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Was Epstein Simply a Tinder Swindler of Billionaires?

Bromance is sadder than conspiracy theory

By Scott Christenson🌴Published 5 months ago • Updated 5 months ago • 9 min read

The internet is swirling with rumors that Jeffrey Epstein was either a Mossad agent or a CIA asset -- both alluding to a vast conspiracy run by intelligent and powerful men.

What if the reality is the opposite?

Jeffrey Epstein was a run-of-the-mill swindler, and the rich and important billionaires he swindled, were simply lonely old men who were easily exploited?

Going through his background and modus operandi, the person he most resembles is "Tinder Swinder" Simon Leviev. Both grew up in working class Jewish families in Brooklyn, possesed effortless superficial charm, presented themselves covered in the trappings of wealth, and had a vast appetite for talking others out of their money.

Jeffrey Epstein would, at odd moments, give out hints it was all a charade:

In 2001, journalist Michael Wolff, upon entering Epstein's magnificent Upper East Side townhouse, exclaimed, “Wow, this is an incredible place!”

“Fake,” Jeffrey Epstein replied, rapping his knuckles on a wall, “It’s all fake.”

Jeffrey was a predator who targeted people with influence. His main focus was the country’s wealthiest men, most of whom, like Leslie Wexner and Leon Black, were philanthropists with ties to Israel. Others, like Larry Summers and Alan Deshowitz, were influential in the fields of government, academia and the judicial system.

No witness has ever mentioned him pursuing a political agenda. His schemes were driven by personal greed.

His methods relied on charm, lies, and exploiting the trust of bored, wealthy elites. His journey into their world began with a fabricated resume that landed him a teaching job and a friendship that opened doors to Wall Street.

Donald Barr — Wikimedia Commons

The First Scam — From Brooklyn to the Dalton School

In his first big lie, Jeffrey Epstein would fool ex-intelligence officer Donald Barr.

From 1964 to 1974, Donald Barr was the head of the Dalton School, an elite private school attended by the children of New York’s wealthiest families. He is also the father of the future US Attorney General, William Barr, and was an ex-OSS intelligence officer, the precursor of the CIA.

Donald Barr came from a Jewish family and so did Jeffrey Epstein, and they must have immediately shared this in common.

The year before Jeffrey was hired in 1974, Donald Barr had also published his SciFi novel Space Relations, a book filled with explicit depictions of sexual violence and underage exploitation. Did Jeffrey and Donald perhaps share another common interest?

And he also lied about his resume. Epstein had dropped out of both Cooper Union and NYU’s Courant Institute without gaining a degree. Despite later having an office at Harvard University, Epstein would never obtain a college degree. His charisma and self-assured demeanor convinced Donald Barr, an ex-intelligence officer, to hire him, despite his lack of formal qualifications.

At Dalton, Epstein cultivated an image of intellectualism, impressing students and parents alike. His time there was short — 1974 to 1976 — but it was a stepping stone. The school gave him access to Manhattan’s elite, and he leveraged this exposure to make connections that would propel him forward. His teaching stint ended amid allegations of inappropriate behavior and lackluster performance, but by then, Epstein had already set his sights on a bigger stage.

Befriending Power — The Bear Stearns Connection

Alan Greenberg — Wikimedia Commons

Epstein’s next leap came through a fortuitous relationship forged at Dalton. Among the parents of his students was Alan “Ace” Greenberg, the CEO of Bear Stearns, a prominent Wall Street investment bank.

Several sources, including The New York Times and Miami Herald, report that Epstein’s interactions with a parent led to a recommendation to Greenberg, who subsequently hired Epstein at Bear Stearns in 1976 after his dismissal from Dalton for “poor performance.” Greenberg’s daughter Lynne herself recalled to the Miami Herald that Epstein persuaded another parent to advocate for him to her father, highlighting his charisma and ability to “schmooze.”

Epstein’s charm and knack for self-presentation worked their magic on Greenberg, who saw potential in the young teacher. By 1976, Epstein parlayed this into a job at Bear Stearns, starting as a junior assistant to a floor trader. Once again, he misrepresented his qualifications, glossing over his lack of a degree or formal financial training.

At Bear Stearns, Epstein quickly climbed the ranks, becoming a limited partner by 1980. His role was nebulous, often described as a “financial troubleshooter,” but he excelled at cultivating relationships with wealthy clients. Greenberg, a no-nonsense executive with a reputation for spotting talent, reportedly took a liking to Epstein, giving him the latitude to network with the firm’s high-net-worth clients.

Epstein left Bear Stearns in 1981 under murky circumstances, with some reports suggesting he was investigated for improper trading practices. But by then, he had gained enough credibility and connections to strike out on his own, setting the stage for his larger schemes.

Steven Hoffenberg — A Pyramid Scheme

Steven Hoffenberg — WIkimedia Commons

In 1987, Jeffrey Epstein joined Steven Hoffenberg at Towers Financial Corporation, introduced by British defense contractor Douglas Leese, who described Epstein as a financial genius with no moral compass.

Hoffenberg was born in Brooklyn, New York to a Jewish family on January 12, 1945 according to Wikpedia.

According to Hoffenberg’s later court claims, Epstein played a pivotal role in encouraging and shaping the Ponzi scheme that would bilk investors out of $475 million.

Hoffenberg alleged that Epstein, hired at $25,000 a month plus a $2 million unrepayable loan, was the architect of the scam, pushing for aggressive financial maneuvers and using Towers funds to fuel a lavish lifestyle, including private jets and multiple properties.

Despite their collaboration, Epstein left before the scheme’s collapse in 1993 and avoided criminal charges, leaving Hoffenberg to face a 20-year prison sentence alone.

Leslie Wexner — Victoria’s Secret

Leslie Wexner — Wikimedia Commons

Leslie Wexner, born in 1937 to Russian-Jewish parents in Dayton, Ohio, built a retail empire through L Brands, encompassing brands like Victoria’s Secret and Bath & Body Works.

By the 1980s, he was a billionaire and a prominent Jewish philanthropist, co-founding the Mega Group, a network of Jewish-American businessmen supporting Israeli causes. Wexner met Epstein in the mid-1980s, and their relationship quickly deepened. Epstein became Wexner’s financial manager, gaining power of attorney over his fortune by 1991 — a remarkable level of trust for a man with no formal financial credentials.

Epstein lived in Wexner’s Manhattan mansion, managed his charitable efforts, and even replaced Wexner’s mother on the Wexner Foundation board.

Wexner’s reliance on Epstein has puzzled observers. As a self-described outsider — a Midwestern Jewish man navigating New York’s elite circles — Wexner may have been drawn to Epstein’s charisma and promise of social access. Epstein, a master manipulator, reportedly exploited such vulnerabilities, offering “glamour and smoothness” to a man who felt socially isolated despite his wealth. People at L Brands referred to him as “Leslie’s boyfriend.”

In a 1985 New York Magazine profile, Wexner described feeling haunted by a “dybbuk,” a Jewish folklore spirit that prodded him toward success, hinting at deep-seated insecurities that Epstein could have leveraged.

Investigations later suggested Epstein misappropriated tens of millions from Wexner, funneling funds into his own accounts while maintaining the facade of a financial genius. Epstein’s famous Manhattan townhouse was transferred to him from Wexner for zero dollars. All in exchange for what? No one is certain.

Leon Black — A Wall Street Fortune

Leon Black as depicted by Grok AI

Leon Black, was born in New York in 1951, a child of a Jewish businessman who emigrated from Poland.

Black founded Apollo Global Management and amassed a fortune estimated at $7.5 billion. Like Wexner, Black was a significant Epstein client, paying him $158 million for vaguely defined “financial advisory services” between 2012 and 2017. Black, like Wexner, was a prominent Jewish philanthropist with a history of supporting Israel-related causes. Epstein’s ability to ingratiate himself with such figures relied on his knack for exploiting their trust, offering access to exclusive social networks and the promise of financial growth.

Black’s decision to continue working with Epstein post-conviction raises questions about the nature of their relationship. Epstein’s ability to maintain influence over Black, a sophisticated financier, suggests a dynamic beyond mere financial advice. Some speculate that Epstein’s knowledge of personal or professional secrets may have kept Black tethered, though Black has denied any blackmail or wrongdoing.

No Political Agenda, Just a Con

Despite the conspiracy theories surrounding Epstein, no credible evidence or witness testimony points to a political agenda, whether pro-Israel or otherwise. His actions were driven by self-interest, not ideology. He exploited the vulnerabilities of his targets — often older, successful men who were bored or seeking new opportunities — using his curated image as a connected, brilliant financier. His luxurious properties, private jets, and high-profile friendships were props in a performance designed to dazzle and disarm.

Epstein’s methods mirrored those of modern con artists like Simon Leviev, the Tinder Swindler, who used a fabricated persona to extract money from trusting victims. Epstein’s “product” was access: to elite networks, financial opportunities, and a glamorous lifestyle. For men like Wexner and Black, he offered a sense of excitement and exclusivity, all while siphoning their wealth.

Blackmail as a Tool of Control

Epstein’s wealth, estimated at nearly $600 million at his death, is attributed largely to his relationships with Wexner and Black, with Forbes estimating Wexner paid him over $200 million and Black $170 million. Epstein’s tactics, as alleged by victims like Virginia Giuffre, included recording compromising activities to exert control over powerful individuals. Wexner’s 2019 letter to his foundation claimed Epstein misappropriated “vast sums” of money, yet he never reported this to authorities, raising questions about why he remained silent.

The Hulu docuseries Victoria’s Secret: Angels and Demons suggests Epstein may have held blackmail material on Wexner, possibly related to his personal life, though both Wexner and Epstein denied any such relationship.

Bill Gates Didn’t Pay (until he did)

Bill and Melinda Gates — Wikimedia Commons

Bill Gates has no Jewish ancestry, but as the world’s richest man, Jeffrey Epstein couldn’t help luring him close. Using his ‘salon’ gathering of prominent political and intellectual figures, Epstein lured Gates into his Manhattan townhouse and many numerous occasions.

In 2017, Epstein attempted to blackmail Microsoft co-founder Bill Gates over an alleged 2010 affair with Mila Antonova, an attractive Russian bridge player who had been sponsored by Jeffrey Epstein. According to The Wall Street Journal, Epstein sent Gates an email demanding reimbursement for tuition he had paid for Antonova’s software coding school, implying he could expose the affair if Gates didn’t comply.

This was seen as an effort to pressure Gates into supporting a multibillion-dollar charitable fund Epstein was pitching to JPMorgan Chase, from which Epstein sought a commission for funds raised. Gates, who met Epstein several times since 2011 for philanthropy discussions, refused to pay or join the fund. His legal team, wary of Epstein’s criminal history and reputation, strongly advised against any association, with a Gates spokesperson confirming no financial dealings occurred.

Gates later called his meetings with Epstein a “huge mistake,” driven solely by philanthropy talks. The affair and Epstein’s threat, coupled with his legal team’s disapproval of Epstein, heightened scrutiny of Gates’ ties to him, contributing to marital strain, as Melinda French Gates cited discomfort with Epstein in their 2021 divorce.

The Fallout and the Legacy

Epstein’s death in 2019 left many questions unanswered, but the financial trail reveals a man who thrived on deception. His early lies — about his education to secure the Dalton job, about his expertise to win over Greenberg — set the pattern for his later cons. The fallout from his schemes continues to haunt his victims, with Wexner and Black facing scrutiny for their associations with him. Lawsuits and investigations have exposed the extent of Epstein’s financial misdeeds, but they also underscore a timeless truth: even the most powerful can fall prey to a skilled swindler.

Jeffrey Epstein was no ideological crusader or political operative. He was a con artist who began with a fabricated resume, who charmed his way into Wall Street and spent decades preying on the trust of the ultra-rich.

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About the Creator

Scott Christenson🌴

Born and raised in Milwaukee WI, living in Hong Kong. Hoping to share some of my experiences w short story & non-fiction writing. Have a few shortlisted on Reedsy:

https://blog.reedsy.com/creative-writing-prompts/author/scott-christenson/

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Comments (4)

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  • Sid Aaron Hirji5 months ago

    These con artist stories freak me out. This story is still unravelling too but the wealthy preventing truth coming out. Scary indeed

  • JBaz5 months ago

    We all know there is more to be told and revealed, but as long as the wealthy have control (everything), they seems to be ok with talking about it, and trying distractions. I notice you had nothing on Trump and their relation in this article. Then again this could probably gone on for another 10000 words.

  • Rachel Deeming5 months ago

    So he fed off the rich? However he's being portrayed, he's not coming out of it all looking like an innocent and neither are the people linked to him. Interesting insight, Scott.

  • I have not really seen much about this, only hearing about the "Epstein Files" through some news emails I get. But this seems like a pretty likely scenario. Sometimes, the simple solution is the correct one, and the pieces align pretty well here, it seems.

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