In this episode of Gangland Wire, retired Kansas City Police Intelligence Unit detective Gary Jenkins interviews Eddie Inserra about the Boston Mafia. He is the author of Confidence of the Mob: The IRS Agent Who Took down the Mob – Then Advised Them, a deeply researched account of his grandfather, Fred G. Pastore, a key figure in early IRS efforts to dismantle organized crime.

Fred Pastore was part of the IRS’s early “racket squad,” targeting Boston Mafia enterprises. His work paralleled the groundbreaking financial investigations that helped bring down figures like Al Capone, demonstrating how financial crimes could succeed where traditional policing struggled. Then, he leaves the IRS and advises the Boston Mafia.

Eddie recounts how he uncovered his grandfather’s story through a remarkable archive of family documents, photos, and recordings. These materials revealed a complicated dual life: Fred was both a relentless investigator and, later, a trusted confidant to certain Boston Mafia figures. This paradox sits at the center of the book and this conversation.

A major focus of the discussion is the “pinball racket”—a widespread illegal gambling operation hidden in plain sight within bars and storefronts. Fred’s investigations exposed how these machines generated significant underground revenue streams for organized crime, particularly in Boston. Eddie details the innovative and often risky techniques the IRS used to infiltrate these operations, including undercover work within corporations like Raytheon, where illegal gambling rings had taken root among employees.

The episode also explores the institutional challenges Fred faced. His aggressive tactics and unconventional relationships eventually brought him into conflict with IRS leadership and political figures, forcing his resignation.

In a striking turn, Fred leveraged his deep knowledge of organized crime to advise former mob associates—highlighting the blurred moral boundaries that often exist in this world. Eddie adds a personal dimension, sharing memories of growing up around his grandfather and describing the cultural landscape of Boston’s North End, where family, community, and organized crime often intersected.

These stories provide insight into how relationships between law enforcement and mob figures could be shaped by proximity, respect, and shared environments. The conversation concludes with a look ahead at Eddie’s upcoming podcast, which will expand on these themes through interviews with former IRS agents, mob associates, and others connected to Fred Pastore’s extraordinary life. This episode offers a rare look at the gray areas of justice—where the line between hunter and ally becomes increasingly difficult to define.

Check out the book: Confidence of the Mob: The IRS Agent Who Took down the Mob – Then Advised Them,
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Gary Jenkins: [00:00:00] hey, are you wire tapers? Good to be back here in the studio. Gangland wire. This is Gary Jenkins, retired Kansas City Police Intelligence Unit Detective. Glad to be back in the studio. I have a man on the line who’s written a really interesting book called Confidence of the Mob, the RIRS agent who took down the mafia and then advised him.
So that’s what’s interesting about this. Here’s a man. The, it was part of the early racket squad with the IRS intelligence who were the guys that went after the mafia and in all the different cities, most famously in Chicago, and took down Al Capone, and he ends up in a conflict with his bosses over informant and then.
He goes into business as an accountant and ends up advising Jerry Angelo and some and childhood friends, really. ’cause he grew up in the north end of Boston. So this is his grandson Eddie and Sarah. Welcome Eddie.
Eddy Inserra: Hey, thanks Gary. Glad to be here.
Gary Jenkins: All right guys. Now there’s the book and I’ll have [00:01:00] links to it in the, the show notes as well as you can see the book over Eddie’s right hand shoulder there. You’ll get it. Now. First thing I wanna bring up about this book, Eddie, is I’m gonna ask you a little bit about how you got into this, but about this QR code you have in there, guys, there’s a QR code in there.
I don’t know, about a quarter of the way in. Tell us about that and what was your idea to do there?
Eddy Inserra: Yeah, so the QR code takes you to our website, which is it links to confidence of the mob.com. And this project started off as me interviewing a bunch of people about. My grandfather’s story. So I have all these audio clips, I have all these documents that I found in the box that my mother gave me that really had my grandfather’s complete career in there.
So it’s more of a evidence-based website where if you scan that QR code, you can access some of the documents. Listen to some of the clips by the book, just learn more about the story overall. So it’s, the QR code is meant to be interactive, so you can take from what’s on the book into your phone and just explore more, [00:02:00] right?
Gary Jenkins: Really interesting that with the new internet and you can do so much more and make your, what used to be just a hardcover. Paperback or hardcover piece of, a bunch of papers together and you can go onto the internet and you can find so much more with really not that much effort and a little bit of effort on your part.
I know that I did something like that with a book I did. And it is a little bit of effort, but it’s not as much effort as is really, I think for that to further instruct people, teach people what that life was like for your subject. ’cause that’s what you’re trying to do, is you wanna tell people what.
Your grandfather’s life was like, and so that’s I think it was just ingenious of you to doing that. I haven’t really seen that. I don’t think there’s probably other books that I didn’t notice, but I had not seen that before. Anyhow Eddie, let’s let’s go back. You’re the grandson.
Fred g Pastor, tell us how you got into this, your earliest memories of this. Did you know your grandfather when you were a little kid and probably didn’t get the stories you wish you’d gotten? More than likely [00:03:00] I’d have him. But tell us a little bit about that.
Eddy Inserra: Yeah, so he actually passed away when I was eight years old, so I got to know him for eight years.
He passed away in 1988, and then, I knew my grandfather was always, when you see your grandfather, he is always happy when you’re, a little kid. One side of him, always happy, generous smile on his face, always laughing. Typical grandfather give you candy when no one’s looking.
Things like that. So typical grandfather, I found out later on that his life was much more complex than I had thought. And when I was younger, he had an office. So I’d go into the office and I’d, everybody would be doing accounting work. He’d have probably about, he had about six or seven employees, maybe more at some, sometimes I’d go into the office and I’m just a kid running around the hallways and sitting at the desks.
My father worked there as well. And yeah, I’m just watching them push papers and write down numbers and stuff like that. So I didn’t think it was too, I thought it was pretty boring. It was cool, but it was boring. But later I found out much more about him.
Gary Jenkins: Interesting.
Eddy Inserra: Yeah.
Gary Jenkins: So later on in life, how did you stumble [00:04:00] across this whole dualistic life He had in a way I would maybe dualistic not at the same time but these two careers that he had how did you stumble across that?
Eddy Inserra: There was a box that my mother had in her attic, and it was a, an old Florida citrus oranges box carton and overflowing with papers. And she, about 10 to 12 years ago, she gave it to me and said, Eddie, I want to give you these documents that your grandfather’s documents. I don’t know what’...