Money, Women and Taxes: Jeffrey Epstein’s Fiery Friendship with a Wall Street Titan

Jeffrey Epstein was furious. For years, he had relied on the billionaire Leon Black as his primary source of income, advising him on everything from taxes to his world-class art collection. But by 2016, Mr. Black seemed to be reluctant to keep paying him tens of millions of dollars a year.

So Mr. Epstein threw a tantrum.

One of Mr. Black’s other financial advisers had created “a really dangerous mess,” Mr. Epstein wrote in an email to Mr. Black. Another was “a waste of money and space.” He even attacked Mr. Black’s children as “retarded” for supposedly making a mess of his estate.

The typo-strewn tirade was one of dozens of previously unreported emails reviewed by The New York Times in which Mr. Epstein hectored Mr. Black, at times demanding tens of millions of dollars beyond the $150 million he had already been paid.

The pressure campaign appeared to work. Mr. Black, who for decades was one of the richest and highest-profile figures on Wall Street, continued to fork over tens of millions of dollars in fees and loans, albeit less than Mr. Epstein had been seeking.

Of all the relationships that Mr. Epstein built with the rich and powerful, his friendship with Mr. Black was arguably the most important. After Mr. Epstein served jail time for soliciting prostitution from a minor, many of his contacts backed away. Not Mr. Black, who kept Mr. Epstein afloat for years.

The new emails, along with court documents and interviews, provide the most complete picture yet of that relationship. They come at a time of renewed interest in Mr. Epstein, stoked by the Trump administration’s refusal to release government records related to investigations into him. The president, who was once friends with Mr. Epstein, has sought to deflect attention onto “hedge fund guys” and other prominent men who he says were much closer to the predator than he once was.

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