Charlie

            Charlie "Lucky" Luciano was born in Italy in the last years of the 19th century, and emigrated to the United States as a teenager with his family. His first brush with the law was in 1915, when he was convicted on a charge of drug possession. Upon his release, he became part of the Joe Masseria game, and he became known as "Lucky" after surviving a particularly brutual beating from a rival gang. Shortly after, he joined up with the men that had assaulted him, and put out a (successful) contract on the life of his former boss, Masseria. He was one of the top bosses in New York during the roaring twenties, but was sentenced to prison for assisting prostitution in 1930. He remained in prison throughout WWII, but served as an informant on Italian politics, and once the Allies defeated Italy he was released on "good behavior". He returned to his homeland soon after but managed to play a significant role in the American mafia until his death in 1962.
             Roy DeMeo was one of the most successful Mafia hit men ever to work in the Syndicate, with a victim count estimated in the hundreds. As a young boy, he worked in a butcher shop, and he managed to transfer his learning into his adult occupation, allegedly educating hit-men-in-training on how to efficiently dismember and conceal victims. He began working for the Gamboni crew in the late sixties and soon gained a reputation as a professional, but as his reputation grew so did his bloodlust. He managed to gain the attention of the FBI by the early eighties, when he was ordered by the clan boss to stay under the radar screen. He continued to kill with abandon, infuriating his superiors, but no one was willing to knock him off. Frustrated, the Don ordered an second-level boss to stop DeMeo for good, and his body was found in the trunk of his car in 1983.