The Epstein Diaries: When I First Met the Devil
The first installment...
This is the first of an extended series about my interactions with Jeffrey Epstein. The discipline here is that I’m only going to talk about what I personally saw or heard. That’s necessarily an incomplete Epstein story, of course, but at the same time, I hope it adds a layer of first-person detail to what day by day is becoming a tale that fits all purposes, views, and agendas.
Jeffrey Epstein has come to represent a Rosetta Stone truth about the corrupt times we live in and the invisible powers that control us—a tale of vast conspiracies and extreme depravity. My business here is not to challenge any of that, but to see it through a different window— not a theoretical window, but one I actually looked through. And to hope that an observed account might cast the story in a clearer light.
My plan is to publish a new installment every Monday until my story is done.
Context is everything. Revisit where we left off in the previous installment, This Is My Jeffrey Epstein Story.
By utter happenstance, and with zero expertise, I was, by 1994, an early entrant in the internet business. Among the other effects of this unexpected life turn was a near-daily introduction to a set of unlikely, random, unfamiliar, and, as it often turned out, dubious people. The nature of success, or the trick to success, seemed to rest on the ability to be open to all comers—everyone was a potential genius or funder. The world was being remade by new technology and by vast amounts of money, crazy money, that for no clear reason, strange people might want to give to you.
I myself—up until this point a writer but suddenly, in that anybody-who-put-their-hand-up atmosphere, recast as a tech CEO—got a bunch of it. Neither the people getting the money nor the people giving it appeared to question the logic of any of this too closely. What seemed obvious was that a new type of person, outside of ordinary rules and measures—with a greater grasp over the shape of the future or, just as possibly, a charlatan—was emerging.
I shortly lost all the money I had been given, along with my CEO title. Chastened, I returned to writing, without riches but with a new subject: the wild west gold rush and its strange characters.
The TED conference (technology, education, design), held annually in Monterey, California, had become something of an official celebration of all this. Richard Saul Wurman, who in his previous life had been an architect, designer, mapmaker, publisher, and travel book writer, was the host and impresario, with one of the great Rolodexes (still then Rolodexes) of the rich and the willing, and the cool and deserving. To give a sense of the novelty, hubris, and guiltlessness of the moment, one of the conference’s high points was, with much more self-congratulation than self-consciousness, an event called the Billionaires Dinner. Of note, billionaires were still a small lot and could not yet fill many seats—so, more accurately, this was a billionaires-and-would-be billionaires dinner.
Wurman, in 2000, had arranged for a contingent coming from New York City to be flown out on one such billionaire’s private plane. Private planes were not yet ordinary business, and the nervous anticipation of our group, instructed to gather at a remote terminal at JFK, was hard to contain. What’s more, no one quite knew whose plane this was. (It rather felt like the beginning of a mystery plot.) The exception was the literary agent John Brockman, who represented many of these new tech and science personalities, and whose influential newsletter, Edge, with its biology-explains-it-all view, was quietly being funded by our plane’s mysterious billionaire. (Behind every great fortune there might be a great crime, but increasingly there was also a lot of science.)
Among our small group: Malcolm Gladwell, the New Yorker writer; Stephen Pinker, the evolutionary psychologist and science writer; Brockman, with his wife Katinka Matson; David Rockwell, a well-known New York architect; Geraldine Laybourne, the creator of Nickelodeon and a top television executive, with her husband, Kit; Daniel Dennett, the cognitive scientist; Richard Dawkins, the biologist and evangelizing atheist; and Caroline Miller, then the editor-in-chief of New York magazine, where I was writing a column about the media.
The Damnation of Jeffrey Epstein’s Friends
Around the world, people in the “Epstein files” have been unable to explain what they were doing in Epstein’s company without appearing ever more guilty. Their apparent only recourse is to intensely regret being there, to publicly confess to the monumental misjudgment that placed them there, and to wish harder than they have ever wished for anything that they might never have been.
We were shown out onto the tarmac but redirected from the line-up of smaller corporate jets to a 757 painted entirely black—with, for me, and I’ll bet for all of us, the sense, not without some trepidation, that occurred so often in those years, that everything was just getting more and more.
Private planes—those attended by decorators, specialty craftsmen, and engineers—with overhead bins removed, seating reconfigured into lounge areas and entertainment space, color schemes of muted pastels, and, on this one, a mirrored and lacquered bedroom cabin (we all peeked in), certainly suggested excess, but also an experience that, if you were trying to participate in the new world, you were grateful not to miss out on. Still, it was hard not to feel the unlikeliness and undeserved privilege of being here, and hard to summon the confidence that might seem to be required—it was just so not middle class. But there was a willing suspension of disbelief, too. We were here after all, so that meant something—perhaps that we should be.
Read more: Why Trump Feared a Humiliating Death on Jeffrey Epstein’s Plane
Twenty or 30 minutes in—still with the sense heavy in the air that we might be party crashers—the unknown, unnamed billionaire (billionaire had basically become a catchall for fortunes whose outward display seemed to surpass normal accounting) stepped onto the plane and stood in the door. Late forties, I guessed, great hair, good-looking in a sort of Ralph Lauren lounge-lizard way, radiating satisfaction and sangfroid. Three model-tall young women stood behind him—and towered over him.
Yes, yes, the dodginess could not be missed. But in so many ways, a tolerance for dodginess was more and more the price of admission.
We each got a direct, open, personal, big smile, full eye-contact greeting: “I’m Jeffrey—really, really glad you could make the trip with us.” Dodgy had manners and charm. Well, you could at least see dodgy that way, if you wanted to.
The three young women with him—unaccountable in any social or business sense and with a quick first-name introduction—transformed themselves into flight attendants and began serving a steady menu throughout the flight of drinks and hors d’oeuvres, tea sandwiches, and petit fours.
Epstein, sunny, affable, relaxed—this was long before his jail sentence, without a cloud in the air of public opprobrium—seemed to engage each of his passengers with interest and amusement. The plane was his easy ice breaker. It was almost as though he was his plane. He wanted you to ask about it. He wanted to talk about it. You didn’t have to pretend it wasn’t exceptional. You didn’t have to be cool with it. The plane was a central character on the trip. This was its story: where he had gotten it; who had had it before him. And this was his explanation for it: you lived faster with your own plane, so you lived more; and a bigger plane meant you could do it with more people—a bigger life. And then, here were all the ways he had improved and retrofitted it: indeed, do you hear that? No, you don’t. The quiet? Isn’t it amazing. And he described the engineering challenges of muting the sound and vibrations when you fly at 600 miles per hour.
It was quite a movable salon, with the hovering confusion about maybe being on a Bond villain jet but with the sense that there was a joke here that you ought to be smart enough to appreciate—not to mention the comfort of it all. Epstein somehow embodied the joke by playing the entirely deferential, interested-in-everyone, I’m-here-for-you, self-effacing host: the villain as, actually, a good guy.
Read more: Listen To The Jeffrey Epstein Tapes: ‘I Was Donald Trump’s Closest Friend’
At one point—I was listening in—Epstein engaged in a particularly eager way with David Rockwell, the architect. He couldn’t have been more interested in Rockwell’s various hotel projects (and seemed to know investors in each of them), and was full of real estate and design questions (the favorite and connecting topic, in my experience, of rich men). With modesty and enthusiasm, he asked if Rockwell wouldn’t mind taking a look at the plans for an island he was developing in the Caribbean. Epstein unfurled his handy blueprints and schematics. Rockwell, like a doctor asked for medical advice at a social gathering, seemed to unenthusiastically settle in, peeling back the big sheets.
He clearly became more confounded as he looked more closely, and as Epstein chattily describing the extent of his other-worldly seeming project. “What are these little rooms here?” a puzzled Rockwell finally asked, pointing to an area that might seem to resemble a medieval cloister.
“That’s where the girls stay,” said Epstein, without affect.
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