LUCKY LUCIANO: Criminal Mastermind

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Luciano also led the trend in gangster chic. He lived large, in a suite at the Waldorf Astoria. Expensive and elegant suits, silk shirts, handmade shoes, cashmere topcoats and fedoras enhanced his executive image. There was always a beautiful woman, a showgirl or a nightclub singer on his arm. Sinatra and actor George Raft were pals.

The good life ended in 1935. Thomas E. Dewey was appointed New York City special prosecutor to crack down on the rackets. He targeted Luciano, calling him "the czar of organized crime in this city," and charged him with multiple counts of compulsory prostitution. The trial was sensational. Tabloids went wild. Lucky vehemently denied being a pimp. "It's a bum rap," he said, a lament echoed down the years to modern Miami, where a few aging mobsters remember the man. "Nobody had anything bad to say about Charlie," one of them told me. "He's the one who put it all together. A gentleman. He'd give a girl a hundred dollars just for smiling at him. That pimp charge was a frame just to get him off the streets." Convicted on 62 counts in June 1936, Luciano got 30 to 50 years in prison.

It took Hitler to win Lucky his freedom. After Pearl Harbor, German U-boats off the U.S. coast were sinking merchant ships regularly. U.S. intelligence suspected they were aided by spies or Nazi sympathizers. Then the Normandie, a French liner being retrofitted into a troop ship, sank in the Hudson River, sparking fears of sabotage.

Stymied intelligence agents turned to the underworld for help. Lansky, known in the '30s for breaking heads at pro-Nazi meetings, acted as liaison and was allowed to visit Luciano. Lucky put the word out to cooperate, and formerly mute dockworkers, fishermen and hoodlums became the eyes and ears of naval intelligence. Soon eight German spies, who had landed by U-boat, were arrested, and explosives, maps and blueprints for sabotage were seized.

When the invasion of Italy was planned, the Allies needed intelligence for the landing at Sicily. Lucky for them, again. On V-E day in 1945, Luciano's lawyer petitioned for clemency, citing his war efforts.

Eventually, a deal was reached that included deportation--Luciano had never become a citizen--and he was sent to Italy in February 1946. He surfaced months later in sunny, pre-Castro Cuba. Lansky, Sinatra and other pals paid visits--so many, in fact, that the press took note, and in February 1947 the U.S. Bureau of Narcotics learned of Luciano's reappearance in the Americas. U.S. authorities claimed that he planned to headquarter a worldwide drug-smuggling operation in Cuba. Lucky was again packed off to Italy.

He died there, in homesick exile, on Jan. 26, 1962. Unlike so many of his predecessors and colleagues, he expired of natural causes, a coronary--an occupational hazard common to hard-driving executives. Or maybe he was just lucky. Italian and U.S. officials quickly announced they had been about to arrest him in a $150 million heroin ring. The fatal attack came at an airport, where he had gone to meet a Hollywood producer.