Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (9 page)

At Lewisburg, Whitey was housed in a single cell and worked as a sanitation clerk. Now even closer to home, he received ten visits during his eighteen months at the Pennsylvania prison. On January 16, 1964, he saw his father for the last time when he showed up at the prison with Whitey’s brother Jack.
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Two months later, on the same day the parole board had rejected Whitey’s second request to be freed, the prison’s Catholic chaplain received a call at 5:00 p.m. from Bill Bulger, who told him his father, James Bulger Sr., had died of pneumonia the previous day at St. Elizabeth’s Hospital in Brighton, Massachusetts. He’d been given last rites while surrounded by his family. The chaplain broke the news to Whitey a half hour later. Whitey’s imprisonment had taken a huge toll on his father: Bill Bulger told a friend his father never had a good day after Whitey went to prison.
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Whitey asked to go home for his father’s funeral, which was to be held two days later at St. Monica’s Church, but was told there wasn’t enough time to make arrangements.
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He had, the prison chaplain reported, “an excellent attitude despite some bitterness” and did not tell his mother about his parole denial when he was allowed to call her the next day. They spoke for five minutes about his father’s death while the prison’s Catholic chaplain listened in on the conversation at Whitey’s request.
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Whitey seemed to be growing impatient with the parole board’s reluctance and yearned for his freedom. Prison staff reported that he “maintains some questionable associates and is among the group who are always watching the rear gate and the towers and other vital parts of the institution.”
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Yet they also referenced the fact that he had influential friends, noting: “He seems to have a good outlook and to be quite proud of members of his family who are in politics. It is also noted his family have a very close relationship with the speaker of the House of Representatives [McCormack].”

Bill Bulger’s persistent requests for McCormack’s help, and McCormack’s strategy of going over the heads of individual institutional authorities directly to the Federal Bureau of Prisons, were finally paying off. In a note to the Lewisburg warden that seemed sympathetic to Whitey, Bureau of Prisons assistant director H. G. Moeller wrote that Whitey’s adjustment was good and “and he is trying very hard to make a good record in order to be granted parole.”
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For a third time, Whitey went before the parole board, telling them he had a job waiting for him, earning $1.50 an hour at Farnsworth Press, a graphic arts company on the waterfront in Boston. He planned to live with his mother in South Boston. His parole adviser would be Father Drinan. The third time was the charm, and the board finally relented.

Whitey had gone to prison with a plan to get educated, and one thing he had learned was that relying on your own wits and cunning was not enough; that it was important to have friends in high places. Having spent nine years in some of the most fearsome corners in America, he had come to realize that power, even just the perception of it, accomplished more than fear. On March 1, 1965, at 10:55 a.m., Whitey strolled out of Lewisburg prison with $64.27 in his pocket. He’d be back in Southie in plenty of time for St. Patrick’s Day.

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Becoming Untouchable

H
e had persuaded everyone
—his family, his priest, his best friend in prison, and finally the parole board—that he would go straight when he was released. But if Whitey Bulger meant it, he didn’t mean it for long. He got work in construction when he returned to Southie, but he also began looking for work of a more familiar kind. If timing is everything, Whitey’s was impeccable. The nine years he’d spent in prison hadn’t just served as a finishing school for his mind, they had dramatically improved his chances of thriving in the Boston underworld.

Whitey was still in Alcatraz in 1961 when the Irish mobsters in Boston turned on each other with unprecedented vengeance. The bloodletting would go on for years, and when it was over, just as Whitey was getting out of prison, some sixty gangsters lay dead. A few dozen others were serving long prison sentences for violence connected to the war. The city had never seen anything like it. On the street, Whitey would have been either a potential victim or a perpetrator or, more likely, both. Tucked away in prison, he moved closer to power without lifting a finger. The war had drastically remade the criminal landscape in Boston, creating a vacuum of power and a wealth of opportunity that Whitey, older now, less impetuous and more tactically savvy, would exploit.

Like many things involving Boston’s Irish gangsters, the war was ignited by the combustible mix of alcohol, women, and a warped sense of loyalty. In sheer numbers, the Irish gangsters should have been the dominant ethnic organized crime group in the Boston area, but they tended to group themselves by neighborhood, and sometimes even within smaller neighborhood subsets, diluting their citywide power and causing fights, even desperately bloody ones, over small questions of territory and pride. The Italians, by contrast, benefited from having an organization, La Cosa Nostra, whose main requirement for membership—Italian heritage—cast a wider net and limited, at least in a smaller city like Boston, the risks of factionalism.

The Irish gangs also demonstrated a remarkable propensity for fratricide, posing a greater risk to each other than the Italians ever mustered. This paradigm for organized crime in Boston extended back to the era of Prohibition. Even the 1931 Mafia ambush of Frank Wallace, leader of Southie’s then-dominant criminal group, the Gustin Gang, did not persuade the Irish to coalesce. Instead, they retreated to their respective ghettos, making pacts and alliances that almost invariably collapsed over personalities and peccadilloes.

The Boston gang war of the 1960s involved criminals of all stripes, but it had a disproportionate impact on the Irish and, not surprisingly, was started by them. By war’s end, the Italians had increased their power and dominance, mainly by having held their fire and let the Irish go at each other. Not only did the devastating mayhem give Whitey Bulger an opening to rise through the depleted Irish underworld, it created an enduring illusion in Boston of Mafia omnipotence. The Mafia, with its national and international tentacles, was the most powerful criminal organization the city had ever seen when Whitey got out of prison. The FBI had a national mandate to take out La Cosa Nostra, and thus the bureau’s Boston office went after the New England Mafia with great zeal. Pursuing Irish gangsters took a backseat. Whitey was able to cement his power precisely because the FBI considered the Mafia the only worthwhile organized crime target for law enforcement. Agents got commendations and promotions for developing informants against the Mafia, not for taking down murderous, small-time Irish thugs.

The war was a critical bend in Boston underworld history, and it all started because George McLaughlin couldn’t keep his hands to himself.

George was the youngest of the three brothers who controlled the rackets in Charlestown. With just fifteen thousand residents, Charlestown is Boston’s smallest “big” neighborhood, the site of one of the most important battles of the Revolutionary War, and the center of Boston’s maritime industry. As in South Boston, the Charlestown shipyard docks provided jobs for longshoremen and opportunities for criminals, and the McLaughlins controlled not just all the gambling in town but the thievery along the docks. Their bookies walked the wharves like supervisors, taking bets from longshoremen who played “the number,” an illegal lottery. Meanwhile, the mob enforcers behind the bookies were free to select the goods they wanted to steal and fence. The McLaughlins had a mostly peaceful relationship with their fellow mobsters on Winter Hill in the neighboring city of Somerville—Irish, most of them—but that was about to change.

Perhaps because he knew his big brothers would always have his back, George McLaughlin often started fights he couldn’t finish, and he started a doozy during a liquor-soaked Labor Day weekend in Salisbury Beach, just south of the New Hampshire border. According to various accounts by gangsters and law enforcement officials of that era, George McLaughlin staggered up to the wife of a Winter Hill mobster from Somerville and grabbed her breast. The Somerville mobster and his friends took offense. George McLaughlin was beaten unconscious and had to be hospitalized.

Bernie McLaughlin, George’s older brother and the leader of the Charlestown gang, wanted justice, so he sought out James “Buddy” McLean, leader of the Winter Hill Gang. Bernie McLaughlin thought his demand was perfectly fair and reasonable: Whoever beat his little brother should be killed, and Bernie wanted McLean to set the guy up. But Buddy McLean shook his head. His men, he asserted, had acted nobly, while George McLaughlin had flagrantly insulted the honor of a woman, in front of men from both Somerville and Charlestown. George McLaughlin had gotten what he deserved.

Bernie McLaughlin drove back to Charlestown nursing a grudge, and an idea. He dispatched some men to put a bomb in McLean’s car, but McLean caught them in the act and chased them off. Not long after, McLean approached Bernie McLaughlin outside the Morning Glory bar in Charlestown, in the middle of the afternoon, and this time it was not to discuss the niceties of gangland protocol. He pulled a gun and shot Bernie in the head.
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It was Game On.

Besides clearing the playing field for Whitey Bulger, the gang war of the 1960s brought into prominence, and into the welcoming arms of the FBI, the man who would become Whitey’s closest associate: Stevie Flemmi. A wiry 5 feet 6 inches, Flemmi was never the tallest guy in the room, but he was usually the deadliest.

The son of Italian immigrants, Flemmi grew up in the Roxbury section of Boston and seemed born to be a criminal. At fifteen, he was arrested on a charge of “carnal abuse,” a charge usually applied to juveniles who have underage sex, and was locked up briefly on assault charges.
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Even when doing the noblest thing in his life, signing up with the army in January 1952, he wasn’t on the level: as a seventeen-year-old high school kid, he was too young to enlist, so he stole the identity of a childhood friend. With the Korean War on, army officials apparently didn’t notice or didn’t care. Flemmi, serving in the 187
th
Airborne, displayed a prowess with firearms. He claims to have killed five Chinese soldiers during his first taste of combat,
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and his crack shooting led his Airborne buddies to dub him “The Rifleman,” a moniker that stuck. His battlefield stardom also gave him the opportunity to tell his commanding officers what his real name was; Flemmi said he revealed the deception so his parents would get survivor’s benefits if he was killed during the war.

Flemmi went on to kill many more Chinese and North Korean soldiers, and thus, in addition to his high school equivalency diploma and a nickname, he took home from Korea an identity he valued more than being a criminal: military veteran. Proud of his service, he would raise money for veterans’ memorials and regularly attend Airborne reunions and functions as he rose in criminal eminence. He also discovered he was really good at, and seemed to enjoy, shooting people. This was the extent of his professional training when he returned to Boston in 1955. For what he had in mind, it would be enough.
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Back in town, he opened a convenience store, Jay’s Spa, in Dudley Square, the main commercial district in Roxbury, and soon met Edward “Wimpy” Bennett, a racketeer who used a nearby storefront as a cover for his extensive gambling operation. Bennett asked Flemmi if some customers he had loaned money to could leave repayments off at his store. In gratitude, Bennett later staked him to some money that Flemmi used to extend credit, on steep terms, to gamblers, launching his career as a loanshark.

By 1958, Flemmi was already drawing notice from local law enforcement as an up-and-coming wiseguy. He was approached by Paul Rico, the FBI’s prime local cultivator of confidential criminal informants and the agent who two years earlier had arrested Whitey Bulger after an informant spotted him in a nightclub. Rico showed up at Flemmi’s store out of the blue and asked him if he had been involved in a recent bank robbery. Flemmi was stunned. He denied he was robbing banks—in fact, bank robbery was one of the few criminal activities Flemmi wasn’t engaged in at the time. Rico took his word for it, but not long after, Rico was back, this time accusing Flemmi of driving a Roxbury bank robber to Los Angeles. This time Rico had it right; Flemmi had, in fact, made the drive in the company of the bank robber, and it was suddenly clear to him that the agent must be talking to Wimpy Bennett, who knew about the cross-country road trip. Flemmi also surmised, correctly, that Rico was trying to recruit him as an informant, letting him know how vulnerable he was to arrest, that others whom Flemmi had trusted were talking about him, and that his best hope for protection might come from the FBI itself.

Rico started visiting Flemmi’s store every day, pumping him about the Mafia in the North End, where Flemmi was a frequent and respected presence. He’d come to know many local Mafia figures, including those who dropped by an after-hours club he’d opened in Roxbury. But if Rico and his FBI partner, Dennis Condon, irritated Flemmi at first, they became an asset after the Somerville-Charlestown gang war erupted. It was obvious to Flemmi that these guys weren’t on the level, that they were up to their own game, even if at that stage he couldn’t quite discern what the game was. The agents were playing favorites, trying to dictate not only who would win the war but who would die in it.
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Flemmi wanted to be counted among the winners, and so, at the urging of Rico and Condon, he changed sides, aligning himself with Somerville’s Winter Hill organization. He did so gladly, for he had grown to scorn the McLaughlins. He considered them arrogant, undisciplined in their drinking, and unreliable allies. It was a critical turning point for him and for the city. Flemmi would survive the wars and go on to team up with Whitey Bulger in a match made by the FBI.

Watching the way Rico and Condon
schemed to tip the balance of power in the gang war was Flemmi’s first lesson in how deeply intertwined the FBI was in Boston underworld doings, and how blurred the line was between crime and crime fighters. It would not be his last. In 1965, Flemmi met Buddy McLean at the Winter Hill leader’s hangout, Pal Joey’s, a bar in Somerville, and mentioned what he’d learned. McLean surprised Flemmi by acknowledging that he talked to Paul Rico and Dennis Condon all the time. This wasn’t a dread secret; it was an open alliance.

Rico and Condon hated the McLaughlins. But they also had calculated that Winter Hill could win the war, especially with their help. The agents’ motives were then, and remain, a puzzle, a source of uneasy speculation among Boston mobsters. But the connection was clearly rooted in something personal.

Frank Salemme, who later became the head of the Mafia in Boston, grew up with Flemmi and was his partner in crime before Flemmi teamed up with Whitey Bulger. Salemme thought Condon, a Charlestown native, wanted to get rid of the McLaughlins because they had threatened his brother in a barroom dispute. But he also thought that Rico had an even more personal vendetta. Salemme claims Rico’s animosity toward the McLaughlin gang stemmed from the McLaughlins’ typically careless and insulting ways—specifically their bawdy claims that Rico and FBI director J. Edgar Hoover were lovers. Insinuations about Hoover were rife at the time, and linking the rumored scandal to Rico became a running joke for the McLaughlins.

Rico ignored the taunts, but he got even by helping Winter Hill pick off the McLaughlin gang, one by one. He helped Winter Hill set up the 1964 murder of Ronnie Dermody, who had robbed a bank with Whitey Bulger in 1955. Dermody was also one of Rico’s informants, but when Rico found out that Winter Hill had Dermody on a hit list, he ingratiated himself with Buddy McLean and assisted with the disposal of Dermody, a far less significant player.

Rico arranged to meet Dermody about a mile from Rico’s house. It was supposed to be a routine meeting between an agent and his informant, but Rico didn’t show up; Buddy McLean did, with a gun. Rico picked McLean up after the hit and let McLean stay at his house for couple of days.
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But Dermody was small change. Rico and Condon wanted George and Edward “Punchy” McLaughlin to join Brother Bernie McLaughlin in the grave. They decided to get Winter Hill to do their dirty work.

As his name suggested, Punchy McLaughlin was a boxer, quick on his feet. He’d dodged two assassination attempts in the mid-1960s. Rico meant to ensure he wouldn’t survive the third. George McLaughlin was on trial for murder, and Punchy was dutifully attending the court proceedings in Suffolk Superior Court every day. Rico followed Punchy to find out how he was getting to court, then drove to Dudley Square and told Flemmi that Punchy was taking the bus from a stop in West Roxbury to the courthouse downtown every morning. Flemmi disguised himself and went to the bus stop. He covered a .38-caliber long barrel revolver with a newspaper and fired six times into Punchy’s chest as he was boarding the bus. The next time Flemmi saw Rico, the FBI agent told him, “Nice shooting.”
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