The Daily Beast Podcast

Episode: How the Epstein Files Backfired on Trump: Wolff
Date: December 24, 2025
Host: Joanna Coles
Guest: Michael Wolff

Episode Overview

This episode dives into the chaotic release of the Jeffrey Epstein files and how unexpectedly, they may pose more harm to Donald Trump and close associates than his adversaries had planned. Host Joanna Coles and guest Michael Wolff explore the implications of the document dump, the proliferation of fake evidence, what’s actually hiding in the files, and the unraveling political, media, and business ramifications — from Congress’s exodus to Trump’s personal branding obsession and questionable alliances. The episode maintains its trademark blend of sharp analysis, skeptical wit, and newsroom banter.

Key Discussion Points and Insights

1. The Epstein Files: A "Garbage Can" of Chaos

• Unmanageable Document Dump

  • The release resembles a flood of undifferentiated material — not a discrete, curated archive.
  • Wolff: “The Epstein file turns out to be a funnel of everything undifferentiated. So the file is essentially a garbage can of everything mentioning Jeffrey Epstein.” (02:42)
  • No guide, index, or context: searching for truth is nearly impossible.

• Transparency Paradox

  • Calls for transparency (“release everything!”) have led to a glut of information that obfuscates more than it reveals.
  • Wolff: “Rather than solve the mystery, it increases the mystery. ... How do we obscure what we don't want to see? Well, then we give you too much.” (16:44, 24:08)

• Questionable Content and Fakes

  • The files contain purported evidence, much of it either unverifiable or clearly fabricated (e.g., staged Epstein suicide video, suspicious "Larry Nasser" letter).
  • Coles: “There’s now all sorts of fakes which are confusing people. … As if taken from a camera in his jail cell — which of course was never there.” (18:41)

2. Direct Implications for Trump

• Trump’s Ties and the Backfire

  • Contrary to GOP hopes, the files reinforce or raise questions about Trump’s connections to Epstein.
  • Notably, he appears on Epstein’s flight logs far more than previously thought.
  • Wolff: “Epstein always used to say that Trump wanted to be on his plane because he didn’t want to spend the money on the gas.” (20:15)
  • There are also threads suggesting Trump’s role in the initial Palm Beach police investigation of Epstein after their real estate fallout.
  • Wolff: “Did the beginning of the Jeffrey Epstein investigation involve a confidential informant whose address was Mar-a-Lago?” (26:37)

• Murky Communications

  • Discussion centers on possibly faked or misinterpreted correspondence (such as Epstein/Ghislaine Maxwell legal strategy allegedly involving Trump).

3. Congressional Exodus & Income Inequality

• Congress Has a Retention Problem

  • Record numbers of representatives leaving, citing low pay versus private sector, safety, and harassment.
  • Wolff: “Congresspeople make $174,000 a year, which should be a perfectly respectable sum…compared to peers who are making millions…they feel they can’t stay.” (07:36, 10:03)

• Hostility and Public Scrutiny

  • Visibility and wealth inequality (e.g., Jeff Bezos's lavishness) demoralize public servants and workers alike.

4. Age, Health, and Presidential Fitness

• Biden vs. Trump: It’s About Age, Not “Psycho” Status

  • Pushback on audience critiques equating age with mental fitness, not personality.
  • Wolff: “If there's a health concern with the President…whether he’s a functional good guy or a functional asshole doesn’t make any difference. It's a health concern.” (12:17)

• Armchair Diagnoses

  • Reiterates the public’s burden to “diagnose” candidates given zero transparency from the White House.

5. Trump’s Influence, Grift, and Branding

• Businessmen Running Diplomacy

  • Wolff and Coles dissect Steve Witkoff’s improbable role as a Trump-favored diplomat (possibly picked by Putin) for Russia-Ukraine — no credibility but a useful jet.
  • Wolff: “His entire credential for now being one of the most pivotal people involved in questions of world war and peace is that he's Donald Trump's friend. ... A guy with a plane.” (32:12–33:00)

• Trump’s Personal Branding: The Trump Battleship

  • Trump’s compulsion to put his name on everything, now affixing it to government property and military hardware, becomes a metaphor for impermanence vs. attempted legacy.
  • Wolff: “The foundation of his career is slapping his name on everything.” (42:52)

• Resistance to Naming Rights

  • Legal and grassroots pushbacks (e.g., Congresswoman Joyce Beatty opposing rebranding of the Kennedy Center).

6. Media, Propaganda, and Social Media Influence

• Staged ICE Videos as “Entertainment”

  • Deep dive into the Trump White House and Homeland Security churning out TikTok-ready ICE arrest videos, set to popular music, targeting a social media audience.
  • Coles: “They've really created these videos largely for social media…set to music, ... as if they are some kind of rap video.” (54:54)
  • Discussion of the ethical, strategic, and aesthetic insanity of this approach.
  • Wolff: “People in masks ... acting as a paramilitary force ... but you can’t characterize it in a way that’s going to make people feel good.” (51:00)

• Social Media Outrage—But Massive Views

  • TikTok posts like “That deportation feeling” drawing 45 million views.
  • Coles: “We don’t know how many people were just looking at it thinking, I can’t believe they’re putting this out. We don’t know that.” (58:17)

• Polarization vs. the “Middle”

  • The hosts discuss whether the U.S. remains deeply divided or if the noise is from the margins, with most Americans remaining moderate and independent in sentiment. (59:31)

7. Power, Media Ownership, and Backchannel Influence

• Washington Post, Bezos, and Elite Proximity
  • Dissects how Bezos’s personal involvement (or lack thereof) influences The Washington Post’s coverage.
  • Wolff: “It usually works that they are semi-distracted and absentee ... until someone slaps them.” (62:23)
  • Amazon, Melania documentaries as soft power currency in the Trump orbit.

8. Final Thoughts: Trump and Television, Legacy, and What’s Next

• Tease for Next Episode
  • “A special on Donald Trump’s relationship with television….He just does not exist as a human being outside of television.” (66:28–66:35)

Notable Quotes & Memorable Moments

• On the Epstein Files’ Value:

  “Rather than solve the mystery, it increases the mystery.” — Michael Wolff (16:44)

• On document dumps as strategy:

  “How do we obscure what we don't want to see? Well, then we give you too much.” — Michael Wolff (02:42, 24:08)

• On political dysfunction:

  “This is part of now, this is part of the democratic process. ... You have to make your own diagnosis because you’re never going to get an accurate one.” — Michael Wolff (14:07)

• On the ICE “Content Machine”:

  “I guess he thinks ... it looks like ICE is very busy, that they’re doing a lot of work. … If you’re a sociopath, you do think it’s fun. So it’s like a video game.” — Joanna Coles (57:00–57:34)

• On Trump’s branding:

  “The foundation of his career is slapping his name on everything. ... This is the fundamental insight. He may never have had any other insight…” — Michael Wolff (42:52)

• On branding’s downside:

  “Putting your name up there means someone can remove your name, and that’s not going to feel very good ... it’s going to be a signal that ... he’s a loser.” — Michael Wolff (45:26)

• On U.S. polarization:

  “I refuse to believe that we’re quite as divided as everybody said. ... Most people are somewhere in the middle.” — Joanna Coles (59:31)

Timestamps of Important Segments

• Epstein Document Dump & Release Problems: 02:42–04:27, 15:09–24:33
• Trump-Epstein Fallout, Plausible Connections: 20:15–29:33
• Congressional Pay & Mass Exodus: 05:07–11:52
• Biden/Trump Age and Fitness Comparison: 11:52–15:09
• Steve Witkoff as Diplomat & Oligarch Influence: 32:12–36:39
• Trump Grift & Expansion of Branding: 42:31–45:26
• ICE Videos and TikTok Propaganda: 49:57–59:43
• Media Ownership, Bezos, and the Post: 61:30–64:30

Tone and Language

The discussion is lively, sometimes sardonic, with both hosts alternating between biting analysis and newsroom sarcasm. Wolff’s dry, incisive style pairs with Coles’s quick-fire repartee and pop culture references, maintaining a pace that feels both informed and irreverent.

Summary

This packed episode leverages the chaos of the Epstein files to frame larger questions about transparency, propaganda, personal legacy, and the state of American democracy and media. Trump looms as both subject and symptom: from dubious files to performative patriotism, a presidency defined by spectacle and branding — now facing the blowback from its own operatic excess.

Next up: A special on “Donald Trump, Television, and His Manufactured Identity.”