Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (17 page)

In contrast, Ray Flynn was able to move his political career beyond the confines of South Boston, despite being as closely associated with the anti-busing movement as Bill Bulger had ever been. Flynn was elected mayor of Boston in 1983, during a campaign against a black candidate that was notable for its conciliatory tone. Bill Bulger accused Flynn of abandoning the neighborhood for political gain. That didn’t, however, stop him from asking Flynn to make John Connolly, Billy’s old friend and Whitey’s FBI handler, the police commissioner of Boston. Flynn declined to do so, as he had his own preferred candidate: Mickey Roache, whose brother had been shot and paralyzed during the Southie gang war and who would focus as commissioner on racial reconciliation. Flynn’s snub of Connolly earned him Bill Bulger’s lasting enmity. Whitey also hated Flynn. His man, Kevin Weeks, bragged of punching the future mayor when Flynn dropped into Triple O’s for a drink in the 1970s.

Busing also changed, irrevocably, the Bulger brothers’ relationship with their old friend Father Drinan. The priest had been an active booster of Whitey’s rehabilitation, and even served as his parole adviser, a gesture that facilitated Whitey’s release. But Drinan, who served in Congress from 1971 to 1981 and filed the first impeachment resolution against President Nixon in 1974, had also been the driving force, and legal mind, behind Massachusetts’ efforts to desegregate its schools. After busing, Bill Bulger’s and Drinan’s relationship was strained, at best.

Drinan died in 2007, and his sister-in-law, Helen Drinan, said he sometimes lamented that his efforts on Whitey’s behalf had come to so little. Helen Drinan was married to Father Drinan’s brother, a doctor, and it was over Sunday dinner at their Newton home, not far from the Boston College campus, that Father Drinan would sometimes talk about his lost sheep, Whitey Bulger. Father Drinan corresponded with, and intervened on behalf of, many convicts, but Whitey stood out because of his supportive family and because of his intelligence. Whitey’s letters from prison, Father Drinan told his family, were written with almost perfect grammar. Father Drinan “kept track of people who came to him for advice. And he took it personally when they failed,” Helen Drinan said. “He invested a lot of his personal time in Bulger. He knew the family, and when Whitey Bulger went to prison, Bob wrote to him very regularly. Bob said he [Whitey] was very intelligent, and that he could have been anything he wanted to be, but apparently he wanted to be a criminal.”

“Bob was very sad,” Helen Drinan said. “He spent a lot of time trying to keep him straight. And at one point, he thought the man had gone straight. But it all changed. He felt he was a flop.”

Father Drinan’s outspoken support for busing alienated more than the Bulgers. “There were many people in Boston who disagreed with Bob about that,” she said. “The Bulgers might have been more outspoken, but they weren’t alone.”
⁴⁰
And the ranks of the critics of the integration experiment, and Garrity’s order, would only grow, for if the intention behind busing was noble, its implementation was an utter disaster. Thousands of white families moved out of Boston for the suburbs, so that within a few years of busing’s introduction the schools were more segregated than ever. Even the
Boston Globe
, busing’s leading media champion, admitted as much. “Busing has been a failure in Boston,” the paper editorialized on the twentieth anniversary of Judge Garrity’s order. “It achieved neither integration nor better schooling.”

Twenty years after Whitey firebombed JFK’s birthplace,
FBI agents searching Whitey’s home office in Southie seized a stash of books and papers. One of the books was
Southie Won’t Go
, a diary of a teacher at South Boston High during the first two years of busing. Whitey had circled a paragraph on page 117 of the book that describes news accounts of the firebombing of the kitchen of John F. Kennedy’s birthplace and the spray painting of “Bus Teddy” on the front sidewalk. In the book’s margin were the neatly printed words:
MaryJo K. wishes Teddy was in the kitchen having coffee that evening—so do others.

Mary Jo Kopechne was the passenger in Ted Kennedy’s car who drowned when he drove off a bridge on Chappaquiddick Island in 1969. In Whitey’s world, Ted Kennedy’s death would have avenged her. And Southie, too.

PART TWO

THE REIGN

7

A Beautiful Friendship

W
hen Steve Flemmi finally came home
in 1974 after five years on the lam, it was time for hoodlums of a certain standing in town to celebrate the prodigal’s return. And that meant at Chandler’s. The party that night at the South End bar where peace had been brokered in the Southie gang war a few years back attracted a particularly rich cross-section of Boston’s underworld, a mix of Flemmi’s old partners from Winter Hill and a bevy of local Mafiosi. Loud men in loud shirts slapped Flemmi on the back. Made guys in leather jackets kissed him on both cheeks. Women in tight dresses kissed him on the mouth. As at a political function or high-society event, it was important to be there, to be counted in that number. In the dim light of the room, Flemmi noticed someone standing off to the side, leaning against the mahogany bar set on an antique brick base. It was a face he hadn’t seen for years: Whitey Bulger.
¹
They shook hands. Whitey said they should talk soon. Flemmi said he’d like that. They agreed to meet at the Marshall Street garage.

In Flemmi’s absence, Whitey had become a core member of the Winter Hill Gang. He was now, with Flemmi’s return, one of six partners in a lawless firm—a senior partner, in fact. In addition to the proceeds from the Killeens’ territory, he was getting a cut of Winter Hill’s extensive gambling and loansharking business. Some gangsters would have been jealous; Flemmi was impressed, not only that Whitey had survived the war with the Mullens but that he had emerged as the leader of the merged Southie gangs, handpicked by Howie Winter, the Winter Hill boss. If Howie thought Whitey was the most capable of the Southie gangsters, that was good enough for Steve Flemmi.
²

He had met Whitey only a couple of times before the encounter in Chandler’s, but Flemmi remembered him as an ambitious guy who, while still on parole, used to drop by his after-hours club on Dudley Street in Roxbury. Flemmi’s club was more than a spot to get booze after the bars closed; it was something of a recruiting stall for gangsters, a place to find criminal partnerships and broker opportunities. When Flemmi first met him, Whitey had been trolling for a partner. Now, back in town after five years, it was Flemmi who was looking. He had to reestablish himself not only within Winter Hill but beyond it.

Not long after the welcome-home party, Flemmi bumped into Paul Rico’s old FBI partner, Dennis Condon. Rico was now posted in Miami, but Condon told Flemmi he had nothing to worry about. Condon had removed the old federal fugitive warrants for the murder of Billy Bennett and the car bombing that maimed John Fitzgerald, the lawyer—the crimes that had forced Flemmi to flee town.
³
Flemmi knew that Condon’s assurances implied a quid pro quo. He was expected to resume providing information to the FBI. What he didn’t know was that the FBI wanted to pair him with Whitey.

While the Winter Hill Gang had dozens of associates and scores of bookies working for it, the hardcore membership was small: Howie Winter, the leader, plus Jimmy Sims, Joe McDonald, John Martorano, Whitey Bulger, and Steve Flemmi. Within the gang itself, there was no rigid hierarchy of capos and soldiers after the fashion of the Mafia; members were free to break off and make separate partnerships as long as common interests weren’t impaired. In the mid-1970s, Winter Hill began extorting independent bookmakers, shaking them down for the privilege of taking bets on Winter Hill’s sprawling turf. Whitey and Flemmi volunteered to take on this new front, to go out as a team and squeeze the bookies.

They were kindred spirits, their instincts and their taste for brutality remarkably in sync. One day early in their dealings, Flemmi looked on approvingly as Whitey threatened a bookie named Bernie Weisman with an ax. Weisman collapsed, clutching his chest. But he recovered, and he started paying.
⁴
And they were alike in other ways. Loners in a dangerous trade, they were men with an incongruous need for domestic tranquillity who could yet never settle for one woman. And they were men who considered themselves principled and patriotic, even as they murdered with equanimity and corrupted law enforcement. Over time, they became partners who trusted no one but each other.

As kids, they had both floundered at school, not from lack of intelligence but lack of interest; both got their GEDs in the military. As criminals, they were wary of affiliating with big groups, preferring to maximize their profits while minimizing the risk of being cheated or informed on. For all their troubles at school and in large organizations like the military, they were clearly smarter, and wilier, than most of their criminal associates.

Together, they represented the two main ethnic strands of organized crime in Boston in the twentieth century, which made them an attractive tandem for an FBI that needed eyes and ears in both camps. Bulger’s parents were the children of Irish immigrants, while Flemmi was the oldest son of Italian immigrants who settled in the Roxbury section of Boston. Unlike Southie, where the Irish formed a substantial majority, and the North End, which was almost exclusively Italian in those years, Roxbury was a hodgepodge of ethnic groups and races. Italians, Irish, and Jews shared the neighborhood throughout the first half of the twentieth century, and then, as African Americans began to move north in great numbers, Roxbury evolved into the city’s most populous black neighborhood. Some Italian kids from Roxbury, including Flemmi’s first criminal partner, Frank Salemme, hoped, like their North End peers, to join the Mafia. But Flemmi didn’t share that aspiration. He was more comfortable with the ethnic blend and freedom of maneuver he knew in Roxbury, without the restrictions of the relatively stratified Mafia hierarchy. His after-hours club drew a noticeably integrated crowd in a starkly segregated city. Some of the bookies who paid him to operate were black, and many of the gamblers were, too. He was an enthusiastically equal opportunity gangster and extortionist.

Flemmi’s father Giovanni was a bricklayer and also owned a pushcart from which he sold costume jewelry and quahogs. Anything to make a buck. Giovanni was also famously frugal. When he died in 1991 at the age of ninety-eight, his sons were stunned to learn that he had amassed from his humble labor seventy thousand dollars in savings.
⁵

The Flemmi boys were living proof that in the working-class neighborhoods of Boston, the same household could produce a cop and a criminal. Flemmi and his younger brother Jimmy “The Bear” were prolific killers, while their younger brother Michael joined the Boston police. Stevie was, in matters of business, far more circumspect than Jimmy. A few days after Christmas in 1964, Jimmy got into an argument with a smalltime hood named George Ashe, and he wasn’t one to end an argument just with words. As Ashe remonstrated from the front seat of his car, Jimmy pulled a gun and shot him through the open window. Two police officers watched the whole episode, but instead of arresting Jimmy, they went directly to Steve Flemmi’s store and told him what had happened. Flemmi handed the cops a thousand dollars, a late Christmas present, then went and chastised his brother, saying he was lucky to have shot Ashe in front of two cops on the take.
⁶

But it was Jimmy who introduced Flemmi to the world where the interests of cops and criminals intersect, where the two sides could happily coexist for mutual benefit. Jimmy had worked as an informant for Rico and Condon in the 1960s, and not only had the agents turned a blind eye to his many murders, they had framed four men, two of them Mafia leaders, for one of his killings.
*
Steve Flemmi would come to know this dark, compromised side of the FBI—its blinding fixation on the Mafia—better than Jimmy could have imagined.

Whitey and Stevie mirrored each other in still other ways. They stood out from other gangsters in being obsessed with eating healthy food and with keeping themselves in top physical condition. They worked out daily, and while they spent inordinate amounts of time in bars—Whitey at Triple O’s in Southie, Flemmi at the Marconi Club in Roxbury—they drank very little. Too vain to let booze make them puffy, they were fonder of wine with meals than beer, the favored beverage of many criminal comrades who had gone to fat. Their fastidiousness did more than set them apart: they viewed other gangsters as their inferiors, weak-willed, prone to mistakes, more likely to cheat their partners, statistically more likely to get caught. “The rest of the guys were kind of party-type guys. We liked to party also,” Flemmi said, noting that he and Bulger were hardly teetotalers. “We weren’t square. But we weren’t extreme.”
⁷

While many of their associates read, at most, the racing section of a newspaper, Whitey and Flemmi read books. They were intrigued by military history and were students of Machiavelli. While their associates considered long-distance travel a flight to Miami or Vegas, Whitey and Flemmi were more likely to jet off to Europe, touring old battlefields. But in the end, what really made their partnership unique in town, what brought them together and kept them together for twenty years, was their relationship with the FBI. Their informant status conferred on them a belief that they could do anything as long as they weren’t sloppy—and they prided themselves on not being sloppy.

FBI agents Paul Rico and Dennis Condon had put Flemmi on the winning side in the Somerville-Charlestown gang war. They had also helped set up rival gangsters, potential competitors, to be murdered. Whitey had risen and prospered without the FBI’s assistance but had quickly taken advantage of his newfound status as an FBI informant to engage in a self-serving propaganda effort, giving information about his rivals and covering his own tracks as he killed off what was left of the Mullens gang. And all the FBI wanted in return was for Whitey and Flemmi to tell them whatever they knew about the Mafia.

When the two men got together at the garage after that spirited evening at Chandler’s, Whitey took Flemmi aside and, out of earshot of the other Winter Hill members, explained how John Connolly had recruited him and why. It was a stunning disclosure, not to mention a potentially deadly one, but Whitey had a specific purpose. Flemmi read between the lines, and got it: Connolly must have told Bulger that Flemmi, too, was an informant, and that the FBI wanted him and Whitey to join forces. It would be their little secret, and their huge advantage. Theirs was a partnership envisioned, encouraged, and sanctioned by the FBI.
⁸
It would make them unstoppable.

Unlike other Boston criminals,
the Winter Hill Gang was not afraid of the Mafia. There was an uneasy alliance between the two organizations. The Mafia had all the trappings of power, and they had popular culture cachet, but the Winter Hill boys were not much impressed. They knew their Mafia counterparts and considered them soft and spoiled, living on their reputations. In New York, the Mafia was unrivaled. In Boston, the Irish gangsters’ wild, unpredictable violence, and their superior numbers, forced the Italian organization to appease or even employ them. “If we had a competition with the Mafia, we would absolutely, positively destroy them and they knew it,” Flemmi said.
⁹

Because he was Italian, and because of his reputation as a moneymaker who could handle a gun, Flemmi was frequently courted by the Mafia. But he always demurred. He told Whitey his anti-Mafia attitude could be traced to the late 1950s, when Larry Baione, a Mafia leader, refused to honor a three-thousand-dollar winning number one of Flemmi’s gambling customers had picked. Baione contended that because the bookie carrying the slip was arrested before depositing the wagers with the North End, the bet was technically never made.
¹⁰
Flemmi concluded then and there that, if the likes of Baione would chisel him on such a small matter, the Mafia’s claim to prestige and to being “men of honor” was nonsense, a finely constructed myth. He humored Mafiosi like Baione when they tried to recruit him, and whatever they told him went straight to the FBI.

Not long after he agreed to be an informant for John Connolly in September 1975, and had intimated to Flemmi that he knew of his arrangement with Dennis Condon, Whitey suggested that Flemmi meet with Connolly. “All of us?” Flemmi asked.
¹¹
No, Whitey replied. Go alone. Get your own read on Connolly. Whitey put the meeting together like a social secretary, picking a coffee shop in Newton, believing it unlikely that other gangsters would be anywhere nearby.

There had been a changing of the guard at the FBI office in Boston. Rico, who had developed Flemmi as an informant, had retired. Condon, Rico’s partner, who had inherited Flemmi as an informant, was about to retire, too. Connolly was the new sheriff in town, the FBI agent who handled the top-echelon informants, gangsters who provided information to the FBI even as they remained criminally active. When Flemmi arrived at the coffee shop, he saw that Condon and Connolly were there, waiting for him. Their pitch to him was noticeably similar to the justification that Whitey had given Flemmi when he had divulged his relationship with Connolly: They could save themselves by giving up the Mafia. Flemmi was friendly with Gennaro “Jerry” Angiulo, who led the Mafia in Boston but reported to the boss of the New England Mafia family based in Rhode Island. Flemmi also knew Baione, the Mafia’s consigliere. His access was unmatched. But as he sat there, stirring his coffee, Flemmi quickly grasped that the new deal would be different from the one he’d had in the 1960s. He was going to be part of a team with Whitey, something new and strange for both of them.
¹²

Flemmi said he’d think it over, but he didn’t really think he had any options. He couldn’t very well go back and tell his Winter Hill partners that Whitey wasn’t just getting information from Connolly but giving it; Whitey could simply out him as an informant as well, and neither of their lives would be worth much. The risk was less in joining forces with Whitey than in defying him. Flemmi was in, and Connolly would be his handler, too. It was two for the price of one. While the rest of Winter Hill knew that Whitey was talking to Connolly, they had no idea that now Flemmi was, too, at least a couple of times a month. Whitey and Flemmi kept their secret close. Connolly’s arrangement, to have two gangsters working in concert with each other, was highly unusual for the FBI. He even admitted that, when he sat down to type up reports, he would sometimes confuse and conflate the contributions of the two.
¹³
But it was not an innocent mistake; it was a conscious effort by Connolly to make Whitey appear Flemmi’s equal as a source of information on the Mafia, when the truth was that Whitey had little to give. He didn’t trust the Italian mob, and the feeling was mutual. Mafia leaders respected Whitey, but they didn’t like him because he was violent and independent, which made him unpredictable, a man to be feared more than welcomed.
¹⁴