Black Mass

by Dick Lehr

Shortly afterward, Killeen was called away from his son’s fourth birthday party. As he was starting his car, he saw a lone gunman racing at him from the nearby woods. As Killeen went for his gun under the seat, the gunman pulled open the driver’s door and jammed the machine gun near his face. He then fired off a fifteen-bullet burst. The gunman fled down the driveway to a revving getaway car. No one was ever charged with the shooting, but it became part of Southie lore that it was Bulger. The finishing flourish occurred a few weeks later when Kenneth, the youngest brother in the Killeen family, jogged past a car parked near City Point with four men in it. A voice called out “Kenny.” He turned to see Bulger’s face filling the open window, a gun tucked under his chin. “It’s over,” the last Killeen bookmaker standing was told. “You’re out of business. No other warnings.”

  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.

  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 while 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 to jokingly call him “Canolli” because he dressed and acted like a slick mob dude. Jewelry. Chains. Pointed shoes. 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 a coup for 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 hitman immediately. Martorano ambled over and sat down, while the other two gangsters hung back. The former school chums shared a drink and got to jiving each other about their opposite lots in life. Johnny Martorano jabbed Billy Delahunt about there being more honor in his world than in the one populated by bankers and lawyers. Delahunt just chortled and did not argue the point with him. But when it was Delahunt’s turn to dish it out, he touched a nerve. Delahunt urged his old classmate turned gangster to stay out of Norfolk County. Stick to Boston, “for both our sakes,” Delahunt cautioned.

  Martorano told Delahunt to pound sand, and the repartee got animated enough that one of Martorano’s companions joined them at the table to see what was going on. Bulger hung back, waiting by the entrance and out of sight, but Delahunt certainly recognized Martorano’s companion, Stevie Flemmi. Then the odd encounter ended suddenly, and amicably enough, when Delahunt’s dinner companion, federal prosecutor Martin Boudreau, arrived at the table. When they were alone, Delahunt rolled his eyes and said, “You’ll never guess who I was talking to.”

  Meanwhile, Bulger joined Martorano and Flemmi, and the threesome picked a cocktail table against the back wall and set up there. Arms folded, they sat waiting for the owner to appear. They had come to see Francis Green because Francis Green had some explaining to do.

  About a year earlier Green had borrowed $175,000 from a high-interest Boston finance company for a real estate investment. The problem was that Green had not paid back a dime and, while he didn’t know it, was stiffing a friend of Winter Hill’s. Whitey knew a way to solve such bad debts. It was not genteel.

  Green came into the large central room, spotted the three gangsters, and slid into an empty seat. As was his wont, Bulger skipped the small talk. “Where’s our money?” he asked. Green, a glib salesman with a checkered past, tried a salesman’s tap dance. His finances were in shambles. His business deals had gone bad. He was in bad shape. This had to count for something.

  But Bulger would have none of it. No money is no answer. It didn’t matter that two prosecutors were seated across the way. Bulger leaned into Green’s face, his eyes cold marbles. Understand this, Bulger told him, “if you don’t pay, I will absolutely kill you. I will cut off your ears and stuff them in your mouth. I will gouge your eyes out.”

  Then Bulger leaned back. He told Green he really should make an appointment with his loan officer to arrange a schedule for repayment. And Flemmi, playing the good cop to Bulger’s tough cop, advised Green to pay something real soon. That way, comforted Flemmi, no one would get hurt. Then it went back to Bulger, who made one final chilly comment: make it $25,000 within a few days.

  An ashen Green said he would see what he could do. The brisk business meeting was over. An FBI report afterward recorded in leaden government prose that the conversation “greatly upset” Green. It was an understatement. Green was in fear for his life, and it was fear mixed with bewilderment. He was aware that Martorano and Delahunt had earlier been mingling at the bar, and the entire scene that night left him confused about what exactly he was up against.

  It was all pretty bizarre, the kind of odd occurrence that comes with life in and around a big small city like Boston. For their part, the two prosecutors were oblivious to the extortion nearby. Over at their table, Delahunt and Boudreau joked during dinner about winding up at the same restaurant with Martorano and Flemmi of the Winter Hill gang. They hadn’t realized that the third man in the entrance shadows was the notorious Whitey Bulger. But Delahunt had no idea at the time that the business activity at the cocktail table was actually a prelude to the bad relations to come between the rest of law enforcement and the Boston office of the FBI. In the future it would seem like the world was divided between the FBI and Bulger, on the one hand, and all the other police agencies on the other. At the moment, though, the chance meeting just seemed to be one of those crazy things that happen but don’t really mean anything.

  The Bulger ultimatum—pay or die—quickly sent Green scrambling to seek out his own contacts in Boston’s law enforcement community. He started with Edward Harrington, who was the former chief prosecutor at the federal Organized Crime Strike Force for New England. Green not only had had some dealings with the strike force over the years but had raised money for Harrington’s unsuccessful run for state attorney general in 1974. Harrington was about to rejoin the ranks of government service as the new U.S. attorney in Massachusetts, but he was in private practice at a law firm when Francis Green came calling in full panic.

  Green wanted Harrington’s counsel. What should he do? Harrington, according to an FBI report, was blunt. He told Green he had three options: Pay the money. Get out of town. Or testify against Bulger.

  Green took stock of the situation. Repayment was out of the question. He had squandered the money. Relocation was not appealing. Testifying against the reputed killer seemed even worse. But it was this last option, the one that perhaps carried the highest risk, at least to life and limb, that Green began to contemplate.

  In the weeks that followed Green asked Harrington more questions about coo
perating, and Harrington decided that because the extortion occurred in Norfolk County, the matter could best be pursued through a state investigation. He told Green that the case should be developed out of District Attorney Delahunt’s office. But what about Delahunt? Green was worried about Delahunt’s ties to Martorano. He had seen the two men sitting there at the Back Side Restaurant sharing a drink and having a laugh.

  Harrington phoned Delahunt and briefed him about Green and Bulger’s threat. Then he mentioned Green’s concern about the county prosecutor bantering with Martorano. Delahunt assured Harrington that it was only a chance meeting, that there was nothing between the two men beyond faded boyhood memories. Arrangements were made for Green to take his evidence to Norfolk County prosecutors.

  Soon afterward Green met with Delahunt and his top staff. In gripping detail, Green re-created the dramatic night at the Back Side. The story stunned Delahunt. He’d had no idea that this conversation was happening just out of earshot of his dinner with Boudreau.

  Later Delahunt huddled with his staff. Green’s story was explosive, and Delahunt was personally involved. He had, after all, been in the restaurant that same night and could provide eyewitness corroboration that Martorano and Flemmi were present. Could he be both witness and prosecutor? Unlikely. Plus, the county prosecutors wondered if Harrington had been wrong to conclude that this kind of case should be pursued at the state level. They knew that federal extortion laws carried stiffer penalties than they could ever hope to win under Massachusetts law. So Delahunt consulted with Boudreau, the federal strike force prosecutor and law school classmate he’d dined with that night at the Back Side, who agreed with Delahunt’s analysis. He even offered to personally walk the case over to the FBI office to get the ball rolling. With Delahunt’s approval, the case was forwarded to the FBI.