Prince Street Hitman - THE BIG SLEEP - Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)

Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)


I do my best to protect you and I may break a
few rules, but I break them in your favor



Prince Street Hitman

Around midnight, long after agents had followed Gennaro Angiulo home and reported back that the Mafia boardroom was a dark office on a still street in the North End, the FBI entry team began to move out from headquarters about a mile away in downtown Boston.

A dozen agents had whittled the night away in the big, open squad room, sitting on desktops, drinking coffee, trading wisecracks. Some talked about the Celtics’ tight victory over Los Angeles that afternoon, a good win despite Larry Bird’s bad game. Others wondered why the boss, Larry Sarhatt, was going on the mission that night. Did it mean he lacked confidence in the game plan? Or was Sarhatt doing what most twenty-year FBI men would do—getting involved on a big night? No one was sure.

After everyone was in place in the North End, John Morris, as the Organized Crime Squad supervisor, called the shots over a two-way radio from a car on the other side of a small hill from Angiulo’s office. He was now spending 98 percent of his time on the case and 2 percent worrying about Whitey Bulger’s standing within the bureau and his own relationship with the disdainful John Connolly.

Nervous as a cat and bundled against the frigid January night, Morris sat in the front passenger seat as he fielded reports from agents in cars around Prince Street. At two o’clock the word from the other side of the hill was “all’s quiet.” Morris turned to the backseat and dispatched agents Ed Quinn and Deborah Richards and an FBI locksmith, sending them down the hill to 98 Prince Street. They were to break into Angiulo’s small suite on this crisp, clear night. Surveillance had revealed that early Monday morning was the quietest time of the week in a neighborhood of double-parked cars outside restaurants, bakeries, pizza joints, and apartment buildings. Even the wiseguys stayed in on Sunday nights. Now the usually watchful neighborhood of narrow streets and five-story tenements had finally turned in.

Quinn turned his collar to the night and started down Snow Hill Street to Prince Street, linking his arm with the uninhibited Richards, who carried a bottle of scotch that Quinn brought from home so the trio could look like revelers sharing a drink and looking for an after-hours party. They meandered down the hill but stepped lively when they hit the street, moving quickly to the faintly lit doorway at 98 Prince Street. Quinn and Richards, no longer the party seekers, stood with arms folded across bulletproof vests while the third agent dropped to one knee to pick the front-door lock. Across the street, freezing in the trapped arctic cold of a parked van, two other agents watched the trio’s backs as they entered the foyer. One more door to go.

Using radio code, Morris issued orders for FBI cars to shut down a section of Prince Street. Blocks apart, hoods were popped and agents stood by “disabled” cars to make sure no traffic drove by 98 Prince while agents were making their way into the Mafia’s sanctuary. Larry Sarhatt stood outside his blue Buick until word came that Ed Quinn was standing in the garlic-saturated darkness of Jerry Angiulo’s office. Inside, the inner sanctum came slowly into view—restaurant stoves against the back wall, a table in the middle, and cheap vinyl chairs by the television near the front windows.

Morris then ordered a second team of agents inside. No meandering down the hill with scotch this time. These were the “techies”—this was a military operation now. The three techies hit the ground running, lugging heavy satchels of equipment and looking like paratroopers taking a beachhead. Agents in vans and cars now blocked all the paths to 98 Prince Street as Quinn opened the door for the reinforcements. Suddenly there were six agents inside of Jerry Angiulo’s impregnable domain. They all stood still for ten minutes to make sure no hidden alarms had gone off and to acclimate themselves to the dark room.

Then the techies got out their cloth-covered flashlights and got to work. It took three hours to plant two microphones at the top of the side wall and wire them to big batteries the size of logs that were hidden on top of the ceiling. The bugs would transmit a scrambled signal to foil scanners and send Angiulo’s conversations across Boston Harbor to an apartment in Charlestown that was jammed with agents. After several problematic tests of the signal, Ed Quinn was finally able to talk clearly to agent Joe Kelly from Jerry Angiulo’s kitchen. The tape reels that would prove so lethal to Angiulo were mounted and ready to roll.

At first light a drained Ed Quinn walked out of the Prince Street office. The last thing he did was make sure sawdust from drilled holes was swept up. At five in the morning he climbed back up Snow Hill Street and clambered into the backseat of Morris’s car. They pumped each other’s hand, but it was a quiet jubilation. Wide grins but no loud yelps. It was the FBI, after all.

Four hours later Frankie Angiulo, the Mafia’s day shift manager whose job was to stay on top of local bookies, made his short commute across Prince Street. While agents had worked in the dark office, Frankie had slept about thirty yards away in a ramshackle apartment in a vacant building that concealed wads of cash stuffed in heavy safes. As he did every morning at 9:00 a.m., Frankie started the day at 98 Prince Street by spitting in the kitchen sink and putting on the coffee.

By the time Jerry Angiulo showed up for work at 4:00 p.m.—working the night shift as he had for three decades—about the only thing on his mind was a trip to Florida to beat the unusually prolonged cold spell of a bitter January. But nasty weather would soon be the least of his problems.

▪ ▪ ▪

After more than a year of secretly gathering evidence in an edgy neighborhood, the new enemy in the FBI’s pursuit of the Angiulos was the deafening din inside 98 Prince Street. Listening in a Charlestown outpost five miles away, agents struggled to decipher the fractured syntax of the five Angiulo brothers and their henchmen as they all talked at once against the background of a blaring all-talk radio station that was on around the clock.

Some, like John Morris, never got the hang of it. John Connolly never even tried, ducking out on the tedium of listening to mob talk, protesting that he was needed more on the street. But the rest of the agents managed to master the maddening argot of Prince Street, getting so they could follow staccato bursts of profane half sentences, snatches of Italian vernacular, gutter slang, and lightning changes in subject. The star in every way was the domineering Gennaro. For one thing, he shouted and could be heard over the incessant radio. For another, he mostly made sense. He was self-absorbed and bloodless and opinionated, but you could follow what he was saying. There was no mistaking his message, for example, when he talked about some underlings who were arrested after a gambling raid. “We find that one of these individuals that we use becomes intolerable, we kill the fuckin’ motherfucker and that’s the end. We’ll find another one.”

Usually the bugging at Prince Street didn’t reveal much until Jerry’s four o’clock arrival from his waterfront mansion in Nahant, north of Boston. His red and silver AMC Pacer or his baby blue Cadillac would pull up, Angiulo would enter the building, and the mood changed immediately. There was almost no small talk. Angiulo walked in the door barking questions about food and gambling and money and murder, holding court with the imperious impatience of a judge too long on the bench. At seven-thirty he took a supper break, frequently cooked by the youngest Angiulo brother, Mikey. The only other break was for the public television series The Wild, Wild World of Animals. The underboss never missed an episode and provided a running commentary on the wonders and strength of reptiles.

Having successfully fought off conspiracy charges in long trials in state court during the 1960s, Angiulo was ever wary of law enforcement’s reach and tools. His were prescient concerns: the FBI bugs captured a frustrated Angiulo shouting, “They can stick RICO.” But no one else in the office knew what he was talking about. Angiulo worried out loud about the ease with which a racketeering case could be made against his long-running criminal organization. He alone saw the jeopardy.

Over the years Angiulo had come to view himself as shrewd beyond his merit, but he was right about the power and danger of the RICO statute. Reading out loud to indifferent henchmen, Angiulo dissected newspaper articles about a Massachusetts defendant’s appeal of his twenty-year racketeering sentence that was before the US Supreme Court. He lectured his brothers about the danger posed by federal prosecutors only having to prove the Angiulos committed two of thirty-two federal and state crimes over a ten-year period to establish a pattern of racketeering. He lamented that “if you break one of those crimes this year and within the next ten years you break the other one, they will take your fuckin’ head off.”

But Angiulo, whose high school ambition was to be a criminal lawyer, took delusional refuge in a mistaken belief that RICO applied only to those infiltrating legitimate business, as the Mafia in New York City frequently did. Oblivious to the finer points of RICO, Angiulo railed on, with hidden microphones picking up every word.

Then, in a fateful misstep that sealed his fate, Angiulo unwittingly outlined the racketeering case against himself in a colloquy with Zannino. The rambling recitation of his criminal endeavors was the bare bones of the indictment he would face just two years later.

“Our argument is we’re illegitimate business,” he said to Zannino.

“We’re shylocks,” answered Zannino, the family’s consigliere.

“We’re shylocks,” echoed Angiulo, warming to the litany.

“Yeah,” said Zannino.

“We’re fuckin’ bookmakers,” Angiulo added.

“Bookmakers,” confirmed Zannino.

“We’re selling marijuana,” said Angiulo.

“We’re not infiltrating,” replied Zannino.

“We’re, we’re, we’re illegal here, illegal there. Arsonists. We’re every fuckin’ thing,” said Angiulo, warming to his own argument.

“Pimps, prostitutes,” added Zannino, bringing the discussion back to where it belonged.

“The law does not cover us,” Angiulo declared. And then quizzically: “Is that right?”

Zannino again brought the discussion back to reality. “That’s the argument,” he said glumly.

The truth was that the argument was a big-time loser. Later that same night a talked-out Angiulo confronted the cruel reality. “The law was written for people like us,” he said wearily.

▪ ▪ ▪

As Angiulo surveyed his ebbing domain, he noticed one small thing. Stevie and Whitey hadn’t been around since they last visited Prince Street, when some of their indebtedness to the Mafia was discussed. Angiulo beefed about the pair not coming around “for two fuckin’ months”—or since the time of their secret FBI reconnaissance mission in November 1980. As with nearly all mob matters, Angiulo thought their absence was about money. But it wasn’t that simple. Bulger and Flemmi could have cared less about any money they owed a dead duck with microphones in his walls. They stayed away because their handlers tipped them off. Bulger and Flemmi knew their loose confederation with Angiulo would be discussed while the tapes reeled it all in. But it would only be hearsay for investigative leads if there was no talk about crimes from their own mouths.

From the beginning the agents did the best they could to cover up for Bulger and Flemmi as their misdeeds tumbled off the tapes in 1981 and, later, when the tapes were transcribed for Angiulo’s racketeering trial. With Morris in charge, the agents distorted the meaning of raw information coming into headquarters about Bulger’s gambling, loan sharking, and potential use as a hitman by the Mafia. Running interference, Connolly raced headlong into the record. For example, the FBI tapes caught Zannino urging Angiulo to use Whitey and Stevie to kill a fringe mobster. The tapes also had Zannino paying homage to Winter Hill as a formidable partner in some loan-sharking and gambling enterprises. Indeed, the tapes revealed the Angiulos routinely discussing what the thwarted state police were after—a racketeering case based on a joint venture between the Mafia and Winter Hill. The Mafia leaders talked frequently about how best to divide gambling and loan-sharking territory with Winter Hill. Jerry Angiulo himself summed it all up when he referred to the millions of dollars in extorted payments by the FBI’s pair of prized informants: “Whitey has all of South Boston, and Stevie has all of the South End.”

But the FBI not only left alone those fiefdoms; they protected them. And the FBI’s protection was hardly confined to nonviolent gaming crimes. The bulk of the business was from extorting drug dealers and bookies who faced ultimatums every month to either pay or die.

Zannino knew Stevie’s work firsthand as a killer from the gangland wars of the 1960s. He reminisced with gusto about how Stevie murdered Dorchester loan shark William Bennett after Bennett crossed the Mafia. (Willie Bennett was one of three Bennett brothers murdered at Zannino’s behest over financial and territorial disputes.) The bloodthirsty consigliere knew about Bulger’s work only by reputation, aware of his use of selective violence from afar.

But Zannino knew a job for the pair when he saw one and immediately pushed them as the solution to Angelo Patrizzi. A dim-witted mobster on the periphery, Patrizzi had just come out of jail vowing vengeance against two Mafia soldiers who had killed his brother for holding back on loan-shark payments. It was a widely known threat that put the Mafia leaders on the spot. They decided to stop Patrizzi in his tracks. Patrizzi was a thirty-eight-year-old escaped convict with an eighth-grade education, a drug and alcohol problem, and a bullet fragment in his head. But he knew what it meant when Zannino had Freddie Simone start coming around the garage where he worked, making nice. Patrizzi went into hiding in Southie. Zannino offered Angiulo a suggestion for a threat living on Bulger’s home turf: “Whitey and Stevie will clip his fuckin’ head.”

But Angiulo didn’t want to owe Bulger a favor, especially when Bulger had his $245,000 outstanding bill due to the Mafia. Angiulo, who saw the nettlesome problem as internal housekeeping, preferred the safer course of using several Mafia soldiers to execute the foolish man making rash threats. And Angiulo was always thinking about who could testify against him if something went wrong: Bulger was not “one of us” who would automatically stand up if caught. Angiulo even rejected the idea of having soldier Connie Frizzi team up with Bulger so Frizzi could identify Patrizzi and then get out of Bulger’s way.

Connolly cleverly took the whole incident out of context and claimed that the internal Mafia debate debunked the law enforcement rumor that Bulger was sometimes used as a hitman. He reported to his boss that the Prince Street eavesdropping operation had established two “indisputable facts”—one that papered over Bulger’s standing as a killer for hire and the other that jabbed the state police for overstating the general knowledge about Bulger’s rat status. Connolly offered two bulletins from Prince Street to a boss just in from Knoxville.

“A. That source [Bulger] is not a hit man for Jerry Angiulo as has been contended.

“B. That the hierarchy of the LCN do [sic] not consider source to be an FBI informant as Col. O’Donovan of the Massachusetts State Police has stated.”

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. Because 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 Jerry related 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 craps 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 an FBI in denial ignored the profusion of mob talk about LCN joint ventures with Winter Hill. 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.

To be sure, John Morris had coordinated a seven-days-a-week bugging operation that required around-the-clock staffing by forty agents. He’d handled a crisis a day for four months. Operation Bostar wiped out the Angiulo crime family, an enduring law enforcement triumph that Morris hoped would carry him to a job as special agent in charge in a major city.

But Morris was also failing just as surely as he was succeeding. He left telling signs of his slowly unfolding destruction behind in the Colonnade room. Besides emptying more than two wine bottles, Morris had stumbled out of the hotel, leaving behind the top-secret government tape recording he had so proudly played for Bulger and Flemmi. Indeed, the tape was retrieved only when Flemmi realized it was being left behind and went back for it himself.

Though the turning point had been long before, perhaps nothing so summed up just how masterfully Bulger had turned the tables on the FBI and just how corrupted the FBI had become than the end of the Colonnade night. A drunk Morris was driven home in his own car by Whitey Bulger. Flemmi followed in the black Chevy. Morris and Connolly may have once thought they were in control of the relationship, but they and the FBI were now just intoxicated passengers. It was midnight in Boston.