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A lawyer for Mr. Epstein, Reid Weingarten, did not respond to messages seeking comment.

Early Influences

Mr. Epstein’s big break came when he was teaching math at the Dalton School, a prestigious Manhattan private school, in the mid-1970s. He had tutored the son of Alan Greenberg, the chairman of the mighty investment bank Bear Stearns, and ended up joining the firm.

He left after a few years. Mr. Epstein told Securities and Exchange Commission lawyers in an insider-trading investigation that there were three reasons, according to a 2003 Vanity Fair article. He had been disciplined over lending money to a friend to buy stock, and there were irregularities with his expense account and rumors he was having an affair with a secretary. (Mr. Epstein testified that he had known nothing about any insider trading, and neither he nor anyone else at the firm was charged.)

In 1981, he struck out on his own. He founded his own advisory firm, Intercontinental Assets Group, which he ran out of his apartment on East 66th Street. In 1987, he met Mr. Hoffenberg, then the chief executive of Towers Financial Corporation.

Mr. Hoffenberg said in an interview that he had met Mr. Epstein in New York at the height of the 1980s takeover boom, when Ivan Boesky’s “Merger Mania” was a national best seller. Towers Financial was buying unpaid debt from hospitals, nursing homes and phone companies and trying to collect it — a distinctly unglamorous niche. Mr. Hoffenberg hired Mr. Epstein as a consultant for $25,000 a month, and the two men refashioned themselves as corporate raiders.

Two takeover efforts were spectacular failures. They made a run at Pan Am, and a news release issued by Towers in November 1987 listed their advisers as John Lehman, a former secretary of the Navy; John N. Mitchell, the attorney general during the Nixon administration; and Edward Nixon, former President Richard M. Nixon’s brother. But the bid collapsed after a jetliner exploded over Lockerbie, Scotland, which sent Pan Am into bankruptcy.

Mr. Epstein and Mr. Hoffenberg also made a run at Emery Air Freight — an “epic failure,” according to an affidavit filed by Mr. Hoffenberg in a 2018 lawsuit against Mr. Epstein, which was brought by investors defrauded in Mr. Hoffenberg’s Ponzi scheme. The suit was dismissed.