Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (3 page)

After the Old Harbor project was opened and another housing project broke ground right across from it, Roosevelt’s popularity soared even higher in Southie. In 1940, he won more votes in the district than Al Smith, the first Catholic presidential candidate, had in 1928.
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By 1940, McCormack was the House majority leader and he would later become the first Catholic Speaker of the House. Old Harbor was eventually renamed in honor of McCormack’s mother, Mary Ellen.

South Boston’s growing political influence, critical in winning Old Harbor, would be demonstrated repeatedly over the next quarter-century, until the neighborhood was home to two more housing projects and several subsidized apartment buildings for the elderly. For much of the second half of the twentieth century, South Boston had a little more than 5 percent of the city’s population but 20 percent of the city’s subsidized public housing stock.
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It wasn’t just McCormack; Southie’s Irish ward bosses, and state representatives like Jimmy Condon and state senators like Johnny Powers, were expert at delivering votes for Democrats on local, state, and national ballots, although the neighborhood’s resolute insularity made it hard to elect a native son citywide. Politicians won enduring loyalty by securing housing and jobs for their constituents, and Southie pols, if they wanted to survive, had to be skilled at delivering both.

In Old Harbor, everyone was poor—the average rent was twenty-six dollars a month—and everyone, it seemed, was Irish. In the Bulgers’ building, there were six families—the Bulgers, the Pryors, the McCarthys, the Drinans, the McKeowns, and the Walshes—with twenty-seven kids among them.
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In all, there were six thousand people living in Old Harbor, most of them children. There was always something to do. Games like tag and hide-and-seek started, and grew, spontaneously.

Unlike so many other desolate and isolated housing projects that would follow, in Boston and across the nation, many of the apartments at Old Harbor boasted ocean views, with Carson Beach just across the way. There was sprawling Columbus Park sandwiched between the project and the beach, where kids played baseball into the dusk on summer nights and football when those nights turned cool. On Saturdays, the maintenance building was converted into a cinema. For five cents, kids got to see a movie, a cartoon and one of the serials. Kids from the project would sneak into the storage yard of a barrel factory on nearby Dorchester Street and pull staves off used barrels returned by Baker’s, a chocolate manufacturer. They’d eat the chocolate right off the staves, picking splinters from the hardened candy.
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During World War II, Italian POWs were housed at Camp McKay, at the end of Carson Beach. Kids from Old Harbor, many of them with brothers or uncles fighting overseas, would cross the fields to stare at the POWs behind the wire. Italians from the North End came, too, and the American guards did nothing to stop them from pushing a taste of home—Italian cheeses and cold cuts—through the fence to the POWs.
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After snowstorms, the kids from Old Harbor would run across Columbus Park up toward Dorchester Heights. They would block off Telegraph Street, a steep hill that rose to Dorchester Heights, and coast down on makeshift toboggans. Traffic wasn’t an issue; there wasn’t any.
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It was rare to see a car drive through or around Old Harbor during the war years. A car was a symbol of making it, and few here would reach that level. Whitey’s younger brother Bill and his contemporaries remember the Old Harbor as something of a haven, a place where, for all the lack of wealth, it was considered rare and scandalous when a man walked out on his family. He, like many of his peers, remembers a neighborhood and a childhood that was idyllic. And he remembers that South Boston viewed itself as separate and distinct from the rest of the city. Indeed, when people from other neighborhoods took the trolley into the heart of the city, they said they were heading into town, just as in Southie people referred to their neighborhood as the Town.

Bill Bulger remembers the South Boston of his youth as a place where people swept their sidewalks and washed their windows, where the churches and schools were stable institutions, where divorce was rare. Southie had its share of bars and bookies, but it was also widely considered the safest neighborhood in the city. “And,” he noted, “on the rare occasions when someone crossed the line into heavy felony, he alone was condemned. The neighborhood was wonderfully free of the star-chamber mentality that indicts or ostracizes entire families.
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It was, however, famously quick to distinguish outsiders from insiders and cherish its tradition of deciding for itself who belonged. “It takes a lot to incite South Boston people, but beware when that happens,” said Patrick J. Loftus, a political opponent of Bill Bulger who nonetheless shared his view of Southie’s essential character. “When Charlie Do Right or Mr. and Mrs. Nice Guy who know nothing about us come riding into South Boston from out of town and try to change us, our jobs, our neighborhood, and our traditions, without our accord, war is declared.”
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For some, including the Bulgers, “outsider” was an elastic term. Bill Bulger says he never understood why his family escaped being labeled as outsiders.
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In fact, the construction of public housing in the neighborhood introduced to Southie dozens of families who, like the Bulgers, had no previous or familial connection to the Town. It was a melting pot of the poor. The rest of the city, though put off or amused by Southie’s preening pride, more or less bought into the view of the neighborhood as a place apart, and its physical isolation meant few outsiders passed through unless they had reason to. Many outsiders saw Southie as a rough place with a disproportionate number of bars and the problems that accompanied them. But it was more complex than that.

When Whitey Bulger was growing up, there were three distinctive parts of Southie: City Point, a leafy section on the east side, bounded by the ocean; the hardscrabble Lower End, on the west side, where tenements stood near factories and the fish warehouses that stretched up from the waterfront; and the projects. While the projects were on the west side, they were considered distinct and apart from the Lower End. Southie’s population was about twenty-three thousand during the Civil War, but it had nearly tripled in size by the beginning of the twentieth century. From the apex of around eighty thousand before World War I, the population steadily dwindled to about fifty thousand in 1920 and remained fairly constant until 1980, when it fell to today’s roughly thirty thousand. It was an overwhelmingly blue-collar community, thick with tradesmen, laborers, and longshoremen. Southie’s lawyers and doctors and small businessmen peopled the brick town houses in City Point. A stretch of East Broadway had so many doctors living in the brownstones that the locals called it Pill Hill. The waterfront provided many jobs, legitimate ones to those who loaded and unloaded ships, illegitimate ones to those who trafficked in the goods that were stolen off those ships. If the waterfront gave James Bulger his only steady job, it would one day give his first son and namesake his first crooked one. Not long after the Old Harbor project opened, they dedicated a huge sculpture in the project’s courtyard showing three workingmen—a fisherman, a longshoreman, and a foundry worker—flanked by a boy and girl at play. Those were the sorts of people who lived in Old Harbor.

The Cliffords of O’Callaghan Way,
who were close to the Bulgers, were considered almost royalty: Billy Clifford was the first priest ordained out of the projects, while his sister Marilyn was the first nun.
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Such was the ideal for ambitious Catholic families, but it was hardly the rule. It was not unusual—indeed, it was probably more common—for the same household in South Boston to produce a cop and a criminal, a priest and a politician, a firefighter and an arsonist. That duality left people less judgmental and more empathetic about those who went astray. When Whitey Bulger started getting into trouble as a young teenager, snatching and reselling stolen goods, no one suggested he came from a bad family; in fact, they knew just the opposite. The rest of the Bulger kids were well behaved and studious; Whitey was just the wild one, the black sheep, and there were few clans in Southie who could credibly claim their family tree never knew the backhand of a cop or the inside of a jail cell. It wasn’t considered just poor form in Southie to hold a family accountable for its bad seed; it was considered hypocritical.

Jean Bulger, Whitey’s mother, was infused with an optimism that defied a depression and a world war. Neat in appearance, invariably pleasant, she was a master at the art of stoop talking, by which news and gossip spread from one building to the next. She handed out freshly baked cookies to the neighborhood kids.
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Viewed with great fondness by her neighbors, she was also a different person in different settings. In the presence of her husband, who was quiet, she was retiring and demure, even deferential. But on her own, she stepped forward. Her sometimes reticent demeanor hid a street-smart sagacity. You could not pull anything over on Jean Bulger, and she did not like phonies.
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“When she put her mind to something,” her son Bill said, “she usually got it.”
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As the family patriarch, James Bulger cut something of a sad figure. He was self-conscious about his missing arm and eventually stopped wearing his prosthetic. No matter what the weather, he slung a coat over the missing appendage. But he liked a well-cut cigar and was a good conversationalist, a staunch New Dealer who believed that FDR saved the country, and especially the workingman. At the very least, FDR gave his family a good place to live for $29 a month, about a third of their monthly income.
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In part because he never held a full-time job after losing his arm, in part because of his introverted nature, James Bulger was fond of long, solitary walks along the beach. When he did stop to talk, it was usually about politics. He was politically astute, and a staunch supporter of James Michael Curley, Boston’s empathetic if ethically challenged mayor.

Curley’s rise from poverty to power was a potent symbol to Boston’s ethnic poor of what could be done, and what they could hope for. He personified a defiant, anything-is-possible ethos that resonated in Old Harbor. And while there is no evidence that Whitey paid much attention to Curley, Whitey’s little brother Billy grew to idolize him, to want to be like him, first as a student, then as a politician. He patterned his rhetorical style and wit after the master.
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Curley, who grew up poor but was a learned man, had been caught in the early 1900s taking a civil service exam for an Irish immigrant. This transgression landed him in jail briefly and marked him forever as a scoundrel to the ruling Protestant Brahmin establishment. But to the working-class ethnics he was a hero. They returned him to office despite repeated acts of graft and corruption. Curley turned his criminal record into a campaign slogan: He Did It for a Friend. He was shameless and savored hard-nosed tactics. When he found out that Boston mayor John “Honey Fitz” Fitzgerald had had an affair with a cigarette girl named Elizabeth “Toodles” Ryan, he announced that he would be giving a public lecture entitled “Great Lovers in History: From Cleopatra to Toodles.” The public had never heard of Toodles but Honey Fitz had; he withdrew from the race, and Curley canceled his lecture and cruised to victory in the 1914 mayoral election.
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He was Boston’s most charismatic and resilient politician, and, in a career that stretched well beyond a half century, he served terms in the mayor’s office, the governor’s office, Congress, and a federal penitentiary. Long after the Irish became the most powerful force in Boston and Massachusetts politics, Curley exploited class divisions to create an us-versus-them narrative that helped sustain his wild popularity with his blue-collar base.

In places like Old Harbor, Curley was especially loved. During the Depression, he received constituents at his mansion, located on the main, winding tree-lined boulevard in Jamaica Plain. Its shutters were decorated with shamrocks. The line of supplicants formed early in the day, and Curley listened to stories of hardship and handed out cash or jobs. In the projects, his roguish ways engendered only affection. If he stole, many reasoned, he stole from the Brahmins and the banks—and what have they ever done for us? Curley was especially admired in Southie because he built the L Street Bathhouse on Carson Beach and greatly expanded City Hospital, which served the lower classes. He was known, with justice, as the Mayor of the Poor.

James Bulger, while a Curley loyalist, had no connections in City Hall, no political patron to wangle him a secure job, and so he struggled to keep his family out of poverty. It was an era, Bill Bulger recalled, when there were no special programs or opportunities for the disabled. His father had to work when others wouldn’t. “If it were very, very cold, he would be the night watchman. If it were Christmas, or New Year’s, when no one else wanted to work, he would take whatever jobs he could get. He wasn’t a complainer, though. He was happy to get the job. It was a grind.”
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World War II changed both the Bulgers and South Boston. For Southie, the war brought a sudden end to the Depression. Thousands of neighborhood men enlisted, and both men and women filled new jobs in factories and shipyards.
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O’Connor, the Boston historian, argues that Southie came out of the war more unified than ever, more recognized as a special place than ever. The old vaudeville song “Southie Is My Home Town,” which praised a neighborhood where “they’ll take you and break you but they’ll never forsake you,” was ubiquitous. It was sung at military posts, PXs, “and barrooms from South Carolina to Georgia, Texas to California. . . . By the time the war had ended South Boston, for better or worse, had become the only one of the city’s two dozen neighborhoods to epitomize the ‘Boston Irish’ at their open-hearted, ebullient best, or their brooding, belligerent worst,” O’Connor said. “The single image of ‘Beacon Hill’ comes close to encapsulating the notions of the Yankee heritage, the Brahmin influence and the conservative Protestant tradition of Boston. In much the same way, ‘South Boston’ had come close to symbolizing, in a single community, the ‘other’ Boston—the immigrant spirit, the Irish character and the Catholic influence in the city.”
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