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

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

From Gangland Wire by Gary Jenkins: Mafia Detective

May 11, 2026 · 29 min

About this episode

Gary Jenkins interviews Eddie Inserra about the Boston Mafia and his grandfather's dual role as an IRS investigator and advisor to mob figures.

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…

People in this episode

Host: Gary Jenkins

Guest: Eddie Inserra

Topics covered

Keywords

Mentioned in this episode

Organizations: IRS, Boston Mafia

Books & works: Confidence of the Mob: The IRS Agent Who Took down the Mob – Then Advised Them

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