Keystone Press/Zuma Press/Newscom/File
Crime boss Charlie Luciano redefined New York City organized crime in the 1930s, pushing for its infiltration of legitimate businesses and for a more orderly chain of command. Although he was a murderer, he was convicted of leading of a prostitution ring in 1935.
Luciano was sentenced to 30 to 50 years in prison, but received a shorter term in exchange for helping the U.S. military during World War II. Luciano used his underworld connections to help U.S. intelligence agents locate German spies. He later used his Italian connections to help the U.S. Navy plan its invasion of the country. In 1946, New York Gov. Thomas E. Dewey pardoned Luciano, under the stipulation that he would be deported to Italy. Luciano died there in 1962.