How I Know Trump's at His Most Dangerous: Wolff

How I Know Trump's at His Most Dangerous: Wolff

From Inside Trump's Head by The Daily Beast, Michael Wolff and Joanna Coles

May 29, 2026 · 1h 3m · Season 1 · Episode 118

About this episode

The episode explores the panic and volatility surrounding Donald Trump as he navigates political challenges and personal grievances.

Michael Wolff and Joanna Coles trace the panic, paranoia, and raw volatility swirling around Donald Trump as he insists he “doesn’t care” about the midterms while privately sounding trapped, furious, and increasingly dangerous. From comparisons to Stalin’s inner circle and the cult-like loyalty inside Trump’s cabinet, to the political gamble of backing scandal-plagued Ken Paxton in Texas, the episode dives deep into a presidency that appears to be running on grievance, chaos, and reality-show instincts. They unpack Trump’s escalating obsession with E. Jean Carroll as the Justice Department targets her after she beat him twice in court, explore how Iran may be outmaneuvering him in the Strait of Hormuz crisis, and examine why Trump’s promise to avoid endless wars is collapsing in real time. Plus, Michael reveals another surreal chapter from his Jeffrey Epstein encounters involving Bill Gates, billionaire fantasies, and the strange power games unfolding inside Epstein’s Manhattan mansion. Visit https://ffrf.us/TRUMP or text TRUMP to 511511 to learn more and join. #ad Learn more about your ad choices. Visit podcastchoices.com/adchoices

People in this episode

Hosts: Michael Wolff, Joanna Coles

Topics covered

  • Trump's volatility
  • political loyalty
  • midterm elections
  • legal battles
  • foreign policy
  • celebrity encounters

Keywords

  • Trump
  • midterms
  • E. Jean Carroll
  • Ken Paxton
  • Iran
  • Epstein
  • politics
  • chaos
  • loyalty

Sponsors

FFRF

Mentioned in this episode

Organizations: Justice Department, Epstein, The Daily Beast

Places: Texas, Strait of Hormuz

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