Ivan Boesky's first uncomfortable nickname came from his wealthy in-laws, who referred to him as "Ivan the Bum" for his lack of direction. No ring to it, but some truth. The young Boesky had put in stints at three different colleges before finally earning a degree from Detroit College of Law. Later he drifted from job to job, working unhappily as a law clerk and then as an accountant. "My father always considered him a ne'er-do-well," claims his estranged sister-in-law. But once the restless 29-year-old Boesky arrived on Wall Street in 1966, he would never again be indifferent. He was taken with a specialized form of stock speculation called risk arbitrage. It was a sleepy game then, but Boesky learned to play it with such daring and ruthlessness that he horrified the old hands. Who was this scary overachiever, this Russian revolutionary in their midst? "Ivan the Terrible," they called him. )
Boesky (pronounced Bo-ski) was terribly good indeed, thanks to frantic 20-hour workdays, obsessive research and a natural trader's ability to talk on several telephones at once. It was as if he had stored up millions of kilocalories of energy during his aimless years and was now unleashing them on an unwary Wall Street. "Boesky did not really need to cheat," observes Corporate Raider T. Boone Pickens. And yet he did. His relentless drive to get an edge appears to have pushed him right over it. Boesky seemed to expect something like that might happen. "I can't predict my demise," he once said, "but I suspect it will occur abruptly."
His tragic story might be called "The Great Boesky." No amount of money seemed to convince him that he had finally arrived, even when his fortune reached $200 million or more. "He wanted so much to be accepted," says a friend, "and he thought money was the only way." Observes another: "He never realized that really making it means being at peace with yourself." Boesky has now suffered what he probably feared more than anything else: being portrayed as a fraudulent genius. "I always thought he was a rat," declares one investment banker. The disgrace kept welling up for Boesky last week. His book Merger Mania (subtitled Arbitrage: Wall Street's Best Kept Money-Making Secret), a scholarly tome he published last year in an effort to dignify his profession as a science, was abruptly dropped by its current publisher, Henry Holt & Co.
The arbitrager was born and reared in Detroit; his father was one of five Russian-immigrant brothers who operated a succession of popular delicatessens and restaurants in the city. Boesky was known from childhood for his intense desire to excel -- almost to the point of not knowing when to stop. Recalls Roger Boesky, a second cousin who attended the same prep school, Cranbrook, in suburban Detroit: "He had this capacity for single-mindedness. He drove himself mercilessly as far as exercise goes," performing hundreds of push-ups at a time.