Among twentieth-century gangsters, few combined ruthlessness with bizarre personal habits quite like Vincent "the Chin" Gigante. A former hit man who climbed to the top of the New York crime world, Gigante ran the powerful Genovese family in the 1980s and 1990s. But he also drew attention. For unlike the stereotype of grim and dapper Mafia leaders, Gigante's image bordered on the absurd. "The Oddfather," as some called him, was famous for strolling Greenwich Village in his pajamas and slippers, muttering and relieving himself. He attended court dates in a bathrobe. Whenever legal trouble beckoned, the mobster checked himself into psychiatric clinics. Was it all an act? After several efforts, federal prosecutors finally convinced a court that he had been feigning insanity for more than thirty years.

Born on March 29, 1928, Gigante, the son of a jewelry engraver father and seamstress mother, tried boxing in his twenties. He joined...