Born John Riccobono in New York City to Sicilian American parents. His father Nat Riccobono had earlier moved with his brothers from Sicily and made a living through involvement with various shady businesses throughout New York in the late 1940s. After his father was deported and his mother died, Roberts moved from home to home until he was 16 and later became an enforcer for a loan-sharking operation run by his uncle, "Staten Island" Joseph Riccobono, a Gambino crime family consigliere who attended the 1957 Apalachin Conference. By the time Roberts was 26, in 1978, he was a practiced criminal — committing robberies and dealing cocaine in New York City. After being apprehended by police for kidnapping (a debtor who escaped from a basement "with a chair tied to him and no clothes on"), Robe