[2][4] Nat Riccobono was deported from the United States following a federal crackdown on the Mafia in the late 1950s, after which Roberts' mother had his surname changed.

[4] Roberts' mother died during a medical operation when he was thirteen years old, and he subsequently lived with his stepfather and then with various relatives, including a sister in Brunswick, Maine.

[4] At the age of sixteen, he returned to New York and began working for his loan shark uncles as an enforcer and debt collector.

[2][3][4] In 1965, at the age of seventeen, Roberts was arrested for kidnapping and attempted murder after a severely beaten debtor escaped from a basement "with a chair tied to him and no clothes on".

[3][4] Roberts made claims that was given an opportunity to expunge his criminal record with military service and subsequently joined the United States Army, serving for five years.

[1] He made claims that he had served on a long-range reconnaissance patrol team and was selected for missions to carry out assassinations in Cambodia.

"[2] Despite all of Roberts' claims about his time in Vietnam, journalist Evan Wright who profiled his life in the book American Desperado found absolutely no records of him ever serving in the military.

This included a Freedom of Information request to the National Archives which showed no data on him ever fighting in the War in Vietnam or serving in the military.

[7] Nevertheless, Roberts and Munday began working under the supervision of Max Mermelstein, who had an agreement with Salazar to manage the transportation of cocaine from Colombia to Miami.

In American Desperado, Roberts describes: "After I made my first big score selling coke to Bernie Levine in California, Danny Mones told me racehorses were a good way to launder money."

He recounts prominent people he met through his racehorse connections, such as "Judge Joe Johnson, who hosted horse auctions", and through him, "We got friendly with Cliff Perlman, who owned Caesar's Palace.

[11][12] Mermelstein acted as a high-level trafficker working under cartel member Salazar and with the Munday transportation group.

[7] According to his ex-wife and various other sources, Roberts used his past to gain trust within the criminal community and report their activities to the authorities in order to maintain his prison-free status.

When I told him last week this story would be published, the craggy, gray-mustached ex-gangster vowed, "You will never write another word in this town again...

"The outburst is in character with Roberts' gangster-flick biography, which he described in an on-the-record interview before changing his mind about publication".

For example, they share that Roberts was not completely reformed in his later days: Garcia-Roberts: In the book, you write that Jon--who as a felon is not allowed to have guns--showed you silencers he kept buried in his backyard.