Connolly’s parents—John J. Connolly, a Gillette employee for fifty years, and his stay-in-the-background mother, Bridget T. Kelly—lived in the project until John was twelve years old. In 1952 the family moved “up” to City Point, which was Southie’s best address because it looked out to sea from the far end of the promontory. Connolly’s father was known as “Galway John,” after the Irish county of his birth. He made the church, South Boston, and his family the center of his life. Somehow the father of three children pulled the money together to send John to the Catholic school in the Italian North End, Columbus High. It was like traveling to a foreign country, and John Jr. joked about a commute that required “cars, buses, trains.” The Southie instinct for patriotic duty and a public payroll also led Connolly’s younger brother James into law enforcement. He became a respected agent with the U.S. Drug Enforcement Administration, a subdued version of his swaggering older brother.
The Connollys and Bulgers reached adolescence in a clean, well-lit place by the sea surrounded by acres of parks and football and baseball fields and basketball courts. Sports were king. Old Harbor had intact families, free ice cream on the Fourth of July, and stairwells that were club-houses, about thirty kids to a building. The twenty-seven-acre project was the middle ground between City Point, with its ocean breezes and lace curtains, and the more ethnically diverse Lower End, with its small box-shaped houses that sat on the edge of truck routes leading to the factories and garages and taverns along the Fort Point Channel. To this day the neighborhood consistently maintains the highest percentage of long-term residents in the city, reflecting a historic emphasis on staying put rather than getting ahead that engenders fierce pride. As South Boston bowed slightly to gentrification along its untapped waterfront in the late 1990s, its city councilor sought to reaffirm traditional values by outlawing French doors on cafés and roof decks on condos facing the sea.
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.