HOWL

HOWL

The Epstein Diaries

The Epstein Diaries #2: When Jeffrey Met Bill—and Bested Donald

The media spotlight is a dangerous drug, particularly for those with dirty laundry...

Michael Wolff's avatar
Michael Wolff
Mar 30, 2026
∙ Paid
Photo credit: William J. Clinton Presidential Library/Handout via REUTERS

This is the second installment in a series detailing my nearly twenty-year acquaintance with Jeffrey Epstein. It is a story told only on the basis of what I have seen or heard, and therefore might serve as a counterpoint to a tale that has ballooned out of all proportions and come to serve all agendas. The Epstein story has become a reflection of so many of the great fears of our time—all the conspiracies, depravity, and secret forces that control us. This account, I hope, can bring it back to a street-level view.

Last week’s chapter was about my happenstance introduction to Epstein as part of a New York group he was flying on his plane to a California tech conference.

I plan to publish a new chapter every Monday.

Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries: When I First Met the Devil

In 2002, seeing an opportunity for a singular friendship, Jeffrey Epstein put his plane at Bill Clinton’s service. The plane was Epstein’s currency, a bond; the giving of his plane was the giving of himself. He felt this, but so did the recipients. Free, accommodating, convenient, commodious travel was a way to even jaded hearts.

Out of office, in semi-disgrace, radioactive and yet magnetic, the singular political talent of the age yet liable to shoot himself in the foot (in the head!) at any moment, Clinton was the most public ex-president perhaps ever, and had launched his new chapter as a worldwide humanitarian. Through his girlfriend, partner, associate—usefulness long since overshadowing romance—Ghislaine Maxwell, Epstein had offered to ferry Clinton, and his entourage, including the actor Kevin Spacey, on a week-long trip to Africa to support AIDS prevention initiatives.

This was social climbing of a determined order. Clinton was a high get—among the highest—in politics and in international circles. But it was not just calculated. Epstein had, like so many others of the time, a Clinton crush, a childlike awe of his political talents and for the ways he had flown so near the sun. Epstein’s friend, Donald Trump, had a Clinton crush, too.

Indeed, proximity to Clinton and, potentially, a friendship with Clinton had become another measure of Epstein and Trump’s more than a decade of friendly-not-so-friendly (toxic-friendly) competition. Perhaps they both saw themselves in Clinton, and saw their race to be noted as friends of Bill as a way to have it all—legitimacy and, as Epstein put it, “lifestyle.” Anyway, on the Clinton point, because of the plane, Epstein, to his friend Trump’s annoyance, had now won.

Former President Bill Clinton is pictured with Jeffrey Epstein in this image released by the Department of Justice in Washington, D.C., U.S., on December 19, 2025.

Part of the proof of this victory was that the New York Post, keeping a record of Clinton’s post-presidency excesses, highlighted the trip and put the mysterious Epstein, with his ready plane, in the close Clinton circle.

This was, Epstein would come to believe, the beginning of his long downfall—not so much Clinton and the trip, but the New York Post’s notice of it.

“You have to remember how much people hated Clinton, for being as popular as he was and for what he had gotten away with. Clinton was the guy who made it all so personal, every public attack. I walked into that, collateral damage,” Epstein, ever an attentive witness to his own demise, and largely obtuse to his own part in it, reflected years later.

This Is My Jeffrey Epstein Story

This Is My Jeffrey Epstein Story

Michael Wolff
·
Mar 19
Read full story

After he ferried a group that I was part of out to the TED conference in 2000, it hadn’t crossed my mind that there would be a “follow-up” between us. But several months later, I got a call from Epstein’s office—as in, “This is Jeffrey Epstein’s office”—asking if I might be available to have tea with him at his house. Tea.

His Brobdingnagian bachelor mansion—a former school he’d turned into a palace—and my crowded apartment, maxxed out with three children, were only a few blocks apart on Manhattan’s Upper East Side. His block, however, off Central Park, was real estate that would take a leap of time, space, and hedge fund dealings to occupy. And his own house was three or four times the size of the nearby $30 or $40 or $50 million homes. In years hence, as his name became a curiosity and then a curse, I’d often direct people’s eyes to the house if we were passing by, producing, always, involuntary guffaws.

But be cool. You might chart your advance in New York, and your motivation, by how much real estate you saw that was better than your own.

Keep reading with a 7-day free trial

Subscribe to HOWL to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2026 Michael Wolff · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture