Inside Trump's Head

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.