The Daily Beast Podcast: “How Trump Can Bury Epstein Files Shame: Wolff”
Date: November 21, 2025
Host: Joanna Coles
Guest/Co-host: Michael Wolff
Overview
This episode dives deep into Donald Trump’s maneuvering around the Jeffrey Epstein files, examining the power dynamics at play in their (non-)release, and unpacks the mix of spectacle, incompetence, and impunity defining Trump’s White House. Joanna Coles and Michael Wolff dissect Trump's media strategies, his inner circle (including disastrous legal representation), and the ongoing resonance—and elusiveness—of the Epstein scandal. The episode oscillates between gallows humor and exasperation, providing sharp commentary on both the files and the wider absurdities of the Trump era.
Key Discussion Points and Insights
1. Trump and the Epstein Files: Illusion of Transparency
- Joanna Coles summarizes Trump’s tactic: “Although in that Trump jiu jitsu, he is now saying he directed the release of the Epstein files. What we of course know is that he has done everything… not to release the Epstein files. I think he’s gotten, if not a hundred percent of what he wants, he’s pretty close to it.” (01:29)
- Interpretation: Despite public statements, Trump has maneuvered himself into total control over what—if anything—is made public. The new legislation simply lets him curate the files, not actually release them.
- Congress’ role: Congress gave the appearance of transparency but left curation at the executive branch's discretion.
- End result: “At the end of the day...we have actually probably just more distractions in the process of getting to the bottom of the Epstein story.” (01:29, 07:07)
- Coles and Wolff agree: The mainstream headlines promising a release are misleading.
2. Inside Trump’s Head: Government as Reality Show
- Wolff on covering Trump: “Other reporters…cover this Donald Trump as they would any other president…It doesn’t work that way.” (02:40)
- Coles’ philosophy: “He’s a reflection of what he got up in the morning, what was on his mind...It is all about him. It is a government of one.” (03:21)
- Wolff riffs: “Politics has become pop culture...Because we've got a president who spent 14 seasons on a very popular reality show, he has made winning and losing elections almost as exciting as who was gonna win American Idol.” (04:46)
3. Mechanisms of Secrecy & Control
- Legal Loopholes: Trump can classify anything or designate it as part of an ongoing investigation—thus withholding it indefinitely.
- Coles: “They don’t have to turn over files which are relevant to an ongoing investigation. Everything can be an ongoing investigation…they can classify anything." (09:00)
- Selective Leaks & Weaponization: Any files released will likely target Trump’s rivals (Bill Clinton, Larry Summers, “any Democrats or people he has some issue with”) (12:44)
4. Why Weren’t the Files Released Under Biden?
- Lack of Urgency: “I think nobody [was] clamoring for it...they probably didn’t know what it was...No one was particularly interested.” (13:21)
- Democratic Liability: Many Democrats were associated with Epstein. The Biden administration saw no upside in releasing material that could implicate their own.
- Bigger Priorities: “They certainly wanted a silver bullet which they thought that they had.” (15:00)
5. Political Fallout: Will It Matter in the Midterms?
- Perceptions of Coverup: “Does it seem like he is stonewalling? That’s the classic cover up…Never underestimate the incompetence of the Trump administration to appear to be actually a cover up…” (15:35)
- Coles points out: Even failures or U-turns become opportunities for narrative repositioning.
6. Trump, Musk, and the Gulf Connections
- Social Media Maelstrom: Elon Musk’s tweets (“Trump is in the Epstein files”) briefly destabilized the alliance but faded fast. (16:40)
- Trump-Saudi Money Links: Discussion of Jared Kushner’s “Affinity Partners” backed with $2 billion from Saudi Arabia, and Jeffrey Epstein’s own deep ties in the Persian Gulf. Epstein spent time with MBS (Saudi crown prince), “playing video games” to curry favor. (18:00)
- Epstein’s Gulf Ties: “Epstein is one of the people who saw the opportunities. The Pickens were ripe. And he spent an enormous amount of time in the Persian Gulf with MBS playing video games with him.” (18:00)
7. Legal Follies: Lindsey Halligan and Trump’s Incompetent Team
- Trump’s Lawyers: “As you pointed out, Trump often says he may not have the best lawyers, but he has the hottest lawyers…Pam Bondi, he had [Lindsey] Halligan…” (06:10)
- Pure Spectacle: Halligan is “singly the most incompetent lawyer...her function was entirely to be a picture on his phone that he could show people.” (06:27)
- Judicial Rebuke:
- Wolff reads judge’s comment: “It’s challenging to unpack the DOJ letter he wrote because it contains so many factual, legal, and typographical errors…legally unsound, baseless, erroneous, ham fisted, and a mess.” (26:00)
- Justice Department—at war with itself: “This is kind of the Justice Department against the Justice Department…One is competent and one is utterly incompetent and has presented a mess to the judge.” (28:21)
8. Trump’s Reflex: Double Down and Distract
- On failure: “He distracts from his failures, often with other failures... he feels no shame. He’s able, in the face of shame, to summon enormous righteousness, a kind of righteousness that no non sociopath would be able to summon.” (33:30, 34:52)
- Narrative pivots: Each debacle simply sets the stage for another outlandish storyline.
- Comey as perennial scapegoat: “He’ll double down…Comey is a plot by the Democrats, his enemies within the government, on and on and on...” (30:21)
9. Epstein Saga: Why It Persists
- New York high society: Trump was “Jeffrey Epstein’s best friend for 15 years...each had never had a relationship as close as the one they had with each other.” (36:23)
- Irony: “It is remarkable that Larry Summers...is forced to recuse himself...and yet Donald Trump, Epstein’s best friend...is in the White House and the most powerful man in the world.” (34:52)
- No closure: “The Epstein, Epstein, Epstein of it all is going to continue and it won’t stop with answers because there won’t be any answers. But it will continue as often scandals do, precisely because there are no answers.” (37:57)
Memorable Quotes & Moments
On Trump’s Tactics and Mindset
- “He is a reflection of what he got up in the morning, what was on his mind... it is a government of one.” – Joanna Coles (03:21)
- “Politics has become pop culture…enthralling, exasperating, and potentially terrifying.” – Michael Wolff (04:46)
- “Failure, another failure...he distracts from his failures often with other failures.” – Joanna Coles (33:30)
On Trump’s Legal Team and the DOJ
- “I may not have the smartest legal team, but I have the hottest.” – Paraphrased by Coles and Wolff (06:10)
- Judge’s takedown: “DOJ letter... so many factual, legal, and typographical errors...legally unsound, baseless, erroneous, ham fisted, and a mess.” (26:00)
- “This is kind of the Justice Department against the Justice Department…one is competent and one is utterly incompetent and has presented a mess to the judge.” – Michael Wolff (28:21)
On the Epstein Files
- “We are no farther along than we have been. The headlines are wrong. The headlines should be files are not going to be released.” – Joanna Coles (11:09)
- “You can classify anything. Whether that would hold up in a court is...irrelevant.” – Joanna Coles (09:41)
On Trump’s Shamelessness
- “There is never a moment...in which there is a kind of taking stock...and you sense the underlying shame…That never happens with Donald Trump.” – Joanna Coles (33:30)
- “He’s able, in the face of shame, to summon enormous righteousness, a kind of righteousness that no non sociopath would be able to summon.” – Joanna Coles (34:52)
Notable Listener Questions (Ask Melania Section)
(40:00+)
- Sandra Sundrad asks: Would you marry your husband if you had the information you have today, back then when you first met?
- Questions about Melania Trump’s background in modeling and her connections with Paolo Zampoli’s agency.
- An 84-year-old listener points out: “During the timeline when Trump and Epstein were buddies, Trump himself was very much a Democrat…So when he wants all these Democrats in the files identified, he was a Democrat.” (41:06)
Timestamps for Key Segments
| Time | Segment/Topic | |------------|------------------------------------------------------------------| | 01:29 | Trump’s control of the Epstein files & the illusion of release | | 03:21 | Analyzing Trump’s impulsivity and ‘government of one’ dynamic | | 04:46 | Politics as pop culture; Trump’s reality TV presidency | | 06:10 | Lindsey Halligan: Trump’s lawyer for image, not competence | | 07:07 | Constraints and loopholes over “release” of Epstein files | | 12:44 | How the files' release will likely target Trump’s political rivals| | 18:00 | Epstein and Trump’s financial/personal ties to Saudi Arabia/MBS | | 26:00 | Judge’s public dressing-down of Trump’s legal submission | | 28:21 | DOJ as a battleground: Incompetence vs. competence | | 33:30 | Trump’s shamelessness, distraction strategy, and righteousness | | 36:23 | Reiteration of the Trump-Epstein close personal bond | | 37:57 | The enduring absence of resolution—or accountability—in the scandal| | 40:00+ | "Ask Melania" Q&A, listeners’ observations |
Conclusion
This episode critically examines how the much-hyped release of the Epstein files is, in fact, a masterclass in misdirection and control by Trump—one enabled by legislative sleight-of-hand, legal incompetence, and a media environment eager for spectacle. The hosts paint a picture of a presidency defined by distraction, personal vendetta, and shamelessness in the face of perpetual scandal. The Epstein saga, they argue, remains an open wound: subject to endless intrigue, but unlikely ever to yield real answers or closure, especially with Trump in charge of the vault.
For more context, see: thedailybeast.com