In this episode of Gangland Wire, host Gary Jenkins sits down with author Daniel Zimmerman, whose investigative works dive deep into the dark corners of Boston’s organized crime world. Zimmerman has written two gripping true crime books that reveal the raw and often tragic realities of life on the fringe of the Mafia. He recounts his research for his book, Shots in the Dark, which led him to an informal meeting with former New England boss Peter Limone.

His first book, Shots in the Dark, tells the harrowing tale of Rocco Anthony Balliro, a Boston mob associate whose desperate and poorly planned rescue mission turned into a deadly shootout. Believing he was storming into danger to help a friend, Rocco unknowingly walked into an ambush set by Boston police. When the smoke cleared, the cost was unimaginable—his girlfriend and her young son lay dead. Zimmerman takes us behind the headlines, exposing the chaos, confusion, and heartbreak of that fateful night.

Zimmerman’s second book, Chasson’s Run: The Prison Break That Captivated America and the Love Story That Fueled It, shifts focus to one of Boston’s most violent and manipulative criminals. This is the story of a man so dangerous, yet so persuasive, that he convinced a woman to help him escape from the infamous Walpole State Prison. It’s a tale of charm, obsession, and reckless loyalty—set against the backdrop of one of the most dramatic prison breaks in U.S. history.

Join us as Daniel Zimmerman unpacks these explosive stories and reflects on the twisted loyalties, romantic delusions, and violent consequences that define Boston’s mob lore.

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transcript
[0:00] Hey, welcome all you wiretappers. Good to be back here in the studio of Gangland Wire. I have today Daniel Zimmerman, a little bit different sort of a story. Now, he has another book a lot of you guys might be a little more interested in. We’re going to talk about that just a little bit. But the main book we’re going to look at is Chasson’s Run. I think I pronounced that right, Daniel. It’s actually Chasson. Chasson’s Run. Chasing somebody, which kind of fits the picture here. I think it’s a story that, well, Daniel Zimmerman, welcome. I really appreciate you coming on. Well, thank you. I appreciate you having me for this talk. Yeah. Now, Daniel, tell the guys a little bit about yourself. So tell the guys a little bit about your story. Well, oddly enough, I am a newspaper writer, but not the type you would think. I’ve been writing for over 25 years now, actually, a column or columns for local newspapers. And I cover, of all things, high school sports. I go out to area high schools. I watch the games. I take notes, take interviews, grab comments from players

[1:00] and coaches, go home and write it. And a couple of days later, it’s in the newspaper. Is that in the Boston area? Yes. Great Boston area. 25 years I’ve been doing it. You know, it’s funny you say that because I did a library presentation for my first book. And one of the questions in the audience from a woman was, how do I translate writing high school sports into writing mob books? Yeah. And I told her, you know, there’s two aspects of both. You have to, number one, be able to research, find out information.

[1:29] Keep track of information, and be able to do an interview with your subjects. And in this case, it would be athletes and coaches. On the book writing side, you’re reaching out to suspects and police officers and so forth. So there’s a technique and there’s a skill you learn in both. And I think they translate well into each other. You’re really both just trying, in both situations, you’re trying to get people to tell you a story and give you some interesting little sound bites in both stories. Trust me. Trust me. I get that a lot. As far outside of the newspaper writing, my full-time work over the last five decades has been the first part of my life I worked as an EMT, emergency medical technician, for a private ambulance service, but it happened to be a private ambulance service located within a 15, 20-minute range of two of the most notorious prisons in Massachusetts, MCI Walpole and MCI Norfolk. And the company that I worked for as an EMT, was tasked with transporting inmates to the hospital for a wide assortment, whether it be illness or injuries, stab wounds, you name it. We were the ambulance service that handled that. The second half of my life, I transitioned from being an EMT to working for a major utility, a gas company. And I was a supervisor who would oversee crews that would repair gas leaks in the street. So pretty dangerous work.

[2:49] And it’s kind of funny. I mentioned library talks. Another audience member had said to me, she said, so let me get this straight. You were an EMT going in and out of prisons on a regular basis. And then you switched to dealing with potentially explosive gas leaks and interview mob guys to write a book.

[3:09] You know, how do you sleep at night? Sleep better. Sleep better that way. Get your adrenaline out during the day. So there’s another book, Shots in the Dark, The Saga of Rocco Ballero. Okay, good. Tell the guys a little bit about that, then we’ll get into this book. Well, Rocco was a small time, I describe him as a petty criminal. He was part of a mafia family out of the north end of Boston. His family, the Balleros, worked directly under the main family, the major family in the Boston area, and that was the Anjulos. The Anjulos, in turn, answered Patriaca, who was out of Providence, Rhode Island. So that was the tear. Rocco’s family was two down from the top. And Rocco was at the time that this story took place, only in his early 20s, early to mid-20s. And again, just coming up in the business, so to speak. The same business that his five brothers and father were all involved with all through their lives. Unfortunately, he got swept up into a double murder that he was framed for. Two people perished, a 21-year-old woman and a two-year-old toddler killed in a crossfire.

[4:16] And they were my aunt and my cousin.

[4:18] That’s how I knew the story. It was 1962. I was a toddler myself. I was only two years old, so I don’t have direct memory of the incident. But obviously, I grew up, family members would tell me. And then when I got to a point where I was writing on a regular basis, I decided that I was going to tell the story. And I spent a year researching it, making sure that I had the material to do what I wanted to do. And then I reached out to Rocco. He was incarcerated at MCI Norfolk at the time.

[4:46] And more or less, I wrote a letter and asked him if I could come see him. And he couldn’t get me there fast enough. He wanted the story told. Yep. And so I went to visit him at the prison. And a few years later, you have the book written and done. And Rocco’s story is told. Unfortunately, he didn’t live long enough to see it happen. He died from c...