into a taxi at gunpoint and bark at the bewildered cabbie to drive to the nearby FBI headquarters at East Sixty-ninth and Third. His boss chided him good naturedly about the handcuffs, but there were envious smiles and back slaps all around for bagging one of Boston’s most wanted mobsters. Some were amazed that Connolly had been able to recognize Salemme, but in fact it wasn’t quite as lucky as it first appeared. An old pro in the Boston FBI office had taken a shine to Connolly and earlier had sent him photographs and likely locations for spotting Salemme, gleaned from informant reports. It was a perfect example of how valuable informants could be. Connolly’s apprehension of Cadillac Frank resulted in a transfer back home, an unusually quick return for an agent with only four years of duty under his belt.
By 1974 Salemme was off to fifteen years in prison and Connolly was back to the streets of his boyhood. By this time Bulger was the preeminent Irish gangster in the flagrantly Irish neighborhood of South Boston. When Connolly returned, Bulger had just solidified his hold on Southie’s gambling and loan-sharking network, the culmination of a slow, steady climb that began in 1965 with his release from the country’s toughest prisons.
The two men spoke the same language and shared deep roots in the same tribal place. They came together as book ends on the narrow spectrum of careers available to Irish Catholics who lived in splendid isolation on the spit of land jutting into the Atlantic Ocean. Their cohesive neighborhood was separated from downtown Boston by the Fort Point Channel and a singular state of mind. For decades Southie had been immigrant Irish against the world, fighting first a losing battle against shameful discrimination from the Yankee merchants who had run Boston for centuries and then another one against mindless bureaucrats and an obdurate federal judge who imposed school busing on the “town” that hated outsiders to begin with. Both clashes were the kind of righteous fight that left residents the way they liked to be: bloodied but unbowed. The shared battles reaffirmed a view of life: never trust outsiders and never forget where you come from.
A retired cop once recalled the constricted choices a young man had coming of age in the South Boston of the 1940s and 1950s: armed services, city hall, utility companies, factory work, crime. “It was gas, electric, Gillette, city, cop, crook,” he said. The decades of travail made Southie residents quick to fight for limited opportunities.
Bulger and Connolly, crook and cop, grew up in the first public project in Boston, a spartan village of thirty-four tightly spaced brick tenement buildings. A contractor friend of the legendary Mayor James Michael Curley built it with money from the Public Works Administration of Franklin Delano Roosevelt. Both men were revered in the Bulger home on Logan Way—Curley for his roguish repartee and Roosevelt for saving the workingman from the ravages of capitalism.
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 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 US 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 clubhouses, 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.
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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 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 Southies 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 according to their 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. And 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