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

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.

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.

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)

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

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.

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.