Black Mass - Dick Lehr

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graduated from high school, but he always had a car when everyone else took the bus.

      

      One Bulger contemporary, who grew up in Southie before going into the Marines and law enforcement, played in the ferocious no-pads football games on Sundays and recalled Bulger as an average athlete but a fierce competitor. “He wasn’t a bully, but he was looking for trouble. You could sense him hoping someone would start something. There was some admiration for the way he handled himself. At least back then, there was a sense he would be loyal to his friends. That was the culture of the time. It was incredibly tribal, and the gang affiliation meant so much to poor city kids.”

      Bulger did most of his tailgating with the Shamrocks, one of the successor gangs to the mighty Gustins. The Gustins had had a chance to be Boston’s dominant crime organization during Prohibition, but its leaders reached too far in 1931 when they sought citywide control over bootlegging along Boston’s wide-open waterfront. Two South Boston men were murdered when they went to the Italian North End to dictate terms to the Mafia and guns roared out at them from behind the door of C&F Importing. Law enforcement still views the Gustin gang’s fate as a demarcation point in Boston’s crime history. Boston’s stunted Mafia would survive in Italian sections of the city, and the more entrenched Irish gangs would retreat to South Boston, ensuring a balkanized underworld in which factions stayed in ethnic enclaves. Sometimes, for the sake of high profits, the two groups collaborated. But Boston, along with Philadelphia and New York, would be one of the few cities where persistent Irish gangs would coexist by putting the Mafia loan-shark money out on the streets of their neighborhoods.

      The Gustin gang’s standoff with the Mafia also gave Whitey Bulger the freedom to move around South Boston’s freewheeling crime circuit, graduating from tailgating trucks in Boston to robbing banks and, at age twenty-seven, doing hard time in the country’s toughest federal prisons. His prison file portrays a hard case who was fighting all the time and doing long stretches in solitary. He was viewed as a security risk and once did three months in the hole in Atlanta before being moved to the ultimate maximum-security prison, Alcatraz, because he was suspected of planning an escape. He wound up in solitary there too, over a work stoppage, but finally settled down to do his time, moving east to Leavenworth in Kansas and then to his last stop—Lewisburg, Pennsylvania—before returning to Boston. Bulger went to prison when Eisenhower was still in his first term in 1956 and returned home in 1965 when Lyndon Johnson was firing up the Vietnam War. His father, who had lived long enough to see Billy elected, had died before Whitey’s release.

      Bulger came home as a hard-nosed ex-con who nevertheless moved back in with his mother in the projects. For a while he took a custodian’s job, arranged by Billy, at Boston’s Suffolk County Courthouse. The job reflected the politics of South Boston—a magnified version of Boston’s old-style ward system in which bosses built fiefdoms by controlling public jobs. In the old days this system had been a lifeline for unskilled immigrants with large families, but in the 1960s it could result in a janitor’s job for an ex-con. After a few years of keeping his nose clean on parole, Whitey took a deep breath and jumped back into the underworld, quickly becoming a widely feared enforcer. The Southie barroom patrons from whom he collected gaming and shylock debts were seldom late again.

      The disciplined, taciturn Bulger was clearly a cut above in the brutal world he so readily reentered. For one thing, he was well read, having used his decade in prison to focus on World War II military history, searching for the flaws that had brought down generals. It was part of an instinctive plan to do it smart the second time around. This time he would be a cagey survivor, mixing patience with selective brutality. He would no longer provoke police with flip remarks but rather present himself as someone who had learned the ropes in prison, someone who would assure detectives during routine pat-downs that they were all good guys in their small gathering and he was just a “good bad guy.”

      A couple years after being released from prison in 1965, Whitey Bulger did much of his work with Donald Killeen, then the dominant bookmaker in South Boston. But after a few years Bulger developed misgivings about Killeen’s faltering leadership and incessant gangland entanglements. More important, Bulger began to fear that he and Killeen would be killed by their main rivals in South Boston—the Mullen gang of Paul McGonagle and Patrick Nee. One of Bulger’s closest associates had been gunned down in a desperate run for his front door in the Savin Hill section of Boston. It seemed a matter of time before Killeen or Bulger himself met the same fate.

      In May 1972 Whitey’s dilemma about standing with the beleaguered Killeen was resolved when he ruthlessly chose survival over loyalty; even though he was Killeen’s bodyguard, Bulger entered into a secret alliance with his enemies. In order to survive, Bulger had to make a hard choice about business partners in Boston’s bifurcated underworld: subordinate himself to the Italian Mafia, which he detested, or forge a deal with the Winter Hill gang, which he distrusted.

      But Bulger was in a bind that could never be resolved, with stubborn Donald Killeen calling the shots and the Mullen gang bent on revenge. There would be no truce with the Killeen brothers, what with Paulie McGonagle’s brother being murdered, Buddy Roache paralyzed for life by gunfire, and the nose that got bitten off Mickey Dwyer’s face.

      Desperate for mediation, Bulger chose the lesser of two evils and went, hat in hand, to Winter Hill. In the spring of 1972 he sought a secret truce with the Mullens through the aegis Winter Hill boss, Howie Winter. The terms: Bulger would help arrange the end of Donald Killeen, and Winter would guarantee the end of the Southie gang war and sanction Bulger as the town’s new boss. Bulger’s wedge was that he controlled the lucrative gambling and loan-sharking business and the Mullens were hand-to-mouth thieves.

      The clandestine meeting, held at Chandler’s Restaurant in the South End, ran several hours into the early morning. Bulger faced off with four Mullens, with Winter sitting in the middle of the table and ultimately ruling that the conflict was long past the point of diminishing returns and, not incidentally, there was plenty of money to go around. Whitey agreed to cut truck hijackers into the steady income to be had from hard-luck Southie gamblers.

      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 Bulger was behind it. 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 by nightfall would be known throughout Southie, a formal notice to the underworld that Bulger was soon to manipulate and control.

      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.

      Though 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 an

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