Does the MyPillow Guy Think He’s a Governor?

Michael Wolff joins Joanna Coles to unpack why the release of the Epstein files has backfired on Donald Trump, obscuring key facts while amplifying the one question that won’t go away: what Trump knew, and when. Wolff explains how the chaotic document dump fits Trump’s flood-the-zone instincts, while Coles probes how branding, spectacle, and confusion remain his core political defenses. They also examine the risks of sidelining institutions—from Ukraine diplomacy to ICE-as-content—and ask whether Trump’s belief that chaos protects him is finally working against him. Hosted on Acast. See acast.com/privacy for more information.

24 Dec 1h 1min

Mary Trump joins Joanna Coles to explain how Donald Trump’s accelerating cognitive and psychological decline is rooted in a childhood defined by cruelty, fear, and the absolute ban on showing weakness. Drawing on her training as a clinical psychologist and her firsthand experience inside the Trump family, Mary argues that Trump’s belligerence is routinely mistaken for strength, even as his physical health, cognitive deterioration, and untreated pathology collide. The conversation ends with a stark question: What happens when a country is governed by a man trying to fill a void that can never be filled? Hosted on Acast. See acast.com/privacy for more information.

23 Dec 54min

Psychologist Dr. John Gartner joins Joanna Coles to dissect Donald Trump’s latest White House speech and explain why its manic pace, rigid teleprompter discipline, and sheer velocity alarm mental health professionals. Drawing on decades of clinical experience, Gartner argues that Trump’s hypomania, malignant narcissism, and advancing dementia are no longer abstract theories but visible patterns—accelerating, measurable, and increasingly unmanaged. They examine why repeated cognitive tests suggest monitoring decline rather than routine screening, and how sleepless nights, impulsive decisions, and compulsive posting point to a leader edging toward a cognitive cliff. Hosted on Acast. See acast.com/privacy for more information.

22 Dec 41min

Michael Wolff joins Joanna Coles to tackle the question Washington won’t confront: what happens when a president’s cognitive decline is visible but systematically rationalized by those around him. Wolff describes how Trump’s inner circle shields alarming behavior as “Trump being Trump,” even as voters recognize familiar warning signs from their own families. He also explains the significance of Susie Wiles’ long-standing relationship with Marco Rubio, and why her influence still shows in his disciplined, professional posture as Trump spirals. As Trump’s grandiosity accelerates—from galloping speeches to branding national institutions—Coles asks why no one is willing to take the keys away, and what that silence means for the country. Hosted on Acast. See acast.com/privacy for more information.

21 Dec 57min

Michael Wolff joins Joanna Coles with a story Trump World would rather bury: his legal pursuit of Melania Trump after she threatened a $1 billion libel suit over his reporting on her ties to Jeffrey Epstein. Wolff details the surreal effort to serve the First Lady—lawyers refusing papers, process servers turned away, Trump Tower staff claiming she lives there while she avoids being found—and explains why he sued first under New York’s anti-intimidation law. The legal farce opens onto something larger: a family operating in secrecy and fear, a president trying to “serve” his wife even as control slips, and a White House where avoidance has become strategy. As Trump’s foreign policy grows more erratic and Europe edges toward war, the question lingers: is Melania’s disappearance just legal gamesmanship—or another sign of a presidency retreating from accountability? Hosted on Acast. See acast.com/privacy for more information.

19 Dec 59min

Stacey Williams joins Joanna Coles as the anticipated release of the Epstein files throws fresh scrutiny on Donald Trump’s long-denied proximity to Jeffrey Epstein. Williams recounts how a dinner invitation led to a relationship with Epstein—and, she says, to being deliberately walked into Trump Tower where Trump groped her while Epstein stood by, a moment she now believes was staged. Does her account expose how power, silence, and sexual coercion were normalized at the highest levels—and why Trump remains untouched as others in Epstein’s orbit fall? Hosted on Acast. See acast.com/privacy for more information.

18 Dec 45min

Michael Wolff joins Joanna Coles to break down the Vanity Fair profile that may have pushed Trump chief of staff Susie Wiles into dangerous territory, and the newly surfaced Epstein diaries that reveal fixation more than revelation. But the episode turns darker with Trump’s grotesque response to the murder of Rob Reiner and his wife—a moment that shocked even his own insiders. Wolff argues this wasn’t calculation or cruelty, but something giving way. And it leaves an unavoidable question hanging in the air: how long can a presidency survive when self-destruction is no longer strategic, but instinctive? Hosted on Acast. See acast.com/privacy for more information.

17 Dec 47min

Chris Whipple joins Joanna Coles as his explosive Susie Wiles profile sends shockwaves through Trump’s White House. After 11 months of on-the-record access, for Vanity Fair, to Susie Wiles, Whipple explains why the facts can’t be denied—and why her description of Trump’s “alcoholic personality” has triggered cabinet-wide panic and presidential pushback. Does this unprecedented candor reveal how Trump 2.0 actually functions, or mark the moment the West Wing turns on its most powerful gatekeeper? Hosted on Acast. See acast.com/privacy for more information.

17 Dec 40min