Gennaro Angiulo: Boston Mafia Underboss, FBI Takedown, and Trial

Gennaro “Jerry” Angiulo was the underboss of the New England Patriarca crime family and ran Boston’s Mafia operations from the 1960s until his arrest in 1983. Federal prosecutors convicted him in 1986 on racketeering charges built largely on secretly recorded FBI tapes from his North End headquarters, and he was sentenced to 45 years in prison. He served about 21 years, was paroled in 2007, and died in 2009 at age 90.¹

Who He Was

Angiulo was one of seven children born to Italian immigrant grocers in Boston’s North End. He served in the U.S. Navy as a chief bosun’s mate in the Pacific during World War II, despite an initial rejection for flat feet.² After the war he rose through the New England Mafia and became underboss, the number-two position, under Raymond Patriarca Sr., who ran the family from Providence, Rhode Island.

What He Ran in Boston

By the 1960s Angiulo effectively controlled all Mafia activity in the Boston area, operating out of 98 Prince Street in the North End.¹ His operation covered illegal gambling, loansharking, extortion, and adult bookstores, and produced substantial revenue for the Patriarca family.³ Four of his brothers, Francesco, Donato, Michele, and Vittore, worked in the organization alongside him.

The gambling side included numbers, barbooth games, and organized “Las Vegas Nights.” Loansharking loans ran into the hundreds of thousands of dollars. Angiulo was also tied to murder. In 1981 he took part in a conspiracy to kill Angelo Patrizzi, who had been planning to murder two Patriarca members he blamed for his half-brother’s death. After earlier attempts failed, Angiulo helped coordinate the hit. Patrizzi disappeared on March 13, 1981, and his decomposed body turned up months later in the trunk of a stolen car in Lynn, Massachusetts.⁴

How the FBI Brought Him Down

The case that finished Angiulo rested on court-authorized FBI bugs planted at 98 Prince Street and a second location at 51 North Margin Street. Between January and May 1981, agents recorded roughly 29 hours of Angiulo and his associates discussing murders, gambling, loansharking, and other business in detail.⁴⁵

Getting the bugs into place is where the story turns dark for the FBI. Key intelligence used to plan the surveillance came from two rival gangsters: James “Whitey” Bulger and Stephen “The Rifleman” Flemmi. Agent John Connolly had recruited Bulger as a “top echelon informant” in 1975, and Flemmi had been feeding information to the Bureau since the mid-1960s.⁶ The trade was simple. Bulger and Flemmi supplied intelligence on their Italian Mafia rivals, and in return the FBI shielded them from prosecution for their own crimes.⁷

Connolly and his supervisor, John Morris, then chief of the FBI’s Boston organized crime unit, kept the arrangement running for close to 30 years. Morris later admitted taking more than $6,000 from Bulger and confirmed that he and other agents had protected Bulger and Flemmi from investigation for two decades.⁸ Connolly was later convicted of obstruction of justice for tipping Bulger off about an impending indictment, allowing Bulger to flee and remain a fugitive for 16 years. A later congressional report concluded that the Boston office had used Bulger and Flemmi, allegedly involved in at least 19 homicides, as informants for nearly a quarter century.⁹

Arrest, Indictment, and Trial

On the evening of September 19, 1983, FBI agents arrested Angiulo at Francesca’s Restaurant in the North End. As they took him out, he reportedly told the other diners, “I’ll be back before my pork chops get cold!”¹ His brothers Francesco and Michele were arrested at the same restaurant. Donato was picked up elsewhere in the North End.¹⁰

A federal grand jury indicted seven men the next day: Gennaro, his brothers Francesco, Michele, Donato, and Vittore, and lieutenants Ilario Zannino and Samuel Granito. The charges included racketeering involving murder, loansharking, illegal gambling, obstruction of justice, and interstate travel in furtherance of racketeering.¹⁰

Trial began in June 1985 before U.S. District Judge David S. Nelson and ran eight months, the longest federal trial in Massachusetts history at that point. The government called more than 100 witnesses, but the Prince Street tapes were the spine of the case, capturing Angiulo and his associates talking freely about murders, gambling, loansharking, and extortion.⁵ Angiulo was a loud presence in court, drawing repeated reprimands from the judge for sarcastic comments.¹

On February 26, 1986, the jury convicted all five defendants on 29 of 44 counts.³ Gennaro was convicted of racketeering, multiple counts of running illegal gambling businesses, conspiracy to make extortionate loans, obstruction of justice, and conspiracy to murder Angelo Patrizzi.⁴ On April 4, 1986, Judge Nelson sentenced him to 45 years in prison and fined him $120,000.⁵ The jury also ordered forfeiture of hundreds of thousands of dollars in real estate, cash, bonds, and a yacht.

Appeal and Why the Case Mattered

Angiulo and his co-defendants appealed to the U.S. Court of Appeals for the First Circuit. Their strongest argument was that RICO’s “pattern of racketeering activity” element was unconstitutionally vague, leaning on Justice Antonin Scalia’s concurrence in H.J. Inc. v. Northwestern Bell. In its March 5, 1990 decision, the First Circuit rejected the challenge, holding that whatever ambiguity the statute might carry in other contexts, its meaning was clear when applied to organized crime families, the very target Congress had in mind. The court affirmed all convictions and sentences, upheld the trial judge’s refusal to change venue, and rejected claims of juror misconduct. It did reverse parts of the forfeiture order on technical grounds.⁴

The prosecution became a landmark RICO case. It showed that electronic surveillance, asset forfeiture, and broad racketeering charges could be combined to dismantle an entire crime family in a single proceeding, and it set a template federal prosecutors used against organized crime for decades. The Patriarca family’s Boston operations never recovered. Former federal prosecutor Fred Wyshak later said the Mafia’s leadership had been “destroyed” by the succession of federal cases that began in the 1980s and that “nobody really has the strength to step in and fill that void.”¹¹

Parole and Death

The U.S. Parole Commission granted Angiulo parole on June 22, 2007, and he was released on September 18, 2007, at age 88, after about 21 years of his 45-year sentence.¹² He returned to his home in Nahant, Massachusetts, where he had lived with his wife, Barbara, since 1948. His old Prince Street headquarters had been replaced by an upscale pizzeria.¹³

Angiulo died at Massachusetts General Hospital on August 29, 2009, of renal failure caused by kidney disease. He was 90. Funeral services were held at St. Leonard’s Church in Boston’s North End on September 3, 2009.¹¹⁴

1
WBUR. Obit Angiulo
2
Boston Herald. North End Says Goodbye to Former Gangster
3
The New York Times. 5 Are Sentenced for Major Roles in New England Organized Crime
4
United States Court of Appeals. United States v. Angiulo, 897 F.2d 1169
5
UPI. Boston Mob Boss Given 45 Years
6
The New York Times. The Underboss Excerpt
7
NPR. Bulger Case Changed FBI’s Role With Informants
8
Los Angeles Times. FBI Agents Shielded Bulger and Flemmi
9
GovInfo. House Report 108-414
10
The New York Times. U.S. Investigation of Boston Mob Yields Indictments Against 7 Men
11
Boston.com. As New England Mafia Fades Away, FBI Boston Disbands Organized Crime Squad
12
Telegram & Gazette. Boston Mafia Leader, 88, to Be Released
13
UPI. Aging Boston Mobster Gets Early Parole
14
Legacy.com. Gennaro Angiulo Obituary