Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (10 page)

The gang war that started in 1961 gradually petered out in the mid-1960s, but not before Flemmi had killed McLaughlin loyalists Wimpy Bennett and his two brothers. Wimpy Bennett had given Flemmi his start in the underworld, but he had also given Flemmi up to Rico. Flemmi had put down a marker; this was how he would deal with informers.

The McLaughlin gang got a bit of revenge before it was over. In October 1965, they ambushed the Winter Hill leader Buddy McLean as he walked out of Pal Joey’s—a hit that was eerily reminiscent of McLean’s shooting of Bernie McLaughlin outside the Morning Glory four years before. The assassinations of the gang leaders bookended the war, but taking out McLean proved a Pyrrhic victory for the Charlestown gangsters. He was replaced by Howie Winter, who was even more cunning, ruthless, and efficient. With Winter at the helm, the Somerville gangsters mopped up what was left of their Charlestown rivals.

With the McLaughlins vanquished, Paul Rico formalized what had been an unwritten arrangement for seven years: In 1965, Steve Flemmi became an official informant for the FBI.

Whitey left Lewisburg Penitentiary in 1965
and moved back in with his mother at 41 Logan Way. He was a skinny twenty-six-year-old when he went into prison; he came out a man of middle age at thirty-five, more muscular after all those years hitting the weights but, more important, with a sturdier sense of himself—he was older, wiser, harder. His famously light locks were slightly darker, robbed of years of sunlight. And the post-incarceration plan of employment he had provided to the parole board changed almost the moment he was free. The $1.50-an-hour job his brother Bill had arranged at Farnsworth Press, a graphic arts company on the waterfront, never materialized. Instead, a family friend who was head of the compressed air workers union got him his first job out of prison as a laborer at construction sites. One of his first tasks was working at St. Mary’s, the residence hall for Jesuits at Boston College. Among those who lived in the spartan dormitory was, coincidentally, Father Drinan, Whitey’s prison pen pal and parole adviser. The work at BC would also bring him into contact with another acquaintance from his Old Harbor days: John Connolly.

In 1961, Connolly had taken Bill Bulger’s advice and gone to Boston College. Closing in on graduation day, he was walking across campus with John Cunniff, the BC hockey star from Southie, when Cunniff suddenly waved and went over to a guy who was carrying slabs of granite outside St. Mary’s.

“Johnny,” Cunniff said, motioning Connolly over, “you know Jimmy Bulger?”

John Connolly shook the hand of the guy who had bought him an ice cream cone all those years before at The Druggie.

“Sure,” Connolly said. “We grew up in Old Harbor.”

The skinny teenager Connolly remembered was now an ex-con, his physique bulked-up and toned. “I’m good friends with your brother Bill,” Connolly said. There was a little more small talk and some handshakes, and then Cunniff and Connolly walked away and Whitey went back to work.

“How do you know him?” Connolly asked.

“We worked construction together,” Cunniff replied.
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Connolly looked back over his shoulder. He wouldn’t see Whitey Bulger again for some ten years, by which time he was an FBI agent, looking to make a deal.

Whitey liked the construction work only because it kept him in shape. He was hoping for something else, and his brother Bill, by now a three-term state representative, was able to arrange for him to work as a janitor in the Suffolk County Courthouse.
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It was an odd place for an ex-con to find work, but politics trumped security concerns in 1960s Boston. Luckily for Bill, Whitey’s hiring did not draw attention, but the risk that his brother could cause him political embarrassment was a lurking concern.

Whitey was fiercely proud of Bill’s political success, and when his brother ran for state senate in 1970, he volunteered for the campaign. He ferried people and campaign literature all over Southie. One day, when campaign workers were standing in the rain at the rotary across from St. Monica’s, holding campaign signs, Whitey showed up with a bunch of umbrellas he had bought on impulse.
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No one remembers Whitey doing anything overtly to help his brother’s political career after that first senate campaign. His apparent disappearance from the campaign trail coincided with his reemergence in the criminal world. Whether his lowered profile was a matter of plan or coincidence remains unclear. There was always the risk that his temper, and passionate loyalty to Bill, could lead to an embarrassing incident. Politics was a contact sport in Southie, but at some point during that senate campaign, Whitey went too far. Pat Nee, who has spent most of his life as, by turns, Whitey’s rival and criminal associate, says Whitey took it upon himself to intervene on behalf of his politician brother, often intimidating people perceived as political enemies. One of them, Patrick Loftus, was more than a perceived enemy. In 1970, he challenged Bill Bulger for the open state senate seat. Loftus, a fraud investigator for the state, and later the author of a rose-colored memoir about Southie, had a gift for piercing oratorical flourish. He was Bill Bulger’s match in rhetoric and enjoyed sparring with him. After one heated debate, Whitey marched down to the Loftus campaign headquarters and lit into the candidate, accusing him of insulting his family. Whitey was more than vaguely threatening, and when Bill Bulger found out, he was appalled. He later told a congressional committee that it was the one instance of his brother’s having taken on a political opponent, and that he had urged Whitey to refrain from such partisanship. “Billy told him to stop,” Nee said. “Whitey hated the Loftus family because they had challenged Billy. Billy told him to knock it off. I don’t think Billy asked him to do this stuff. Whitey did it on his own.”
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In winning parole two years
after becoming eligible and eleven years before his sentence officially ended, Whitey had convinced the parole board that he was going to leave crime behind him. But he didn’t abide by the conditions of his parole for very long. As late as March 1969, his parole officer reported that Whitey was quite happy working as a custodian. “He remains on the job and seems to enjoy this type of work as a custodian,” the parole officer wrote. “James is still working and not being involved in any difficulty so far.”
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But none of that was true. Whitey had stopped showing up for work at the courthouse. He was hanging in Southie’s myriad taverns, not to drink but to network. He was reconnecting with the sort of men he had associated with before he went to prison. Players. People who made their money in the rackets. It was only a matter of time before he came to the attention of the Killeen brothers.

Donnie and Kenny Killeen were, at the time, the preeminent gangsters in South Boston, and they had taken a liking to Whitey, with his smarts and prison-honed toughness. His time in Alcatraz, which shut so many doors elsewhere, opened a door at the Transit Cafe, the seedy bar on Southie’s West Broadway that served as headquarters for the Killeen gang.

The Killeens made most of their money off a lucrative gambling and loansharking business that was patronized by longshoremen and factory workers and warehousemen on the waterfront. It was a trade not without its risks. George Killeen was gunned down in the North End in 1950. Eddie Killeen was shot dead in 1968. That same year, the surviving brothers, Donnie and Kenny, decided to add Whitey to their roster of enforcers. The Killeens were products of Southie’s rougher and poorer west side, and Whitey’s reputation preceded him in the Lower End and the projects, where many of the Killeens’ customers hung their hats. Donnie Killeen led the group and saw to it that Whitey came under the tutelage of his top enforcer, Billy O’Sullivan.

Billy O, as he was known, was an ex-marine, someone who was quick with his fists and quicker with a gun. As would soon be the case with his protégé, whenever someone ended up dead in Southie the collective, if not always accurate, wisdom was that Billy O had done it. The truth of such talk was irrelevant; a reputation for ruthlessness was very good for business. Billy O was also a gifted teacher. He taught Whitey how to follow his prey unobserved and, just as important, how to lose a tail. His military skills were invaluable, and Whitey would in later years profess a debt for all that Billy O had taught him.
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But in another way, O’Sullivan set an example to avoid, for if he had a vice, it was his fondness for drink. One of the conditions of Whitey’s parole was that he not consume alcohol to excess. That was never an issue, because he didn’t drink heavily, and considered those who did weak and unreliable. The streets of South Boston and Charlestown were littered with the corpses of men too drunk to avoid or elude their assassins.

The Somerville-Charlestown gang war had been over for just a few years when a smaller but similarly lethal conflict broke out in July 1969. This war would be limited to Southie, and like the earlier upwelling of Irish fratricide, it began after copious amounts of alcohol had been consumed. There had been a long, simmering feud between the Killeen gang and the Mullens, a group of South Boston toughs who took their name from a street corner in City Point named for a World War I hero. Mullen Square was hardly a square. It was just a corner, with Mullen’s name adorning a sign attached to a black pole.

Pat Nee was with the Mullens. Born in Ireland, he moved to Southie when he was eight years old and had an accent, not to mention a stutter that made him stand out. He was picked on but responded by attacking his tormenters, which was the surest way to gain respect in South Boston. By his teens, he had cast his lot with the Mullens, which, in the beginning, was more Our Gang than a real gang. They stole donuts from the corner store, collected bottles they could turn in for money, searched for junk they could sell. But as they grew older they began stealing things off the trucks that left the docks near Castle Island. Scrap metal, especially tin, was a favorite and lucrative target.
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In 1962, Nee joined the marines. By the time he returned to Southie in 1966, after seeing combat in Vietnam, he noticed that the Mullens had become less deferential to the Killeens, who were, at the time, the only really organized criminals in Southie. “I think part of it was so many of us had been in the service,” Nee said. “A lot of Mullens had been in Vietnam and were like, ‘We just fought the Viet Cong in the fucking jungle. Why should we take shit from Donnie Killeen in Southie?’”

The war was a generational feud as much as anything. In the late 1960s, young Americans had begun to question the establishment, and it was no different in the criminal milieu. The Mullens considered the Killeens the establishment, The Man, the disdained status quo. Their taste ran to more freewheeling mayhem. “We were just criminal opportunists, wharf rats. The Killeens had a hierarchical structure, and we had just a loose federation,” Nee said. “We saw something we wanted and we’d steal it. They were organized crime. We were disorganized crime. We robbed anything and everything. We weren’t very respectful of them, and that eventually led to serious conflict. We ran up debts with them. We’d bet on everything and tell the Killeens, ‘Oh, we’ll pay you back as soon as we get the money.’ But we had no intention of ever paying them back. That aggravated them. So a war was inevitable.”
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Tensions between the two groups had escalated, so that by the summer of 1969, the littlest thing could launch a war, and the littlest thing turned out to be Mickey Dwyer’s nose. Dwyer, a Mullens member, was drinking in the Transit Cafe, which was asking for trouble. He was also popping off, talking of how the Mullens weren’t afraid of the Killeens anymore, which was begging for it.

Tired of such insolence, Kenny Killeen jumped Dwyer. Dwyer was a boxer, but he was also drunk, and Killeen was much bigger. At some point, as they tussled on the barroom floor, Killeen bit off a chunk of Dwyer’s nose. Then he pulled a gun and shot him in the arm.

Mickey Dwyer’s humiliation at the Transit was the final straw for the Mullens, who’d previously been known as brawlers, not shooters. That changed after the maiming of Dwyer. The Mullens started arming themselves, and the war was on. “Up to that point, we used our fists and maybe a baseball bat,” Pat Nee said. “We didn’t have shooters. But that had to change.”

Few gave the Mullens a chance. There were only about twenty of them, and none were known as killers. The Killeens enforcement team boasted Billy O’Sullivan and Whitey Bulger, who were considered stone-cold killers. It was a reputation they deserved, and soon they offered a vivid reminder why. Whitey and O’Sullivan were hunting for members of the rival gang one night when Whitey saw the Mullens leader Paulie McGonagle alone in a car, driving up East Seventh Street in City Point. McGonagle parked in front of his house, and Whitey pulled right alongside him going in the other direction.

“Hey Paulie!” he called.

When McGonagle turned, Whitey shot him in the face. As soon as he fired, he realized his mistake.
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It wasn’t Paulie McGonagle but his brother Donnie, who looked a lot like him. Donnie McGonagle had two kids and was not involved in criminal activity. Whitey, aghast, raced away to O’Sullivan’s house a couple of miles away. O’Sullivan led Whitey to the kitchen, where Whitey slumped in a chair. If he was expecting a reprimand, he got something else. O’Sullivan pulled some pork chops from the refrigerator and threw them into a frying pan.

“I shot the wrong one,” Whitey said, almost in disbelief. “I shot Donald.”

Whitey prided himself on doing his job right, of never drinking when he needed to be shooting. He had patience, and he had no problem with passing on a potential target if something didn’t feel right. Everything had felt right, until the moment he’d squeezed the trigger and killed the wrong man. O’Sullivan was blasé about the whole thing, telling Whitey to forget about it, because Donnie McGonagle was a heavy smoker and was going to die anyway. “Now,” O’Sullivan said, rubbing his hands together, “how do you want your pork chops?”
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