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 matter. 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.