Jeffrey Epstein’s rise began far from Wall Street. In the mid-1970s, he was teaching math and physics at New York’s elite Dalton School, with no college degree and little exposure to finance. An invitation to an art gallery led to a fateful introduction to Ace Greenberg, a senior executive at Bear Stearns. Within months, Epstein had landed a job at the investment bank, despite having no formal training in the field, the New York Times reported.
Greenberg was known for favouring unconventional hires, and Epstein’s confidence and ambition appealed to him. That relationship would shape the rest of Epstein’s life.
Protected inside Bear StearnsAt Bear Stearns, Epstein quickly learned how power operated inside financial institutions. He benefited from Greenberg’s patronage and from a brief relationship with Greenberg’s daughter, which gave him informal protection. When the firm later discovered that Epstein had lied about earning college degrees, he admitted the deception but suffered no serious penalty.
Colleagues later recalled this episode as an early sign of Epstein’s ability to disarm authority figures. Despite repeated rule violations involving expense accounts and trading privileges, he remained insulated from consequences.
Learning how to bend the systemBear Stearns gave Epstein more than a salary. It gave him credibility. He learned how elite clients were cultivated, how deals were structured, and how rules could be stretched without triggering real punishment. Even after the firm investigated him for misconduct in 1981, Epstein was allowed to resign quietly rather than face suspension.
Crucially, former colleagues continued to vouch for him, introduce him to investors and route business his way long after he left the firm.
Early scams and quiet paydaysOutside Bear Stearns, Epstein began experimenting with increasingly aggressive schemes. He persuaded acquaintances to invest in dubious ventures, including a crude-oil deal that cost one investor hundreds of thousands of dollars. Civil lawsuits followed, but Epstein avoided personal liability on technical grounds.
He also began marketing himself as a specialist in tracking hidden wealth through offshore banks. Some clients paid handsomely for these services, even when the results were unclear.
By the mid-1980s, Epstein had embedded himself in elite social circles. He cultivated financiers, politicians, academics and philanthropists, often using young women as intermediaries to gain access. Strategic donations helped him secure board positions and institutional affiliations that enhanced his credibility.
These relationships allowed Epstein to present himself as a trusted insider, even as questions about the source of his wealth persisted.
The Wexner turning pointEpstein’s fortune expanded dramatically after he gained the confidence of Leslie Wexner, the billionaire behind brands such as Victoria’s Secret. Wexner granted Epstein sweeping authority over his finances, including power of attorney. From that point on, Epstein’s wealth and lifestyle escalated rapidly.
Former associates would later say Epstein appeared to take tens of millions of dollars from Wexner’s accounts with little oversight, financing properties, private aircraft and offshore tax arrangements.
Institutions that kept enabling himAs Epstein grew richer, major banks continued to service him, influential lawyers defended him and political connections deepened. Even as allegations of sexual abuse emerged, he retained financial legitimacy in elite circles.
Investigators who later retraced his rise concluded that Epstein was not a financial genius or a covert operator, but a skilled manipulator who exploited institutional blind spots and personal loyalties.
Second chances that had lasting consequencesAgain and again, Epstein benefited from second chances that others would not have received. Those chances did more than enrich him. They protected him, enabled him and allowed his power to grow unchecked for decades.
By the time his crimes became widely known, the system that had allowed Jeffrey Epstein to amass wealth, influence and immunity was already deeply entrenched.
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