to create massive fortunes and the
billionaire class outpaced entail and
primogeniture, women like the
one in Southampton were necessary
accessories, and learning how to
acquire them was part of many a
high-level trader’s skill set. There’s a
temptation to say that the world has
always worked this way—ambitious,
beautiful young women have often
sought to climb rungs via powerful
men, and powerful men have
partly craved power in order to access
beautiful women—but this era
in New York was unique. A rapidly
increasing workforce of women
in black slip dresses, knee-high black
boots, and flatironed hair had
come to seek the Sex and the City
lifestyle, not husbands—but with
most of their professions (fashion,
publicity, publishing) paying far
less than men’s, they were not averse
to someone footing the bill.
Beautiful women also had currency
in the city’s “models and bottles”
scene, as the post–9/11 era of downtown
nightlife was called. Manhattan’s
legendary club scene of hip-hop stars,
painters, and graffiti artists, where
one gained entrée by virtue of one’s art
rather than the size of one’s wallet,
was going capitalist. A new nightclub
formula had been devised: Ice
buckets of Cristal and Cîroc bottles
were set up at leather banquettes,
alongside every kind of model—
Victoria’s Secret model, runway model,
supermodel, “just-off-the-boat
model”—and if you were a rich older
guy who wanted to take a seat, it could
cost up to $10,000, though Puffy and
Leo didn’t pay a thing.
Like his billionaire friends, Epstein
ran a highly compartmentalized
life. “He’d say he was going somewhere
for work, and then I’d see pictures
in a British tabloid of him on a yacht
with supermodels,” says a woman
who dated one of his close friends. The
women of consenting age with whom
Epstein became involved weren’t
gold diggers, per se—they were models,
or Amy Winehouse’s “Gucci bag crew”
flying to Miami for free, or postcollegiate
women who didn’t care about a
30-year age difference. Some wanted to
open a door to the world of private
The women who dated Epstein,
many of whom now have high-profile
careers, didn’t want to be identified in
this article, some because they feel the
press would mangle their relationships
and describe them as prostitutes,
not a reputation a professional woman
can surmount. Some were getting
something from Epstein—a trip on a
private plane with Bill Clinton
is not without value. But more often
they were, to some degree, the
commodities—tradable objects. That
was part of the grift. Epstein traded
men for acceptance, always trying
to show other men how many
important people he knew: politicians,
billionaires, former Harvard president
Larry Summers, top scientists.
Women were another instrumentality.
Everyone had their price.Epstein’s ex-girlfriends say he was
quiet and charming, for the most
part, Jay Gatsby in a monogrammed
sweatshirt. He spent most of the
day on speakerphone, and he liked
them to listen in, rolling calls from
financiers to heads of state. He
did not drink or take drugs or smoke,
and he didn’t like to be around
people who did. He practiced Iyengar
yoga. He showered many times
a day. He abhorred restaurants and
ate whole grains, proteins, and leafy
greens 30 years before the rest
of America. He tied body to mind,
physical self to mental aptitude;
he believed in transhumanism and had
a theory that if you had too much
muscle mass, you wouldn’t be as smart
as you could be. He liked to sleep in
54-degree chill because he believed
you’d get the most restful sleep at
that temperature. “I was like, ‘I’m
fucking freezing. I’m going to die of
hypothermia,’ ” says an ex-girlfriend.
He also had an instinct for what
people wanted. “Jeffrey was brilliant
in understanding how people felt,”
says the same ex-girlfriend. “He could
feel energy very clearly. But I think
because he’s a sociopath, he would
manipulate that for his own needs. The
average human population just doesn’t
operate that way, and thank God.”
The man who contributed to
Epstein’s riches, Les Wexner, the ownerplanes and the global elite. In later
years, he favored a different kind
of Eastern European woman who was
more expressly for sale. “There are
almost as many people involved over
18 as under 18—it’s not 50-50, but
it’s in that ballpark,” says David Boies,
the attorney for some of Epstein’s
accusers. He describes two different
types of of-age women involved
with Epstein. “There were women who
were not underage, but usually in
their younger 20s, who became part
of what we’re calling Epstein’s
sex-trafficking orbit—they’d either be
trafficked or lent out, describe it
as you will, to other people,” he says.
“Then there were young professional
women of comparable age whom
Epstein sort of dated, and then hemight or might not recommend
them to other people.” Young women
like the one I came across in
Southampton were presumably part
of that second set. (She did not return
messages for further comment.)
Epstein’s recommendations for these
young women were romantic, or
professional, or some uneasy mix of
both; Charlie Rose, disgraced after
sexual assault allegations, received
suggestions for several assistants on
his TV show from Epstein.“He could
feel energy
very clearly....
Because he’s
a sociopath,
he would
manipul ate
that for his
own needs.”
OCTOBER 2019 VANITY FAIR 43