Black Mass

WHEN John Connolly was a toddler on O’Callahan Way, Whitey Bulger was already tailgating merchandise off the back of delivery trucks in Boston’s minority neighborhoods. He was thirteen years old when first charged with larceny and moved on quickly to assault and battery and robbery, somehow avoiding reform school. But he was nevertheless targeted by the Boston police, who frequently sent him and his fresh mouth home more battered than they’d found him. His parents worried that the bruising encounters would only make him worse, and indeed, the stubborn teenager exulted in his confrontations at the police station, swaggering around the tenement and daring younger kids to punch his washboard stomach so he could laugh at them. In a few short years he became a dangerous delinquent with a Jimmy Cagney flair, known for vicious fights and wild car chases. His probation files reveal him to have been an indifferent student who was lazy in school, the polar opposite of his brother Bill. He never 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 recalls 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 stand-off 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 before returning to Boston—Lewisburg, Pennsylvania. 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 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 of 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 Mullin 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. There would simply be no patching up the Mullin rift with Killeen, what with Paul McGonagle’s murdered brother and the nose that got bitten off Mickey McGuire’s face. Howard “Howie” Winter, who ran the dominant Irish gang out of a garage in nearby Somerville, was friendly with Mullin gang members and mediated its dispute with Bulger. Once the fiercely independent Bulger had taken hat in hand and gone to see Howie, it was the end of Donald Killeen.

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.”