Inside Trump's Head

Michael Wolff joins Joanna Coles to focus on one of Donald Trump’s most revealing tools: the telephone. Drawing on decades of firsthand experience—from Trump’s landline calls to New York Magazine in the 1990s to rambling, unsolicited calls as president—Wolff explains why Trump is almost never off the phone, why he hates email and paper trails, and how calling isn’t about exchanging information so much as asserting dominance, rehearsing grievances, and never being alone. It’s a portrait of a man who governs, leaks, vents, and connects almost entirely by voice—using the phone as both comfort object and command center—and a revealing look at how Trump’s constant talking shapes his politics, his relationships, and his presidency. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff and Joanna Coles unravel a week in Trumpworld that veers from grotesque to outright dangerous, starting with Donald Trump’s late-night Truth Social spiral and the racist meme depicting the Obamas that even members of his own party scrambled to disown. They dig into what aides privately describe as Trump “going over the edge,” why the media still struggles to describe these moments honestly, and how this behavior is no longer an exception but the operating system. From there, the conversation turns to Trump’s jaw-dropping demand to rename Penn Station after himself—holding billions in federal infrastructure funding hostage in exchange for another monument to his name—and what that reveals about power, domination, and his obsession with owning physical and psychological space. The episode also explores the next weaponized phase of the Epstein files, Ghislaine Maxwell’s looming testimony, and how conspiracy, grievance, and raw racism are colliding at the center of Trump’s presidency—so is this just another scandal to scroll past, or a warning sign of something far more unstable still to come? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles as Trump aids declare the White House an “Epstein-free zone” where his name cannot be spoken. Wolff reveals how Trump’s go-to tactic of personal attacks and distraction still works just enough to avoid answering the one question he can’t touch, why the Epstein revelations are quietly reshuffling internal crises, and how figures from Deepak Chopra to Peter Mandelson to Silicon Valley’s self-styled gurus keep orbiting the same corrupt universe. Then comes Trump’s most compulsive, self-destructive obsession yet: his push to rebrand the Kennedy Center, justified by his own near-assassination fantasy and driven by a need to overwrite history with his name—even as artists flee, audiences vanish, and the politics make no sense. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles as Trump predictably lashes out in the fallout from the Epstein files—targeting Wolff as his latest nemesis, threatening lawsuits he can’t afford to file, and insisting the real conspiracy is against him. They unpack Trump’s rambling, defensive response to questions about Epstein flights, island denials, and the newly resurfaced claim—now echoed in official documents—that Epstein introduced Melania to Trump, a detail Trump world once tried to bury with billion-dollar legal threats. From Bill Gates and elite denial to Epstein’s role as an information broker, the conversation widens to Trump’s current obsession: federalizing elections, re-litigating 2020, and quietly laying the groundwork to undermine the 2026 midterms. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff and Joanna Coles step inside Donald Trump’s head at a moment when spectacle, grievance, and power collide. They unpack what Melania’s glossy new documentary really reveals about her marriage, money, and leverage. Wolff explains why the newly released Epstein files are reopening uncomfortable truths inside Trump World. They then discuss how the federal response in Minneapolis offers a stark window into how Trump understands authority and force. As these threads converge, Wolff and Coles wonder: is Trump tightening his grip on power—or revealing the fractures that could define what comes next? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to unpack Melania’s high-profile movie premiere flop and Trump’s crumbling White House operations. As Minneapolis reels under paramilitary forces and DHS overreach, Wolff reveals how Trump’s aides point to the president’s “cabinet of morons” as the root of the administration's flailing incompetence as they scramble to keep him happy and dodge accountability. Meanwhile, the First Lady leverages her office to secure a $40 million documentary deal, sparking questions of corporate bribery. With resignations, lawsuits, and the looming midterms, Wolff and Coles map the power plays, personal agendas, and unraveling strategy behind the headlines. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to unpack the Minneapolis ICE shootings that have sent the Oval Office into a frenzy—and exposed the real tripwire in Trumpworld. As Susie Wiles, Stephen Miller, Kristi Noem, and Corey Lewandowski turn on each other in a furious blame game, Wolff reveals why the president is suddenly “wobbling” on immigration, how ICE quotas and untrained agents led to disaster, and why Miller is now dangerously exposed with no bureaucratic buffer left. Looming over it all is a furious First Lady, whose long-planned Melania movie rollout has been eclipsed by bloodshed and scandal—and whose displeasure, Wolff argues, matters more to Trump than polls, politics, or public outrage. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles as a winter blizzard barrels toward Washington and a political storm gathers inside the White House, where Trump’s second term is no longer defined by dominance but by drift, bad polls, and creeping loss of control. From a Davos appearance that Trump insists was triumphant—but clearly wasn’t—to a rare and dangerous moment of international pushback led by Canada’s Mark Carney and echoed across Europe, Wolff argues the strongman illusion is cracking. The question hanging over it all: Is this just another chaotic chapter—or are we witnessing the first chapter of the end of Trump’s reign? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to unpack why Trump’s latest global theatrics—from the Greenland takeover threat to the billion-dollar “peace board”—were never meant to happen at all. Drawing on Davos, disastrous polling, Minneapolis blowback, and Trump’s endless talent for distraction, Wolff explains how bluster without cost is the core of Trumpism: set fires, bask in the sirens, then walk away before consequences arrive. The question lingering after Greenland fades: Is this the moment the world finally stops chasing the fire engines, or is Trump already lighting the next match? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to take apart the most durable myth of Trump’s presidency: the idea that there is some master strategist at work. As Ukraine remains unresolved, the economy wobbles, and Trump’s promised “day one” deals evaporate, Wolff argues that what actually sustains Trump is not strategy but performance — a relentless projection of dominance learned on reality television and refined in politics. They trace how Trump’s refusal to retreat, apologize, or show weakness keeps him squeaking through moments that logic says should break him, from Greenland to Epstein to Minneapolis, each distraction layered atop the last. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to unpack Trump’s latest high-stakes drama: the Insurrection Act and his escalating presence in American cities. From Minneapolis as ground zero to ICE agents wielding “absolute immunity,” Wolff breaks down how conflict and chaos have become Trump’s strategy, not his mistake. Joanna and Wolff explore the administration’s doubling down, the Democratic Party’s faltering response, and the curious absence of figures like Barack Obama and George W. Bush—two leaders with the authority to counter Trump’s moves. They also trace Trump’s foreign entanglements, from Venezuela to Iran, and the surprising ways reality continues to diverge from his proclamations. With Trump’s threats backfiring at home and abroad, the conversation exposes a presidency ruled by drama, distraction, and the relentless pursuit of power. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to trace how a president cornered by Epstein, ICE violence, collapsing polls, and mounting legal exposure responds the only way he knows how: by grabbing territory, media, and attention at scale. From the Foxification of CBS News and the quiet corporate bargain behind it, to Trump’s fixation on Greenland, Venezuela, Iran, and elite cities he loves to demonize, this episode maps a presidency fueled by distraction, intimidation, and an audience of one. Wolff unpacks why Trump’s pressure-point politics now extend from network newsrooms to foreign policy theater, why even loyal institutions are bending under threat, and why the nightmare Trump is trying to outrun—Epstein. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to trace the oddly revealing logic now driving Donald Trump’s presidency: a man who knows the midterms are coming, knows the numbers are bad, knows Epstein, jobs, ICE videos, and his own health chatter are bleeding into the public consciousness—and who believes the only solution is something that “plays.” From Pam Bondi’s visible strain as Trump treats the Justice Department like his personal law firm, to his lifelong conviction that nothing is ever his fault, Wolff explains why loyalty always curdles into blame. The conversation moves outward to the foreign-policy theatrics he sees as risk-free wins: Venezuela as a headline-grabbing show of force, Greenland as a performative threat designed to make Europe bend, and war as branding. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to unpack the central illusion of Trump’s presidency: that someone, somewhere knows what is going on—when in fact nobody does, least of all Trump himself. From Iran’s uprising to Venezuela’s phantom “invasion,” Wolff explains how Trump exploits uncertainty by announcing conflicts he has no intention of prosecuting, using noise, grandiosity, and endless talking to stay at the center of attention while avoiding real risk or consequence. The conversation ranges from ICE and Minneapolis to Greenland, shoes, height, and the limits of loyalty, before landing on the most dangerous question of all: What happens when Trump’s talent for manufactured crises collides with a real one—Russia, Iran, or a nuclear threat he cannot simply talk his way out of? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to unpack one of the most confounding political inversions of the Trump era: the moment when lying stopped being a liability and became a source of power. Wolff argues that while past presidents were undone by exposed falsehoods, Trump’s credibility has never been weaker—and yet it has only strengthened him. Together, they examine how shamelessness, repetition, and brute insistence on an alternate reality have replaced truth as a governing tool, leaving institutions, media, and public protest strangely inert. From the collapse of shared reality to the media’s inability to name what’s happening in plain language, this episode digs into why transparent lies no longer undermine authority—and what it means when reality itself stops working as a check on power. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to examine how Nicolás Maduro’s dance mocking Trump became a genuine trigger for the president — and why humiliation lands harder than policy. Wolff explains how Trump turns foreign affairs into personal vendettas, and when Maduro refuses the deals, dances, and laughs, it pierces Trump at the level of ego, not ideology. Also, the conversation widens to Trump’s fixation on the MOCA test as proof of competence, the way distraction becomes a governing tactic, and how figures like Mark Kelly are pulled into the narrative to shift attention, rewrite the stakes, and keep the spotlight where Trump needs it most, namely away from Epstein. Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to probe the growing mystery around Melania Trump — the first lady who rarely appears, rarely speaks, and yet increasingly shapes the atmosphere around Donald Trump. Wolff explores why Melania’s absence feels deliberate, how lawsuits and the threat of depositions have sharpened attention on her, and why Trump’s team appears determined to keep her out of reach of process servers and cameras alike. Wolff examines why discovery terrifies Trumpworld more than accusation, why Melania’s distance reads like leverage, and how one reluctant witness can destabilize a carefully managed narrative. If the quietest person in Trump’s orbit may also be the one who knows the most, what happens when the courts — not the campaign — decide who gets to ask the questions? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles for part two, continuing their forensic account of Donald Trump’s long, combustible friendship with Jeffrey Epstein. Drawing on years of interviews and firsthand reporting, Wolff argues that Trump and Epstein were not casual acquaintances but intimate allies, bonded by money, sex, models, and a shared outsider resentment of New York’s elite. The episode traces how that alliance curdled into rivalry and fear—through real estate betrayals, private planes, kompromat, and the moment Epstein believed Trump turned the authorities on him. Wolff details why Epstein obsessed over Trump even after their rupture, why other powerful men fell while Trump survived, and how Epstein’s arrest and death intersected with Trump’s presidency. If Epstein was the man who knew Trump best, what does it mean that this is the one story that still visibly unnerves him? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to trace the unsettling origins of Donald Trump’s relationship with Jeffrey Epstein, long before public scandal or denial. Wolff begins with their bond in the late-1980s New York, where Trump was chasing Manhattan legitimacy and Epstein was emerging as a fixer fluent in money, women, and leverage. From Trump introducing Epstein as “my associate—Jeffy,” a pattern forms of shared ambition, cruelty, and secrecy. Wolff links those early dynamics to Trump’s financial near-collapse in the 1990s and Epstein’s claim that he helped Trump survive bankruptcy while keeping his tax returns hidden. If Epstein helped shape Trump’s instincts before power, what does that say about the secrets that still follow him now? Hosted on Acast. See acast.com/privacy for more information.

Michael Wolff joins Joanna Coles to peel back what Christmas looks like inside Donald Trump’s carefully staged world at Mar-a-Lago — a holiday less about family and warmth than performance, attention, and control. From the bored, rope-off table at the center of the patio to Trump’s late-night torrent of Truth Social posts, Wolff maps how even Christmas becomes another arena for validation. They examine Melania’s rare flash of animation beside her father, the eerie surge of hyper-religious messaging from Trump-world, and the rituals that feel rehearsed rather than heartfelt. As the conversation widens, they trace how sagging TV ratings, Hollywood power plays, and proximity to Trump himself still dictate the action around him. Hosted on Acast. See acast.com/privacy for more information.