Black Mass

Just about the only cautionary note amid the froth in the manual reflects longtime director J. Edgar Hoover’s obsession with the bureau’s public image. FBI agents, above all else, were never to shame the FBI, a commandment that covered their work with criminal informants. FBI handlers were not to sponsor an informant until they were “convinced that the potential informant [could] be operated without danger of embarrassment.”

In early 1976 Bulger reported to Connolly about business meetings between the Winter Hill gang and the Mafia’s Larry Zannino and Joe Russo. In March 1976 Bulger reported that underboss Angiulo had sent an emissary to Winter Hill in Somerville “in an attempt to establish contact with Stevie Flemmi.” The continued Mafia courtship of Flemmi was good for relations between the two criminal outfits—and good for the FBI. Bulger added that there was word that gang leader Howie Winter was going to meet with Angiulo, and then godfather Patriarca, “to create a better relationship.” Later in 1976 Bulger told Connolly about the betting lines his gang and the Mafia had agreed to so that bookmakers for the respective organizations were working in sync.

Flemmi served a key role in all of the Bulger-Connolly meetings, given his easy access to Angiulo, Zannino, and the rest of the Mafia crew. Flemmi passed along what he picked up to Bulger, who would pass it along to Connolly. Bulger’s reports were flavored with underworld tidbits —who was meeting with whom, who was mad at whom, who wanted to whack whom. For example, he told Connolly that a senior Mafia associate had faked a heart attack to avoid a federal grand jury subpoena. In April 1976 Bulger passed along a tip about a murder in an attempt to direct attention away from an enforcer who worked for him, Nick Femia. Bulger told Connolly: “Nick Femia had nothing to do with the hit of Patsy Fabiano.” Despite his earlier insistence that he would never inform about the Irish, Bulger regularly reported to Connolly about the jockeying of various Irish gangsters in his own South Boston.

All of this information was helpful, though it wasn’t as if Bulger’s inside track was going to topple the House of Angiulo. Most of it amounted to underworld gossip, and it was often flat-out self-serving. Often the reliability was questionable, but Connolly did not challenge it. Instead, just as Rico had before him, he filed reports that served to divert suspicion away from Bulger and his gang.

THE OLDER agents Paul Rico and Dennis Condon belonged to the city’s first generation of FBI Mafia fighters, and they, along with their counterparts in every major U.S. city, had worked feverishly in the late 1960s to turn around the bureau’s ignorance about all things Mafia. These agents had been instructed to get information, and to get it fast. One of the best techniques had proved to be electronic surveillance—even if the use of “gypsy wires” had required agents to bend the rules of law, or even break them.

In cities around the country, agents had burglarized the offices of local mobsters to install microphones, often crude devices planted behind a desk or a radiator with the wires, hidden as best they could, snaking out to a nearby location where agents secretly recorded the mobsters’ conversations. In Chicago the bug secretly installed by agents in a tailor’s shop used by mobster Sam Giancana operated for five years, from 1959 to 1964. In Providence, Rhode Island, agents made secret recordings of the New England godfather Raymond Patriarca. In Boston agents Condon and Rico were part of a crew that secretly bugged the basement office of Jay’s Lounge, a Tremont Street nightclub where underboss Gennaro Angiulo often conducted Mafia business.

The FBI was not above engaging in dirty tricks—some silly, some far worse—in those hectic days of catch-up. In New York City agents one night grew tired of following a mob figure who’d picked up two women and was seen heading for a motel. The agents, wanting to go home, let the air out of the subject’s tires, hoping that would keep him in place for a while. There were also stories about agents who rattled suspected mobsters by visiting and questioning their friends and family; the aggressive, full-court press may have been designed to gather information, but it was also used to harass the targets.

Far more serious was an incident in Youngstown, Ohio: FBI agents monitoring their makeshift bug picked up Mafia talk about a plan to kill the one FBI agent the mobsters most disliked. In short order, and with Hoover’s approval, about twenty FBI agents, the toughest batch that could be assembled from nearby offices, were sent to Youngstown for a private audience with the Mafia boss. The agents crashed into the mafioso’s penthouse, trashed the place, and issued a warning that considering harm to an agent was truly unwise.

These were some of the FBI tactics of the time—before the 1968 passage of federal legislation authorizing court-approved electronic surveillance. None of the information obtained during these warrantless break-ins and bug installations could be used against the mobsters in court, but the bugs provided a windfall of intelligence that put the FBI on a fast track to closing its information gap. Eventually the FBI drew up a list of twenty-six U.S. cities that were identified from then on as “LCN cities.” Among those cities was Boston.

The whole premise of the top echelon informant program rested on the bureau’s understanding, even acceptance, that its informants were active in crime. It was what made them top echelon informants: they were criminals with access to the LCN. Bulger’s gambling and loan-sharking constituted the threshold crimes that the FBI was generally aware of going into the deal, eyes wide open. The challenge was, what about other crimes? Then what?

In the late 1950s the FBI had developed a set of regulations for the development and handling of informants. Over the years the regulations were revised and refined, most notably in the late 1970s when U.S. Attorney General Edward H. Levi crafted for the Justice Department a series of informant guidelines that the FBI incorporated into its manual of operations. By decade’s end the FBI was reporting that it had 2,847 active informants on board in its 59 field offices, an unknown number of them serving in the hot-ticket top echelon category.

For handlers the guidelines were the bureau’s soup-to-nuts primer. For example, when developing an informant, an agent was required to conduct a suitability review to assess the informant’s reliability and motive. Motivation could vary: money or revenge or the competitive edge against other gangsters. If the FBI succeeded in taking down the underworld competition, an informant obviously stood to gain.

There was also a section on the admonishments an FBI handler was required to convey regularly to his informants—warnings intended to prevent an informant’s deal from softening into a cozy, protective cover. The informant was not to consider himself an employee of the FBI or to expect the FBI to protect him from arrest or prosecution for crimes he committed on his own time. Furthermore, the informant was warned against committing any acts of violence and was not to plan or initiate a crime.