Black Mass: The Irish Mob, the Boston FBI, and a Devil's Deal (17 page)

So far the investigation had focused on loan-sharking and gambling, but the troopers now began to make out the hint of a drug connection. The troopers didn’t know at first who Frank Lepere was; in fact, a number of photographed wiseguys were written up in their logs as “unknown white male.” But showing one such photograph around, the troopers learned it was Lepere, a former Winter Hill associate who’d gone into the business of marijuana trafficking with Kevin Dailey of South Boston. Lepere had shown up at Lancaster Street carrying a briefcase; looking back, Long and his troopers realized “it wasn’t full of candy bars, that’s for sure.” After Labor Day the troopers had followed Bulger and Flemmi from the pay phones to South Boston, where the two gangsters met up with Kevin Dailey. This time Flemmi was the one carrying a briefcase. They met for an hour in the parking lot of a closed-down gas station across from the Gillette Company plant along the Fort Point Channel.

The next day at HoJo’s, on Friday, September 5, Femia caught the troopers’ attention when he tucked a small automatic handgun in his pocket before locking up his blue Malibu. Bulger and Flemmi pulled in, and then a short while later a gray Mercedes 450SL rolled into the lot. Driving the car was Mickey Caruana, who at forty-one was reputedly the biggest drug trafficker in New England. Caruana was the Mafia’s own drug kingpin, a brash high roller who answered to no one except Raymond L. S. Patriarca, the Providence-based godfather of New England. (In 1983 he would become a fugitive, fleeing a federal indictment for drug trafficking that charged him with netting $7.7 million between 1978 and 1981.) Bulger and Flemmi greeted Caruana. Femia stayed back while the three men went into the restaurant. The meeting lasted about ninety minutes. Outside, Bulger and Caruana shook hands heartily before splitting up.

It was all tantalizing stuff. There was another meeting with Kevin Dailey in Southie, and yet another encounter with the Mafia’s Larry Zannino, who arrived at HoJo’s in his blue Continental. Compared to the flophouse, the troopers’ command post was posh. They’d set up in a fourth-floor bedroom at HoJo’s overlooking the pay phones and were photographing and videotaping Bulger’s comings and goings.

Pulling all their intelligence together, the troopers went back to court. On September 15, 1980, Judge Barton approved their second bid to capture Bulger’s and Flemmi’s incriminating words. The troopers had all five pay phones tapped. The wiring was done two nights later, on a Wednesday night.

But once again the troopers came up empty. Eager and optimistic, they took up their position in their hotel room the next afternoon, awaiting their targets’ regular arrival. But one o’clock came and went. Two o’clock. Three o’clock. The hours passed. Bulger and Flemmi were no-shows. They didn’t show up the next day either, or the day after, or the day after that. Once again Bulger was gone.

Inside their hotel room the sullen troopers had a lot of empty time on their hands. The court order they had lasted until October 11, but Bulger never reappeared. They could have screamed and yelled, cursed the high heavens, but they didn’t. They didn’t trash the room. But they did talk obsessively about their plight, talk that went in dizzying circles. What the hell was going on?

MAYBE they were crazy, or at least too stubborn for their own good, but Long and his unit reviewed the intelligence they had amassed against Bulger and Flemmi and, despite their setbacks, decided to launch a third and final try. They all felt some pressure to produce something tangible—a prosecutable case—after investing more than six months of manpower and resources in the investigation. They also weren’t naive: with each failure the chances for success narrowed. Bulger and Flemmi were on high alert. But Long and the troopers were still fired up, and they decided to take a final shot at the high-riding crime bosses. “We didn’t think our chances were good,” Long recalled, “but we figured what the hell—go for it. If it doesn’t work out, we close the books on it and move on.”

Their target would be the black Chevy—installing a bug in the car would be their “Hail Mary” pass. The troopers had chased Bulger from the Lancaster Street garage and from the pay phones outside HoJo’s. From their surveillance, they now saw that Bulger was using the car as a mobile office. For a few weeks in the fall the troopers once again eased off to give Bulger and Flemmi some breathing room. Resuming their surveillance in late 1980, they saw that Bulger and Flemmi continued to conduct most of their business in the Chevy.

Bulger’s new routine was to drive into the North End in the early afternoon and park outside of Giro’s. The restaurant, located on one of the neighborhood’s busier streets, Commercial Street, was only a few blocks from Angiulo’s headquarters at 98 Prince Street. Giro’s, like the garage before it, was a hub of underworld activity: wiseguys were moving in and out of the restaurant throughout the early afternoon. Sometimes Bulger or Flemmi went inside and sat at a table for a meeting with various underworld figures, but most of the time they sat in their car and hosted a stream of wiseguys who climbed into the Chevy, talked a bit of business, and then got out.

Following Bulger into the North End, it was a wonder the troopers did not bump into the FBI. The troopers, of course, didn’t realize it at the time, but for most of 1980 the FBI had been putting the finishing touches on its sophisticated plan to bug 98 Prince Street. The operation, code-named “Bostar,” targeted Gennaro Angiulo and the top tier of Boston’s Mafia. Throughout the year FBI agents had been combing the North End, documenting the daily rhythms at 98 Prince. John Morris, as supervisor of the Organized Crime Squad, was in charge, along with case agent Edward M. Quinn. John Connolly and a dozen or more agents were part of the top-secret team.

By the fall of 1980 strike force attorney Wendy Collins had already gone through several drafts of the Title III application to win the federal court approval the FBI needed to break into 98 Prince Street to install bugs. Even though Bulger and Flemmi were Connolly’s prized informants, the two had not been used to develop the probable cause the FBI needed for Wendy Collins’s Title III work-in-progress. Instead, the FBI was mostly relying on five or six other informants—all of them gamblers and loan sharks—who, unlike Bulger and Flemmi, regularly met with Angiulo inside 98 Prince Street.

Of course, it wasn’t as if Bulger had not been discussing the Mafia in his surreptitious meetings with Connolly. He had, but Connolly’s FBI reports for those sessions contained mostly secondhand Mafia gossip. Early in 1980, for example, Bulger described a “brawl” that had erupted at a Mafia wedding reception after a young hothead made the stupid mistake of “ridiculing Larry Zannino.” Instantly some of Zannino’s men attacked the young man, who “suffered multiple lacerations and a couple of broken bones.” Bulger told Connolly about Nick Giso, who was Bulger’s daily Mafia contact at the Lancaster Street garage and then at Giro’s. The Mafia, said Bulger, “is supposed to be upset with Nick Giso ... because of Nick’s continual use of cocaine.” To his credit, Bulger did provide some information about the activities of the drug traffickers Caruana, Lepere, and Dailey. “Mickey Caruana and Frank Lepere were behind the load that was interrupted recently in Maine,” Bulger told Connolly in April. Bulger even gave Connolly Caruana’s phone number. But these Bulger reports did not include any disclosures by Bulger about the extent and nature of his own growing business ties to the marijuana and cocaine traffickers.

At Giro’s, Bulger and Flemmi met with a who’s who of Mafia associates of Gennaro Angiulo’s—Zannino, Danny Angiulo, Nicky Giso, Domenic F. Isabella, Ralph “Ralphie Chong” Lamattina, Vincent “Fat Vinnie” Roberto, and a steady stream of bookmakers and loan sharks. In March, armed with a 102-page, sworn affidavit authored by Rick Fraelick and with accompanying surveillance photographs of Bulger and his Mafia contacts, the troopers went back to court.

Superior Court Judge John T. Ronan authorized their third bid for electronic surveillance on March 19, 1981; that court order gave them five days to get their bug in the car. But five days later the troopers were back in court seeking an extension to the original court order. They hadn’t been able to get near the car long enough to install their one-watt transmitting microphone along with a tracking device. Flemmi kept the Chevy at night, either in Milton or in Brookline at the apartment complex, Longwood Towers. Neither location was accessible. In Milton, each time the troopers approached the car under the cover of darkness Flemmi’s dog went nuts. At Longwood Towers the state police technician actually got into the Chevy, but then a delayed car alarm went off. Fraelick threw a rag over the security camera, grabbed the technician, and fled, just ahead of a security guard and Flemmi himself.

The judge approved an extension, and the troopers, their hopes waning, devised their most ambitious plan. A trooper would stop Flemmi for a phony traffic infraction. The trooper would run Flemmi’s plate, inform him the Chevy had been reported stolen, and then order the car towed away. With the car in their possession, the troopers could install a bug before Flemmi retrieved it.

The trooper, Billy Gorman, stopped Flemmi one afternoon as he drove the Chevy through an intersection in Roxbury. Hidden but nearby, Long and the other troopers watched and monitored the cruiser’s radio. Gorman had been handpicked for the assignment; he was unflappable, and the mission called for a trooper who would not be drawn into an ugly exchange with the volatile gangster.

The cruiser’s lights flashed, and Flemmi pulled over. The trooper got out, and so did Flemmi. They headed for each other right there in the street. The trooper spoke first: “Did you see that old lady there you almost ran over?”

The many months of only being able to study gangster body language now ended abruptly, and at long last the troopers finally heard actual noise from one of their targets. Flemmi’s first words were hardly pleasant ones.

“What the fuck is this shit?” he shouted. No ordinary citizen, the gangster was not impressed by a trooper’s uniform and badge. His temper raced from zero to sixty in an instant. “Do you know who I am, you fuckin’ jerk? This is harassment!”

Methodically, Gorman asked Flemmi for his license and registration. “I don’t got no fuckin’ registration,” Flemmi yelled. “These are dealer plates, can’t you see?” The trooper calmly told Flemmi he should still have a registration. The trooper explained he was going to have to run the plate and that Flemmi would have to wait patiently. Gorman headed back to his cruiser, and Flemmi stormed off into a convenience store where he began making telephone calls.

In the cruiser Gorman consulted with Long. The tow truck was summoned. The installation crew was waiting in the back lot of the nearby abandoned Mattapan State Hospital. Flemmi came back out of the store, and Trooper Gorman explained that the car had been reported stolen. Gorman and Long even play-acted on the cruiser’s radio, with Long telling the patrol trooper, “Please be advised that the vehicle comes back as stolen from Nassau County, New York, in July 1979.” Gorman told Flemmi the Chevy was going to be towed.

Flemmi was apoplectic. Then he uttered the words that made Long’s and every other state trooper’s stomach turn to mush. “You tell fuckin’ O’Donovan that if he wants to bug my car so bad, I’ll drive it right up to fuckin’ 1010.” “O’Donovan” was obviously Lieutenant Colonel John O’Donovan, Long’s commander, and “1010” was a reference to state police headquarters. Flemmi knew.

It was over.

Flemmi went back inside the convenience store. The car was towed away, but even before its arrival behind the hospital Flemmi’s lawyer was telephoning O’Donovan screaming about the blatantly absurd seizure of the car. The state police commander kept a stiff upper lip and didn’t give the lawyer anything, saying the car had come back as reported stolen. But the troopers all knew the ruse was up. Long told the troopers not to even install the bug. Don’t give Bulger and Flemmi the satisfaction of taking apart the car and finding the bug, he said. Let them wonder, maybe they’ll get a little paranoid.

This was the troopers’ only consolation. They’d thrown the Hail Mary, and it had fallen woefully short. Despite their many months of successful surveillance, they’d lost in the streets against Bulger and Flemmi. They may have seen Bulger and Flemmi joined at the hip to the Boston Mafia, but they would not be taking them to court. They’d been outmaneuvered at every turn. But even in failure the state police had triggered, unbeknownst to them, a massive internal crisis over at the FBI, a crisis that, more than any other in the FBI’s long history with Bulger and Flemmi, posed the biggest threat to the cherished deal Connolly and Morris had with the two gangsters.

Responsibility
for the stunning breach in security in the potentially devastating state police bugging of Bulger and Flemmi fell squarely in the FBI’s lap, and on one agent in particular. “It was Connolly,” Flemmi later admitted. But Connolly wasn’t the only FBI agent watching out for Whitey Bulger like a lifeguard monitoring shark-infested waters. Morris, Flemmi added, had also tipped them off. The supervisor, said Flemmi, had told Bulger that another agent had come to him looking for background information on the two gangsters. Morris interpreted the inquiry as groundwork for another group’s plan to launch electronic surveillance.