Black Mass

Morris, as the supervisor of the Organized Crime Squad, weighed in with an addendum that also distorted the record being compiled in the Charlestown tape room and from a steady stream of FBI informant reports. He proclaimed that the Winter Hill gang was dead. The passé, empty shell that foundered when Howie Winter went to jail, Morris concluded, “does not merit further targeting at this time or anytime in the foreseeable future.”

Angiulo’s preference for an all-Mafia hit team on Patrizzi may not have been included in Connolly’s FBI memo to Sarhatt, but the FBI tapes were still damaging to Bulger if anyone paid attention or was pointed in the right direction. Angiulo’s true sentiments were recorded earlier in the bugging when he talked about all the people who would kill for him. Talking to a soldier about Bulger and Flemmi, Angiulo said, “We could use them. If I called these guys right now, they’d kill any fuckin’ body we tell ’em to.” Connolly had no choice but to steer people away from such damning declarations.

In the end, nine men dragged Patrizzi, nicknamed “Hole in the Head” (and proclaimed “real dumb” by the likes of Freddie Simone), out of a private club. They hog-tied his legs to his neck, put him in the trunk of a stolen car, and let him slowly strangle himself to death. His body was found months later in the far corner of a parking lot behind a little-used motel north of Boston. The listening FBI agents heard the plotting against Patrizzi and Zannino’s concerns that the state police would find the parole violator before the Mafia did, but they did virtually nothing to intervene. Federal prosecutors convicted Angiulo of the murder seven years later, but nothing was ever done to stop it from happening.

THE FBI also turned a deaf ear to Angiulo’s monomania about Bulger’s $245,000 debt, incurred when he took over the Winter Hill gang in 1978. The money was being used for loan-sharking; Winter Hill charged 5 percent a week but was not paying Angiulo his 1 percent. Bulger claimed the debt was $195,000, and Angiulo became convinced that he was never going to be paid. Since there was nothing he hated more in his tightly controlled world, the debt could mean war. But it would put more blood on the sidewalk than the frustrated Angiulo was willing to shed.

Beyond the much discussed dispute over the loan-shark money, Angiulo and Bulger clashed over who controlled Watertown bookie Richie Brown. After Howie Winter went to jail, Bulger had begun clamping down on any bookie who strayed onto his playing field. Pay or die. Whitey told Brown that it would cost him $1,000 a week to stay in business and that his boss, Mafia bookmaker Charles Tashjian, should come see him. Following standing orders, Tashjian said to Bulger that he “belonged to Prince Street. Talk to Danny Angiulo.”

Both sides had given the mobster version of a Miranda warning. A confrontation was now inevitable. Whitey and Stevie had no choice but to go see Danny, the one truly tough Angiulo, a killer who had made his bones on the street, unlike the short, voluble Jerry. The brothers were not on the best of terms. Every once in a while Danny would throw it in Jerry’s face and their estrangement would result in Danny avoiding Prince Street. Then he would work out of his own office around the corner in the back of the Cafe Pompeii.

In a breach of protocol that left the sensitive Jerry fuming, Bulger and Flemmi made an unannounced visit to Danny’s office, asking about Richie Brown. In a conversation related by Jerry to cohorts at Prince Street, he quoted Danny as challenging Bulger when Bulger claimed that Winter Hill was short of funds and needed Brown’s money. “Don’t say you’re broke,” Danny told Whitey. “I know of fifty guys that claim they give you one thousand a month ... fifty thousand a month.” In the end it was agreed that Brown would stay put with the Mafia. But Danny Angiulo’s financial analysis of Bulger’s extortion portfolio hardly reflected the moribund Winter Hill mob that John Morris told his boss was not worth targeting now or in the foreseeable future.

Despite the posing and preening along the underworld’s borders, both sides knew that the wary collaboration between Bulger and the Mafia was the cornerstone of organized crime in Boston. Late one night a drunk Zannino chastised a subordinate when he learned that he had cheated Bulger and Flemmi out of $51,000. Jerry Matricia had been asked to do some Winter Hill business in Las Vegas. He was supposed to put the money down on a prearranged winner in one of Winter Hill’s fixed horse races but lost it at the crap tables instead. Years after the fact Zannino was berating Matricia over a breach that could unravel the tenuous peace with Winter Hill. It also had the potential of a shooting war. Zannino declared, “If you fuck someone close to us, I’m going to give you a shake now. Do you know the [Winter] Hill [gang] is us?”

Zannino then sent Matricia out of his office and conferred with his top two associates, who agreed with Zannino that Bulger was “going to hit him.” They called Matricia back and read him the riot act. Get some money quick to Stevie, they told him. A few hundred will do but start paying the debt down. Zannino ended his tirade with some fatherly advice about the little-understood virtues of collaboration. “These are nice people,” he told the quaking Matricia. “These are the kind of fuckin’ people that straighten a thing out. . . . Anything I ever asked them. What happened? They’re with us. We’re together. And we cannot tolerate them getting fucked. Okay?”

But the profusion of mob talk about LCN joint ventures with Winter Hill was ignored by an FBI in denial. The tapes were used exclusively to pursue mafiosi, and the FBI put a score in jail, including all the Angiulo brothers and Jerry’s son Jason. The only action Connolly took after the Prince Street bugs ended was to tell Bulger it was safe to go back in the water.

DESPITE the smashing success of his Prince Street operation, supervisor John Morris was now flying blind. Even with the afterglow of the Angiulo case lighting his path, Morris’s compass was broken. Within days of the bugs being turned off, he arranged a private celebration with Bulger and Flemmi at the Colonnade Hotel in Boston. Bulger brought two bottles of wine for “Vino” at the gathering in the upscale hotel. In the next two hours Bulger and Flemmi each had only a glass or so and Morris finished off the rest.

Feeling no pain, Morris played a tape from Prince Street for the two informants. They heard Angiulo and Zannino talking about the need to deal with the loose-lipped girlfriend of Nicky Giso because she’d shown bad judgment in talking openly about how one of Angiulo’s henchmen had cut up a North End man.