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. Click here to find books by mob expert Gary Celemente

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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[0:00] Hey, all you wiretappers, Gary Jenkins back here in the studio of Gangland Wire. I am a former Kansas City Police Intelligence Unit detective and now turned podcaster and documented filmmaker. We record the mafia, everything we can about the mob. And today I’ve been wanting to do this story, guys, as a man named Nicola Gentile. Did I get that right, Gary? Beautiful. All right. This is Gary Clemente, and Gary’s been on before, or GP Clemente. He’s been on before. His father was Peter Clemente, who was one of the original Sicilian-born FBI agents in the United States and did a lot of translation work with Bellacci. And he’s written, he’s writing books. So we talked about the first book, but tell just a little bit more about it. And guys, I’ll have links to that book. And then tell me a little bit about the two more you have coming out. The first book that I wrote in a series of books about my father’s lengthy FBI career is called Untold Mafia Tales from the FBI Top Hoodlum Squad.

[1:04] And it’s about my father’s career in the mafia from 1950 to 1976. And in 1957, he became a part of the Top Hoodlum squad, which is an elite group that J.H. Goober started as part of the Top Hoodlum program. And what happened was in 1957, they had a big mafia conclave meeting in Appalachian, New York.

[1:30] And they had about 60 members of the mafia throughout the country, all the bosses that attended this meeting. And it became publicized. The cops were there. They confiscated their identification, their wallets, the money, everything. And it got released into the news. This was a big story.

[1:50] So what happened was J. Edgar Hoover at that time had been denying the existence of the mafia for a number of reasons. Probably because he didn’t want to get involved with all of the muck of trying to prosecute these gangland people because he knew that they had a lot of buffers between the bosses and the guys committing the murders. So he knew it was going to be difficult, and it would blemish their conviction record and rate. So he kind of stayed away from it, denied the existence of the mafia, And along comes this Appalachian Conclave meeting. It got released into the news, and everybody was up in arms about this. That’s when Hoover decided to start the Top Hoodland program, because there was absolutely no denial of what was going on here, that there was some sort of vast criminal organization that was highly organized, and he had to do something about it. So in 1957, my father became part of the Top Hoodlum program.

[2:54] And in particular, the Top Hoodlum squad in New York City, which is really a hotbed of mafia criminal activity. You couldn’t get any more hotter than what they had. They had five mafia families alone in New York. And the first book was really about how my father confronted Carlo Gambino, how Carlo Gambino became one of his original subjects for him to study and to profile.

[3:24] He was ordered to do that, and he was happy to do that. The book is really about him confronting face-to-face with Carlo Gambino, and then afterwards wiretapping him at the Golden Gate Hotel in Miami Beach, Florida. He was on the other side of a wall. From Gambino for six weeks. Gambino did not know he was on the other side of the wall wiretapping him with another agent. So that’s what the first book was about. And the second book is about really the backstory of my father’s life before he got into the FBI a little bit. Then his first years in the Bureau, when he was a part of the investigation of the Communist Party and the Workers’, Party and the few offices that he was in, like the Springfield, Illinois office, and also Cleveland. And then he became a part of the New York office. He was still investigating communist activities at the time. And then he became a part of the Top Woodland squad. And his milieu, his wheelhouse, became organized crime and the mafia. So that’s generally what has happened so far. The second book is being released this coming month, and it will We’ll have book two and book three talking about these sorts of things.

[4:44] Interesting. Interesting. All right, guys, I’ll have a link to the old book down there in the show notes and look for that new book coming up and we’ll get back together. I’ll get back with Gary after the book comes out sometime and we’ll do another show. And we’re not going to talk about the mafia so much. We’re going to talk about these activities, which I think is interesting, of the FBI against the Social Workers Party and the Communist Party USA because they did a lot of work. When I was growing up, Gary, do you remember I Led Three Lives, the TV show about, his last name was Phil Brick. It was a weekly TV show about an undercover FBI agent who supposedly was working as a member of the Communist Party. He would go to these meetings and things like that. Do you remember that? I Led Three Lives. I do remember that. That show goes way, way back. What year was that show? Oh, that had to be 1953, 54. I had to be like 9, 10 years old, 55. I was 10 years old, so it probably may be 1955. I do remember the show. I think I’ve seen reruns of it. Yeah, I bet it’s on YouTube. I have to look that up for fun one of these days.

[5:52] Issue Machine’s show back then, we will talk about this later on at another time as regards to the second book. Back in the 1950s, J. Edgar Hoover’s main enemy was the Communist Party. It wasn’t organized crime. That was his top focus. He wrote a book called Masters of Deceit. And people, I think everybody, they should have this book in public school system, but they don’t want to do that today. Today’s public school system, they try to inculcate youngsters in more social activities and social warriors and not learning about the perils of Marxism and communism.

[6:33] Okay, today we’re going to talk about Nicola Gentile. Now, 1903, he was a Sicilian immigrant that came to the United States, and he found a lot of opportunity among the other Sicilian immigrants because he was a blackhander, if you will, when he first got here. He was a criminal who came over from Sicily, but he was able to move among all the different families, all the different cities, and settle disputes and help people get organized and do things like that. Gary, start telling us a little bit about what you remember about Nicola Gentile. First of all, I want to tell people that Nicola Gentile was an uber jovelace. He was jovelace on steroids. Somebody later on in his life, toward the end of his life, he wrote his memoirs down. This was in 1963. So what happened was he published his memoirs in Italy. He had a co-author, he had another journa...