1. He had no idea how to read a balance sheet.

2. He liked to know a woman’s measurements, and although he otherwise had a problem with numbers, he was good at accurately guessing them.

3. He hated his mother.

4. He liked Black women—“a little chocolate”—but his father was a racist, so he had to keep that desire carefully under wraps.

5. He was afraid if he took a drink he’d instantly become an alcoholic.

6. One night at the China Club, a 90s celebrity night-scene on the Upper West Side, he pushed up behind a waitress at the bar, pinning her there, and, without her protesting or anyone in the place being any the wiser, entered her—or so he said.

7. The only vegetable he liked was a potato.

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Jeffrey Epstein, along with everyone else, watched Donald Trump’s announcement that he was running for president in 2015.

In some sense, he saw it like the rest of us: as a preposterous bit of mugging for the cameras. But, unlike the rest of us, he was aware that this could be something unique hurtling through the political and existential universe—and, not incidentally, directly towards him.

The Jeffrey Epstein story is the Donald Trump story. We might like to believe, as a form of moral flattery, that it is about the victims. But Jeffrey Epstein achieves his worldwide significance in the reflection of Donald Trump. He’s a Trump proxy.

While he certainly didn’t anticipate that, he understood that having spent more than a decade witnessing behavior that would have logically disqualified anyone from the presidency, this meant he was bound to Trump in a potentially troublesome way for both men.

Here, too, still like the rest of us, he did not yet, in 2015, see the presidency as a plausible outcome for Donald Trump.

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“Are you a spy?” I asked, hoping to catch Epstein off guard with the question.

“Of course I’m a spy,” he happily replied.

“But…if you actually were a spy, you wouldn’t admit to it, would you?”

“Why not? Everybody’s a spy.”

JD Vance recently went on Joe Rogan’s podcast and said that, indisputably, Jeffrey Epstein was working for the Israelis as an intelligence asset, and, he added, probably for the CIA. Now… as the Vice President of the United States, he might reasonably know if Epstein was working for the CIA—and, by the by, if he was working for the CIA in a clandestine role, revealing that would be a federal crime. Likewise, the United States government would certainly have a pretty good idea if Epstein was an Israeli spy. So here too, Vance is either revealing some top-flight intelligence or talking through his hat.

I can tell you, Epstein wasn’t an Israeli spy, certainly not in the deep state, cross-allegiance, John Le Carre sense that Vance was implying. Vance was instead nodding to a general MAGA conspiratorial view of Epstein, and of a more specific idea of the Israelis working to subvert the U.S., and, arguably, of Jews as deeply suspect in all regards.

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“The Epstein Diaries,” my window on Jeffrey Epstein and the culture of American wealth and entitlement, now reaches the pivotal turn when Epstein begins to watch his former best friend, Donald Trump, become a plausible, albeit ridiculous, political contender.

This is the seventeenth installment. Now, though, as the story approaches its Trump election denouement, I’m shifting to a biweekly schedule in order to introduce a timely limited series on Melania Trump—who, of course, very much intersects with the Epstein story—and how she impacts her husband’s presidency. Join me next week, Monday, July 20, for the first installment of “Melania! The Wild Card.” (And then back on July 24, for the next “Epstein Diaries” chapter.)

Epstein wanted an outing. Sometimes, like a prince closed in his castle, he seemed to have a sudden need to break free. So, we turned around as soon as I got to his house on 71^st Street and headed down Madison Avenue.

The destination was the Viand Diner on 61^st Street, which, in Epstein’s view—and in the consensus of the Upper East Side—had the best turkey sandwich in Manhattan. I believe this was in early 2014, though I can’t quite be sure. But certainly, we were discussing the open 2016 presidential race, which had begun with the overwhelming default likelihood that it would be Hillary Clinton against Jeb Bush.

Epstein discussed presidential politics with the greatest giddiness and intimacy, as though he was personally involved in the drama and had an inside, even proprietary, track on it.

Hillary Clinton was very bright, perhaps the best-prepared candidate in history, he said, but had no political gifts and would always suffer in comparison to Bill. She should have been a McKinsey partner rather than a politician. Jeb Bush, on the other hand, was, in his view, not only an adept politician but, unlike his brother, a thoughtful student of government. But there were too many Bushes.

Did I know who Bernie Sanders was? Epstein asked…

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This Is My Jeffrey Epstein Story

The Epstein Diaries #15: The Godfather

The Epstein Diaries #14: What Epstein Knew About Bill and Melinda

Jeffrey Epstein would ask a frequent and peculiar question: “Am I having fun?”

This was, of course, rhetorical. Obviously, a man who had everything he could possibly want and access to everyone he wanted to know was having fun. But in another obvious sense, he was always taking stock, measuring the risks of an unchecked life (existential, as it turned out) against the rewards of getting all he believed he wanted.

The question was also an excuse to catalog the actual fun he was having, and it would be followed by a list of the places he was going, the people of great influence he was seeing, and the global dilemmas he was entertaining.

It was, too, a knock on everyone else’s seriousness. Epstein had achieved a personal remove which made life an amusing spectacle.

But it was also weirdly open-ended and certainly prompted the question: “Was he having fun?”

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #14: What Epstein Knew About Bill and Melinda.

Jeffrey Epstein was a universally repellent creature. There is, by universal acknowledgment, no plausible explanation for how any person of any decency could spend time with him. And by extension, anyone who did is complicit and corrupt—as the New York Times, gathering its skirts, opined shortly after his death: “anyone who has shaken hands with Mr. Epstein in recent decades should be scrutinized.”

Since so many people who spent time with him were among what is now designated as the elite class, the elite itself must be complicit and corrupt (if you needed to look for a reason). This remains the ground zero of the Epstein matter: to have supped with him is to have supped with the devil.

When I first came to New York in the 1970s, one of the glamorously brazen or reckless things to do among writers, journalists, and Hollywood people was to rub shoulders with mobsters. If you hadn’t, you were out of it. If you did, you had stories to tell—it was a lucrative substratum of journalism and a reliable movie genre—and it lent you a certain kind of knowing, real-world authority to throw around.

I spent one skittish evening—indeed, long into the evening—at a card game at a social club in the Bronx among people who, for good reason, I had never imagined might cross my middle-class life. That was the point, not just bragging rights, but a glimpse, again for a middle-class boy, into the human abyss when you peeled the illusions away and exposed the true animal element (save a discussion of the class issues here for another day).

The Godfather became the central metaphor for success in the world.

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #13: The Tabloid Tide.

Bill Gates, whose fortune and good works had turned him into an American saint, had a serious crush on Jeffrey Epstein, who, while quite a dubious figure on the periphery of American business life, had a carefree way with his own wealth and influence in stark contrast to Gates’ own repressed and throttled world.

For Epstein, his progress toward social and public rehabilitation after his plea bargain and jail sentence, and amidst his efforts to deal with a mounting number of accusers and their tenacious lawyers, had become closely related to how successfully he could insinuate himself into Gates’ life and business.

The impediment for both men was Gates’ wife, Melinda.

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #12: The Social Network.

Jeffrey Epstein emerged from his years-long legal travails, his conviction, and his prison sentence, and slipped back into his extraordinary life. The former seemed to have no relationship to the latter. He continued, as though uninterrupted, carefree. This could be seen as tempting fate—not appearing to pay the price meant you hadn’t paid the price. But it could also be seen—as I think many of the people around him saw it—as not giving in to fate. Here was a superior act of will, his untroubled state.

What is the greatest fear of people who have it all? Losing it all. But Epstein, by the sheer (or forced) buoyancy of his personality, had overcome ignominy and disgrace, somehow maintaining his humor—and his wealth—and requiring pity from no one.

But this was the surface life, the created life. The act of will had not so much put his troubles behind him as merely disguised them, sparing his friends from any discomfort.

There was the front rooms life and then the backstairs life. In the front rooms, there was the exchange of power, influence, and information, and on the backstairs a constant consultation with lawyers—there would be more than 75 by the time his legal saga and life were done—and the whispered strategies required by each new claim against him.

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #11: The Girls.

Jeffrey Epstein turned his interests, aspirations, and sense of himself into a lifestyle marketing scheme. He was an early “influencer,” in effect, although within the most exclusive of social networks.

A key Epstein perception was that in a world run amok with naked ambition, his version of wanting it all, with an ironical self-awareness, and a casual flaunting of the restraints of respectability, could be novel and charming.

At the age of 22, he submitted a fudged resume claiming he’d graduated from Cooper Union (he hadn’t) to a catch-all of Manhattan private schools, and got a hit from the Dalton School, which had a sudden opening for a math teacher. (This striking feature of the Epstein story—that he was hired by a prestigious private school without a college degree—may actually say more about the laxness of private school vetting and the difficulties of finding teachers who will work for minimal salaries than about Epstein’s perfidy and audacity.)

His scheduled 30-minute interview with Donald Barr, the head of the school—whose son, Bill Barr, in an inevitable conspiratorial turn, was the Trump attorney general who sanctioned Epstein’s final arrest—went on for two hours.

“I told him,” Epstein later recounted, “that I wanted to be a private school teacher to see how the other half lived. He said, ‘Unhappily, entitled, screwed up, don’t know where to turn, desperate for people to solve their problems.’ Sign me up, I thought.”

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #10: The Invitation.

In every situation—every situation—Epstein came with multiple girls. They surrounded him like a mist of cologne. There but not there; part and parcel; the background music.

The long-time investigative reporter Edward Jay Epstein (no relation), whose acquaintance with Epstein went back to the 1980s, describes walking in Central Park with Epstein—nearby his home, the Park was one of Epstein’s few outings in New York—with two girls “like Russian Wolfhounds” behind them.

Consider the cognitive dissonance of it all: most of the men around him were older, highly focused, mostly Jewish, with wives and children at home and, in pretty much every way, no matter their own considerable wealth, living by every repressed middle-class convention. Epstein, however, who by all appearances was their equal, a man of great status and wealth, with interests at a heady level of intellect and finance, who knew presidents and prime ministers, yet lived a life of open and even debauched indulgence—nothing hidden here.

These men around him, in their fifties, sixties, seventies, and even eighties, buttoned down and uptight, were of a generation to believe such lifestyles, an age of heterosexual license, existed—in Hollywood, in other glamourous precincts, in the 1960s and 70s, at the Playboy Mansion, for rock stars, at Studio 54—and if not for real, certainly in their imaginations. This, of course, was Epstein’s fantasy too.

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #9: The Baby Elephant in the Room.

It was never clear what Epstein’s invitations were about, but every four or five weeks I’d get one. His assistant, Leslie Groff, sunny and cheerful (was she straining to be?), who commuted in from Connecticut every day, sat in the anteroom off the foyer in his giant house on East 71^st Street, and whose primary job seemed to coordinate comings and goings, would shoot you a chirpy email:

Can you have lunch with Jeffrey…

Jeffrey would love to see you if you can come for breakfast….

Can you join Jeffrey after lunch….

Why? Maybe no reason. Part of why you went, and looked forward to going again, was the lack of agenda. The traffic in his house—I’d guess a dozen or more people a day coming and going—was a showcase of power and influence, attracted, not only by the serendipity of other people of power and influence, but because there were very few places in Manhattan, with its cast of maximally busy people, where there was no purpose.

I had never seen Epstein do a lick of work. Or, perhaps his work, the literal interactions and transactions that produced a mighty income for him, might have woven seamlessly into the colloquial that took place around his dining room table from early breakfast until dinner time. This was his true work—and his true seduction.

You’d wait in the anteroom—a library of sorts featuring books that had been presented to Epstein by their authors (he’d buy copious copies of books by authors he knew and then hand them out)— where Groff sat and went on pleasantly about the weather or the traffic on the Upper East Side, interspersed with updates about Epstein’s schedule: “Jeffrey’s just running a few minutes behind… Jeffrey’s just finishing up a call.”

Or you’d find yourself waiting with someone else.

“Governor,” Groff on one occasion addressed a large man whom I had not exactly been introduced to, but who I suspected, and then had confirmed, was Bill Richardson, Governor of New Mexico.

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #8: Epstein Goes to Jail—For the First Time.

I had come to Manhattan in the 1970s and lived through the transformation of the broke and bohemian city into the Oz of wealth in the 80s and 90s. I’d hardly say Epstein was the most dubious person I’ve met. That list was long. It would take quite a work to convey the hall of mirrors in the new moral universe created by the yuppie-financial-entrepreneurial class.

But Epstein, a vivid exponent of this class, seemed notable in how he treated it, both to take whatever it would give him and, at the same time, to mock it, even dare it to take back whatever he had gained. His was an elaborate art installation project in aping and blaspheming respectability. The girls (usually three) who accompanied him, the show-off plane and the show-off house, his study in intellectual pretension… was it real? Was it a joke? Well, both, sort of.

You could dine out on Epstein. He was a story that would hold people’s attention: The mysterious billionaire—if he actually even was a billionaire—with his made-up life.

That he had become a sex criminal certainly complicated this picture. And yet, another aspect of this time and the people who defined it is that so many seemed on the edge of ruin and disgrace. Success went hand in hand with the risk of being caught in the headlights.

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He has turned down the offer of a misdemeanor and a slap on the wrist, and is now, instead, facing the possibility of a life sentence. In the eighth installment of the Epstein Diaries, Jeffrey Epstein and his legal dream team wrangle out of the most serious immediate consequences only to fall into a bottomless pit of legal settlements, a slippery slope of conspiracy theories, and an ultimately mortal legal battle—the World vs. Jeffrey Epstein.

Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #7: From ‘Bad Boy’ to Trafficker.

As the federal government threatened to indict him on sex trafficking charges—and to hold him indefinitely, because trafficking is one of the few crimes with a presumption against bail—Epstein certainly regarded himself to be in a Kafkaesque situation. He was also jaunty about it.

I saw him perhaps four or five times during the 2006-2008 period, usually for tea at his house in New York City, in front of the baronial fireplace. I had never known anyone to be the subject of a sex crimes investigation and was, I confess, a curious witness to how he would handle this disgrace and humiliation.

He was matter-of-fact, blithe, incapable of not making a joke about his situation, and as well, resigned to people not understanding or refusing to accept the nature of his desires. (“I’d be in much better shape if this were a gay thing.”) But he was also a general in command. He coolly laid out the field of play: the various characters both in Palm Beach and in the Justice Department; the legal maneuvers on his part and against him; his dream-team lineup of lawyers; and a defense of his own position. It was quite a Clintonesque equivocation: He did not have sex, he never had sex, he didn’t like sex—that is, penetrative sex. He only liked hand jobs.

A by-product of his command-and-control attitude—that the force arrayed against him demanded an equal or greater force against it—meant he was spending more money than any other criminal sex defendant had ever spent in the state of Florida, producing a gusher of cash for the lawyers he kept hiring.

The outcome of the case—the way-too lenient outcome, in the favored telling—would come to be seen as the result of the nefarious influence that Epstein’s money and power were able to summon. And he certainly was trying to summon any he could. But money, at this level, affects everything. The system is transformed by it, and not just in his favor. Jeffrey Epstein created his own legal ecosystem, enriching his lawyers and, ultimately, much of the South Florida bar. The money was a variable that tilted almost every factor both for him and against him.

He had a specific model here: his former friend, and now nemesis, Donald Trump. Among all that Epstein derided Trump for, one thing he admired was Trump’s striking ability to get out of a jam—to beat the system at its own game.

But so far, Epstein’s efforts only seemed to get him into a deeper jam—from a local prosecution in Palm Beach now to the weight of the federal government on him.

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In the seventh installment of the Epstein Diaries—an account of how I saw the Jeffrey Epstein story unfold over nearly twenty years—the legal system closes in on Epstein in a way that will satisfy no one, neither Epstein nor his accusers, and that will launch a thousand conspiracy theories. It is, too, the beginning of a stark intrusion into Epstein’s sybaritic and solipsistic world—the voices of women suddenly describing the details of their experience in it.

Context is everything—especially when it’s this sordid. Revisit where we left off in the previous installment, The Epstein Diaries #6: When Alan Dershowitz Came to Town.

I was having one of my occasional lunches with Mortimer Zuckerman—just the two of us in his Fifth Avenue penthouse (Zuckerman wasn’t capable, I don’t think, of eating alone), surrounded by staff, looking over Central Park. Zuckerman was the New York billionaire who, in 2004, had put together a group, including Jeffrey Epstein and Harvey Weinstein, to buy New York magazine, where I then worked, and with whom I’d aligned myself (inopportunely, because they didn’t get the deal).

“Jeffrey’s been a bad boy,” said Mort, whose interest in me, I thought, was partly because he liked to talk about Epstein, as a shared taste, or, perhaps, a joke.

Even with the local Palm Beach paper starting to register details of an investigation into the “part-time Palm Beacher” and “money manager,” whatever Epstein had done—which seemed unsavory but not clear—was still being related as sniggering gossip rather than scandal. Epstein’s proclivities, Zuckerman seemed to be saying, should not have come as a surprise, certainly, and, given Epstein’s open lifestyle, you might make an allowance for him getting caught out—this was his nature. Plus, there was the assumption that whatever had happened would be handled, albeit with some discomfort. And discomfort would be the price he would have to reasonably pay for his bad-boy behavior.

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #5: The House in Palm Beach Where the Trump-Epstein Fallout Starts.

Epstein was embroiled in his bitter pissing match over a piece of prime real estate with Trump, both openly vowing and secretly plotting Trump’s destruction.

Just then, Epstein and his girlfriend-slash-house manager, Ghislaine Maxwell, noticed an increased police presence cruising by his house on El Brio Way in Palm Beach. And then there was a police car, parked on the road. Maxwell sent out cupcakes.

Epstein had been diligent—in fact, overboard—in his support of the Palm Beach police. This was something he’d picked up from Trump, who got all kinds of special police favors at Mar-a-Lago for his contributions. This was not so much bribery—not technically—as lavish generosity of a community-minded sort. Wealthy individuals could support the police and, in return, expect more from the police. Naturally. (You might then say that you owned the police, as Trump often did—and believe it.) Epstein figured the special attention he was getting now was his due, and probably a reminder that more contributions should be forthcoming.

It was a particular kind of denial and a feature of his own weird bubble life not to connect the police monitoring his gated Florida-pink home with the criminal enterprise going on inside—indeed, to somehow lack a conscious awareness of that criminal enterprise.

Or even to consider the questions that might be raised by the scores of young girls coming and going at 358 El Brio.

And it took a while for him to realize, amidst all his threats to expose his friend Trump as a money launderer for stealing his dream house, that, as he would be told later, the police had their eye on him because “Mr. Trump dropped a dime.”

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Here, in the fifth installment of the Epstein Diaries, as Jeffrey Epstein reaches a pinnacle of wealth and social standing, he confronts his friend and Palm Beach neighbor Donald Trump—an altercation that may well have set in motion events that will come to haunt both men, mortally so for Epstein, and ongoing to this day for Trump.

Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #4: Epstein and Trump— Everything Was Permissible.

Palm Beach is about many things: society; privacy; a certain order of class and taste; state taxes (none in Florida), and bankruptcy rules (they can’t take your house in Florida). But it is also about—perhaps mostly about—real estate. Real estate is a principal interest of rich men because a good property represents high status, and Palm Beach is certainly a status-obsessed place. It is an asset class, too, one that, particularly in an enclave of the rich, has a high safety threshold. And, because real estate, in a largely unregulated market, is a good way to hide money.

But, even beyond all this, it is really hard to fully express how much emotion and identity are vested by the rich in their real estate.

For Jeffrey Epstein, his homes—in Manhattan, Paris, Palm Beach, New Mexico, and the Caribbean—were the stage set of his life, the personification of all he had achieved and how far he had come. Indeed, Ghislaine Maxwell, the closest relationship he would ever have and the closest he would ever get to having a wife, was much more of a house manager than a wife (or prospective wife). Real estate is intimacy.

For Donald Trump, real estate was no less important, but it was more transactional, and ultimately fungible.

It was these two sensibilities that collided in 2004.

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This is the fourth installment of my effort to tell the story of how Jeffrey Epstein became the mirror of all that is corrupt and diabolical about our age. It is based only on what I personally saw or heard as I got to know Epstein during the early 2000s, and then as I began to discuss with him writing his story and to use him as a source about Donald Trump, political candidate and then president, based on their long relationship.

This is, I believe, a story about society, wealth, success, hubris, and the inevitable fall that implies. For me, Trollope comes to mind. And so it seems fitting to tell it not as so many are trying to tell it, as one-dimensional journalistic scoop and revelation, but as a slow unfolding tale of character and fate. Join me here, on Substack, every Monday, for a new chapter in the story that sometimes seems to tell us all we need to know.

Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #3: When Jeffrey Epstein—and Harvey Weinstein—Almost Bought New York Magazine

Jeffrey Epstein and Donald Trump had their big falling out in 2004. The consequences of their break-up, in Epstein’s account, would directly determine his fate. But this is not yet that story. In order to properly tell it, we first need a sense of their relationship, symbiotic and toxic, before they visited the piece of Palm Beach real estate which would cause the blood feud between them.

Epstein vaguely put the beginning of that relationship as sometime in the late 1980s. It certainly makes sense in the Manhattan of that time—when the fundamental ethos of New York City was being reinvented, from the creative, rebellious, living-on-the-edge city to a deliriously amoral, on-the-make city—that Trump and Epstein, covetous and materialistic, would have rubbed up against each other. At the very least, we know that they both frequented the China Club, a demi-monde bar of models and celebrities in the basement of the Beacon Hotel on the Upper West Side.

Both were there cruising for women, of course.

The first time I can directly put them together is one night on Fifth Avenue in what was most likely 1987 or 1988, when Charlie Allen, founder of Allen & Company, the less-than-blue-chip investment bank catering to the new generation of less-than-investment-grade entrepreneurs (a far-from-respectable Rupert Murdoch was Allen & Company’s leading client), was getting into a black car, along with two friends, one a journalist who would later tell me this story.

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Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #2: When Jeffrey Met Bill—and Bested Donald

New York magazine, where I wrote a weekly column, was owned by an odd-lot private-equity-backed company that bought magazines but yet had no apparent interest in them. By 2003, the industry’s slide could hardly be missed—even by people not paying very much attention—and New York was put up for sale.

It seemed to me prudent to at least make an effort to try to have some hand in the magazine’s fate—and my own. I called Mort Zuckerman, owner of the New York Daily News, and the one person I know with millions to spare and, however nostalgic, an attachment to the title of publisher.

Zuckerman had made his billions on real estate, achieved social prominence by buying the Atlantic Monthly, and had become a Manhattan character of high establishment bona fides and civic superiority. I’d written meanly about him as one more arriviste pretender of the era a few years before, but he had called me up and invited me to his triplex apartment on Fifth Avenue for lunch (served by his butler) to convince me that he was really alright. After lunch, I got a tour—one that would be repeated many times—of his art collection. And then I got put on an invitation list for soirees held at his apartment, populated by the great and the good—Henry Kissinger, Barbara Walters, Hillary Clinton heading the list—where worthy topics were earnestly discussed. These were deadly affairs, but, apparently, how the other Manhattan .01% lived.

Anyway, I figured it was better for your owner to be the devil you knew rather than a fund or a rich man you didn’t, and I pitched Mort on buying New York. He was leery, as he should have been, about the magazine business, but yet, willing, sort of. But he didn’t want to do it alone. So, who else?

There was a sense of him contemplating the known world of men with easy millions to throw around and a taste for media influence. “There’s a guy, a terrific guy, wants to do things, a friend of Clinton’s,” he said. “An original… he’s really an original… Jeffrey Epstein.”

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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.

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.

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.

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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.

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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