insight into

why Donald Trump operates the way he does than Michael Wolfe, 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? 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.

He does keep giving. He is a larger-than-life character. He is a character that defies expectations. Every day he defies expectations. 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. Well, and almost if you're a citizen of anywhere in the world, right,

you are untouched 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. Yeah, no. I mean, you can make comparisons, but you're not going to find somebody to compare him to in the modern age. 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. Well, 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 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. His wilderness was a short little piece of lawn, actually, I think. 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. No, I mean, again, and I think whatever you have to say about this guy, I mean, whatever your views are, we know our views, he's been an incredible success. 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. We always think you Brits have had an affairs with several people in the same family, yes, and in the royal family, yes. 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 have a... I'm not going to have this discussion. I'm just going to let you... Anyway, we're talking about Andrew Loney'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 Etienne. right back central with Donald Trump and with Andrew. 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 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, and Trump are not exactly, you know, triple A businessmen. Right. And so the question is, how do you get, how do you, how do you, how do you get money? How do you raise capital? How do you get, how do you raise, how do you, you get loans when you are not debt worthy? 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. Yes. It's a very transactional city. 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, a lot of people who 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. 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.

Yeah, well, that was part of his grift. I mean, and I think that's how he began to see this, see the possibilities of New York life by teaching us. 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. Well, and it was a parent at Dalton who got him his job at Bear Stearns, his first job in the financial market. Yes, no, and he became friends, which is not widely known, with the publisher of the New York Times. His daughter was one of Epstein students. Was that Arthur Salzberger? Well, they're all named Arthur, so it's...

But this is Punch Salzberger. I did not know that. So Jeffrey Epstein was friendly with the publisher of the New York Times. Yes, no, no. I mean, you know, very close, very taken into 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 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've got to offer something. And it's partly just – 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 that Prince Andrew was a currency in this transaction. Right. And actually, Stacey Williams, who 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 and 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. 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 there for none of those reasons, and they are because they enjoyed his company and also enjoyed the flow of information. And the flow of information was partly a byproduct of being a social climber. And how do you, and so 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 for, or supply you with the wherewithal to get money to move into, 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.

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 siblings. But of course that made him more accessible for somebody like Jeffrey Epstein and Donald Trump. And no less of interest to people in, to people who were interested in the royal family.

Of course. He comes to America. 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. Yeah, well, you know, both of these guys, you know, and Epstein and Trump functioned as a, as a duo. They were, you know, you know, grifter buddies, basically. I mean, they had, they had, they had, the same interest, interest in women and also in money. How do you get money? How do you, these two guys who are not, who don't work for major corporations, don't have relationships

with major banks or don't have good relationships? And the other person who needed money in this triangle was Prince Andrew. Yes, exactly. And now, and so Prince Andrew, I mean, they perceived that Prince Andrew had two weaknesses, women, who apparently he had an utterly insatiable appetite for. Well, one of the astonishing things in the book, Michael, hold on, we're just going to take a break. We love our advertisers, but we're back to talking about what else Donald Trump and Jeffrey Epstein? One of the astonishing things in the book is that Jeffrey Epstein says, I'm a perfect. but you are the king of kink. Yeah.

It's just, oh my goodness, Jeffrey Epstein, the ultimate, die of bollicle. But that is a line certainly that sounds like Jeffrey Epstein. 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 roundy 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, they're 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. And 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. had a competition, Trump and Epstein, who would be the first one to sleep with Princess Diana? You know, this was all, 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. 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... It was a competition, yes, whether it was a...

I knew Donald 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. 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

He was a chair-warmer. Jeffrey Epstein was a chair-warmer for Diana. I did not know that. Like one of those people that fills a seat filler at the Oscars, so they 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? We do not. 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. No, I mean, this was, you know, this was part of this. They, the royal family amused them or amused,

it amused them that they had access. They had broken this, the code there. And they had broken the code. Also, Galane is the important connection here. How did they, how did they

initially get to the royal family through Galane Maxwell, who was deeply connected throughout British society. One of the revelations in the book also is that Gillen was sleeping on and off with Andrew and sleeping on and off with Epstein, and Epstein got a great thrill from this. Yeah, I mean, I can't, I never had that conversation 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 apparent friction. So let's bring this back to Donald Trump, which is why we're interested in there. 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, to become an icon of the evangelical set while for so long living a life absolutely antithetical to people who 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. And the MAGA God at one point, Elon Musk also pointed this out to them. When he was having his fit of peak with Trump after he'd left Doge, he tweeted out, Trump is in the Epstein file. But it is, you know, 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 we can, the, the plan is women and money. And let's just take a break for these messages.

And we're back talking about Donald Trump with Michael Wolfe. 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 Andrews. Loney, the author points out there is endless photographic evidence. They're playing golf together. They're hanging out together. 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 at this moment, again, in the Trump presidency, this is the Epstein

moment. Will he get out from under this? Or will he more and more connections tie him to Epstein and the life they lived together. Well, and I was very interested to see a report this week that Gillen Maxwell had approached the Biden administration with dirt on Donald Trump, and they hadn't taken her up on it. And that would have been, from the Biden's standpoint, honorable, of course, if someone, a convicted sex offender approaches us with information, you would, if you were a reasonable, decent person, reject that. Well, they may also have known that Democrats were also frequent visitors to Jeffrey Epstein's private club.

Well, I actually don't think we should go there because that's not 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, you know, if you're a decent person, you say no, this is a first thing, how could we ever trust this? And secondly, we have no truck with convicted criminals. Well, we know they're not releasing the grand jury files from the Gillen-Mexwell 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... Who's the family member? I hadn't heard of it. She has a sister who lives in Texas. Curious, and we should come back to that because once I was almost in business with the Maxwell sisters. 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? Well, as I remember when before his last one-on-one was in Helsinki,

and he refused to do any preparation for that. So no preparation for a sit-down with Vladimir Putin on how to resolve the war in Ukraine. Yes, and even then I remember Steve Bannon pointing out that certainly at that point in time, Trump would not have been able to locate Ukraine on the map. 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.

Yeah, no, I mean, I think, I think, I mean, Friday, the conversation that he is going to have with with with with with with put in Alaska tomorrow is is it's it's it's frightening because basically they will divvy up Ukraine what a week what a week Michael thank you very much how did we find our second episode we're rolling right along Joanna oh we're rolling right along it's there's so many strange little caverns and potholes in Trump's head. I feel very confident we're going to need grappling hooks. And who knew that Prince Andrew occupied a space in Donald Trump's head, a privileged space?

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?

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