Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (5 page)

For many in the neighborhood, St. Monica’s, the local parish, was more than a church. It was a youth center. Its pastor, Rev. Leo Dwyer, was more like a social worker than a priest. He could talk baseball with anybody. He took the kids on the trolley down to Mattapan Square, then on hikes in the Blue Hills. Sometimes he’d hitchhike with the kids to get out of town for the day.
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Bing Crosby would have played him in a movie. But Dwyer never had a chance with Whitey, who stayed clear of the church, even as his brother Bill became an altar boy and a standout second baseman on the parish baseball team. Being an altar boy, not to mention a good ballplayer, carried a lot of status in the neighborhood, another reason John Connolly looked up to Bill Bulger. And even after Connolly’s family moved out of Old Harbor, Bill Bulger remained a mentor, a constant, one of the most important people in Connolly’s life, encouraging him to take the same route he took, to Boston College. “I didn’t know a lot of people who went to college growing up,” Connolly said. “Bill Bulger planted the idea. He knew education was the way up and out.”
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It may have been the way up but it was not the way out. You never left South Boston. You might move away. But you never really left. Connolly only left for five years, cutting his teeth as a young FBI agent, and when he came back Whitey was already the biggest gangster in town. He decided to repay Bill Bulger’s kindness by protecting Whitey, by protecting the Bulger family from scandal. It was an act of loyalty, of fealty, and of incredibly misguided priorities. It was the sort of blind devotion that puts family and friendship first, something that grows from allegiances born on the stoop of a housing project in Southie. It would be his undoing.

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Stick-up Man

T
he wrong kind of fame came early
to Whitey Bulger. Even as a teenager he was a figure of growing renown in the neighborhood, looked up to by the likes of the young John Connolly, feared by others for his toughness and temper. He also began drawing the attention of police. Whitey was just sixteen when, by his account, the cops dragged him into the back of the South Boston precinct house. They knew him as a notorious tailgater—gifted in the art of stealing valuables off delivery trucks and fencing them for cash on the streets—and they wanted names. Who were his associates? Who were his buyers? He gave them a smart answer instead, and they gave him a beating. His arm was throbbing; he thought it was broken. One of the cops jammed the barrel of a revolver into Whitey’s mouth and drew so close that he could smell the booze on the officer’s breath. “I thought I was dead,” Whitey told a friend years later.
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But the moment passed and Whitey was released. He was proud of himself. Even expecting a bullet, he insisted he had given no one up. There would be other backroom episodes with police officers, though apparently none quite as dramatic. But Whitey’s interactions with the law became increasingly adversarial, and with good reason. With every year that passed, he veered more deeply into trouble. The crimes he was accused of took on a more sordid edge.

In June of 1948, when he was eighteen years old, Whitey was charged with assault with intent to rape after the twenty-three-year-old wife of a marine got into a car with Whitey and two other young men. The woman told police she joined the men willingly after watching a movie downtown. But instead of driving her home, they took her to Malibu Beach in Dorchester, where she had to fight her way out of the car and flee. A month later, the charge was reduced to assault and battery. Whitey paid a fifty-dollar fine and walked out of court a free man. It was a considerable break. A few months later, he enlisted in the air force.

In Southie, men enlisted enthusiastically. There was a patriotic tradition of joining the service and a solemn sense of pride in the number killed or wounded in war. Whitey’s older sister, Jean, had married a career army man from Southie, Joe Toomey. After graduating from West Point in 1949, Toomey was commissioned as a first lieutenant and sent into combat in Korea the following year.

Whitey’s military career followed a less impressive trajectory. Not surprisingly, the boy who never had much patience for rules had a hard time taking orders from superiors. In the nearly four years he was in the air force, from January 1949 until August 1952, he worked as an aircraft mechanic and managed to get his high school degree, but he also kept getting in trouble. His rule breaking, however, proved both a blessing and a curse: He never got promoted, but neither was he deemed fit for combat in Korea. Whitey’s brother-in-law was not so lucky. He was wounded and captured by Chinese troops in Korea in November 1950. Like other POWs, he endured harsh conditions, and Jean Bulger later received a letter from the army telling her that her husband had been starved to death by his captors. Whitey’s sister was a widow at twenty-three. Her dead husband’s body was never recovered. Joe Toomey is the last name of the twenty Southie natives listed on the Castle Island Korean War memorial that Whitey helped underwrite some forty years after Toomey’s death.
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Joe Toomey’s capture and horrific death traumatized the Bulger family. It also increased their concern that Whitey, too, might see combat in a conflict that would take the lives of more than thirty-six thousand US servicemen. But the Bulger family’s worries proved misplaced; Whitey’s disciplinary issues kept him comfortably stateside. “He wrote me often,” his brother Bill said.

It was clear he was enjoying himself. The Air Force apparently had more rules than planes, and he delighted in breaking or circumventing a great number of them. It appeared from his letters that he contrived a new system each week for being absent without leave and did so with impunity. His conduct was not from any lack of patriotism. He was just being Jim. I believed then, and I believe now, that he would have performed well in combat.
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The part about going AWOL was not hyperbole. In January of 1950, Whitey was arrested in Oklahoma City and charged with being absent without leave. A year later, while stationed at an airbase in Montana, he was charged with rape by police in Great Falls. The details of the alleged incident are unclear, but he was released to military authorities. The disposition of the case, while not specified in available records, favored Whitey. He left the air force with an honorable discharge. A prison report later recounted his adult arrest record and remarked on Whitey’s charmed life: “He has been arrested on charges of unarmed robbery, investigation, AWOL, rape, grand larceny and vagrancy. However, in no case did he ever receive a sentence or serve any time.”
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Whitey returned to Logan Way
at the end of the summer of 1952 and picked right up where he’d left off, stealing and selling hot merchandise. This gave him cash and a certain cachet. Boys of a certain age would watch Whitey, sporting a pearl-gray fedora, drive by in his blue Oldsmobile with a buxom hairdresser named Jacquie McAuliffe beside him in the front seat. They wanted to be like him, but most of them couldn’t imagine what that meant. He had begun by boosting goods off the back of trucks parked up and down Broadway. It was petty thievery, but it was profitable enough for Whitey to dress the way he wanted, to always have a car, to always have a girl.

A Boston police intelligence report noted that Whitey had become one of the city’s preeminent tailgate thieves. “However,” the report states, “sometime in 1955, it was reliably reported that he had stopped this activity and decided to go in for more serious crime.” While he was never a drinker, police reports describe Whitey frequenting the myriad barrooms in Southie. In the bars a small-time thief, especially one with ambitions, could latch onto a group of like-minded criminals. Bank robbery in those days was considered the next step up the criminal ladder. It was also a team sport. A typical crew consisted of three men, one of them to drive the getaway car, another to vault the counter, the third to keep his gun drawn while his accomplice scooped the cash.
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Whitey would, in time, master all three roles, though he proved especially good with the gun.

But even as he was moving on to bank robbery, or because he was, Whitey seemed unusually sensitive about his reputation within Old Harbor. George Pryor, whose family lived in the apartment beneath the Bulgers when he was a boy, remembers Whitey apologizing for not going out of his way to drive Pryor home. “I felt bad,” Whitey told him, “because I didn’t want you to think I drove by you.”
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During the early to mid-1950s, Mickey McGonagle had the paper route in the Old Harbor project, and every day he delivered a paper to the Bulger apartment. The weekly bill was fifty cents. Whitey paid McGonagle every week, handing him a dollar and telling him to keep the change. Whitey was the biggest tipper in the project by far.
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He had begun cultivating the image of the benevolent wiseguy. Of course, as a bank robber, he had more disposable income than just about anyone else. He later told his criminal associates that he robbed seventeen banks in all.
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But it was for three very specific heists that Whitey, for the first time, found himself suddenly and very seriously wanted by the law.

Bank robbery was the sort of thing
you fell into because of the people you had fallen in with. Whitey had been hanging in the taverns on and off Broadway, where ex-cons and wannabes dreamed of big scores. But he had to go downtown to find his first crew. He later claimed to prison authorities that he came under the tutelage of Carl Smith, an experienced bank robber from Indiana who used Boston as one of his bases of operation.

In an interview with prison authorities in 1956, Whitey suggested he was duped into committing his first bank robbery. He said he was introduced to Smith in May 1955 at the Stage Bar in Boston’s theater district by an ex-convict. Smith encouraged Whitey to drive for him but was vague about what he had in mind, other than saying it was easy money. Whitey’s explanation for going along with a robbery sounds implausible—even at that young age his smarts and self-awareness stood out—but it is also suggestive of the importance he placed on his reputation among other criminals. He wasn’t about to retreat from the action, no matter what it might entail. “When he learned that this deal concerned a bank robbery he wanted to back out but did not want them to know he was afraid,” a prison official wrote. “He claims that he was even more afraid when he learned he had to go into the bank since two persons who [were] involved backed out. He stated that the bank robbery was successful and afterwards he was in on three more bank robberies.”
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In May of 1955, Whitey walked into the Darlington branch of the Industrial National Bank in Pawtucket, Rhode Island, with Smith and Ronnie Dermody, an ex-con from Cambridge, Massachusetts. There were five customers and fourteen employees in the bank. Whitey pointed a .22-caliber revolver and forced two bank employees to lie on the floor. One of the customers, a Pawtucket housewife, closed her eyes and whispered a prayer, “Blessed Virgin, help us. Blessed Virgin, help us.”
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There were some tense moments when a young man training as a teller lifted his head. “All right junior G-man,” one of the robbers barked, “I said to lay down.”

They were in and out in four minutes, then returned the getaway car to the nearby factory parking lot where they had stolen it and switched cars. If Whitey was somehow duped into his first bank robbery, as he claimed, he acquitted himself well. One of the tellers told police that Whitey “walked like a cowboy.”
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And it was a very good score for four minutes’ work: $42,112.

A few months later, Whitey would show off his newfound affluence, taking his girlfriend Jacquie to Florida, staying at high-end hotels. Besides cutting hair, Jacquie had done some modeling, and Whitey had wooed her relentlessly, often stopping by the Broadway salon where she worked. When he told her he had money to burn, she left her young daughter with her mother and jumped in his Oldsmobile. They pretended to be husband and wife. It was an expensive con. In the year of living dangerously and robbing banks, Whitey estimated he spent twenty-five thousand dollars on clothes and hotels.
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Jacquie, blonde and two years Whitey’s senior, looked a lot like Jayne Mansfield, the pin-up icon of the 1950s. Jacquie was the first of the string of beautiful women who would become his companions. At some point, he started referring to her as his fiancé, but they never married.

In October 1955, Carl Smith told Whitey they had another potential bank job lined up, this one in Hammond, Indiana, where he had once lived. Smith had experience robbing banks in the Midwest and considered them easy touches compared to those on the East Coast. Whitey drove to Indiana with Smith and another member of the crew, Richard Barchard. They cased the Mercantile National Bank and agreed to rob it on October 29. On the appointed day, they stole a car from a shopping plaza and parked near the Mercantile. When they walked into the bank, however, they did not pull their guns; instead they abruptly turned around and walked out. There was a police officer inside. They drove the car back to the parking lot where they had stolen it, and, as they did so, Whitey and Barchard noticed the Woodmar branch of the Hoosier State Bank, unguarded and enticing.

Looks like a soft touch, Whitey said to himself.

A month later, Whitey and a bricklayer from Dorchester named Billy O’Brien robbed a bank in Melrose, a suburb north of Boston. While O’Brien held a gun on the customers and employees, Whitey vaulted the counter and scooped $5,035 out of the tellers’ drawers. They split the money with Barchard, who had picked the bank out and cased it. Two days later, Whitey and Barchard agreed it was a good time to leave town, to let the heat die down. They remembered that little lonely bank they had seen from the parking lot in Indiana and thought two words: road trip.

Barchard took his wife, Dorothy; Whitey took Jacquie. It was a nine-hundred-mile double date. The boys left the women in a motel, cased the bank, and, the next day, the day before Thanksgiving, they returned in a 1954 Oldsmobile 88 with Illinois plates they had just stolen, parked on Indianapolis Boulevard right in front of the bank, and strolled in. They wore blue jeans, plaid work shirts, and hunting caps with the ear flaps pulled down, but no masks.

Whitey held a pistol in each hand, pointing them at the customers and tellers. He went to the nearest customer, stuck the gun in his chest, and pushed him down. “Everybody on the floor!” he shouted. “I’ll shoot the first one who moves!”

There were five other customers, and they all hit the deck. Barchard vaulted the counter and grabbed fistfuls of cash from the tellers’ cages and stuffed it into a bag. Whitey, meanwhile, tried to reassure the terrified customers. “We aren’t going to hurt anyone,” he said. “But we have to make a living. Dillinger did.”

It was a great line, invoking the name of the Midwest’s most famous and charismatic bank robber. It might not have played in Southie, but it played big in Hammond. The customers who were forced to lie on the floor later took to calling Bulger and Barchard “the two Dillingers.”
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The two Dillingers almost hit a housewife in the parking lot of the shopping center as they made their getaway. Their haul was less than a third of what they got in Rhode Island—$12,612.28—but it was still about three times the yearly salary of a Boston firefighter living across the street in Logan Way.

Back in Southie, Whitey told Jacquie to pack: They were going to Miami for another romantic spree. They were only there a couple of days when they were both arrested for vagrancy—a pretext charge, evidently—by the Miami police, who had some reason to be suspicious of Whitey. When the police in Boston said they had no outstanding warrants on Whitey, the charges against him and Jacquie were dismissed after Whitey paid a fine of one hundred dollars.
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The cops had no idea Whitey had just robbed a bank in Indiana. It was a different time. The technology now commonly used to trace bank robbers, or even to photograph them in the act, didn’t yet exist. Whitey and Jacquie headed home for Christmas.