In the 1920s and 1930s, Kennedy was well on his way toward amassing a personal fortune that the New York Times valued at $500 million at the time of his death in 1969. He earned his money through banking, real estate, corporate takeovers and consulting, liquor importing, and movie production, displaying a Machiavellian flair that left a trail of broken companies and smashed careers in his wake. Movie superstar Gloria Swanson, who was Kennedy’s mistress and management client before he double-crossed and abandoned her, recalled that Kennedy “operated just like Joe Stalin”; “their system was to
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