Boston’s Mafia Rackets, IRS Wars, and Mob Secrets

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Boston’s Mafia Rackets, IRS Wars, and Mob Secrets

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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, Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. 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 ...

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