“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

Last week, 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 New York media weren’t complicit, he insists. They were just dumb. They found the story unseemly, were uncomfortable with it, and avoided it out of Upper West Side disdain—not conspiracy. David Remnick of The New Yorker, a model of this type of progressive snob, was “dismissive of the whole thing.” The word Wolff keeps coming back to is “ick.” Epstein was icky. Except when he wasn’t.
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 a New York story that comes most naturally to him. If you want the closest thing to a firsthand account, Wolff boasts, read “The Last Days of Jeffrey Epstein” in his collection Too Famous. I haven’t. But we all should because whatever one thinks of Michael Wolff, he’s a great writer.
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, Wolff suggests, was at war with his ambition to be respectable. The blackmail theory? “Certainly not true,” Wolff says. People came to the house and the island because they liked being there. He was skilled at being their friend.
And then there’s Trump. Another New Yorker who Wolff knows intimately. His most explosive claim is that Epstein and Trump are the same person—the closest relationship both men had in their uber-middlemen lives were 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 not only so vile but so compelling.
As for the Trump show, Wolff has given up predicting its final episode. It doesn’t end until Trump dies, Wolff predicts (in contrast with the Epstein story). 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, couldn’t give a fuck.
Trump and Epstein. We’ll be trying to figure out how all this happened for the next hundred years. How these two men, born at the hip, shamed America. And how one ends up dead in the darkest prison in America, and the other in the White House.

Takeaways
• The Media Didn’t Conspire—They Were Just Dumb: Wolff says the media found Epstein unseemly and avoided the story out of disdain, not conspiracy. Remnick was dismissive. The word was “ick.”
• No Publisher Would Touch the Book: Wolff tried repeatedly to sell an Epstein book. Every publisher passed. One cited “the ick factor.” Others feared a Trump lawsuit.
• Trump and Epstein Are the Same Person: The closest relationship both men had was with each other. One ends up dead in prison, the other in the White House. Gatsby without the romance.
• Epstein Was a Middleman Who Was Genuinely Interested: The blackmail theory is “certainly not true.” People came because they liked being there. His depravity was at war with his respectability.
• The Trump Show Doesn’t End Until He Dies: Wolff concedes Trump is sui generis. No one will replace him. He doesn’t understand legacy. We’ll be figuring this out for a hundred years.

About the Guest
Michael Wolff is the author of Fire and Fury, Siege, Landslide, All or Nothing, and Too Famous. Two-time National Magazine Award winner. He lives in Manhattan.

References
Too Famous by Michael Wolff: https://www.amazon.com/Too-Famous-Powerful-Wishful-Notorious/dp/125014762X
Fire and Fury by Michael Wolff: https://www.amazon.com/Fire-Fury-Inside-Trump-White/dp/1250158060
About Keen On America
Website: https://keenon.tv/ Substack: https://keenon.substack.com/ YouTube: https://youtube.com/@KeenOnShow

Chapters:
00:00:41 Introduction: The media elite and Epstein
00:02:16 The media didn’t conspire—they were just dumb
00:04:18 Wolff knew Epstein: why the story fascinated him
00:05:15 No publisher would touch the book—“the ick factor”
00:08:21 The Trump problem: fear of being sued
00:08:34 What’s the story? A middleman in a city of middlemen
00:10:01 What Epstein was actually like
00:12:00 “The Last Days of Jeffrey Epstein”: the best thing written about him
00:15:40 Epstein as one of the elites—or the man who fed off them
00:16:29 Trump and Epstein: the same person
00:17:49 Gatsby without the romance
00:20:53 The publishing industry’s failure of nerve
00:22:04 How does the Trump show end?
00:24:59 No legacy: Trump is sui generis