Long before Jeffrey Epstein boasted of his billionaires-only client list—and long before his arrests for molesting underage girls in Florida and New York—the perverted financier was an eligible bachelor in the glossy pages of Cosmopolitan.
In July 1980, Epstein was featured as the magazine’s “Bachelor of the Month,” a tiny section advertising successful single men across the country. At the time, the future sex-offender was a Bear Stearns trader and asked potential dates to write him at the investment bank's former headquarters in Lower Manhattan.
Epstein also claimed to speak only to millionaires, a prelude to his high-rolling lifestyle that included hobnobbing with Donald Trump, Bill Clinton and Prince Andrew, and amassing a collection of posh homes in Palm Beach, New York, Paris, and the U.S. Virgin Islands.
The personals ad, which included a photo of Epstein in a suit, portrayed him as a “New York dynamo” seeking “a cute Texas girl.”
“Financial strategist Jeffrey Epstein, 27, talks only to people who make over a million a year!” the listing declared. “If you’re ‘a cute Texas girl,’ write this New York dynamo at 55 Water St., 49th floor, N.Y.C. 10041.”
It’s unclear if anyone met Epstein through the Cosmopolitan writeup. Media representatives for the magazine didn’t return messages left by The Daily Beast.
One month after Epstein’s Cosmo debut, Bear Stearns placed an ad in The Wall Street Journal naming employees who made limited partner, including Epstein. But the former Dalton teacher left the firm in 1981, sometime after he was accused of financial chicanery that allegedly involved lending a friend $20,000 to buy stock.
According to Vanity Fair's Vicky Ward, after his departure from Bear Stearns, Epstein had insisted that he exclusively managed money for billionaires, though his only known client was Limited Brands chairman and Victoria’s Secret mogul Leslie Wexner. “I was the only person crazy enough, or arrogant enough, or misplaced enough, to make my limit a billion dollars or more,” Epstein reportedly bragged.
Ward also touched on the “many women in his life, mostly young,” while noting Epstein never committed to anyone. In the 1990s, Epstein was in a relationship with British socialite Ghislaine Maxwell—his accused madam and the daughter of the late media tycoon Robert Maxwell, who was as dark and mysterious as Epstein.
The Mail on Sunday published a yarn on their supposed romance under the headlines, “The mystery of Ghislaine Maxwell’s secret love.”
“His name is Jeffrey Epstein, a shadowy, almost maverick New York ‘property developer’ who, for over a year, has helped Ghislaine become a coveted fixture on the Manhattan social scene,” the British tabloid reported in 1992. “During the last year, say friends, she has fallen in love with him, and the couple are inseparable.”
“Despite the dubious fame of having been nominated as Cosmopolitan magazine’s Bachelor of the Month,” the report added, “Epstein walked into her life at a time when she was desperately lonely.”
The Mail described Epstein as an enigmatic figure, rumored to be a concert pianist, a math teacher at an elite girls’ school, and connected to the CIA and Mossad, Israel’s intelligence agency. “The most intriguing rumor is that he was a corporate spy hired by big businesses to uncover money that had been embezzled,” the article stated.
In 1993, the Washington Times depicted Epstein as a “maverick investor and Clinton supporter” and “president of the Limited clothing-store empire.” (The New York Times, in a 1991 blurb, identified Epstein as “president of Wexner Investment Company.”)
Epstein called Maxwell his “best friend” in Vanity Fair’s 2003 profile. Once a romantic relationship is over, he said, the woman “moves up, not down” to friendship status. “He enjoys the company of pretty women. Ghislaine is important to him in other ways. She arranges his social life,” one pal told London’s Evening Standard in 2001.
The press started digging into Epstein’s Gatsby-esque rise after the New York Post revealed he flew former President Clinton to Africa on his private Boeing 727 jet. “How Clinton, who took off on Saturday, hooked up with his traveling companions is a mystery—as is his relationship to Epstein,” the Post reported in fall of 2002.
That year, Epstein was even awarded “Best Male Support” at the conclusion of the Stockholm School of Economics’ “Female Economist of the Year” scholarship ceremony. While the business school’s website doesn’t name Epstein, identifying the winner as “an important but for now anonymous Friend,” a Scandinavian magazine did recognize him.
Nordic Reach quoted the scholarship’s founder, New York-based executive Barbro Ehnbom, who said the “Best Male Support” designation was created “to honor a specific Friend who was extra helpful and supportive during the previous year.” The article then listed “New York City Billionaire Jeffrey Epstein” as the 2002 recipient. (IRS records for his charity, Epstein Interests, show a $25,000 donation to the school for the tax year beginning in June 2001 and ending in May 2002. His other nonprofit, the C.O.U.Q. Foundation, donated at least $125,000 to the school from 2005 to 2010, tax returns show.)
Hanna Flodmark, a spokeswoman for the Stockholm School of Economics, said Epstein’s donations were made to a fund run by Ehnbom, who is an alumna and “important patron of the school.” Ehnbom’s scholarship is a “separate business” from SSE, though the school has administrated the funds for her in years past. (Ehnbom could not be reached for comment by The Daily Beast.)
In December 2003, Page Six declared Epstein, then 50 years old, one of New York City’s “most eligible guys” under the headline “Singling Out Apple’s Top Studs.” The list of bachelors included Donald Trump, Jr., modeling agent Paolo Zampolli, and disgraced former Democratic congressman Anthony Weiner.
“Mystery billionaire was a math teacher at Dalton just a few years ago,” Page Six staffers wrote. “Then he started handling Leslie Wexner’s money. Now he lives in Manhattan’s biggest mansion. Pro: Has a private plane which he used to take Bill Clinton to Africa. Con: Was one of Mort Zuckerman’s partners in failed attempt to buy New York magazine.”
But Epstein’s dark secret would come to light in March 2005, when police in Palm Beach launched an investigation into his abuse of underage girls. Attorneys for Epstein’s victims say he molested scores of underage girls after hiring them for “massages.” Some of them, like Virginia Roberts Giuffre, were allegedly recruited by Maxwell.
Epstein was arrested in July 2006, and cops brought their case to the FBI. But the money-manager secured a cushy deal from federal prosecutors in Miami, ultimately pleading guilty to a pair of state charges and spending just 13 months in a county jail—mostly on “work release.” The sweetheart deal, brokered by former U.S. Attorney in Miami Alex Acosta, was kept secret from dozens of Epstein’s minor victims.
This month, one woman came forward to accuse Epstein of sexually abusing her while he enjoyed his work release privileges, and the Palm Beach Sheriff launched an internal investigation into why Epstein was allowed his own private driver and to make unsupervised stops at his mansion during his sentence in 2008 and 2009.
Epstein faces sex-trafficking charges in New York after being arrested on July 6, and a Florida judge will soon decide whether to invalidate the 2007 plea deal that shielded Epstein, and his alleged co-conspirators, from serious charges in Palm Beach.
The New York indictment puts Epstein’s past lives under further scrutiny.
When police recently searched his Manhattan townhouse, they discovered an expired 1980s passport inside a safe, along with diamonds and $70,000 in cash. Federal prosecutors argued the passport (which has stamps from four countries and his photo, but another name) is evidence that Epstein is a flight risk.
But Epstein’s lawyers say the phony passport was a gift from a friend and that he never used it to travel abroad. “Some Jewish-Americans were informally advised at the time to carry identification bearing a non-Jewish name when traveling internationally in case of hijacking,” his lawyer, Marc Fernich, wrote in court papers.
In the 1980s, Epstein palled around with Ford models, including his ex-girlfriend and former Miss Sweden, Eva Andersson. And as The Daily Beast reported, Epstein sought out Juilliard students in 1983 to teach Andersson and his guests dance in Palm Beach. One dancer said Epstein was "obsessed" with the Flashdance soundtrack when he approached the performing arts school looking for a ballet barre instructor.
A decade later, Epstein was a major donor to Michigan’s Interlochen Arts Academy. One former administrator told The Daily Beast that the Epstein visited campus in the 1990s with Ghislaine Maxwell.
Victims have accused Maxwell of acting as Epstein's madam, saying she took part in abusing minor girls and groomed them for Epstein’s wealthy friends, including Prince Andrew and Epstein’s lawyer Alan Dershowitz. (Both men have denied those claims.)