by Dick Lehr
THE us-versus-them mentality at the core of Southie life goes even deeper than its Irish roots. Before the first major wave of Irish immigrants washed over the peninsula after the Civil War, an angry petition to the “central” government had arrived at city hall in 1847 complaining about the lack of municipal services. It would be a couple of decades before the famine immigrants, who stumbled ashore in Boston as the potato blight wracked Ireland from 1845 to 1850, made their way to the rolling grass knolls of what was then called Dorchester Heights. The famine had reduced Ireland’s population by one-third, with one million dying of starvation and two million fleeing for their lives. Many of them headed to Boston as the shortest distance between two points and spilled into the fetid waterfront tenements of the North End. By the 1870s they were grateful to leave a slum where three of every ten children died before their first birthday.
The newly arrived Irish Catholics took immediately to Southie’s grievance list with outside forces. Indeed, it became holy writ as the community coalesced around church and family, forming a solid phalanx against those who did not understand their ways. Over the decades since then, nothing has galvanized Southie more than a perceived slight by an outsider who would change The Way Things Are. In the Irish Catholic hegemony that came to be, a mixed marriage was not just Catholic and Protestant. It could also be an Italian man and an Irish woman.
Although Boston had been an established city for two centuries by the time the bedraggled famine immigrants arrived, South Boston did not become a tight-knit Irish community until after the Civil War, when newly created businesses brought steady employment to neighborhood residents. In the war’s aftermath the peninsula’s population increased by one-third to its present level of thirty thousand. Irish workers began to settle in the Lower End to take jobs in shipbuilding and the railroad that spoke to the era. Soon local banks and Catholic churches opened their doors, including St. Monica’s, the Sunday destination of Whitey Bulger’s younger brother Billy and his tag-along pal John Connolly.
In the latter part of the nineteenth century most men worked on Atlantic Avenue unloading freight ships. Women trekked across the Broadway Bridge after supper to the city’s financial district, where they scrubbed floors and emptied wastebaskets, returning home over the same bridge around midnight. By the end of the century the Irish Catholic foothold was such that residents congregated by the Irish county of origin —Galway was A and B Streets, Cork people settled on D Street, and so on. The clannishness was part of the salt air. It was why John Connolly of the FBI could quickly resume an easy relationship with an archcriminal like Whitey Bulger. Certain things mattered.
Beyond common ethnic roots, the magnet of daily life was the Catholic Church. Everything revolved around it. Baptism. First Communion. Confirmation. Marriage. Last rites. Wakes. On Sundays, a day apart, parents went to early mass and sons and daughters attended the children’s mass at nine-thirty. There was a natural cross-fertilization with politics, with one of the first steps toward public office sometimes being the high-visibility job of passing the hat along the pews.
Like Ireland itself, Southie was a grand place—as long as you had a job. The Depression swung like a wrecking ball through South Boston’s latticed phalanx of family and church. The network that had worked so well collapsed when the father in the house was out of work. A relentless unemployment rate of 30 percent badly damaged the Southie worldview that the future could be ensured by working hard and keeping your nose clean. It changed the mood in a breezy place, and ebullience gave way to despair. It wasn’t just Southie. Boston’s economy had calcified, and well into the 1940s, the formative years for the Bulger boys and John Connolly, the city was a hapless backwater down on its luck. Its office buildings were short and dreary and its prospects dim. Income was down, taxes were up, and business was lethargic. The city was afflicted by the legacy of a ruling oligarchy of Brahmins who lost their verve. The dynamic Yankees of the nineteenth century had given way to suburban bankers indifferent to downtown, a generation of cautious coupon clippers who nurtured trust funds instead of forging new businesses. In tandem, hopeful immigrants became doleful bureaucrats. Nothing much changed until the urban renewal of the 1960s.
It was to this hard time and place that James and Jean Bulger arrived in 1938, looking for a third bedroom for their growing family in the first public housing project in Boston. Whitey was nine, Billy four. The Bulgers would raise three boys in one bedroom and three girls in another. While the Old Harbor project was a massive playground for the children, parents had to be nearly broke to get into it. The Bulgers easily met this criterion. As a young man, James Joseph Bulger had lost much of his arm when it was caught between two railroad cars. Although he worked occasionally as a clerk at the Charlestown Navy Yard, doing the late shift on holidays as a fill-in, he never held a full-time job again.
A short man who wore glasses and combed his white hair straight back, James Bulger walked the beaches and parks of South Boston, smoking a cigar, a coat hanging over the shoulder of his amputated arm. His hard life had begun in the North End tenements, just as the Irish neighborhood of the famine era was giving way to another immigrant wave, this one from southern Italy in the 1880s. He had a strong interest in the issues of the day; one of Billy’s boyhood friends remembered bumping into him on a walk and being waylaid by a long discussion of “politics, philosophy, all this stuff.” But the father was a loner who stayed inside the apartment most of the time, especially when the Red Sox were on the radio. In contrast, the loquacious Jean was usually found on the back stoop at Logan Way, chatting with neighbors, even after a hard day of work. Many of the neighbors recalled Jean Bulger as a sunny, savvy woman who was easy to like and hard to fool. They say Billy was like her, friendly and outgoing, running off to the library with a book bag or to the church for a wedding or funeral, his altar boy cassock flying over his shoulder.
But Billy also shared his father’s concerns for privacy and his solitary ways. In a rare interview about his family, Bulger talked wistfully about his father, his stoic manner and hard-luck fate, wishing that they had talked more and that there had been more shared moments. He recalled the day he went off to the army toward the end of the Korean War, his parents tight-lipped with worry because their son-in-law had been killed in action two years earlier. James and Jean took Billy to South Station for the train to Fort Dix, New Jersey. His father, then nearly seventy years old, walked behind him down the aisle, following him to his seat. “I thought, ‘What’s this?’ You know how kids are. My father, and this was unusual for him, he took my hand and said, ‘Well, God bless you, Bill.’ I remember it because it was quite a bit more than my father was inclined to say.”
BILLY BULGER ran for public office in 1960 because he needed a job as he neared graduation from Boston College Law School and married his childhood sweetheart Mary Foley. John Connolly was one of his campaign workers. Originally, Bulger was going to stay a few terms in the House of Representatives and then leave for private practice as a criminal defense lawyer. But he stayed on, juggling a small law practice, the legislature, and a booming family. The Bulgers would have nine children, about one a year during the 1960s. Billy moved up to the senate in 1970 and went on to be president of the chamber longer than any man in Massachusetts history.
As he progressed through the legislature, Billy came to epitomize South Boston, with his jutting jaw and conservative agenda. He became a provocative statewide figure who delighted in tweaking suburban liberals who thought busing was a good idea for his neighborhood but not for their own. He had a passion for refighting old lost battles, none more emblematic than the statewide referenda he forced on an indifferent electorate in the 1980s to right an ancient wrong he found in the state constitution. An anti-Catholic 1855 provision banned aid to parochial schools and, while Bulger readily admitted it had done no lasting harm, he wanted it smitten because of the original intent. That the correcting amendment was overwhelmingly rejected twice at the polls made no mat
ter. The fight was the thing.
It was all part of what made him one of the dominating politicians of his time, a paradoxical figure who drew on a rare mixture of scholarship and mean streets. At once he was a petty despot and masterful conciliator, a reserved man who loved an audience, a puckish public performer who had a dark side and took all slights personally. His bad side remains a precarious place to be.
Though Billy Bulger was well-known for his scholastic and high-minded style, he could show another side as well. In 1974, when anti-busing protesters were arrested outside a neighborhood school, Bulger was on the scene and denounced the police for overreacting. He went nose to nose with the city’s police commissioner, Robert diGrazia, jabbing his finger at him about his “Gestapo” troopers and angrily walking away. DiGrazia yelled a retort about politicians lacking “the balls” to deal with desegregation earlier when things could have been different. Bulger spun around for more, working his way up to the much taller diGrazia. “Go fuck yourself,” the senator hissed into diGrazia’s face.
As busing turned Southie on its ear, even Whitey Bulger got into the act, but in the incongruous role of peacemaker. He worked behind the scenes to try to bring some calm to the streets among his followers. His exhortations were hardly the stuff of civic altruism. By raising the prospect of a protracted police presence in South Boston, busing was simply bad for business. So Whitey spread the word to his associates not to exacerbate the tensions boiling over in the schools.
Despite the fractious 1970s, Billy rose quickly in the senate and ruled it with an iron hand by decade’s end. But he would struggle with an image steeped in Southie lore, the good and the bad. It made him a hero in the town and anathema in a liberal Democratic state. His dilemma was captured in the late 1980s when he was fighting off the latest reform movement to bring debate and democracy to the senate. A colleague tried to convince him he could be a hero if he loosened his grip on the chamber ever so slightly. But Bulger just shook his head. No, not guys like me, he said. “I’ll always be a redneck mick from South Boston.”
AS A project kid, Connolly got to know both Bulger brothers. He became good friends with Billy, drawn to the maturity and humor that made Billy as distinctive as Whitey was notorious. It was Billy who Connolly tagged along after on the way home from mass at St. Monica’s and Billy who got him into books, though Connolly and his friends generally thought it was a crazy notion in such a sports-mad environment.
Connolly also came to know the infamous Whitey as the hellion of Old Harbor who kept the project in an uproar with his street fights and audacious antics. Indeed, everyone knew Whitey, even eight-year-old kids like Connolly. Once Connolly was in a ball game that turned ugly. An older boy decided Connolly was taking too much time retrieving a ball and fired another one into the middle of his back. His back stinging, Connolly instinctively picked up the ball and fired a high hard one into the kid’s nose. The older boy was all over the smaller Connolly, pounding away, beating him up pretty good. Then, from the margins of the playground, Whitey swooped in to break up the one-sided fight. Bloodied, Connolly staggered to his feet, forever grateful. At some level, Connolly would stay a poor city kid looking for acceptance in a hardscrabble world, permanently susceptible to the macho mystique of Whitey Bulger.
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 detecti
ves 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.
