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

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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