In this episode of Gangland Wire Crime Stories, I dive into the intricate world of the Boston Mafia, focusing on the notorious Gennaro Angiulo family and their operations. As a retired Kansas City police intelligence detective, my fascination with organized crime has led me to some of the most compelling stories in law enforcement history. Today, I’m joined by Ian Cross, an expert on Boston’s underworld, for a deep dive into the city’s mob landscape, the power struggles between the Italian and Irish factions, and the innovative tactics used to dismantle these criminal empires.

We start with a behind-the-scenes look at the FBI’s surveillance methods—how agents installed covert microphones, maintained secrecy, and penetrated the Mafia’s inner circles. I share a striking Kansas City case where a courtroom revelation exposed a long-hidden bugging technique, shedding light on the FBI’s relentless efforts. Ian provides his expertise on Boston’s organized crime scene, detailing how law enforcement’s meticulous strategies put pressure on the Angiulo family’s gambling empire.

Ian also introduces us to The Big Dig, his previous podcast exploring Boston’s controversial tunnel project and its ties to corruption and organized crime. This leads us to the heart of today’s episode—Gennaro “Jerry” Angiulo, the underboss who controlled the city’s illegal gambling operations from the North End. We discuss his rise to power, his strategic avoidance of violence, and the FBI’s elaborate efforts to bring him down through surveillance and legal maneuvers.

As we unpack the Angiulo family’s criminal enterprise, Ian shares gripping details of the FBI’s wiretaps—how agents captured Jerry’s conversations, exposing the inner workings of Boston’s Mafia. We also explore the broader impact of these investigations, including the tensions within the organization and the shifting landscape of organized crime in the city.

Ian previews his upcoming podcast, Scratch and Win, which explores the Mafia’s transition from controlling underground gambling to the rise of state-run lotteries. It’s fascinating how organized crime adapts to new realities while continuing to operate in the shadows. Join us for this in-depth discussion on one of Boston’s most influential Mafia families and the law enforcement strategies that ultimately took them down. Don’t forget to subscribe for more true crime stories from organized crime.

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Gennaro Angiulo Wiretapped