Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (4 page)

The war brought marked improvement to the Bulgers’ finances. With so many men in the military, James Bulger got work at the Charlestown Navy Yard. The work remained steady until the war ended. James Bulger was philosophical about the end of the war and his job. “Look,” he told his family, “even though it’s better for me than it’s been, I wouldn’t want the thing to go on one extra day, because of what it would mean to other people.”
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If finding work was a constant worry, so was his son Jim. Compared to his other siblings and most of his peers, Whitey was notably uncooperative and combative. By nature a nonconformist, he was constantly in trouble with his teachers for acting up or, just as often, for chronic apathy. He seemed ungovernable and unreachable. The nuns at St. Mark’s and St. Margaret’s in Dorchester had had little success in getting him to study. The public school teachers fared no better after the family moved to South Boston and Whitey enrolled in fifth grade at the Thomas N. Hart School, at the corner of H and East Fifth streets. Tommy Moakley, a contemporary of Whitey’s, remembers the public schools and parochial schools as completely different worlds. Whitey didn’t fit in either. In the Catholic schools, a rap on the knuckles was common when you acted up, and that kept outbursts to a minimum for most children. But it was looser in public school. “We went to the Hart School,” Moakley said. In honor of its often unruly students, Moakley said, the kids called it the Nut House.
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Whitey went to the Hart School through eighth grade. A federal probation officer who much later reviewed his report cards and the less than glowing reviews written by nuns and teachers was harsh in his assessment. “His scholastic record was poor. He failed in all of his subjects, receiving poor marks in conduct and effort. The school report shows that he was surly, lazy and had no interest in school work.”
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But he kept getting advanced to the next grade. The available record offers no explanation for the lenient treatment.

Whitey also defied the rules and expectations at home, testing his father’s patience and risking his hand. James Bulger Sr. was a man of solitary pursuits, and child rearing in those years was largely left to women. Still, like many parents of that era, James Bulger sometimes resorted to corporal punishment, especially with Whitey, who later told prison interviewers that his father beat him severely on occasion. The image of James Bulger beating his wayward son was contrary to his character, according to Bill Bulger, who described his father as “instinctively gentle.” But if Whitey’s claim about his father is accurate, the harsh discipline reflected James Bulger’s utter frustration with his scapegrace son. Still, the one-armed beatings seem to have had little or no effect. At his father’s insistence, Whitey gave school one last shot, at the Brandeis Vocational High School downtown, where there was hope he could pick up a trade. He lasted a year.

But he found a trade. It was not a coincidence that Whitey’s last year in school coincided with his first recorded arrest, in 1943, for larceny and delinquency. He was thirteen years old. His sentence was suspended, and he was off probation by the next time he was arrested, two years later, as a wayward youth—a nebulous, catch-all charge reserved for the most incorrigible defendants in the juvenile system. Four more arrests followed, at fifteen and sixteen, on more serious charges, including assault and battery. He was found guilty on only one of the charges, and he won that on appeal; the rest were dismissed or he was found not guilty. He appeared before judges six times as a juvenile, twice for violent offenses, but was not incarcerated. He kept getting a break.
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Perhaps he was the beneficiary of political influence through his Southie connections, or perhaps it was judicial sympathy for the bad apple in a good family; the court files are silent on why. Some who knew him well say some of Whitey’s early criminal forays were motivated by a desire to bring some money to a cash-poor household. He was the oldest boy and felt some obligation. But there were also offenses that don’t fit that pattern at all.
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Trouble wasn’t all that lured Whitey. The Ringling Bros. and Barnum & Bailey Circus came to town one year when he was a teenager, and he ran away with it. He didn’t last long as a roustabout, but his willingness to try it betrayed his desire for something beyond the confines of Southie, the certainties of Old Harbor life that he valued but also felt suffocated by, and the scrutiny of his parents. His mother had just given birth to her sixth and last child, Sheila. Bill Bulger, five years younger than Whitey, recognized the itch, the frustration that in his brother’s case was obvious. “I had seen him change from a blithe spirit to a rebel whose cause I could never discern. He was in a constant state of revolt against . . . I’m not sure what. He was restless as a claustrophobic in a dark closet.”
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Whitey’s rebelliousness was in stark contrast to the behavior and preoccupations of his siblings. They were studious. They strived to conform. His older sister, Jean, was voted the prettiest girl at South Boston High School.
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His brothers and sisters followed the rules.

Not Whitey. Rules were a particular point of contention for him. He would defy them or rewrite them. One day, he came home with an ocelot, a small wildcat that looks like a miniature leopard. He named it Lancelot and kept it in the bedroom he shared with his brothers. Jean Bulger refused to enter her sons’ room as long as Lancelot the Ocelot was there. Bill recalls that whenever his mother reminded Whitey that pets were forbidden in the project, Whitey cited the fine print, insisting that the rules specifically forbade only dogs and cats. “Read the rules,” he told his mother. “Where does it say anything about ocelots?”
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Lancelot the Ocelot grew to such a size that, eventually, even Whitey agreed it had to go to a zoo. He brought it there himself.

Throughout the projects and much of the Lower End, Whitey was known as a good-natured hellion who grew tougher with time and also grew into a figure of real charisma among his peers. Joe Quirk, who grew up across the courtyard from the Bulgers, remembers the teenage Whitey as a physical specimen with a washboard abdomen. “Hit me in the stomach,” Whitey dared him. “Hard as you can.” Quirk was just a kid, six years younger, and he punched as hard as he could. Whitey didn’t flinch. “You can hit me harder than that,” Whitey said.
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He also began building a reputation as something of a gentleman among troublemakers. Sally Dame, who moved into Old Harbor across the street from the Bulgers when the project opened in 1938, remembers Whitey, whom she called Jimmy, as especially solicitous of his elders. If he saw her bumping her shopping carriage down the steps, Whitey would run up to her, saying, “Wait a minute, Mrs. Dame. Wait a minute.” He would then gallantly carry the carriage down the steps for her.
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Bobby Moakley, Whitey’s classmate at the Hart School, said that whenever Whitey saw Moakley’s mother walking home from the store, he would offer to help. When he was young, he offered to carry her grocery bags. When he was older and had a car, Whitey would pull alongside Mrs. Moakley and insist on driving her home. “He was always the perfect gentleman,” said Moakley.
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Whitey also began to stand out for other reasons. Not long after World War II ended, he was a high school dropout without a legitimate job who somehow managed to have a car. Boston police intelligence reports in those years identified him as a tailgater, someone who stole goods and appliances from the trucks that loaded up from freighters on the waterfront. Whitey was hardly alone in this trade. Southie was full of tailgaters, who found willing buyers in the neighborhood for winter jackets or toasters or irons or whatever else they could get their hands on. His neighbors, knowing he didn’t have a job, would doubtless have assumed that Whitey got his money through illegitimate means, but South Boston in general and Old Harbor in particular were not places where people asked questions about such things.

He was also, even as a nascent criminal, preoccupied with appearances, seemingly conscious of creating a public persona that belied his true profession. He dressed neatly, in sports shirts and slacks. The only sartorial nod to his criminal life was a fedora he’d often don while driving—the favored headgear of the hoods of his era. And Whitey, while he could swear like a sailor, was fastidious about not doing so in front of his elders. Sally Dame remembers Whitey asking a neighbor for permission to use a hose to wash his car. He let some of the younger kids help him, giving them a quarter for their trouble, a sizable amount for a young kid in postwar Southie. “One kid swore,” Sally Dame said, “and he grabbed him by the ear, Jimmy did, and he said, ‘Don’t you ever, ever let me hear you swear again or I won’t let you help me wash my car.’”
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After Ann McCarthy moved into Old Harbor in 1947, she noticed that Whitey had a way with animals. “All the dogs in the neighborhood loved him,” she said. “They all ran for him. He always had goodies in his pockets.”
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If Whitey’s image, especially among his elders, was of an affable, gentlemanly teenager, he was seen quite differently by peers. Those his own age knew he was a fierce street fighter, someone not to be messed with. He was, one police officer recalled, the type of kid who would take two punches to land one. And he worked to maintain his chiseled, compact physique. Whitey played football with the Shamrocks, a Southie gang that played other neighborhoods in games where a punch was used as often as a block. But generally he wasn’t drawn to team sports. Instead he lifted weights at home, rare in those days, and ran the beach to stay in shape. His regimen and self-discipline were intense. There was love and stability inside Apartment 756 at 41 Logan Way, but Whitey craved something else: the wild side. Still in his teens, he scandalized his mother when he began dating a burlesque dancer who used the stage name Tiger Lil.
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Bill Bulger remembers his older brother being in search of something far beyond Southie. “‘Where’s Jim?’ my mother was always asking. ‘I turn my back for a second and he’s out the door. He’s always out the door. Where does he go?’ I couldn’t answer. I didn’t know. I don’t think Jim knew where he was going most of the time—just out.”
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Jean Bulger remained relentlessly optimistic about her oldest son. He’s going through a stage, she would say.
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But his restlessness didn’t recede with time. It grew.

Johnny Connolly was sitting on his stoop
on O’Callaghan Way, the longest street in Old Harbor, which loops around the project. It was the summer of 1946 and he was six years old. He looked up, shielding his eyes from the sun, and saw Whitey Bulger walking briskly up the street. He knew it was the kid everybody called Whitey, just by looking at him. In the Old Harbor projects, you learned about Whitey Bulger quickly. He was only seventeen but his legend was taking shape. He was the toughest kid, the wildest kid, in the neighborhood. Being tough meant something in all of Southie, but especially the projects.

From that stoop, Johnny Connolly watched Whitey stride across the courtyard, his short-sleeve shirt revealing a bulging bicep, his dungarees rolled up at the ankles. His hair was somewhere between blond and white, shimmering in the afternoon sun. John Connolly would never really let go of this romanticized image even years later when he knew Whitey as a gangster and a murderer.

Two years later, eight-year-old Connolly and two of his playmates were standing in a drugstore everybody called The Druggie, at the corner of Mohawk Street and Devine Way. The boys had gone to buy penny candy, but one of them spied nineteen-year-old Whitey and another teenager standing at the soda fountain and whispered, “There’s Whitey Bulger.” By that time, even prepubescent boys knew he was a tough guy. Some of them might have even known he was a budding hoodlum. “It was like meeting Ted Williams,” Connolly said. “He was a legend in the project.”
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Whitey noticed the boys staring, so he asked, “You guys want an ice cream?” Connolly’s companions nodded enthusiastically, but Connolly hung back, remembering his mother’s admonition not to accept gifts from strangers. After the other boys had placed their orders, Whitey turned to Connolly and asked, “What kind of ice cream do you want?” Connolly was embarrassed and looked at the floor, but his buddy Robby wasn’t as shy.

“His mom says he can’t take anything from strangers,” Robby blurted out between licks of his cone.

Whitey scrunched up his face.

“Strangers?” Whitey said. He looked down at Connolly.

“Kid,” Whitey asked, “where do you live?”

Connolly pointed down the street, to O’Callaghan Way.

“Kid,” Whitey Bulger said, bending over so his face was level with Connolly’s. “I’m no stranger. Your mother and father are from Ireland. My mother and father are from Ireland. I’m no stranger. Now, what kind of ice cream do you want?”

The families’ immigration history was somewhat truncated—it was Whitey’s grandparents who were from Ireland—but the larger point was made.

“Vanilla,” Johnny Connolly said.

And with that, Whitey Bulger reached down and lifted little Johnny Connolly up to the counter and bought him an ice cream cone.
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It was the first encounter in a relationship that would span more than half a century and become mutually beneficial, though the vector of power would always remain, as it was that day, tilted toward Whitey.

A short time later, Connolly was walking through the courtyard when an older kid threw a ball at him. He instinctively picked it up and threw it back in anger, striking him in the face. Enraged, the other boy pounced on Connolly and began pounding him. He had thirty pounds on Connolly and it wasn’t a fair fight. Whitey Bulger appeared and pulled the older boy off. “Go fight somebody your own size,” Whitey told the kid.

The Connollys moved out of the project and a mile away to City Point when John was twelve years old. Other than buying him an ice cream cone and saving him from a beating, Whitey Bulger played no role in young Connolly’s formative years. But those two acts of generosity and protectiveness were seared into Connolly’s memory, and Whitey’s brother Bill became Connolly’s mentor. Bill Bulger was six years older than Connolly, but he saw something in the younger boy and was solicitous of him, walking him home from church on Sundays. They worked together as lifeguards at the L Street Bathhouse.