The Reason Why Trump Keeps Getting Worse: Wolff

The Reason Why Trump Keeps Getting Worse: Wolff

Author: The Daily Beast, Michael Wolff and Joanna Coles July 8, 2026 Duration: 1:06:34
Michael Wolff and Joanna Coles break down the latest clues to what's really driving Donald Trump, from his attempts to influence FIFA and his obsession with being at the center of every spectacle to the staggering financial windfall he's reaped from his crypto empire while hundreds of thousands of investors have collectively lost billions. They also unpack the scandal engulfing Democratic Senate hopeful Graham Platner, Trump's instinctive defense of embattled public figures, the changing rules of modern politics, the future of NATO as Trump heads into another high-stakes summit, and why Michael believes Democrats still haven't figured out how to capture the country's moral attention in the Trump era. Start your free trial today at https://shopify.com/dailybeast #ad 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
I Know The Truth About Trump's Sex Life: Wolff [not-audio_url] [/not-audio_url]

Duration: 55:55
Michael Wolff and Joanna Coles examine Donald Trump's strange relationships with the women closest to him over the course of his 80 years—from Ivana and Marla Maples to the enduring mystery of Melania Trump's absence fro…
I know Why Trump Is Dreading His 80th Birthday [not-audio_url] [/not-audio_url]

Duration: 1:02:00
Michael Wolff and Joanna Coles mark Donald Trump entering his ninth decade with a special episode revealing new details about private discussions inside Trump’s circle over his age, health, legacy, and the future of his…
White House’s New Epstein Scapegoat Is Revealed [not-audio_url] [/not-audio_url]

Duration: 50:32
Michael Wolff and Joanna Coles unpack a week in which the Jeffrey Epstein saga once again consumed Washington, examining explosive new reporting about panic, leaks, and finger-pointing inside the White House while asking…
Why Trump's Boundless Ego Is Sabotaging Him: Wolff [not-audio_url] [/not-audio_url]

Duration: 59:59
Michael Wolff and Joanna Coles dive into a week that may reveal the limits of Donald Trump’s political dominance, from being loudly booed at a packed Knicks playoff game to turning the White House lawn into a UFC spectac…
Spineless GOP Are Finally Turning Against Trump [not-audio_url] [/not-audio_url]

Duration: 1:14:29
Michael Wolff and Joanna Coles dissect the growing backlash against Donald Trump's inner circle, from Stephen Miller's escalating deportation agenda to the stunning appointment of Bill Pulte to oversee America's intellig…
Why Trump’s Now Losing on a ‘Daily Basis’: Wolff [not-audio_url] [/not-audio_url]

Duration: 1:04:32
Michael Wolff and Joanna Coles dive into what Wolff argues is the beginning of a dramatic unraveling of Donald Trump’s political project, tracing how the fallout from the Iran conflict, slipping poll numbers, congression…
I Know Why Trump Is in His Shameless Cash Grab Era [not-audio_url] [/not-audio_url]

Duration: 58:16
Michael Wolff and Joanna Coles unpack into a week of chaos inside the Trump White House, from a failed attempt to push through what Wolff calls an unprecedented political “grift” to Trump’s growing frustration over a war…
I Know Why Mad King Trump Loves to Sue: Wolff [not-audio_url] [/not-audio_url]

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 I…
How I Know Trump's at His Most Dangerous: Wolff [not-audio_url] [/not-audio_url]

Duration: 1:02:44
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 dan…