Ghislaine Maxwell and Jeffrey Epstein in this image released by the U.S. Department of Justice in December, 2025.U.S. Justice Department/Reuters
How did a college dropout and failed high-school teacher from New York’s outer boroughs, with no discernible investing skills but enormous confidence, charisma and chutzpah, end up acquiring so much wealth, power and influence that his friendship was sought out by those who were even more wealthy, powerful or influential?
Jeffrey Epstein was a convicted pedophile. He preyed on girls and trafficked them, mostly, so far as we know, to himself.
But he was only in a position to exercise this power over the lives of others because of his trappings of wealth and power. He lived in one of the largest homes in Manhattan. He had access to private planes. He owned an island in the Caribbean. A world of boldfaced names were on speed dial.
How he acquired these things – he was the son of a municipal groundskeeper, with neither money nor connections – is a tale as old as time.
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Mr. Epstein was a classic confidence man from F. Scott Fitzgerald. He was also a nihilistic sexual deviant from Bret Easton Ellis. His story is The Great Gatsby, shoved through the pages of Less Than Zero and American Psycho.
He claimed to be a money manager to the ultrawealthy, though for much of his career he appears to have had only one client, retail magnate Les Wexner, whose confidence he abused and whose wealth he pilfered. His real talent, starting with his job interview at investment bank Bear Sterns as a 23-year-old, was to persuade people to like him, to believe in him, to vouch for him, and to introduce him to others as trustworthy and worth knowing.
He basically schmoozed his way into boardrooms and high society.
In a 2003 interview, he said that he realized early on that success didn’t come from “what you knew or how hard you worked.” But neither was it only about “who you knew.”
It was, he said, about “who you came in contact with.”
Mr. Epstein’s primary business was being a connector. Each contact was a new connection, which he used to make other connections. Each time he introduced a contact to a contact, he expanded and solidified his business circle. And access to his connections was something he could monetize.
He had an ability – again, his only real discernible ability – to get people in different worlds to think highly of him, and to make them believe that he had something they lacked and wanted.
When he was a young investment banker, Cosmopolitan magazine named him “bachelor of the month” in 1980, with a photo of the 27-year-old looking somewhere between John Travolta and Lou Reed. He dated a series of models.
His connections in each of these separate worlds gave him credibility with, and advancement in, the other.
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Many colleagues on Wall Street were far more senior and well paid than this junior banker, but his confidence left people outside finance, including those models, with the belief that he had higher status.
Meanwhile, the impression that he had game – and, as he got older and richer, his parties featuring celebrities from the arts, academia and politics – increased his credibility with more moneyed and senior people on Wall Street.
We don’t tend to think that life is just a continuation of high school, but to some degree it is.
We don’t tend to imagine sociopaths as social butterflies, or vice versa. But Mr. Epstein was.
He understood who was a mark to be used and abused, and who was a contact to be cultivated.
And he capitalized on the complementary desires of the worlds he brought together.
The people in his Rolodex with money often wanted things beyond: prestige, friendship, glamour, sex, whatever. His contacts from academia, politics and the arts tended to be after what the finance people had: money.
And everyone wanted a sympathetic ear to listen to and care about their troubles. He could fake that, too.
The Epstein files are a sea of favour-trading, self-dealing, moral corruption and, possibly, criminal corruption.
There is Sarah Ferguson, the penurious former Duchess of York, trying to make a buck by becoming an influencer à la Meghan Markle – and thanking “the brother I have always wished for,” for arranging meetings with rainmakers in finance, entertainment and retail.
There is Lord Peter Mandelson, British politician, sending confidential and market-sensitive information to Mr. Epstein from inside cabinet meetings, and receiving favours and money in return.
Mr. Epstein was a sex criminal, but like American Psycho’s Patrick Bateman – investment banker by day; serial killer by night – this appears to have been mostly a dual existence.
Each release of Epstein e-mails, revealing new and wider Epstein friendship, is always accompanied by a proviso: that appearing in the files, and having corresponded with Mr. Epstein, is not proof of complicity in his crime of trafficking girls.
That proviso is not perfunctory. The people socializing and doing business with Mr. Epstein were trading favours for money, money for favours and access for access. Many may be culpable – but mostly, it appears, of something other than pedophilia.