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
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| - 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
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| - 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"), Roberts was given an opportunity to expunge his record with military service. Roberts claims to have served with the 101st Airborne for four years in Vietnam. He was required to have a metal plate attached to his skull as a result of an injury suffered in an explosion. After working for members of the New York Mafia as a club manager and restaurateur, he moved to Miami to distance himself from business partners he believed were targeted by rival criminals. However, in his book American Desperado, he claims he moved to Miami because both the mafia and law enforcement were after him because he was suspected in the murder of a police officer.
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