Epstein, Trump, and the Elite Obsession

“I have always said that they are the same person. And the drama of this story is that one ends up dead in the darkest prison in America, and the other in the White House.” — Michael Wolff

A few days ago we had Jason Pack on the show suggesting that the Anglo-American media elite had a degree of complicity in the Epstein scandal. Michael Wolff disagrees. The media weren’t complicit, he says. They were just dumb. They found the story unseemly, were uncomfortable with it, and avoided it out of disdain—not conspiracy. David Remnick of The New Yorker was “dismissive of the whole thing.” The word Wolff keeps coming back to is “ick.”

Wolff knew Epstein. He recorded an estimated hundred hours of interviews with him. He has tried repeatedly to sell an Epstein book. Every publisher passed—the last time as recently as autumn 2025. One cited “the ick factor.” Others feared a Trump lawsuit. The man who made fortunes for publishers with Fire and Fury couldn’t get a deal on the story he knows best. If you want the closest thing to a firsthand account, Wolff says, read “The Last Days of Jeffrey Epstein” in his collection Too Famous. He’s probably right.

What emerges from the conversation is a portrait of Epstein as a middleman in a city of middlemen—but one who was genuinely interested in the people he connected, which is rare in that world. His sexual depravity was at war with his ambition to be respectable. The blackmail theory? “Certainly not true,” Wolff says. People came because they liked being there. He was their friend. And then there’s Trump. Wolff’s most explosive claim is that they are the same person—the closest relationship both men had in life was with each other. The drama is that one ends up dead in the darkest prison in America and the other in the White House. It’s Gatsby without the romance. And that’s what makes them both so vile.

As for the Trump show, Wolff has given up predicting its end. It doesn’t end until Trump dies. He is sui generis—nobody will replace him. He doesn’t understand legacy, doesn’t care about it, and when it’s no longer about him, could give a fuck. We’ll be trying to figure out how this happened for the next hundred years.

Five Takeaways

•       The Media Didn’t Conspire—They Were Just Dumb: Wolff dismisses the idea that the Anglo-American media elite knew more about Epstein than they were letting on. They didn’t know anything, he says. They found the story unseemly, were uncomfortable with it, and avoided it out of disdain—not conspiracy. David Remnick of The New Yorker was “dismissive of the whole thing.”

•       No Publisher Would Touch the Epstein Book: Wolff has tried repeatedly to sell an Epstein book. Every publisher passed. One cited “the ick factor.” Others feared a Trump lawsuit. The last attempt was autumn 2025. The man who made fortunes publishing Fire and Fury couldn’t get a deal on the story he knows best. The publishing industry’s failure of nerve, Wolff says, is total.

•       Trump and Epstein Are the Same Person: Wolff’s most explosive claim: Trump and Epstein are the same person. The closest relationship both men had in life was with each other. The drama of the story is that one ends up dead in the darkest prison in America and the other in the White House. Gatsby without the romance.

•       Epstein Was a Middleman in a City of Middlemen: What made Epstein different wasn’t the blackmail—Wolff says that’s “certainly not true.” People came because they liked being there. Epstein was genuinely interested in the people he connected, which is rare among New York’s professional middlemen. His sexual depravity was at war with his ambition to be respectable.

•       The Trump Show Doesn’t End Until He Dies: Wolff has been predicting the end of Trump for years. He now concedes it probably doesn’t end until Trump departs “this veil of tears.” Trump is sui generis—no one will replace him. He doesn’t care about legacy. He doesn’t even understand the concept. When it’s no longer about him, he could give a fuck.

About the Guest

Michael Wolff is a two-time National Magazine Award winner and the author of Fire and Fury, Siege, Landslide, All or Nothing, and Too Famous. He has been a columnist for Vanity Fair, New York, the Hollywood Reporter, and the Guardian. He lives in Manhattan.

References

Books and references:

•       Too Famous: The Rich, the Powerful, the Wishful, the Notorious, the Damned by Michael Wolff — contains “The Last Days of Jeffrey Epstein”

•       Fire and Fury: Inside the Trump White House by Michael Wolff

•       Previous Keen On episode: Jason Pack on the Epstein files and media complicity

•       The Great Gatsby by F. Scott Fitzgerald — referenced throughout as the model for Epstein, “but without the romance”

About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States—hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.

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Chapters:

• (00:41) - Introduction: The media elite and Epstein
• (02:16) - The media didn’t conspire—they were just dumb
• (04:18) - Wolff knew Epstein: why the story fascinated him
• (05:15) - No publisher would touch the book—“the ick factor”
• (08:21) - The Trump problem: fear of being sued
• (08:34) - What’s the story? A middleman in a city of middlemen
• (10:01) - What Epstein was actually like
• (12:00) - “The Last Days of Jeffrey Epstein”: the best thing written about him
• (15:40) - Epstein as one of the elites—or the man who fed off them
• (16:29) - Trump and Epstein: the same person
• (17:49) - Gatsby without the romance
• (20:53) - The publishing industry’s f...