Scratch & Win: Part 4 – The Last Mafia Boss of Boston
Release Date: February 12, 2025
Host/Author: GBH News
Produced by: Isabel Hibbard and Ian Coss
Executive Producer: Devin Maverick Robins
Distributed by: PRX
Introduction
“Scratch & Win” delves deep into the intricate tapestry of American gambling history, focusing on the rise and fall of Boston’s most formidable Mafia family. In Part 4: The Last Mafia Boss of Boston, listeners are taken on a riveting journey from the shadowed alleys of 1970s Boston to the corridors of power within the FBI. This episode meticulously unpacks the FBI’s strategic assault on organized crime, the pivotal role of the state lottery, and the enigmatic figure of James "Whitey" Bulger.
Background: Organized Crime in Boston
The tale begins in the early months of 1979 when FBI photo specialist Bill Sheparly and his colleague John Gill infiltrate Boston’s notorious North End, specifically targeting 98 Prince Street, the epicenter of the local Mafia and illegal numbers game operations.
Nomi Frye [01:00]: "The North End was an isolated and insular place surrounded by water and cut off from the rest of the city by six lanes of elevated highway."
The North End, once a vibrant Italian enclave, was a fortress of tradition where Mafia influence thrived unchallenged, providing a stark contrast to the emerging state-run gambling enterprises.
The FBI’s Strategic Assault
The FBI, under the guidance of Attorney General Robert Kennedy, had been amassing a robust toolkit to combat organized crime, culminating in the Racketeer Influenced and Corrupt Organizations Act (RICO). This legislation allowed for the prosecution of entire criminal organizations rather than just individual members.
Nomi Frye [07:00]: "With RICO, if you could prove a pattern of criminal activity connected by a single criminal enterprise, then you could prosecute everyone involved at once, root and branch."
Sheparly and Gill were integral to this nationwide offensive, representing just two of the many agents mobilizing to dismantle entrenched Mafia operations across the country.
Operation at 98 Prince Street
The operation centered on installing surveillance equipment at 98 Prince Street. Initial attempts to discreetly monitor the premises faced setbacks, including the discovery of hidden cameras by Mafia boss Gennaro Angiulo.
John Gill [03:19]: "We knew it was all over."
Undeterred, the team pivoted to using a specially modified 1968 Chevy with a concealed camera to capture continuous footage from the outside, while simultaneously embedding an audio bug inside the premises.
John Gill [05:29]: "The camera car could get a clean shot up to about 100ft out."
This dual approach was critical in gathering the comprehensive evidence needed to build a airtight RICO case against the Angiulo family.
Key Figures: Gennaro Angiulo and James "Whitey" Bulger
At the helm of the Mafia operations was Gennaro Angiulo, whose leadership was both fearsome and strategic. In parallel, James "Whitey" Bulger, a rising star in the Winter Hill Irish gang, maintained a delicate and clandestine relationship with the FBI.
Nomi Frye [17:28]: "Whitey Bulger was now the top figure in the Boston crime world, and the numbers was never really his specialty."
Bulger, referred to by the FBI as a "strategist" rather than an informant, provided invaluable intelligence that facilitated the FBI’s infiltration and eventual takedown of the Angiulo family.
The Surveillance Operation
The covert surveillance operation was grueling. Agents like Sheparly adhered to a strict routine of swapping and charging multiple batteries daily to keep the surveillance equipment operational.
John Gill [24:05]: "We probably went through 25 to 30 batteries."
This relentless maintenance underscored the operation’s high stakes and the agents’ unwavering commitment. Despite technical challenges, including a near-disastrous battery explosion, the team persevered, capturing crucial audio evidence over months of meticulous monitoring.
John Gill [25:15]: "The battery blew up in his face."
Trial and RICO Case
The amassed evidence culminated in a landmark trial in February 1986, where Gennaro Angiulo and his brothers were convicted under the RICO statute. This was one of the first major RICO cases that successfully prosecuted an entire crime family rather than just individual members.
Ernie Danisko [32:19]: "This was the first one that dealt with an entire crime family like that."
An audibility hearing was pivotal in establishing the legitimacy of the taped evidence, despite initial challenges in presenting the fragmented and often inaudible recordings.
Nomi Frye [33:27]: "Without the tapes, there is no case."
The conviction marked a significant victory for the FBI, signaling the effectiveness of coordinated legislative and tactical efforts against organized crime.
Impact on the Gambling Industry and State Lottery
The downfall of the Angiulo family had a profound impact on Boston’s illegal gambling landscape. The state lottery, having launched its own numbers game as a legal alternative, found itself at a strategic advantage as organized crime’s influence waned.
Kevin Weeks [40:11]: "The government sees money to be made, they get involved in it. They're the biggest gang in the country."
The transition from illicit, community-driven numbers games to state-controlled lotteries transformed the gambling industry, reducing the reliance on violence and fostering a more regulated environment.
Nomi Frye [41:05]: "The game was held together by violence, or at least the threat of violence... It was part of the community in a way that no state lottery could ever be."
However, this shift also opened debates on the ethical implications of state involvement in gambling and its role in perpetuating a legalized form of gaming.
Conclusion
“Scratch & Win: Part 4 – The Last Mafia Boss of Boston” offers a comprehensive exploration of the intricate battle between the FBI and Boston’s organized crime. Through detailed storytelling, firsthand accounts, and archival recordings, the episode not only chronicles the fall of Gennaro Angiulo but also highlights the broader socio-economic transformations influenced by state-run lotteries and the enduring legacy of figures like Whitey Bulger.
Ernie Danisko [40:20]: "You had housewives and little old ladies and everybody... it was well understood."
This episode serves as a poignant reminder of the complexities surrounding legal and illegal gambling, law enforcement’s evolving strategies, and the profound impact of legislative measures like RICO on dismantling entrenched criminal networks.
Notable Quotes
- John Gill [05:29]: "The camera car could get a clean shot up to about 100ft out."
- John Gill [24:05]: "We probably went through 25 to 30 batteries."
- Ernie Danisko [32:19]: "This was the first one that dealt with an entire crime family like that."
- Kevin Weeks [40:11]: "The government sees money to be made, they get involved in it. They're the biggest gang in the country."
- Nomi Frye [41:05]: "The game was held together by violence, or at least the threat of violence... It was part of the community in a way that no state lottery could ever be."
Further Resources
For those interested in a more in-depth exploration, the episode references the book “The Rise and Fall of a Mafia Family” by Gerard O'Neill and Dick Lehrer, which provides a comprehensive account of the events discussed. Additional interviews with FBI agents and prosecutors, including Jane Serene Raskin and John Voorhees, offer nuanced perspectives on the case's complexities.
For more episodes, archival footage, and full transcripts, visit gbhnews.org/scratchandwin or check out the GBH YouTube channel.
Artwork by Bill Miller and Mami Hawa Bao. Closing song "You Made Me Love You" performed by Massachusetts State Treasurer Bob Crane. “Scratch & Win” is a production of GBH News and distributed by PRX.