Inside Trump's Head – Episode Summary

Episode: Real Reason ABC Bowed to Trump on Kimmel: Wolff
Date: September 19, 2025
Hosts: Michael Wolff (Trump biographer), Joanna Coles (Daily Beast)

Episode Overview

This episode delves into the growing tension between Donald Trump, the media, and entertainment giants like Disney/ABC in the wake of Jimmy Kimmel’s indefinite suspension. Michael Wolff and Joanna Coles dissect what this confrontation reveals about Trump’s evolving relationship with power, censorship, and how America’s media and business elite are responding to his second term. The broader context is a media landscape increasingly cowed by political pressure—and what that portends for free speech and democracy.

Key Discussion Points & Insights

1. The Jimmy Kimmel Suspension and the Media Chill

• Kimmel’s Indefinite Suspension

  • ABC suspended Jimmy Kimmel after comments he made about conservative figure Charlie Kirk.
  • The suspension sent a “chill” across the US, symbolizing the clampdown on satiric critique of the administration.
  • Wolff recounts how such censorship is driven by fear of Trump's “wrath and ire.”

    “Everybody running in the opposite direction of controversy, running in the opposite direction of Donald Trump’s wrath and ire.” (Wolff, 04:14)

• The Backstory: Trump and Kimmel’s Relationship

  • Wolff recalls his first political interview with Trump in 2016 in Kimmel’s green room.
  • At the time, Trump and Kimmel were amicable, jokey, and both enjoying their celebrity status. This contrasts sharply with their current antagonism.
  • Trump, post-show, was “delighted” with Kimmel and the two spent hours at Trump’s Beverly Hills home.

    “He was delighted with Kimmel. ...We repaired to his house in Beverly Hills and spent hours and hours each eating a tub of Haagen Dazs ice cream.” (Wolff, 05:30-06:10)

• Shift in Trump’s Persona

  • Over a decade, Trump has transformed from a playful, self-aware celebrity to a “defensive, angry” figure who sees himself as besieged by enemies, including former friends.

2. Media Corporations’ Calculated Retreat

• Business vs. Free Speech

  • Joanna Coles posits Bob Iger (Disney CEO) is motivated by business pragmatism; Disney’s stock is underperforming, and maintaining affiliate relationships (with conservatively-led Nexstar, Sinclair, etc.) is vital.
  • Wolff argues that the result—regardless of motive—is “cowering” before Trump’s administration.

    “Bob Iger... immediately, with hardly a second thought, cowering before the desires of the Trump administration.” (Wolff, 11:16)

• Changing Media Priorities

  • In the past, protecting corporate credibility came first; now, “if you lose Donald Trump, you lose the store.” (Wolff, 12:33)

• The Creative Community’s Alienation

  • Kimmel, a “team player” beloved in LA and by Disney/ABC, is sacrificed for regulatory expedience—potentially alienating artists and writers from the Disney brand.

• Implications for Disney Leadership

  • Wolff predicts this “unforced error” could ultimately cost Iger his job, with Dana Walden (closely linked to Kamala Harris) waiting in the wings.

    “This is probably a deep, deeply, an unforced error that will cost Bob Iger, likely...cost him his job.” (Wolff, 15:05)

3. Censorship, Fear, and ‘Autocracy by Commerce’

• A “Putin Puppet Show” Moment

  • Coles draws an analogy to Russia’s early Putin-era crackdown, noting autocracy sometimes manifests as the quiet cancellation of comedies, not “jackboots in the street.”

    “This could actually be what autocracy looks like, that it’s not people with jackboots marching...it is Jimmy Kimmel being canceled.” (Joanna Coles, 19:34)

• Pattern of Media Capitulation

  • ABC had previously capitulated on settlements benefiting Trump directly (including a $15 million payment).
  • CBS also settled a Trump lawsuit to facilitate a merger, revealing a pattern of pre-emptive surrender to avoid regulatory or legal entanglements.

• Potential Media Consolidation

  • The looming takeover of media behemoths (CBS, Warner Bros Discovery, TikTok) by the pro-Trump Ellison family raises red flags for press freedom.

    “The Ellison family, passionate supporters of Donald Trump, are about to corner the media market.” (Wolff, 23:10)

• Corporate America Bowing to Power

  • Scenes at a white tie dinner—top US tech CEOs and British royalty placating Trump—reflect the performative power games at play.

    “I can only assume that they get together and say, my God, this guy Trump is easy to play...and then we get what we want.” (Wolff, 17:39)

• MAGA’s Schisms and Free Speech Paradox

  • MAGA’s grassroots still demand disclosure on issues like Jeffrey Epstein, while Trump aggressively stonewalls.

    “The MAGA position is, release all the information about Jeffrey Epstein. The Trump position is, do not talk of Jeffrey Epstein. See? And put his fingers in his ears.” (Wolff, 02:03, 26:42)

4. Listener Questions Segment

(From 29:52 onwards)

• Epstein Emails & UK Angle
  • Listeners ask about Bloomberg’s Epstein email leaks and implications for UK figures.
• Stephen Miller’s Influence
  • Stephen Miller remains a central, if “peculiar,” architect in Trump’s White House—trusted to translate MAGA ideology.

    “He may be the most significant policy person in the White House, which is curious because Trump has always regarded him as peculiar.” (Wolff, 31:43)

• Trump’s Legal Defiance & The Supreme Court
  • Questions raised about Trump defying tariffs/troops-related court orders lead Wolff to warn that legal workarounds and a compliant Supreme Court could erode checks on presidential power.

    “Their job is to back the president, apparently.” (Wolff, 35:03)

5. Free Speech in Britain vs. America

• UK authorities arrested activists for projecting images connected to the Epstein story.
• Wolff muses on the more tentative British approach to free speech, contrasting US protections (the First Amendment) with the UK’s more restrictive laws.

  “Free speech has always seemed to me a kind of squeamish relationship [in the UK]...Thank God for the United States of America.” (Wolff, 36:04)

6. Lighter Moments and Personalities

• Anecdotes about Melania’s royal wardrobe, Kimmel’s rapport with Disney, and personal quirks (Trump’s changing ice cream preferences).
• Coles praises Princess Kate and Melania’s fashion at the white tie event.

Notable Quotes & Memorable Moments

• “No one gets out of Donald Trump world alive. I think that’s a reasonable given.”
  — Michael Wolff, 08:58
• “Bob Iger...immediately, with hardly a second thought, cowering before the desires of the Trump administration.”
  — Michael Wolff, 11:16
• “If you lose Donald Trump, you lose the store.”
  — Michael Wolff, 12:33
• “This could actually be what autocracy looks like...it is Jimmy Kimmel being canceled.”
  — Joanna Coles, 19:34
• “The MAGA position is, release all the information about Jeffrey Epstein. The Trump position is, do not talk of Jeffrey Epstein...put his fingers in his ears.”
  — Michael Wolff, 02:03 & 26:42
• “He has always regarded him [Stephen Miller] as peculiar...Do you think he’s strange?”
  — Michael Wolff, 32:08
• “Their job is to back the president, apparently.”
  — Michael Wolff, 35:03

Timestamps for Major Segments

• 02:03 – MAGA vs. Trump on Jeffrey Epstein info
• 03:42 – Kimmel’s indefinite suspension & causes
• 05:40–07:11 – Wolff recollects his first Trump interview (Kimmel’s green room, Beverly Hills, ice cream)
• 08:47 – Trump’s animus extends to inner circle
• 11:30–12:33 – Wolff and Coles on media pragmatism vs. cowardice
• 13:25–15:01 – Kimmel as Disney “team player,” Bob Iger’s dilemma
• 17:15–18:50 – White tie dinner with tech CEOs and Trump, power rituals
• 19:25–20:07 – Putin’s puppet show, Kimmel as a symbol of creeping autocracy
• 21:33–23:50 – Media settlements with Trump, Ellison family’s consolidation moves
• 24:45 – Democratic hopes, Newsom’s attacks, House elections
• 25:55 – Listener question: MAGA & free speech, internal divisions
• 30:35 – Listener question: Epstein emails, UK connection
• 31:27 – Stephen Miller’s status and influence
• 33:53 – Listener question: Trump, court orders, and the Supreme Court
• 35:35 – Arrests over Windsor Castle projection; British free speech laws
• 38:06–39:05 – Royal dinner fashion commentary, closing remarks

Conclusion

This episode paints a sobering picture of Trump’s dominance over media and the increasing accommodation—and sometimes capitulation—of giant corporate and media interests. Wolff’s firsthand anecdotes and candid conjecture, balanced by Coles’ challenging questions, provide a unique, insider’s window into the power dynamics that now define the relationship between Trump, the press, and the business world. The contest between principle and pragmatism, and the slow erosion of free speech (both in the US and UK), echo throughout the discussion—accentuated by stories both astute and absurd, and leavened by the hosts’ dry wit.