In this episode of Gangland Wire, host Gary Jenkins sits down with author and historian Gary Clemente for a deep dive into the remarkable life of Nicola Gentile, one of the most influential yet little-known figures in early American organized crime.
Gentile was no street thug. Born in Sicily in 1884, he immigrated to the United States in the early 1900s and became a roving Mafia diplomat—trusted to mediate disputes among crime families in cities such as New York, Pittsburgh, Cleveland, Kansas City, Pueblo, Chicago, and beyond. Known as Zio Nicola (“Uncle Nick”), Gentile operated as a stabilizing force during the most violent period of Mafia history, including Prohibition and the Castellammarese War.

Clemente reveals that Gentile’s story survives largely because Gentile broke the ultimate Mafia rule: he wrote memoirs. Those writings—published in Italy in the 1960s—were seized by the FBI and later translated by Clemente’s father, Peter Clemente, one of the first Sicilian-born agents assigned to the FBI’s elite Top Hoodlum Squad. The episode offers rare insight into those translations and the intelligence value they held for federal investigators.

The discussion traces Gentile’s interactions with legendary figures such as Carlo Gambino, Al Capone, Lucky Luciano, and Vito Genovese, as well as his behind-the-scenes role in shaping the Mafia’s modern organizational structure—including the creation of the national Commission.
The episode also explores Gentile’s personal contradictions: a lifelong criminal who saw himself as an honorable man, a mediator capable of violence, and a romantic who later believed a lover betrayed him to federal authorities. After fleeing the U.S. under indictment, Gentile returned to Sicily, where he later provided intelligence to Allied forces during World War II—another unlikely chapter in an already extraordinary life.

Despite being sentenced to death by Mafia leaders for publishing his memoirs, Gentile was spared due to the respect he commanded on both sides of the Atlantic. He died peacefully in Sicily in 1970, leaving behind a story so expansive it feels tailor-made for film.


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