In this episode of Gangland Wire, Gary Jenkins, retired Kansas City police Intelligence Detective, is joined by Frank DiMatteo, a man deeply rooted in the Brooklyn mob scene, and his co-author, Michael Benson, a seasoned true crime writer. Frank brings a unique perspective, shaped by his years growing up under the mentorship of mob legends like the Gallo brothers. Together, we dive into the evolution of organized crime in New York, focusing on the rivalry between the Irish and Italian communities as they vied for control of Brooklyn’s Red Hook neighborhood. Frank recounts his early days in the mob, from running simple errands to taking on more significant operational roles. We discuss their latest book, Red Hook: Brooklyn Mafia Ground Zero.
This is a look at the iconic neighborhood, treating Red Hook as a character in the story. The book highlights longstanding rivalries, including how the Irish initially ruled the docks until Italian immigrants arrived and tipped the scales—ultimately leading Frank to conclude that the Irish “lost because they drank too much.”
As we unpack Red Hook’s rich criminal history, Frank and Michael reveal how this area became a breeding ground for notorious figures like Al Capone and Machine Gun Jack McGurn. Through personal anecdotes and broader historical insights, they paint a vivid picture of life in a community that served as both a battleground and home for the mob. Join us as we explore Frank and Michael’s fascinating work, shedding light on the intricate layers of mob life and the neighborhoods that shaped these stories. This episode offers an unfiltered look at the history of organized crime in Brooklyn, revealing the tension between power, loyalty, and survival in a world in the shadows.
To get this book, click here for Red Hook: Brooklyn Mafia Ground Zero.

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Transcript
[0:00] Welcome, wiretappers out there. I’m glad to be back here in the studio of Gangland Wire. This is a retired Kansas City Police Intelligence Unit detective, Gary Jenkins. Gangland Wire is the show, and I know a lot of you guys already knew who I am, but I get some new people every once in a while, so I have a great show for you today. One of these guys, Frank DiMatteo, grew up in the New York families in Brooklyn and around the Joey Gallo gang. He’s got several books out, and Michael Benson is his co-author on this, and Michael Benson, prolific author. And between them, they’ve got books about the mob. I’ve got most of them already. I’ve got The Cigar. We’ve got The Buffy Hitman about Carmine DeBasse. He’s one of the killers of Joy Gallo. A more recent one by Michael Benson and somebody else about moguls in Hollywood. And there’ll be some mob connections. Oops, didn’t have the mob connections to Hollywood. So I want to get Michael on to sometime in the future to talk about that book and Hollywood and the mob, which we know a lot about in Kansas City because we’re so close to Chicago and Chicago are the guys out there in Hollywood and extorted the shit out of them. Anyhow, so welcome guys. Tell us a little bit. Maybe we start with Frank. Frank has this kind of colorful

[1:16] mob history and the way he was raised. Frank, tell the guys a little bit about yourself.

[1:22] Well i was born in my father you know got involved in this life about 1960 i grew up under the under the watch eye of larry gallo joey gallo and alba gallo my godfather is bobby bon Giovanni which is bobby darrow hit guy for the gallo family and my uncle’s joe chapani which was originally with Luciano and Costello and Adonis. These are the mentors and these are the guys that I knew and followed and listened to and picked up everything I had to pick up until I was old enough to move around with them. And when I was old enough to move around with them, I became the driver. I just grew from being a driver for my father and these guys to be more active in the life. Yeah. And I stood there with my life until about 20 years ago. We walked away after it was a big pinch with the last crew we were with. Everybody got arrested. We got some subpoenas. We wound up walking away. And I wound up making a magazine and then now writing with Michael.

[2:33] The magazine is called Mob Can’t Depot. Well, I am a freelance writer. I went to college to learn to be a writer. I was also born in 1956, probably one of the reasons Frank and I get along so well. I started out as a sports writer, wasn’t terribly good at it. I was a pretty good boxing writer. Turns out I was a much better fan than I was a writer when it came to sports. I switched to true crime. I wrote a bunch of books about psycho killers and innocent victims and became a little bit of a TV star doing evil twins and evil kin on the ID network. The market for true crime books softened largely because there were a lot of TV shows, whole networks dedicated to the subject. Books didn’t sell as well. Our editor, Gary Goldstein, found a book that Frank had written called Lion in the Basement. Frank wrote it all by his lonesome. It’s a little bit like a clockwork orange. It’s not quite written in English. It’s written in Frank.

[3:31] So Gary’s idea was to have me take a whack at it and add some new material. I talked to his mom and other people. We put some new things in there and fixed up the English, made the spelling uniform. The result was President Street Boys. And that started a whole thing. We did a bunch of mob bosses. We did a hitman. And then Frank had the idea of, hey, let’s do a book where the hero is the neighborhood instead of one particular mobster.

[3:59] So we start this book, Red Hook, back when the Europeans first arrived. It starts with the slaughter of the Lenape Indians by the Dutch. So, I mean, from the very beginning, the red in Red Hook is for blood.

[4:12] So that’s how Red Hook got its name. I think it has to do with the color of the soil, but it could have been named after the blood that was spilled there. Yeah. I just interviewed an Atlanta-based FBI agent about a case that he did on the Gambino Connected Club called the Gold Club in Atlanta. Michael DiLeonardo took a case, and the owner, Steve Kaplan, had a warehouse in Red Hook. He said, they told me it was in Red Hook. I said, where is Red Hook? I’ve never heard of Red Hook. It couldn’t be more out of the way.

[4:46] It’s one of the reasons it is the way it is because that’s where the docks are. So it’s always been mobbed up, but it’s also geographically isolated more now than ever with the Gowanus Canal, the Atlantic Ocean, the now the Brooklyn Battery Tunnel. It’s a hard place to get in and out of. Interesting. And that’s what I noticed in the book, that Red Hook is the protagonist of this story. It is a character in this story. And you take the readers on a really colorful tour of Red Hook and white hand and black hand gangs, as you said, from the Indians and the white hand, black hand gangs. And those wars between the Irish and the Italians clear up the gas pipe, Casso and got his pal Shorty Masioco, Masioco. I can never get that name pronounced right. But anyhow, you bring them in. You know what? It evokes in me, one of the first mob movies I ever saw when I didn’t realize it was a mob movie was on the waterfront. I think that’s probably where that was set. I would imagine. And that was, that’s what it evokes in me. So yeah.

[5:52] Let’s, maybe we start talking about a little bit about this battle between the Irish and white hand gangs and the black hand gangs and Al Capone is what I’...