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During his career he became a multimillionaire. Until his conviction for sex crimes in , he was well connected with many individuals of the financial, political, and cultural elite. In April , police of Palm Beach, Florida , began investigating Epstein after a parent complained that he molested her year-old daughter.
Epstein was arrested again on July 6, , on federal charges for sex trafficking of minors in Florida and New York. Epstein started working in September as a physics and mathematics teacher at the Dalton School on the Upper East Side of Manhattan ,   where Donald Barr was the headmaster until June Barr may have hired Epstein. Greenberg's daughter, Lynne Koeppel, pointed to a parent—teacher conference where Epstein influenced another Dalton parent into advocating for him to Greenberg.
Epstein joined Bear Stearns in as a low-level junior assistant to a floor trader. In , four years after joining Bear Stearns, Epstein became a limited partner. IAG ,  which assisted clients in recovering stolen money from fraudulent brokers and lawyers. He told friends that he worked sometimes as a consultant for governments and the very wealthy to recover embezzled funds, while at other times he worked for clients who had embezzled funds.
Epstein also stated to some people at the time that he was an intelligence agent. During the s, Epstein possessed an Austrian passport that had his photo but a false name. The passport showed his place of residence in Saudi Arabia. Florida District Attorney Alexander Acosta , who handled Epstein's criminal case in , said to Trump transition interviewers "I was told Epstein 'belonged to intelligence' and to leave it alone" and that Epstein was "above his pay grade ".
During this period, one of Epstein's clients was the Saudi Arabian businessman Adnan Khashoggi , who was the middleman in transferring American weapons from Israel to Iran , as part of the Iran—Contra affair in the s. They had been introduced through Douglas Leese, a defense contractor, and John Mitchell , the former U. Steven Hoffenberg hired Epstein in , as a consultant for Tower Financial Corporation unaffiliated with the company of the same name founded in , and acquired by Old National Bancorp in ,  a collection agency that bought debts people owed to hospitals, banks, and phone companies.