The Daily Beast Podcast — "I Know What Chaos Trump Is Plotting Next: Wolff"

Host: Joanna Coles
Guest: Michael Wolff
Date: March 25, 2026

Episode Overview

This episode tackles Donald Trump’s current strategies in politics, his chaotic approach to the Iran conflict, and the narrative he’s building around a “rigged” American electoral system. Joanna Coles and Michael Wolff discuss not only the real-time confusion surrounding Trump’s actions but how he manufactures chaos to his own advantage, drawing sharp comparisons to his previous manipulation of political narratives and even diverging into cultural commentary about Trump’s peculiar connection to figures like Elvis Presley. The show also explores Wolff's unique perspective, gleaned from personal interactions with figures such as Jeffrey Epstein.

Key Discussion Points & Insights

1. Trump’s Chaos Narrative

• Distraction as Strategy:
  Trump leverages the narrative that the US electoral system is broken, using it to distract from his own political difficulties and lay groundwork to contest future losses.

  “What is to his advantage is just the narrative that the election system in the United States is broken and chaos is to his advantage.” — Michael Wolff [00:31]

• Continual Fantasy Construction:
  Trump’s storylines are ever-changing, unlike the fixed narratives behind, for example, the Iraq War.

  “The weird thing about this fantasy is the fantasy seems to change minute by minute.” — Michael Wolff [18:05]

2. Iran: Confusion and Contradiction

• No Clear Strategy:
  Trump claims negotiations, then reverses, causing widespread confusion internally and internationally.

  “No one knows. All the Arab states are getting together, as they always do in a war... but no one knows who to negotiate with in Iran. Who is the person?” — Joanna Coles [02:25]

• Power Players:
  Witkoff and Kushner are humorously dubbed the “band” behind much of the policy action—or lack thereof.

  “We're in this war, no doubt, because of Witkoff and Kushner.” — Michael Wolff [02:57]

• Iran’s “Compensation” Demand:
  The strange symmetry between Trump’s financial absurdities and Iran's demands is highlighted.

  “The Iranians seem to be giving it back to him.” — Joanna Coles [19:32]

3. The Epstein Plane Story

• Excerpt from Wolff’s Substack:
  Wolff details his first encounter with Epstein on a luxurious, black 757, and the psychological allure of entering Epstein’s privileged world, even amid early misgivings.

  “This appears to be the closest I've ever come to pure evil.” — Geraldine Laban (quoted by Wolff) [06:28] “You want to at least smell this and see this and be part of it... it was hard not to feel the unlikeliness and undeserved privilege of being here.” — Joanna Coles reading Wolff [08:22]

• "The Petting Zoo":
  An unsettling invitation from Epstein, whose meaning becomes clear only in hindsight.

  “Do you want to ride back here in the petting zoo or up front with the pilots?” — Jeffrey Epstein to Michael Wolff [12:33] “But as soon as you agree to that and then you're there, you think, what was that? Did I hear that correctly?” — Michael Wolff [13:10]

4. Reality TV Presidency and the Rigged Election Narrative

• Crafting the Save America Act:
  Trump invents a crisis (mass non-citizen voting) to push legislation requiring strict ID for voters, despite no credible evidence such a problem exists.

  “He creates a problem that doesn't exist. Then he seems determined to find a solution for the problem that doesn't exist, therefore creating chaos in the American election system.” — Joanna Coles [23:16] “The drama... is that the American electoral system doesn't work... Here is Donald Trump saying, I can save this.” — Michael Wolff [25:09]

• Self-Perpetuating Grievance:
  If he wins, the system is legitimate; if he loses, it’s “rigged.”

  “So if he wins, the system is perfect, and if he loses, the system is rigged.” — Joanna Coles [37:20] “Yes, but he's not going to win. So the system is going to be rigged.” — Michael Wolff [37:26]

5. Trump’s Personal Psychology

• Self-Delusion or Calculation?:
  Both speculate whether Trump truly believes his own narratives, ultimately settling that belief is necessary for the performance.

  “You have to believe it. And I have sat with the man as he has gone over these numbers... But nevertheless, he’s in pig heaven with these numbers.” — Michael Wolff [27:13]

• The Pull of the Personality:
  No one—family, advisors, party—buys the story, but they are swept along in the drama he creates.

  “To create this entire world... to bring so many other people inside of it? He has brought, for one thing, he has brought the entire Republican Party...” — Michael Wolff [26:13]

6. Voter Suppression and American Democracy

• Legislation as Suppression:
  The ID requirements would disenfranchise many—particularly the young, poor, and less-educated—groups with complex documentation needs.

  “It's a whole threshold here which an enormous number of people in this country can't get over.” — Michael Wolff [29:15]

• Cynicism & Systemic Undermining:
  Trump’s cynical attacks on the democratic process, even as no problem exists, are called out as “horrifying.”

  “An interesting and cynical and frankly horrifying thing to do to try and get at the very center of democracy by saying it's rotten to its core.” — Joanna Coles [30:19]

Notable Quotes & Memorable Moments

• On Chaos:

  “What is to his advantage is just the narrative that the election system in the United States is broken and chaos is to his advantage.” — Michael Wolff [00:31]

• On Fantasy:

  “The weird thing about this fantasy is the fantasy seems to change minute by minute.” — Michael Wolff [18:05]

• On the Epstein Plane:

  “Do you want to ride back here in the petting zoo or up front with the pilots?” — Jeffrey Epstein, relayed by Michael Wolff [12:33] “This appears to be the closest I've ever come to pure evil.” — Geraldine Laban (quoting) [06:28]

• On Trump & Elections:

  “So if he wins, the system is perfect, and if he loses, the system is rigged.” — Joanna Coles [37:20] “Only I can save this.” — Michael Wolff imitating Trump [25:16]

• On Voter Suppression:

  “It’s... horrifying... to try and get at the very center of democracy by saying it's rotten to its core.” — Joanna Coles [30:19]

Timestamps for Important Segments

• Trump’s Chaos Narrative & Election Plotting — [00:31], [23:16], [25:09], [34:00], [37:20]
• Iran Conflict & Negotiations — [02:04], [08:14], [16:45]
• Epstein Plane Story — [04:40], [06:28], [12:33], [13:10]
• Trump & Elvis/Pop Culture — [20:28]
• Voter Suppression Laws & Impact — [29:12], [30:19], [33:43]
• End Reflection on Democracy — [39:20]

Tone & Flow

The conversation is sharply witty and informed by insider perspectives. Coles and Wolff mix dark humor with deep concern for democratic institutions. Their rapport lends the show a feeling of both urgency and irreverence—“like the best dinner party you’ve ever been to, just without the food.” The storytelling, particularly Wolff’s Epstein anecdotes, breaks up heavy political analysis and gives a privileged window into the psychological world of power and manipulation.

Conclusion

This episode dissects how Trump turns manufactured chaos into political capital, exposes the hollowness and danger of the “rigged election” narrative, and paints a personal, sometimes bizarre picture of the circles of power in contemporary America. Whether you’re following the headlines or seeking a psychological autopsy of the Trump effect, Coles and Wolff deliver both lively anecdotes and sobering warnings about the fragility of democracy in the age of reality TV politics.