How Did Jeffrey Epstein Get So Rich?
Epstein was a ruthless doofus, but a lot of his fellow Jews at the top of the ladder seemed be charmed by his Outer Boroughs moxie.
“When the going gets tough, you don’t want a criminal lawyer, you want a criminal lawyer.” — Breaking Bad
The New York Times runs a long article purporting to explain how Jeffrey Epstein got rich, but mostly winds up shooting blanks. A recurrent theme running through the article is Epstein impressed rich Jews with his working class Jewish moxie and apathy about moral standards:
Scams, Schemes, Ruthless Cons: The Untold Story of How Jeffrey Epstein Got Rich
For years, rumors swirled about where his wealth came from. A Times investigation reveals the truth of how a college dropout clawed his way to the pinnacle of American finance and society.
By David Enrich, Steve Eder, Jessica Silver-Greenberg, and Matthew Goldstein
The reporters, who have been investigating Jeffrey Epstein since 2019, interviewed dozens of his former colleagues, girlfriends, business partners and others. They also dug through archives, reviewed photos, notes and emails and scoured thousands of pages of public records.
Dec. 16, 2025
One evening in early 1976, a bushy-haired Jeffrey Epstein showed up for an event at an art gallery in Midtown Manhattan. Epstein was a math and physics teacher at the city’s prestigious Dalton School, and the father of one of his students had invited him. Epstein initially demurred, saying he didn’t go out much, but eventually relented. It would turn out to be one of the best decisions he ever made.
At the gallery, Epstein bumped into another Dalton parent, who had heard tales of the 23-year-old’s wondrous math skills.
Was Epstein really a prodigy? I’ll get to that question at the end.
The parent asked if he’d ever thought about a job on Wall Street, according to an unreleased recording of Epstein and a document prepared by his lawyers. Epstein was game. The parent dialed a friend: Ace Greenberg, a top executive at Bear Stearns.
Greenberg was CEO of Bear Stearns from 1978-1993, when he was forced out by his protege Jimmy Cayne. Jimmy Cayne sounds like an Irishman, but, nah, he was Jewish, too, just like so many who turbocharged Epstein’s ascent.
Greenberg stayed on as Chairman through Bear Stearns’ collapse in early 2008. (Bear Stearns was the first major domino to topple in 2008, but when that didn’t set off a recession, the Fed grew complacent and then let Lehman Brothers fall too, with disastrous results.)
Epstein, the friend told Greenberg, was “wasting his time at Dalton.”
… Greenberg was impressed — even though the young man didn’t have the foggiest idea of how Wall Street worked. Greenberg had helped build Bear Stearns into one of the industry’s scrappiest firms by eschewing the traditional investment-banking practice of hiring Ivy Leaguers with M.B.A.s. He preferred what he called P.S.D.s: those who were poor, smart and had “a deep desire to become rich.”
Epstein fit the bill. He grew up in a working-class family in Coney Island. Friends described him as a math whiz and a piano virtuoso. And, as Greenberg and his colleagues would soon learn, he yearned for wealth. …
Before offering Epstein a job, Greenberg had him meet another senior executive, Michael Tennenbaum. His son happened to be a Dalton student, who reported to his father that Epstein was popular with students and the school’s young female staff members. Epstein went to Tennenbaum’s office overlooking New York Harbor for an interview. “He was just a hell of a salesman,” Tennenbaum told us. Epstein was hired.
It was an extraordinarily lucky break for him — the first of many. Administrators at Dalton, unimpressed with Epstein’s teaching, had asked him to leave the school after the academic year ended. Now, just like that, he had a new job that paid about $25,000 a year (roughly $140,000 in today’s dollars).
Greenberg viewed the young man as a protégé. Early on, he invited Epstein to a dinner party and seated him next to his 20-year-old daughter, Lynne, who told us that she suspected it was a setup. The two hit it off and started dating. Word of the new guy’s romance with the boss’s daughter spread quickly, granting Epstein something akin to protected status at the firm.
Uh, if you were on the path to shortly becoming CEO of a top Wall Street firm, would you set up your 20-year-old daughter with … Jeffrey Epstein? I’m reminded of how President Obama was proud to have gotten his daughter an internship with … Harvey Weinstein.
We like to think that everything is carefully plotted out ahead of time like in a spy thriller, but a lot of times what we see are instead powerful people making stupid decisions.
Tennenbaum soon became Epstein’s supervisor. “He was proving to be quite talented,” Tennenbaum told us. But in late 1976, he received a disconcerting phone call from the head of Bear Stearns’s personnel department. Employees had belatedly gotten around to checking Epstein’s résumé, which stated that he had received degrees from two California universities.
“Are you sitting down?” the H.R. official asked Tennenbaum. “Neither school has heard of him.”
Tennenbaum was in a delicate spot. He asked Greenberg what to do. The response, Tennenbaum told us, was that he should treat Epstein as if he were a normal employee — an instruction that made clear that, thanks to his relationships, Epstein was in fact not a normal employee.
He summoned Epstein to his office. “You lied about your education,” he said.
“Yes, I know,” Epstein calmly replied. …
“Why did you do it?” Tennenbaum stammered.
Without an impressive degree or two, Epstein said, “I knew nobody would give me a chance.”
This resonated with Tennenbaum. He had benefited from his own share of second chances over the years. And so he agreed to give Epstein one as well.
It was perhaps the first example of Epstein getting caught cheating — and then avoiding punishment thanks to his uncanny ability to take advantage of those in positions of power. This would become a lifelong pattern, one that largely explains Epstein’s remarkable success at amassing wealth and, eventually, orchestrating a vast sex-trafficking operation.
… How did a college dropout from Brooklyn claw his way from the front of a high school classroom to the pinnacle of American finance, politics and society? How did Epstein go from nearly being fired at Bear Stearns to managing the wealth of billionaires? What were the origins of his own fortune? …
What emerged is the fullest portrait to date of one of the world’s most notorious criminals — a narrative that differs in important respects from previously published accounts of Epstein’s rise, including his arrival at Bear Stearns.
Ehh … it’s not particularly full or new.
In his first two decades of business, we found that Epstein was less a financial genius than a prodigious manipulator and liar. Abundant conspiracy theories hold that Epstein worked for spy services or ran a lucrative blackmail operation, but we found a more prosaic explanation for how he built a fortune. A relentless scammer, he abused expense accounts, engineered inside deals and demonstrated a remarkable knack for separating seemingly sophisticated investors and businessmen from their money. He started small, testing his tactics and seeing what he could get away with. His early successes laid the foundation for more ambitious ploys down the road. Again and again, he proved willing to operate on the edge of criminality and burn bridges in his pursuit of wealth and power.
Ehhh, I’d say that it sounds like many of the rich people Epstein dealt with on his way up appreciated that this Outer Boroughs Jewish kid operated on the edge of criminality. Others seemed too obtuse to notice that Epstein was bad news.
But, still, I wouldn’t rule out Epstein having something else going for him, such as an intelligence connection. But …
Paywall here.
