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The Daily Beast Podcast

I Know Why Trump Made Epstein His Best Friend

The Daily Beast Podcast

The Daily Beast

News & Politics

4.67.9K Ratings

🗓️ 31 December 2025

⏱️ 46 minutes

🧾️ Download transcript

Summary

Michael Wolff joins Joanna Coles to trace the unsettling origins of Donald Trump’s relationship with Jeffrey Epstein, long before public scandal or denial. Wolff begins with their bond in the late-1980s New York, where Trump was chasing Manhattan legitimacy and Epstein was emerging as a fixer fluent in money, women, and leverage. From Trump introducing Epstein as “my associate—Jeffy,” a pattern forms of shared ambition, cruelty, and secrecy. Wolff links those early dynamics to Trump’s financial near-collapse in the 1990s and Epstein’s claim that he helped Trump survive bankruptcy while keeping his tax returns hidden. If Epstein helped shape Trump’s instincts before power, what does that say about the secrets that still follow him now?

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Transcript

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0:00.0

At Mar-a-Lago, they have a beauty contest for what they call what they're calling

0:06.0

calendar girls. And they recruit all of these girls to come down to Mar-a-Lago for this beauty

0:12.9

page. When the girls get there, they find that it's an audience that consists of two.

0:18.6

And it's only Donald Trump and Jeffrey Epstein.

0:26.9

Michael.

0:29.3

Joanna.

0:30.6

So this is a special episode.

0:33.7

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,

0:44.1

with Jeffrey Epstein, who died mysteriously, or possibly not, in one of America's worst jails.

0:53.5

And the Epstein, Epstein, Epstein, as Donald Trump refers to it, of it all, is the one thing

1:01.1

that has consistently unsettled him all year.

1:06.7

Well, the other thing is, you know, I mean, we've gone from his complete denial about a relationship with Epstein,

1:17.9

and to a understanding, I think many people seem now to understand this and the evidence in emails in other documentary material

1:33.0

establishes this in fact a very close relationship and certainly in my conversations with

1:41.5

Epstein he was always very particular about the fact that they were the closest of friends

1:49.6

for well over a decade. Right. So where do we begin, Michael? I mean, let's begin at the beginning.

2:00.1

And I actually have a beginning.

2:03.8

Were you there at the beginning?

2:06.0

Nothing would surprise me.

2:10.0

I was not there, but a very close friend of mine was there.

2:15.1

And this would have been in the late 80s, probably 1988.

2:23.3

And it was in a restaurant downtown, and my friend was there with a man by the name of Charles Allen.

...

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