Black Mass - Dick Lehr

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Gone were his days as a crook on the run who dyed his hair black to go into hiding from the FBI, only to be arrested at a nightclub surrounded by agents. No, the second time around he would stay in control and behind the scenes. Those years of reading in prison libraries had sharpened his instincts, and his mind had become an encyclopedia of law-enforcement tactics and past mobster mistakes. Like a chessmaster, Bulger was confident that he knew the moves, that he could watch your opening and lead you straight to checkmate. He vowed to friends that he would never, ever go back to jail.

      Like all mobsters, Bulger worked the underworld’s night shift, starting out in the early afternoon and ending in the wee hours. He presented a studied, icy detachment for those in his world but a small smile for his mother’s aging friends at the project, where he would hold doors for them and tip his hat. For a time he delivered holiday turkeys to families in need at Old Harbor. In his own way he remained devoted to his family and was fiercely protective of Billy. When their mother died in 1980, Whitey kept a low profile for his brother’s sake, fearing that a news photographer would put him and the new president of the Massachusetts state senate in the same frame on page 1. His furtive and alienated life was such that he sat up in the balcony behind the organist during the services and then watched as his five siblings slowly walked the casket out of the church below. As a parish priest summed it up, blood is blood.

      But Bulger had a fearsome mystique about him that terrified Southie’s rank and file. When a resident accidentally bumped into him coming around a corner in Bulger’s liquor store, the cold, hard glare he got was enough to make him soil his pants. As John Connolly conceded, “You cannot have a problem with him.”

      Ellen Brogna, wife of the usually incarcerated Howie Winter, had been around gangsters most of her life, but Whitey Bulger chilled her. Not long after Bulger began working out of the garage in Somerville, they were all having dinner one night. For some reason Bulger had to move Brogna’s Mustang. She flipped him the keys, but he came raging back in when he was unable to turn the car over, not realizing there was a button to press before the key would turn. She tried joking with him that he should be an expert now that he was hanging around Marshall Motors. Bulger just stared daggers at her and then stormed off. Later that night she told Howie that dealing with Bulger was like looking at Dracula. Howie just thought it was funny.

      ▪ ▪ ▪

      The post-Alcatraz Bulger was still a volatile man, but one who had learned the value of controlling himself. He was a poster boy for the stoic, stand-up Southie, with a chiseled, macho look that gave him an instant presence. His ice-cold manner cut like a cleaver to the heart of the matter. This trait, of course, made him the perfect informant, which is why Dennis Condon, the wily FBI agent who worked organized crime for decades, had kept after Bulger in the early 1970s. But though he came from a similar background across the harbor in Charlestown, Condon didn’t come from the unique place at issue—South Boston. Condon closed out the Whitey Bulger informant file with great reluctance, sensing it might work for the bureau if he could just put Bulger with a “handler” from “the town.” The young agent John Connolly was from central casting—streetwise, fast talking, and, best of all, born and raised in the Old Harbor project.

      Condon had first met Connolly through a Boston detective who knew them both. Connolly, finishing up a stint as a high school teacher, was attending law school at night but eager to join the bureau.

      After Connolly signed on with the FBI in 1968, Condon kept in touch with him during his tours of duty through Baltimore, San Francisco, and New York. They talked when Connolly came home to marry a local woman, Marianne Lockary, in 1970. While Bulger bobbed and weaved for survival, Condon took steps that would help Connolly get transferred back to Boston. It was believed that the precise details on Frank Salemme’s whereabouts, given to Connolly by Condon, came from Stevie Flemmi, who had had a falling out with his boyhood buddy.

      Connolly returned to the smaller, more intimate scale of Boston, readily swapping Brooklyn for Southie, Yankee Stadium for Fenway Park. He left an office with 950 agents focusing on New York’s five crime families for one with 250 agents who were barely up to speed on Gennaro Angiulo. He could see that playing field better, and he knew the people by their nicknames. He was a Boston boy and he was back home, raring to fill out the G-man’s suit with style. But Connolly was also an empty vessel who got filled up by those around him. As a teenager he was seen as a “shaper,” a wanna-be who looked good in a baseball hat but was never much of a player. As an agent he was more about playing the role than doing the work. He was always more glib salesman than hard-eyed cop. When he returned home from New York, he was an impressionable young agent suddenly plunged into a movie-script life. His dream assignment became getting close to a bad guy he had long admired. John Connolly fell in love.

      It was a fatal attraction to the seductive personality of Whitey Bulger. Bulger was magnetic in the reverse glamour way of elite gangsters who break all the rules and revel in it. For Connolly it was an enthralling prospect, a future assured. Working with Whitey—what could be better? What could be easier? It sure beat being one of 250 selfless agents riding around in a government car. Whitey would be the head on Connolly’s glass of beer.

      In the first few years of his renewed relationship with Whitey Bulger, Connolly’s “209” informant reports were split between accounts of disenchantment within the ranks of Gennaro Angiulo’s chronically unhappy Mafia family and more concrete tips about Bulger’s rivals within South Boston. Connolly did not remind Bulger that he had originally pledged to inform only about the Italians. And though the Mafia information was mostly generic gossip about problems in the House of Angiulo, the rat file on South Boston came with addresses, license plates, and phone numbers. For instance, Tommy Nee, one of a handful of homicidal maniacs who were regularly committing mayhem out of South Boston barrooms in the 1970s, was arrested for murder by Boston Police, with an assist from the FBI, in New Hampshire—just where Whitey said he would be.

      But the FBI priority was the Mafia, not sociopaths like Tommy Nee. Through Flemmi, Bulger found out that Angiulo had removed his office phone for fear of wiretaps. Angiulo and his brothers, Bulger told Connolly, were talking only on walkie-talkies. Gennaro was “Silver Fox” and Donato Angiulo was “Smiling Fox.” Bulger even recommended a Bearcat 210 automatic scanner to monitor conversations.

      In the button-down FBI office in Boston, such reports were impressing the top bosses even as Connolly’s increasingly brash ways were irritating his colleagues, who began jokingly to call him “Canolli” because he dressed and acted like a slick mob dude, with jewelry, chains, pointed shoes, and black suits. But for his part, Connolly was unconcerned. He knew what he had in Bulger and what it was worth to his career. Bulger’s 209 files were a coup for him and the bureau, a synergy possible only because of who he was and where he came from: South Boston Irish. “Whitey only talked to me,” Connolly bragged, “because he knew me from when I was a kid. He knew I’d never hurt him. He knew I’d never help him, but he knew I’d never hurt him.”

      But sometimes in Whitey’s world, not hurting could be very helpful.

      CHAPTER THREE

       Hard Ball

      As District Attorney William Delahunt was getting into his car to drive to a restaurant near his Dedham office, Whitey Bulger and two associates were barreling down the Southeast Expressway toward the same destination just outside Boston’s city limits. Delahunt was meeting another prosecutor for dinner. The mobsters were planning to terrorize the restaurant’s owner, who had stiffed them on a $175,000 debt. In one of life’s strange split screens, each party would do its business on a different side of the same big room in the Back Side Restaurant.

      It was 1976, and the thirty-five-year-old Delahunt had been Norfolk County district attorney for only a year—just a little longer than Whitey Bulger had been teamed up with John Connolly and the Boston office of the FBI. But the chance encounter was not the only thing the DA and the gangsters had in common. One of the mobsters in Bulger’s crew, Johnny Martorano, had been a grammar school classmate and schoolyard rival of Delahunt’s. They had even been altar boys together.

      When Delahunt looked up from a table near the bar, he recognized the Winter Hill

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