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embrace a level of acute abstraction. “In the past,” says Epstein, “investing was all about reputations and relationships. You invested in a company on the basis of who was running it. Did they have integrity? Were they married? Good family men? It was a ‘50s mentality. But in the mid ‘70s options started to be traded. In essence, the first formal derivatives. The movement of this instrument is not directly attached to the stock price. The world of investing began turning from relationships to math. In a sense I didn’t really make money as much as I tried to create it. This was intellectual activity of a fairly high order.” Intellectual activity aside, he met Helen Gurley Brown and she made him Cosmopolitan Magazine’s Bachelor of the Month in 1980. “What,” I ask, “was your social life like?” “Well, I was a playboy.” “That’s all? Not looking to get married?” “No. Never. I never wanted to get married. I enjoyed sex. I adore women. I wanted freedom. I was attracted to the rich because of their freedom. But I wanted also to avoid their burdens. And I didn’t want to hide. I didn’t want to be a hypocrite. I wanted to be free. I was not remotely ambivalent about what I wanted: to be free. That was the reason to make money.” His rise at Bear Stearns was a swift one. And he soon became the protégée of Jimmy Cayne (also hired by Ace Greenberg on a whim—he met him in a bridge game), who would go on to run Bear and to lose his HOUSE_OVERSIGHT_022880