Black Mass

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.