I Know Why Mad King Trump Loves to Sue: Wolff

I Know Why Mad King Trump Loves to Sue: Wolff

Author: The Daily Beast, Michael Wolff and Joanna Coles May 31, 2026 Duration: 1:03:36
Michael Wolff and Joanna Coles unpack another week of chaos inside Trumpworld, from a judge forcing Donald Trump to strip his name from the Kennedy Center to a court challenge threatening his controversial $1.8 billion IRS settlement fund. They dig into Trump's newly disclosed weight gain, his obsession with public enemies, and why Wolff believes targeting figures like E. Jean Carroll matters more to Trump than winning in court. The pair also explore the growing influence of Todd Blanche, the fallout from the Epstein files controversy, and signs that Trump may already be turning on J.D. Vance as a potential successor. Along the way, they re-open the book on Usha Vance's baffling podcast, the deepening Iran crisis that Trump can't seem to escape, and the reality-show logic that continues to drive the presidency. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What does it actually take to get inside the head of a figure who has so thoroughly reshaped modern politics and culture? That’s the journey undertaken in Inside Trump's Head, a collaboration between The Daily Beast’s Joanna Coles and author Michael Wolff. Wolff, having spent years as a definitive biographer with unprecedented access, pairs with Coles’ sharp editorial perspective to move beyond the daily headlines. Their conversations aren’t just analysis; they’re an excavation of the instincts, motivations, and personal history that drive Donald Trump’s most consequential decisions. Each episode feels like a deep, often surprising dialogue between two people who’ve observed him from uniquely informed vantage points. You’ll hear them parse his public statements against his private history, examine the personal mythology he cultivates, and debate how his character continues to alter the fabric of society. This podcast avoids easy partisan takes, opting instead for a nuanced and candid exploration of the man behind the phenomenon. It’s for anyone who wants to understand not just what happened, but the underlying psychology of why. Tune in for a series that goes deeper than the news cycle, offering a sustained and compelling study of a character whose destiny remains inextricably linked with our own.
Author: Language: English Episodes: 50

Inside Trump's Head
Podcast Episodes
This Is Why Trump Surrounds Himself With Idiots [not-audio_url] [/not-audio_url]

Duration: 1:08:10
Michael Wolff and Joanna Coles look at the latest signs of chaos inside Trump’s White House, from the administration’s fixation on interest rates and the tensions surrounding the Federal Reserve to the startling question…
Why Harp’s Special Perk Stunned Trump Staff [not-audio_url] [/not-audio_url]

Duration: 53:34
Michael Wolff and Joanna Coles take on Donald Trump’s latest fixation with image, power, and excess, from his apparent weight gain and the extraordinary Mar-a-Lago golf club buffet to the increasingly curious role of Nat…
How Melania Has Abdicated Her First Lady Duties [not-audio_url] [/not-audio_url]

Duration: 1:01:04
Michael Wolff and Joanna Coles go inside a White House where Melania Trump’s rare appearances, her increasingly lucrative personal brand, and her complicated relationship with Natalie Harp are raising fresh questions abo…
I Have Natalie Harp's 'Love Letters' to Trump [not-audio_url] [/not-audio_url]

Duration: 1:05:17
Michael Wolff and Joanna Coles go inside the increasingly bizarre inner workings of Donald Trump’s presidency, beginning with Wolff’s extraordinary account of Natalie Harp’s deeply personal letters to Trump and the alarm…
Here’s Everything I Know About Natalie Harp: Wolff [not-audio_url] [/not-audio_url]

Duration: 1:05:47
Michael Wolff and Joanna Coles devote a special episode to Natalie Harp, the Trump loyalist who has risen from campaign aide to one of the most powerful people in the president’s orbit. Wolff traces Harp’s extraordinary…
Why Trump’s Weird Fixations are Exploding Now [not-audio_url] [/not-audio_url]

Duration: 1:01:33
Michael Wolff and Joanna Coles explore Donald Trump’s increasingly intense fixations, from his relentless campaign to put his name on the Kennedy Center to his insistence that the Navy return to outdated technology, and…
I Know Why Everyone Talks About Trump's Diapers [not-audio_url] [/not-audio_url]

Duration: 1:01:12
Michael Wolff and Joanna Coles dig into Karoline Leavitt’s departure from the White House, the scramble to replace her, and what her exit reveals about the brutal demands of working directly for Donald Trump. They also c…
Dark Truth About Trump's Plane Switch Leak: Wolff [not-audio_url] [/not-audio_url]

Duration: 57:45
Michael Wolff and Joanna Coles mark one year of Inside Trump’s Head by dissecting the bizarre story of Donald Trump secretly switching planes while the White House press corps unknowingly flew aboard a decoy Air Force On…
What Trump Is Screaming After Ballroom Humiliation [not-audio_url] [/not-audio_url]

Duration: 1:02:13
Michael Wolff and Joanna Coles get inside Donald Trump’s fixation with the White House ballroom, and why a court ruling stopping the project may only make him more determined to build it. They also look at the growing te…
This Is RFK Jr.'s Explosive Plot for Power [not-audio_url] [/not-audio_url]

Duration: 1:01:54
Michael Wolff and Joanna Coles dive into another astonishing week inside Donald Trump’s head, analyzing the president’s fixation on image—from his infamous hair to a controversial White House helipad—as they reveal how p…