Black Mass

The fast, bloody “Godfather” takeover was the stuff of legends. It was the kind of dramatic, decisive move that would be known throughout Southie by nightfall, a formal notice to the underworld that Bulger was soon to manipulate and control. And it was just the beginning. Within months of Donald Killeen’s death, Bulger joined forces with Winter Hill assassins and, to consolidate Bulger’s power, mowed down South Boston rivals at a breakneck pace. In two days in March 1973, they killed six mobsters. By the end of 1975, the Bulger body count was up to sixteen, including prime movers in the archrival Mullins Gang—Paul McGonagle and Tommy King. Both were buried in Quincy in sandy beaches in view of the busy Southeast Expressway.

It was a new era awash in blood as Bulger eliminated the Killeens and then showed up for work at the Marshall Motors garage in Somerville that served as Howie Winter’s base of operations. Bulger spoke for all the South Boston rackets and was looking for bigger opportunities. Whitey had Southie and, for a short time, Howie had Whitey.

While his wealth grew exponentially, Bulger’s lifestyle would never change. He was the antithesis of the gaudy mafiosi of the North End. No Cadillacs. No yachts. No oceanfront homes. Bulger seldom drank, never smoked, and worked out daily. His one weakness was for a Jaguar that he kept garaged in City Point most of the time. Overall, he lived a quiet life with his mother in the Old Harbor project, staying with her until her death in 1980.

His new agenda was to stay disciplined and not give in to the anger of his youth, when he had been charged with rapes in Boston and in Montana while in the air force. He would indulge neither the restlessness that had led him as a fourteen-year-old to bound impulsively out the door in Old Harbor and join Barnum & Bailey’s circus as a roustabout, nor the recklessness of the young gangster who walked into a bank with a silver gun and other amateurs to take away $42,112 in deposits from an Indiana bank. 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 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 was chilled by Whitey Bulger. 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 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 the 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.