I Know Why Trump Made Epstein His Best Friend

Summary

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Podcast Summary:

The Daily Beast Podcast
Episode: I Know Why Trump Made Epstein His Best Friend
Host: Joanna Coles
Guest: Michael Wolff
Date: December 31, 2025

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Episode Overview

In this special holiday episode, host Joanna Coles and guest Michael Wolff, renowned journalist and author, trace the controversial and complex relationship between Donald Trump and Jeffrey Epstein. The conversation looks back at key moments in their decades-long association, chronicling stories of business, ambition, scandal, and the culture of power and privilege in New York’s elite circles from the late 1980s through the 1990s. Through anecdotes, insider accounts, and analysis, the episode explores how and why Trump and Epstein became so close, what they gained from each other, and how their friendship shaped their reputations and public perceptions.

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Key Discussion Points & Insights

1. Origins of the Trump-Epstein Friendship

• First Meeting ([06:12]):
  • Michael Wolff recounts the earliest confirmed Trump–Epstein encounter:
    • Trump enters a restaurant and greets famed financier Charles Allen, introducing “my associate Jeffrey Epstein… Jeffy.”
    • Wolff notes the intimacy implied:

      "They have a relationship, possibly a business relationship, a flirtatious relationship. That would indicate both 'Jeffy' and 'my associate,' that we are well inside of an established friendship." (Michael Wolff, 07:22)

  • Trump was already rising in the NY real estate scene, keen for greater social standing.

2. Early Adventures Together

• Brooklyn Real Estate Story ([08:01]):
  • Trump, seeking to appease his father Fred, inspects a Brooklyn property, bringing Epstein and two “model-type” women with large Afghan dogs in tow.
  • Trump is averse to the dogs: “No dogs.” Epstein retorts: “No dogs, no girls.” All pile into the limousine anyway.
  • At the site, Epstein jokes:

    “If you buy this, if you become a Brooklyn real estate developer, I don't want to have anything to do with you ever again.”

    • Both men are portrayed as wanting to escape their borough roots for Manhattan glamour.
  • The group is turned away from Mortimer’s, an elite Upper East Side restaurant, possibly due to Trump's lack of status or the dogs, leaving him furious and humiliated. ([13:33])

3. Climbing Social Ladders: The Maxwell Connection

• Involvement with Robert Maxwell and the Daily News ([16:27]):
  • Both Trump and Epstein maneuver around Robert Maxwell, Ghislaine Maxwell's father, then a powerful British media mogul.
  • Trump leverages connections to help Maxwell acquire the NY Daily News and later becomes involved (with Epstein) in its acquisition by Mort Zuckerman.
  • Wolff underscores that both Trump and Epstein were “not blue chip guys trying to make their mark,” outsiders striving for legitimacy. ([18:55])

4. Financial Entanglements and Mutual Support

• Trump’s Business Troubles ([24:08]):
  • Trump faces a wave of bankruptcies in the early ’90s, risking personal ruin.
  • Epstein plays a vital advisory role, allegedly suggesting creative legal interpretations to avoid massive tax liabilities from debt forgiveness.
  • Wolff notes:

    "Epstein chortling his claim that he was the one who told Trump that actually none of this... really hasn't come in as income...that you just don't have to pay it"[27:02]

  • Both are depicted as operating outside traditional financial respectability—“not blue chip,” and often in ethically gray zones.

5. Women, Models, and Power Games

• Their Relationship with Women ([32:59], [35:04]):

  • Joanna details interviews with two former models, Stacey Williams and Cleo Glide, who recall being paraded in front of Trump and Epstein. Trump is described as brazenly groping one of the models in Epstein’s presence.
  • The hosts emphasize how women, especially young models, formed the social glue of the Trump-Epstein friendship—"money and women" being core to their camaraderie.

• The ‘Calendar Girl’ Party ([35:35]):

  • In 1992 at Mar-a-Lago, Trump and Epstein host a beauty contest for “Calendar Girls”—the audience consists solely of the two men.

    "They recruit all of these girls to come down to Mar a Lago for this beauty pageant. When the girls get there, they find that it’s an audience that consists of two…and it’s only Donald Trump and Jeffrey Epstein." —Michael Wolff (35:41)

• Shared Girlfriends & Secrets ([37:41]):

  • They are described as sharing a Norwegian model as a girlfriend/joke, referenced as a “wonderful secret” in a birthday letter from Trump to Epstein.
  • Epstein’s pattern of sharing girlfriends (including Ghislaine Maxwell with Prince Andrew) is discussed:

    "Which makes... the last thing that Jeffrey Epstein wanted with any of these women was permanence." (Michael Wolff, 39:28)

6. Attitudes Toward Domesticity and Family

• On Marriage ([41:19]):

  • Wolff recounts advising Epstein he could rehabilitate his image by marrying and having a family. Epstein’s reply:

    "I would rather go back to jail." ([41:43])

  • This aversion to settling down is considered intrinsic to both men; their lives were fundamentally opposed to the idea of domesticity.

• Trump and Marla Maples ([42:41]):

  • Trump’s relationship with Marla Maples is recounted, with Epstein providing dubious advice upon Maples’ announcement of her pregnancy.
  • Their conversations are painted as emotionally tone-deaf, almost farcical in their lack of sensitivity to the situation.

7. Transition to the Melania Years ([46:50])

• The timeline reaches the point where Trump is with Melania, which both hosts mark as a “new phase” in his life.
• Both agree to resume the conversation in a subsequent episode, hinting at deeper exploration of the later years.

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Memorable Quotes and Moments

• On Trump’s status in the late ’80s:

  "He was very much on the scene and trying to be on the scene." —Michael Wolff (05:32)

• On being turned away from Mortimer’s:

  "It could be because of the dogs or it could be because it's Donald Trump. He has not yet arrived…and he's still looked at as a guy from the boroughs." —Michael Wolff (14:37)

• On Epstein’s legal advice to Trump:

  "How is it possible that we haven't seen his tax returns? How is all of this possible? How is any of this possible?" —Joanna (29:16-29:24)

• Summary of their ethos:

  "Life is not a serious proposition for either of them…It's the sort of both guys on the grift and both guys looking for women who then they're trying to get rid of…" —Michael Wolff (48:31)

• On Epstein and marriage:

  "At one point...I said, well, you could get married and have a family. And he said, I would rather go back to jail." —Michael Wolff (41:19)

• Joanna on Trump’s lifelong motivation:

  "It's a consistent theme throughout his life, revenge." (15:14)

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Timestamps for Key Segments

• First confirmed Trump-Epstein meeting: 06:12
• Brooklyn real estate story & Mortimer's incident: 08:01 - 14:51
• The Maxwell/Daily News subplot: 16:27 - 22:20
• Trump’s financial unraveling and Epstein's advice: 24:08 - 29:16
• Epstein’s & Trump’s attitude on legitimacy in finance: 29:44 - 32:22
• Women, 'Calendar Girl' party: 32:59 - 35:35
• Shared Norwegian girlfriend & “our secret” letter: 37:41 - 39:03
• Epstein’s view on marriage: 41:19 - 41:46
• Marla Maples, Tiffany, and the nontraditional family saga: 42:41 - 44:55
• Transition to Melania and the modern era: 46:50 - 47:06
• Wrap-up: 48:02 - 48:52

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Tone and Language

• Conversational, irreverent, sometimes darkly funny.
• Joanna uses wry British humor; Wolff is candid, occasionally sardonic, relaying stories with a seasoned insider’s nonchalance.
• The tone fluctuates between gossipy storytelling and journalistic detachment with sharp critical insight into privilege, masculinity, power, and scandal.

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Conclusion

This episode provides an unvarnished look at the intertwined histories of Donald Trump and Jeffrey Epstein, exploring how shared outsider status, mutual enablement, and pursuit of women and social ascendancy fortified their complicated friendship. With its mix of unpublished anecdotes, speculative analysis, and bemused critique, the conversation promises more revelations in a planned second part, picking up with the “Melania years” and the later, infamous chapters of both men’s public lives.

Transcript

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Acast.com@mar a Lago there go they have a beauty contest for what they call what they're calling Calendar Girls. And they recruit all of these girls to come down to Mar A Lago for this beauty pageant. When the girls get there, they find that it's an audience that consists of two and it's only Donald Trump and Jeffrey Epstein.

[Joanna]

Michael Joanna so this is a special episode. We thought we would do some special episodes throughout the holidays. And this is one that is going to trace the relationship of Donald Trump, our current president, with Jeffrey Epstein, who died mysteriously, or possibly not, in one of America's worst jails. And the Epstein Epstein Epstein, as Donald Trump refers to it of it all is the one thing that has Consistently unsettled him all year.

[Michael Wolff]

Well, the other thing is, you know, I, I mean, we've gone from his complete denial about a relationship with Epstein and to a understanding, I think many people seem now to understand this and the evidence in emails and other documentary material establishes this. In fact, a very close relationship. And certainly in my conversations with Epstein, he was always very particular about the fact that they were the closest of friends for well over a decade.

[Joanna]

Right. So where do we begin, Michael?

[Michael Wolff]

I mean, let's begin at the beginning. And I actually have a beginning.

[Joanna]

Were you there at the beginning? Nothing would surprise me.

[Michael Wolff]

I was not there, but a very close friend of mine was there. And this would have been in the late 80s, probably 1988. And it was in a restaurant downtown. And my friend was there with a man by the name of Charles Allen. Now Charles Allen is the father of possibly the uncle, it occurs to me, of Herbert Allen who now runs Allen and Company. And Charles Allen was in fact the founder of Allen and Company. So one of the senior, most financiers in New York City. And at this point in the late 80s, Charles Allen was emeritus, I think in the firm. Quite old at this point, but very much still a presence in New York. Someone, anyone who is, who was in the money raising business and Trump was certainly in the money raising business would know and want to know.

[Joanna]

Okay, and Donald Trump at this point was what, a well known real estate developer? Was he sort of at the beginning of peak Trump was this when he was on the front of the New York Post all the time?

[Michael Wolff]

Yeah, I mean this would, I think, I think the art of the deal was in 1989. So that would have been, that would have been the first flowering of Donald Trump's, Donald Trump's fame. But, but he was a person trying to do deals in, in New York, had done a few significant, I think he had done the Commodore Hotel. That was his first major, major project. And he was very much on the scene and trying to be on the scene.

[Joanna]

Okay, so Charles Allen brings them together.

[Michael Wolff]

No, no, no. Charles Allen is just in a restaurant having dinner just without, without nothing to do with Donald Trump except Donald Trump then comes into the restaurant and, and greets Charles Allen and the important part introduces him. I'd like you to meet my, my associate, Jeffrey Epstein.

[Joanna]

Jeffy.

[Michael Wolff]

Jeffy, let's note the Jeffy.

[Joanna]

The Jeffy of it all.

[Michael Wolff]

The Jeffy of it all. So that's the first moment that I can put Trump and Epstein together. A witness, somebody I know, a piece of dialogue There it is. And two people very much at the intersection with an important person in New York City.

[Joanna]

Trump was sufficiently friendly with him that he was calling him Jeffie even in 1988.

[Michael Wolff]

And my associate. So it was a kind of, you know, I mean, clearly they have a, they have, they have a relationship, possibly a business relationship, a flirtatious relationship. I don't know the nature of the relationship, except that that would indicate both Jeffie and my associate that we are not. That we, that we are, that we are well inside of an established friendship.

[Joanna]

Okay. And Jeffrey and Donny are two boys out on the town.

[Michael Wolff]

Two boys out on the town, yes.

[Joanna]

So.

[Michael Wolff]

The next point at which I can put them together is a story that Epstein told. And, and I think this occurs in not long after, maybe 89, possibly 90, Trump's father makes him look at a piece of real estate in Brooklyn. Now Trump's entire thing is to get out of the barrows to establish which is where his father's real estate business has flourished.

[Joanna]

In Queens, right.

[Michael Wolff]

I think in probably all the boroughs. It just is. Fred Trump was active everywhere but in Manhattan because Manhattan was too expensive to glamour. You know, the glamour premium. You know, Fred Trump was a low rent real estate guy, and he was not looking to be what Donald Trump came to look to be, which is a glamour guy. Donald Trump wanted this, wanted the spotlight. Fred never wanted the spotlight, just wanted the profits. And Fred was always unhappy that his son was pursuing this Manhattan dream and at this point in time then was trying to restrain him, go look at this piece of property in Brooklyn. So Trump calls up his friend Jeffie and says, you know, I got to do this. You know, will you come, will you come with me? And possibly, he said, and bring some girls. Because Trump then shows up in the limo in front of where Jeffrey Epstein lives, which is on the east side, not in the big house he would come to inhabit, but in an, in an apartment on, I believe, on 69th Street. But I could be wrong in a.

[Joanna]

Starter apartment, considering what would become of his real estate portfolio.

[Michael Wolff]

Yes, yes, I thought you were going to say in, in the Sinatra apartment, because Sinatra apartment then had a, had an apartment over there also in a, in a, in a, a building that Epstein could have inhabited. But anyway, so Trump, Trump shows up the limousine and the, the, the detail is that the, the limousine has a, a, what is that called?

[Joanna]

Sliding roofing roof. Right. Sunroof.

[Michael Wolff]

Right. And so he pulls up and Epstein is outside waiting for Trump, and he is with two girls and each girl has A large dog on the leash.

[Joanna]

Each girl has a large dog on the leash.

[Michael Wolff]

Yes. And as I recall in the telling, they are Afghans. So. And Trump stands up, puts his head through the, through the roof of the limousine and says, no dogs. No dogs.

[Joanna]

Of course he did. Because Trump is a man who's never had a relationship with an animal, let alone a dog, man's best friend.

[Michael Wolff]

And Epstein says, no dogs, no girls. So that results in them all. Trump makes his decision. Dogs, girls. And they all pile into the limousine and head to Brooklyn to look at this piece of real estate. And, and it's, as I, as I recall in Epstein's telling, it's a, It's a piece of, It's a piece of land. There may be buildings on it, but it's basically a large track. Track of land. And as they look at it, Epstein says to Trump, if you, if you, if you buy this, if you become a Brooklyn real estate developer, I don't want to have anything to do with you ever again.

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What?

[Michael Wolff]

This, this is it. You decide between you, Your decision is between me and Brooklyn. And remember, this can't be true, Michael.

[Joanna]

This must be, this must be apocryphal.

[Michael Wolff]

Oh, I, I don't think so. Why would it be? I mean, it makes perfect sense. Epstein is from Brooklyn. Neither of them want to return to Brooklyn. Brooklyn is glamorous. Now then it was not get me out of Brooklyn. And Trump certainly didn't want to be there because his, you know, he was only there because his father was instructing him. This is what you have to, you have to do. And Epstein doesn't want to be there because he wants to have nothing to do with, with, with Brooklyn. And, and I think this goes to the, Their kind of relationship, which is, which is competitive, but they're kidding each other. But it's. Something is going on, a set of insults back and forth that, I mean, that rings quite true.

[Joanna]

Well, and I suppose it shows a kind of intimacy, too, that Epstein felt comfortable saying to Trump, it's me or Brooklyn. And Trump thinking, of course I don't want to be in Brooklyn. I want to be the center of attention in Manhattan.

[Michael Wolff]

Exactly. And then Trump says, no, I'm not going to. I'm just doing this. My father is just making me do this, and this is never going to happen. And then they head back to Manhattan and I believe. And they end up at a restaurant, a restaurant called Mortimer's, which was on 75th and Lexington, which was peak Upper east side at the time, the society restaurant. Of the 19, you know, of the 80s and 90s. And they are turned away.

[Joanna]

They're turned away. Why are they turned away? Because they have two enormous Afghan dogs.

[Michael Wolff]

Well, it could be because of the dogs or it could be because it's Donald Trump. It's not, you know, he has not yet arrived or. And he's still looked at as a guy from the boroughs.

[Joanna]

Right. An Aravist.

[Michael Wolff]

Right. So they're very, very. So Trump is very unhappy with this. Furious, actually.

[Joanna]

Well. And humiliated.

[Michael Wolff]

Humiliated. And that is. So that's the end of this. That's what I know of that. Of that story.

[Joanna]

So a bad day all round. Forced by his father to go and examine a piece of real estate in Brooklyn he never wants to buy. Forced by his friend to take two Afghan dogs in his stretch limo that he doesn't want. And then he's rejected from a posh restaurant, which would symbolize his arriving in Manhattan. And in fact, he was rejected and humiliated. It's a little bit like what happened to him at the 2011 White House Correspondents Dinner when Barack Obama humiliates him by poking fun at him. It's a consistent theme throughout his life, revenge.

[Michael Wolff]

And the theme. He is always trying to use his own fame and notoriety to counter that. And in fact, that's the next. The next moment that I know of, in. In his relationship with. With. With Jeffrey Epstein and. And I'm unclear on who knows who first, but this is the moment at which Robert Maxwell, the father of.

[Joanna]

The father of Ghislaine Maxwell and the disgraced British tycoon.

[Michael Wolff]

Yes. Steps in. He's not disgraced yet.

[Joanna]

Quite.

[Michael Wolff]

Quite the opposite. He is at the top, the pinnacle of his. Of his moment in time. And I think this is 1990, and he steps forward to buy the Daily News, still a very significant newspaper. I mean, people barely know the Daily News exists at this point, but it was then. It was then, you know, a significant newspaper. You could argue, actually, it's the largest circulation newspaper in New York at the time. And clearly in Donald Trump's interest. I mean, Donald Trump becomes Donald Trump basically because of the attention of the New York tabloids. So he. And again, I'm not sure who knew Maxwell first, whether it was Epstein, whether it was. Whether it was Trump, whether this is the moment that Epstein meets Maxwell, gets introduced to the Maxwell family, which obviously would have repercussions decades later. But Trump becomes or represents himself to Maxwell as someone who can help get this deal done. He knows. He knows the. He knows the real estate interests In New York, real estate is a, is a major advertising category. He also knows union people. Union people. And at that point in time, the newspapers were highly unionized. You couldn't do a deal if you didn't have the cooperations with the unions.

[Joanna]

And Michael, just remind us who owned the New York Daily News at the time? Who was Maxwell buying it from?

[Michael Wolff]

I believe that was still owned at that point by the Tribune Company.

[Joanna]

Michael, I'm enjoying this trip down memory lane. The Maxwells, the Daily News, it all seems so much more innocent then.

[Michael Wolff]

Well, yeah, I mean these were two guys just trying to make it in the big city. I mean it is really not more than that at this point in time. You know, I mean, Trump was building a profile. Epstein didn't have a profile. I'm not sure he did he want one? Maybe. I don't, I don't know. But he was actually interested, you know, this whole idea of, of the Daily News of having an in at a major New York newspaper, knowing the owner, getting involved in whatever. And remember, Maxwell was a crook. He would go on to be one of the great crooks of the time. How much were they attracted to that? Attracted to the, what would we call it? The, the not blue chip side of, of, of someone, someone making his mark. Because they were both of them, not blue chip guys trying to make their mark. And this is fundamental to this, to this, that they were both outsiders. Epstein an outsider, Trump an outsider. The guys from the boroughs trying to make it in Manhattan. So now a couple of things happen here. First, first of all, the, the Max Maxwell buying the Daily News. Maxwell is the crook and he is shortly to be found out. And his ownership of the Daily News collapses. Well, he collapses. First he goes, he kills himself or is killed or slips and falls off of, off of his yacht called the, the Lady Ghislaine. Yes. And then he's. So anyway, so then, then the paper becomes part of the estate which is in bankruptcy. It's a, it's a, it's a disaster. But then Epstein, at this point, actually both Epstein and Trump step forward and get involved in the purchase of the paper by Mort Zuckerman, who's another real estate guy in New York. And Zuckerman and Epstein actually become close friends.

[Joanna]

Meanwhile, we should just point out not only does Robert Maxwell die in mysterious circumstances like Jeffrey Epstein goes on to do, but he pillages the pension fund of his British newspapers to the tune of half a billion dollars, which is an unheard of scam. Just the scale of the scam at the time was almost beggared belief. And of course, he was busy in his own way as an outsider trying to compete with Rupert Murdoch. So in the way that Jeffie and Donnie were hanging out, Robert Maxwell was in a battle to the death with Rupert Murdoch. But it turned out to be his own death.

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[Joanna]

And Michael Wolf and I are back inside Trump's head, examining his relationship with Jeffrey Epstein.

[Michael Wolff]

This is the moment when, when Trump's business empire goes into extremis. So Trump's bankruptcies. Trump's. Trump has to, has to manage and navigate several major bankruptcies at this time. I mean, deeply threatening to all of his, all of his interests, including the fact that he has personally guaranteed money, much of the, of the, of, of the loans that the banks are now calling.

[Joanna]

And when you say his businesses, what were his businesses? Were these simply. I say simply, but were these purely real estate at this point?

[Michael Wolff]

Purely real estate? Well, and I mean gambling, gaming. I mean he has, you know, he, and that he's expanded into Atlantic Cities, he has building projects in the city, but these are all he owns, briefly, an airline. So he has bought Eastern Airlines. Why I remember all these businesses, the names of these businesses from.

[Joanna]

A half.

[Michael Wolff]

A century ago, I don't know. But Eastern ran the shuttle to Washington between New York and Washington, D.C. oh, what a metaphor.

[Joanna]

That he owned that corridor, that shuttle flight to Washington. Right.

[Michael Wolff]

Well, he didn't own it for very long.

[Joanna]

Also a metaphor, as a matter of.

[Michael Wolff]

Fact, as I recall, he missed his first. His first payment, and then that went into bankruptcy. And that was. That was itself a legal kind of. How did this happen? Because if you miss your first payment in a bankruptcy, that means basically, pretty much you've lied about your sources of financing. It's not as if your business, the business as you projected, did not do as well as you thought it would do and put you in extremis, but from the first day, you're an extremist. And so why that was. And actually, Epstein would always chortle about that, how Trump got away with the Eastern shuttle, or as it became, of course, the Trump shuttle. But it wasn't only that. There was a whole set of bankruptcies. You know, the Atlantic City bankruptcies, the, the problems with New York real estate, and the fact that suddenly he owed the banks a billion dollars.

[Joanna]

Wow.

[Michael Wolff]

Now, this is where Epstein gets kind of deeply involved with Trump' swith, Trump's businesses, which is that, you know, what am I going to do? Trump is like, what am I going to do? And it was then Epstein's suggestion, one of the key things. So he managed basically. I mean, his situation was so extreme that effectively the banks had to agree to take a bath on this, that they said, we are going to forgive you these debts. Now, how that came about is enough. Another story, which, which I, I think is completely unclear, but they forgave him these debts up to about a billion dollars. And when. So the problem there, though, is when the banks forgive you your debts, that becomes income. You have to pay taxes on it, in theory. And obviously, if and. Or would seem apparent that if you can't pay, if you don't have a billion dollars to return to the banks, you probably don't have the half a billion dollars that taxes on that money is going to cost. And it was again, Epstein chortling his claim that he was the one who told Trump that actually none of this, because of the nature of this, you really haven't gotten the money. It never has come in as income and exists. And forgiveness sort of exists in a different order of ether, unknown to the irs, that you just don't have to pay it, which Epstein would then come to later maintain was one of the key reasons that we've never to this date have never seen Donald Trump's. Donald Trump's tax returns.

[Joanna]

How is it possible that we haven't seen his tax returns?

[Michael Wolff]

How is it possible? How is all of this possible? How is any of this possible?

[Joanna]

Yeah, it's true. I'm finishing your sentences at this point. It's horrifying. It's horrifying and it's fascinating. So, so what was Jeffrey Epstein doing at this stage? I mean, obviously he was, was he post the Ponzi scheme that he got caught up in but managed to avoid and someone else went to jail at this point.

[Michael Wolff]

So he was Hoffenberg, a man by a gentleman by the name of Hoffenberg. And this, no, this, this would have been just about the same time, right?

[Joanna]

So they were both caught up in weird financial scars.

[Michael Wolff]

Weird, weird financial. No. And it's important, important to understand that that's what these guys do not be blue chip. So everybody understands blue chip is, you know, your financing is in, you know, your collateral was, is, is sufficient. You have relationships with, with established banks and bankers with your, your what you're, what you're supposed to be. You are part of a financial establishment. These two guys are not. And people in the real estate business are often, you know, there's, you know, there's blue chip real estate guys and then there's guys who are not blue chip real estate guys. Trump very much not, not a, a blue chip real estate guy. And remember, this is a moment in time, you know, a great debt bubble which is in the process, at this moment in time of, of bursting, although there will be many debt bubbles afterwards, but in which there was. You. Could you. If, if you were willing to. What would be the. Let's, let's think of the. If you could fake it, if you were of the fake it to. Until you make it variety, it was a pretty good time, except when the bubble bursts, then you get, then you get caught out. And Epstein himself, what did he do? What was his business background? Certainly not, not blue chip. I mean, it's always the questions. The questions equally about Donald Trump and Jeffrey Epstein are always, where did the money come from? How did they get this, this, this, this money? You know, I mean, I mean, Epstein described, would later describe when Donald Trump bought Mar A Lago, he bought it from essentially a loan provided by construction unions in New York against promises of work that he would deliver. All of this, again, is less than blue chip.

[Joanna]

Less than blue chip. Ok?

[Michael Wolff]

And is possibly illegal even. But, you know, you're always straddling the line here. And remember Donald Trump, who's been in litigation throughout the entirety of his career. This became his fundamental talent. I can walk the line. You know, in walking the line means not only that you have to have the, the moral flexibility to do that, but you also have to have the stomach for it because, you know people are going to come after you because you're going to, you're going, people are going to try to hold you accountable for that.

[Joanna]

And Michael, we've had on the Daily Beast podcast over the last few months two women that hung out with Epstein and said that Epstein would take them almost as trophy girlfriends. They were both models, both gorgeous. One was Stacey Williams, who was a Sports Illustrated model. The other, Cleo Glide, who was a model for Yves Saint Laurent. She was a muse there. And they both described going with Jeffrey Epstein walking down Fifth Avenue when he was by this point installed in his big house and walking to Trump Tower. And Donald Trump certainly jumping on Stacey Williams and groping her in front of Jeffrey Epstein, who then did nothing. Did nothing. And then berated her in the elevator on the way down, shouting at her, why did you let him do that?

[Michael Wolff]

You know, I think this would have been just the, in the. Keeping the chronology straight. A bit later, I think that House comes into his possession in and, you know, it could be a year or two off, but I think it's about 96.

[Joanna]

Okay, so this is. So maybe he didn't, maybe they didn't set off from the house then because they were both models in the late 80s, early 90s. But they describe walking down Fifth Avenue and Cleo Glide was wearing a short white dress. And listeners of that podcast will remember he said, oh, my God, you look like a nurse. You look like a nurse, Donald. Like this. Do you have another friend who can wear a similar dress? And I'm going to arrive at his house and pretend you're two nurses.

[Michael Wolff]

Totally. And that was always, I mean, first thing that Epstein was always in a, in a like, like that kind of gag. He was a big gag guy.

[Joanna]

But it was sort of evidence of the. Them playing with women, toying with women and being in. On. In on the joke together.

[Michael Wolff]

Yeah, at this point, that's what I mean, that becomes. I mean, there are two. Two basis of their relationships really. Money and, and money and women and, and matter of fact, in. So in 1992, I believe. I mean, this is right after, you know, this is the Daily News, the Trump, the Bankruptcies doing all of what. Whatever they're doing. But in 1992 is the count, the famous Calendar Girl party, which is that.

[Joanna]

They have what is the Calendar Girl party.

[Michael Wolff]

You know, at Mar a Lago there go they have a beauty contest for what they call, what they're calling calendar girls. And they recruit all of these girls to come down to, to Mar a Lago for this, for this beauty pageant. And when the girls get there, they find that there are only that it's an audience that consists of two. And it's only Donald, Jeffrey Epstein, Donnie and Jeffy. And this would, so this would be at Mar a Lago in, in, in 1992. But again, all, all it's always the, the girls, the beauty pageant girls, the models is a, is a foundation of, of this. And there's a story from about this, this time, you know, 92, 93ish, when that, that Epstein told about Trump at a, at a night place, night clubish down, you know, a sort of a restaurant, but you know, a hot place at that time called the China Club. And, and Epstein says, and this is later he's telling this, he's no longer Trump's friend and is painting Trump as much more despicable than he is. And he describes Trump as going behind the bar and effectively attacking the bartender in rather in public view.

[Joanna]

A woman bartender or a male bartender? A woman bartender attacking a woman bartender.

[Michael Wolff]

Yes, coming up behind her. You know that.

[Joanna]

Oh, that old trick that coming up behind you.

[Michael Wolff]

Yes.

[Joanna]

Right.

[Michael Wolff]

And this is the period. So this comes from 93, 93, 94. And you know, Marla Maples is now coming into this picture. But it is also the, the moment in which Epstein and Trump are sharing a girlfriend. This is a, a Norwegian model and, and who I. Whatever the arrangement is back and forth. I mean again, they're, they're, they are playing with someone and they are, this is their shared, not only girlfriend, but kind of a shared joke. And I think, you know, there's reason it's, you know, I would say sort of likely that his reference to this secret that we have in the birthday letter. So remember, the birthday letter is in 1993.

[Joanna]

Right.

[Michael Wolff]

Jeffrey Epstein's birthday letter from Trump to Jeffrey Epstein. And he refers to our secret.

[Joanna]

A wonderful secret. A wonderful secret. Okay. And that was the Norwegian girlfriend they both shared.

[Michael Wolff]

Well, we can, it would not be unlikely that that is what the reference is.

[Joanna]

It was. And that seemed to be a theme for Jeffrey Epstein too, because he and Prince Andrew. Andrew, formerly known as Prince also shared Ghislaine Maxwell at one point.

[Michael Wolff]

I mean, Trump and Andrew.

[Joanna]

No, I mean Jeffrey Epstein. Epstein and Prince Andrew also shared Ghislaine Maxwell. So this was one of Epstein's things that he was quite happy to share.

[Michael Wolff]

Girlfriends, I think. Yeah, No, I think he was. Which makes, you know, I mean, the last thing that, that Jeffrey Epstein wanted with any of these women was permanence.

[Joanna]

Right.

[Michael Wolff]

That's what he was most. He was allergic to. And let's take a commercial break. Hey, you want to pay just 10 bucks for your phone service at Boost Mobile? Just 10 bucks for your phone service at Boost Mobile? Yeah, I totally do. Yeah, I totally do.

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[Joanna]

And you're back with Michael Wolff and me inside Trump's head, a place you may never have expected to be. But here we are and we're examining his friendship with Jeffrey Epstein.

[Michael Wolff]

At one point in my conversations with with Epstein when he was looking for how to rehabilitate his reputation and what could he do? What could. I said, well, you could get married and have a family. And he said, I would rather go back to jail.

[Joanna]

Well, lucky for him, he made the right choice then.

[Michael Wolff]

Yes.

[Joanna]

He said to you, I would rather go back to jail.

[Michael Wolff]

They lived in this world in which there was no pretense and no value at all to domesticity. Just the very idea was contrary to everything. And this is both Trump and Epstein, everything that they wanted to achieve. And Marla Maples now comes into the picture. Trump is married to Ivana the marriage is, you know, I think probably principally in name only at this point.

[Joanna]

But.

[Michael Wolff]

He becomes involved with Marla Maples there. We've discussed this, I think we've discussed, discussed this before. There's references this to the, in the, in the Epstein emails. Marla Maples becomes pregnant or she tells Trump that she's pregnant. Trump goes to his friend Epstein and says, what am I going to do? Epstein says, she's not pregnant. That's just what they tell you to, to, to get you to marry them. And you know, if she's, if she's pregnant, I'll send you, you know, a year's supply of, I'll bet a year's supply of, I think baby food, diapers, one of them. And at any rate, Trump then actually confirms that she is pregnant and then goes back to Epstein and says, well, what am I going to do now? So at any rate, so, so he, he comes back to Epstein, says, hey, you know, I think I'm kind of screwed here. She really, really is pregnant. And then so they go into a big debate about what can he do in that situation. How do you convince her to get an abortion? How do you, I mean, it's.

[Joanna]

Sort.

[Michael Wolff]

Of both tragic and comical to, to imagine these guys who have no sensitivity to this whatsoever. No, no idea actually of how you think about something, something, something like this. And, but at any rate, it actually, it actually results again here in some kind of old fashioned notion of what you have to do of Trump, of Trump getting married to Marla Maples and she has a child and, and then subsequently, of course, they get a divorce, right?

[Joanna]

So the child is Tiffany and of course he got divorced from Ivana, got married to Marla, got divorced from Marla, married.

[Michael Wolff]

And then we come into the, to the, to the Melania period. And so Epstein and Trump, what they are doing, you know, the fact that suddenly he's become, you know, married to Marla Maples is not an impediment to the life they otherwise lead. I mean, it is a life of inconstant pursuit of women. And Epstein himself at this point is more and more involved with Les Wexner and Victoria's Secret and all of the, and the whole new world of models that, that opens up to him and they become both of them involved in modeling agencies, financing modeling agencies, Essentially establishing this conduit to unlimited number of women girls because they are models of uncertain age.

[Joanna]

So, Michael, we've covered a lot of ground here from them arriving in Brooklyn with two Afghan dogs in a stretch limo to Donald Trump owning a modeling agency, Jeffrey Epstein having an investment in a modeling agency, Trump owning Miss Universe, them having models audition for just the two of them. And now we hit the Melania years. I wonder if this is a good time to, to end this episode and then pick up next time on part two of the relationship between Jeffrey Epstein and Donald Trump.

[Michael Wolff]

It's a good place to end because this is, this is Melania actually begins the next phase of Donald Trump's life, which a phase he's still depending upon how you look at it in.

[Joanna]

Does he wear night goggles? Night vision goggles? Cause Santa likes a green. I can't stop, though. My Instagram feed is full of people miming her reading that book. And it is remarkable that she still struggles so with the English language when she's been here 30 years. I'm not saying I can speak Slovenian and I know that she can speak five other languages, but, but English ain't one of them.

[Michael Wolff]

We have never heard them.

[Joanna]

Well, of course we've never heard them, but we have heard her English. And for someone who's been here 30 years, it's, it's complicated. But obviously she spoke Slovenian to her parents when they were here. Her father's still here and Slovenian to Baron, too. Michael, I hope you're having a very happy holiday season. I imagine you running around with little lanterns up and down the Hamptons high street, singing in parades.

[Michael Wolff]

You know, that's me, Joanna. You got me.

[Joanna]

I've got you. In fact, I know you're probably curled up in your study reading a pile of books and I hope going back through all your notes on Jeffy and Donny, but really, Jeffy, Jeffy puts a whole new, a whole new face on, on their relationship.

[Michael Wolff]

No, I mean, these are two, two, two guys joking around through the 80s.

[Joanna]

And 90s, two bad guys hiding in planes.

[Michael Wolff]

Life is not a serious proposition for either of them, or it certainly doesn't seem because it's, it's, I suppose, not serious. It's, it's the sort of both guys on the grift and both guys looking for, to, for, for women who then they're trying to get rid of and.

[Joanna]

Then both guys bullying and threatening other men. Great guys, the best guys, greatest guys. All right, Michael, go back to your Christmas pudding or whatever else you're eating and let's recommence this conversation in a couple of days time.

[Michael Wolff]

Great. Good. And we, we should thank our top level members. And they are Sandra Clark, methinks, travel with Carl Andrew Beaver, the Capinator Harry Clark Dawn McCarthy Daniel dog lover M. Griner Fulvia Orlando Herbie Andrew Melor Las Conde Bonzo Val Love Francesco Andrea Hodel Bocock D.C. sharon Shipley Connie Rutherford Karen White Heidi Riley thank you all. Thank you Devin, Anna and Jesse, without whom.

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[Michael Wolff]

Want more great listens? Check out our comedy podcast the Last Laugh and our Star Studded the Daily beast [e-mail] podcast if you enjoyed this.

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[Michael Wolff]

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