Preface: This was written in collaboration with Gemini. 

From 1987 onward, Jeffrey Epstein’s life was defined by his transition from a Wall Street "troubleshooter" to a highly connected financier and philanthropist, alongside the development of the criminal activities that would lead to his eventual downfall. As mentioned previously, in 1987, at age 34, Epstein was hired by Steven Hoffenberg as a consultant for Towers Financial Corporation, where he was paid approximately $25,000 per month. In 1988, he founded his own money management firm. He claimed to work exclusively for clients with a net worth over $1 billion. In 1991, Leslie Wexner granted Epstein power of attorney, giving him vast control over Wexner’s personal and business finances. Reports indicate Epstein made over $200 million from this relationship over two decades.

During the 1990s, the line between Wexner’s wealth and Epstein’s assets became almost invisible. Wexner originally bought a massive 9-story mansion on the Upper East Side in 1989 for $13.2 million. By the mid-90s, Epstein was living in it. In a complex series of transactions that were finalized in 2011 but initiated in the late 90s, the house (eventually valued at $77 million) was transferred to Epstein for $0. Wexner’s Boeing 727 was transferred to a company controlled by Epstein. This plane would later become the infamous "Lolita Express." Epstein supervised the construction of Wexner’s 315-foot yacht, Limitless, one of the largest in the world at the time. It became a floating office where Epstein hosted influential guests. 

Wexner introduced Epstein to his most prestigious circles, turning a "college dropout" into a man of high society. In 1992, Wexner appointed Epstein as a trustee of the Wexner Foundation, replacing his own mother. Wexner and Epstein were part of an informal "club" of Jewish billionaires (including Charles Bronfman and Max Fisher) that met to discuss philanthropy and pro-Israel causes. From 1993 to 1997, reports began to surface that Epstein was posing as a recruiter for Victoria’s Secret to lure women. When a female executive at the company complained to Wexner about Epstein’s behavior in 1993, Wexner reportedly said he would "put a stop to it," but their partnership continued for another 14 years. Epstein played the role of Wexner's "intellectual scout." He would bring famous scientists and thinkers to Wexner’s home in Ohio. In 1996, Artist Maria Farmer alleged she was sexually assaulted by Epstein and Ghislaine Maxwell at Wexner’s New Albany estate during this time. She claimed that when she tried to report it to the local police (who were heavily funded by Wexner’s developments), she was ignored. Epstein also co-funded university buildings  and programs at Harvard alongside Wexner, effectively using Wexner’s prestige to buy his own way into Harvard’s elite academic circles. 

During this period, Epstein acquired the assets and social connections that defined his public image. He acquired a massive 9-story Manhattan townhouse from Wexner (valued at over $50 million) and purchased Little St. James island in the U.S. Virgin Islands in 1998 for $7.95 million. Jeffrey Epstein’s purchase of Little St. James in April 1998 for $7.95 million was a major turning point in his life, marking the moment he moved from being a wealthy financier to a man with his own private, sovereign-like kingdom. The purchase was not just a simple real estate transaction; it was a carefully shielded acquisition facilitated by his relationship with Leslie Wexner. 

He used a Delaware-based entity called L.S.J. LLC to make the purchase. It wasn't until much later—specifically in 2011—that public records officially linked Epstein as the sole member of that LLC. He bought the 71-acre island from venture capitalist Arch Cummin, who had originally listed it for $10.5 million. Epstein, a notoriously aggressive negotiator, managed to get it for nearly 25% less than the asking price. By 1998, Epstein was at the peak of his financial power, largely due to his role managing Leslie Wexner's fortune. Investigations into Epstein’s wealth (including those discussed in the February 2026 document releases) suggest that between 1991 and 2007, Epstein was paid approximately $200 million in fees and asset transfers by Wexner. Recent unsealed records from JPMorgan Chase show that the bank began lending Epstein massive sums of money starting in 1998—the exact year he bought the island. The bank regularly allowed him to withdraw large amounts of cash and provided the liquidity he needed to maintain his global property portfolio. 

The purchase of the island was part of a larger financial scheme to avoid U.S. taxes. After buying the island, Epstein set up a company called Southern Trust Co. in the U.S. Virgin Islands. By claiming residency on Little St. James, Epstein was able to take advantage of local tax breaks that slashed his corporate and personal income tax by up to 90%. Experts estimate this move saved him over $300 million in taxes over two decades. 

When Epstein bought it, the island was already a luxury retreat, but it was modest compared to what it became. It already had a main house, three guest cottages, a caretaker’s cottage, and a helipad. Immediately after the purchase, Epstein hired Edward Tuttle (the designer behind the ultra-luxury Aman Resorts) to transform the property into a massive compound. He eventually added the infamous "temple" building, a private desalination plant, and a high-capacity fiber optic cable connected directly to St. Thomas. In February 2026, the U.S. House Oversight Committee released never-before-seen photos and drone footage of the island from the early 2000s. These records confirm that while the island was purchased as a "private residence," Epstein used the same shell companies he used for the island to funnel money to various associates now being scrutinized in the 2026 unredacted FBI files. Other than Little St. James he purchased for $7.95 million in 1998, he also acquired a 7,500-acre estate in Zorro Ranch, New Mexico in 1993, Great St. James in 2016 was purchased for over $20 million to expand his island compound, and his Paris Apartment on Avenue Foch. 

Around 2006, the relationship began to crumble only when the law and Wexner’s wallet were threatened. When the FBI began investigating Epstein in Florida for soliciting minors, Wexner’s legal team began distancing the billionaire from his manager. A year later, Wexner started claiming he discovered Epstein had misappropriated "vast sums" of his money—reportedly around $46.7 million. Wexner says he immediately "severed all ties." According to the recent document releases, Epstein eventually paid back roughly $100 million in various assets and charitable transfers to the Wexner family trusts to settle the "theft" privately. The most recent 2026 disclosures from the Department of Justice suggest that the "breakup" may not have been as clean as Wexner claims. Documents released in late 2025 showed that Wexner signed a "birthday book" for Epstein as late as 2003 with high praise, calling him a man of "excellent judgment." JPMorgan records unredacted in February 2026 show that money was still moving between Wexner-linked trusts and Epstein-linked accounts as late as mid-2007, just months before Epstein's first arrest. 

Severed or not, Epstein cultivated relationships with high-profile figures, including Bill Clinton, Donald Trump, and Prince Andrew through Wexner’s help. He also began funding scientific research, establishing the Jeffrey Epstein VI Foundation in 2000. Prosecutors alleged that between 2002 and 2005, Epstein operated a "vast network" of underage victims at his homes in Palm Beach and New York. In March 2005, Palm Beach police began investigating him after a report involving a 14-year-old girl that led to a federal investigation known as "Operation Leap Year" in 2006. In 2007, Epstein’s lawyers negotiated a controversial deal with U.S. Attorney Alexander Acosta. In 2008, Epstein pleaded guilty to two state charges of soliciting prostitution (one involving a minor) and served 13 months in a work-release program. ☀️