Inside Trump's Head

Michael Wolff joins Joanna Coles with a new window into the volatility inside the West Wing, describing what he says was a secret Situation Room tantrum by Donald Trump, a moment when military briefers could not give him the absolute guarantees he demanded, and the meeting spiraled. Wolff connects that flash of anger to the broader pattern he’s reported for years: a president who hates paper trails, avoids email, and warns aides never to “leave a record,” an instinct that now looms large as the Epstein Files fallout engulfs figures like Prince Andrew and Peter Mandelson. Why, Wolff asks, do so many powerful men have receipts—while Trump seems not to? From the chaos-as-cover strategy to the Iran briefings where strength is performative, and doubt is intolerable, this is a portrait of a leader who equates uncertainty with humiliation and reacts accordingly.

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Michael Wolff and Joanna Coles climb back inside Donald Trump’s mind at the very moment the Supreme Court humiliates him on tariffs—and he responds not with retreat, but with theatrical fury. From calling his own justices “fools” to turning a legal defeat into prime-time spectacle, they unpack how Trump transforms setbacks into legend, why the State of the Union could become a live-wire showdown with Chief Justice John Roberts, and what those colossal presidential banners draped across Washington really signal about dominance and power. Along the way, they dive into the bro-coded videos of Robert F. Kennedy Jr. and Pete Hegseth, the strange silence from Kash Patel on Epstein, and the unsettling mystery of a disappearance gripping the country—asking whether Trump governs as a president, a performer, or something closer to a monarch.

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Michael Wolff and Joanna Coles untangle a week where chaos seems to be the point, including the stunning arrest of Andrew Mountbatten-Windsor in the widening Jeffrey Epstein fallout. Meanwhile in Washington, Trump gathers his Board of Peace to bankroll his grand vision for Gaza while facing a far more combustible reality: a potential military showdown with Iran that he may neither want nor be able to control. As European partners keep their distance and troop buildups raise the stakes, Wolff and Coles probe whether Trump is orchestrating strategic distraction—or simply caught between looking weak and starting a war. With scandals colliding and global order wobbling, is this all part of a master play, or are we watching events slip beyond Trump’s grasp?
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Michael Wolff joins Joanna Coles to examine why Donald Trump’s very public irritation may reveal more than any document dump. As the Epstein files unleash a rolling wave of headlines, Wolff argues the real story is not what’s newly uncovered but how the sprawling release has diffused attention away from Trump and onto a widening cast of peripheral figures—a dynamic he says Trump has repeatedly relied on to survive past crises. Drawing on Wolff’s firsthand encounters with Jeffrey Epstein and his introduction of Steve Bannon into Epstein’s orbit after Bannon’s White House exit, the conversation traces how resentment, rivalry, and obsession with Trump bound those men together, even as Trump now casts himself as the victim of a conspiracy involving journalists and old adversaries.

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Michael Wolff and Joanna Coles unpack the spiraling fallout from the Epstein files, Ghislaine Maxwell’s calculated silence, and the widening circle of elites caught in the “Epstein class,” before turning to something even more alarming: the Trump administration’s brazen willingness to lie in plain sight. From the El Paso airspace shutdown and the balloon-versus-drone fiasco to Fox News alumni now running Cabinet departments at odds with one another, they examine whether the chaos is incompetence—or a deliberate governing strategy built on fear, loyalty tests, and all-or-nothing stakes. As prosecutions stall, investigations fizzle, and reality itself seems negotiable, Wolff argues that the disorder may be the point—and that the risks are existential. Is this simply dysfunction, or is there a dangerous method behind the madness that we’re only just beginning to see? Hosted on Acast. See acast.com/privacy for more information.
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