By the time Bill Bulger began his Senate career in 1970 after a decade in politics, his brother Whitey had been out of federal prison for five years, keeping a low profile in South Boston, living at home with their mother in the Old Harbor project, tipping his hat to neighbors.
But within a year, Whitey left his job as a custodian at the Suffolk County Courthouse and teamed up with Stephen Flemmi, a veteran mobster who survived the bloody gang wars of the 1960s.
Soon, Whitey began showing up at a garage in Somerville that housed some of the roughest mobsters around, signaling that one of the toughest street kids to come out of South Boston was not only back, but a comer in the preeminent Irish gang in Greater Boston.
As the 1970s progressed, both brothers would solidify and expand their power base in South Boston, not knowing that the approaching maelstrom of court-ordered school busing would test them both.
For Bill, busing would be a political hornet’s nest. He had to tread the fine line between opposing what he viewed as unfair government intervention in the lives of his constituents and the perception that anyone from South Boston who opposed busing was a rawboned racist.
Busing would permanently shape Bill’s political agenda and his view of the Boston media. His stand against federal authorities and local police would make him a revered figure in South Boston, but damage his standing statewide, a problem of perception and reality that persists to this day.
For Whitey, busing was a temporary threat to his hold on his hometown power base. While he opposed busing as firmly as any resident of South Boston, he was instrumental in keeping the hooligans from joining irate parents on the street. He knew that such a volatile combination would bring more police, which would jeopardize his hard-won control of South Boston’s gritty lower end.
In light of later events, there is a certain irony about the federal government -- the archfoe of South Boston during busing -- playing a vital if inadvertent role in helping both Bulgers reach the top of their games.
In Billy’s case, federal authorities helped clear a path for his rise to power when, in 1976, they escorted Sen. Joseph DiCarlo into the courthouse in Post Office Square to face corruption charges.
As for Whitey, federal agents paved his way in the late 1970s with the arrest of his boss, Howard T. Winter, for fixing horse races.
By 1983, the top tier of the Mafia family headed by Gennaro Angiulo would be under arrest, leaving Whitey as powerful and feared as any mobster in the city of Boston.
For his part, Bill Bulger is rueful about coming to power on the heels of someone else’s fall.
Whether Whitey lamented the demise of his former boss, Howie Winter, and that of his former associates, the Angiulos, is not known. But just how he and Flemmi escaped prosecution at a time of ferment and downfall in the underworld remains a subject of spirited speculation among law enforcement officials.
Even in prison, Whitey Bulger was not what you would expect. A flamboyant street fighter as a kid, he had his battles in his four years in the Atlanta prison. But, by the time he got transferred to Alcatraz in November 1959, he was less rebellious, more a veteran just putting in his time. One longtime
Alcatraz inmate from Massachusetts, former bank robber and escape artist Teddy Green, was there when Whitey did his three years on The Rock.
“Whitey was very quiet,” says Green, who now lives in Sharon. “A very gentle person. I never found nothing bad about him. He never got in no trouble. He was just a nice quiet guy.”
While in prison, Whitey intensified a fanatical physical regimen of exercise and weight lifting, something he has continued throughout his life. A high school dropout, he became a voracious reader, self-taught in many disciplines. Toward the end of his sentence, when he was in Leavenworth, he studied World War II as a science, dissecting battles and examining military strategy from all sides, a perspective that would later help him keep various segments of law enforcement off balance in his criminal career.
But earlier, when he was first locked up at the Atlanta penitentiary from 1956 to 1959, he took part in a dangerous experimental drug program in exchange for a minor reduction in his sentence. Whitey’s small volunteer unit at Atlanta was part of a CIA project to find out how people reacted to LSD, a program documented in a 1977 book titled “The Search for the Manchurian Candidate,” which exposed medical abuses by the intelligence agency.
While Bill was at law school, his brother wrote him about the drug program. Bill wrote back, urging Whitey to reconsider.
“Who knew about LSD then?” says Bill Bulger. “But I was very apprehensive about it. Imagine, three days a month (taken off his sentence) for running that risk. There were only eight to 10 of them and two guys went stark raving mad. . . . You couldn’t go through something like that and come out improved.”
He says the effects of the drug bother his brother to this day, causing nightmares and often robbing him of sound sleep.
In July 1962, Whitey was transferred from Alcatraz to Leavenworth. In August 1963, he was sent to a prison in Lewisburg, Penn., and paroled in March 1965, in time to get back home for the annual Evacuation Day/St. Patrick’s Day parade.
Although his incarceration had stripped him of his youth and nearly a decade of his life, his timing was somewhat fortunate. At the very least, it improved his chances of surviving Boston’s most notorious gang war. By the time Whitey got out, most of the five dozen hoodlums who were to fall victim to the guns of friends and rivals had been killed.
Whitey rose to power quietly and slowly. Careful not to violate his parole, he tried to stay straight following his release from prison. His brother, by then a three-term state representative, got him a courthouse janitor’s job. But Whitey, an ex-con in his mid-30s without a trade or formal education, would not be content pushing a broom and living from week to week on a meager paycheck.
Soon Whitey was back hanging out on the mean streets of South Boston, wearing sunglasses and sitting in the back of station wagons with thugs from the lower end. But while some hothead hoodlums would scream and swear as the cops patted them down for guns along Broadway, Whitey Bulger would take it all in stride.
“You’ve got a job to do,” Whitey said over his shoulder to one cop, palms pressed against the side of a building. If prison had brutalized Bulger, it had also left him more pragmatic in his dealings with authority. Whitey showed respect for the law, knowing it was the easiest way to go, and perhaps a means to an end.
In the late 1960s, the Killeen brothers were running a gambling and loan- sharking operation in South Boston, and Whitey was their enforcer. If Whitey had a reputation as a tough guy when he went to jail, it was doubly fearsome when he came out. The Killeens, according to police from that era, did not have much trouble collecting their debts with Whitey knocking on doors. Donnie Killeen, the second born of three brothers, ruled over his turf from the Transit, a bar on West Broadway. Police say he and Whitey became firm allies if not close friends.
By decade’s end, however, a group of upstart and vicious South Boston hoodlums known as the Mullins gang challenged the Killeens’ control of the rackets. While the Mullins gangsters gunned down several mobsters, the Killeens felt they had an ace in the hole: Whitey Bulger.
Yet law enforcement officials say that the ever shifting alliances in the underworld worked quickly against the Killeens in the early 1970s. Within a couple of years, Bulger had a falling out with Donnie Killeen and became aligned with a leading Mullins gang member, Pat Nee.
“Donnie hadn’t taken care of Whitey the way Whitey felt he should have been,” said one former law enforcement official who knew South Boston’s underworld.
On the evening of May 13, 1972, Donnie Killeen got a phone call at his home in Framingham. He told his family, who had gathered for the birthday party of his 4-year-old son, that he had to go out for a while. Killeen was sitting in the front seat of his car, about to start the engine, when a gunman ran up, jammed a machine gun in the window and sprayed him with 15 bullets.
Boston and State Police later determined that three men most likely took part in the Killeen execution. Whitey Bulger was among those whom police suspected of being involved, but he was never charged, nor was anyone else. Bulger has told friends he was not involved, and many believe him.
But, in a sense, who murdered Killeen became irrelevant. On the streets of South Boston and among mobsters, it was widely assumed Whitey did it. The Killeen murder was the first of many that were credited to Bulger without any evidence that would stand up in court. The perception of Whitey’s ruthlessness became crucial to his ascendancy in organized crime.
But as the Irish gang war of the early 1960s and the later Mullins gang killings demonstrated, it had become too dangerous for wiseguys, such as the Killeen brothers, to remain completely independent. So, shortly after the Killeen murder, Whitey began showing up, according to police intelligence reports, at a Marshall Street garage in Somerville that was headquarters of the top “Irish” group at the time -- the Winter Hill Gang.
Headed by Howie Winter, a wily survivor of the Irish gang wars of the 1960s, and named for the section of Somerville it called home, the Winter Hill Gang operated independently from but often in concert with the Mafia. Its enforcers collected loan-shark debts, shook down small-time hoods for a share of the pilferage from the docks of Charlestown and South Boston, and took contracts for Mafia hits.
It was during his apprenticeship at Winter Hill that Bulger teamed up with Stephen Flemmi, a mobster nicknamed The Rifleman who got his start loan- sharking around Roxbury and the South End. One of Flemmi’s brothers, James Vincent Flemmi, or Jimmy Bear, was a strong-arm man for the Mafia and confidant to the Boston Mafia’s most notorious hitman -- and later government witness -- Joseph (Baron) Barboza. Flemmi’s other brother is a Boston police officer.
Both Stevie and Jimmy Bear are mentioned on the FBI’s summaries of taped conversations in the Providence office of Mafia boss Raymond L.S. Patriarca, which were recorded by a secret listening device in the early 1960s. Stevie was touted as an up-and-comer with firsthand knowledge of who was getting killed in the out-of-control Boston gangland slayings of the 1960s.
The bonding of Stevie Flemmi, an Italian from Roxbury, and Whitey Bulger from South Boston was a fitting merger of Boston’s criminal heritage. Since the end of Prohibition, when Italian gangsters mowed down two leaders of the Irish Gustin Gang in the North End, there had been an uneasy peace between the two ethnic groups, with the Mafia gradually gaining primacy.
Law enforcement officials who have observed Bulger and Flemmi say they share an extraordinary sense of independence and seem immune to the natural tendency to expand their criminal base. In the underworld, expanding one’s turf is a high-risk business venture, frequently proving fatal, either literally at the hands of rivals, or figuratively at the hands of the authorities.
Bulger and Flemmi proved smarter than their contemporaries, more disciplined, more cunning. And so, during the latter half of the 1970s and early 1980s, while their wiseguy associates were either being hauled off to jail or forced to go on the lam, Whitey and Stevie remained in business, untouched.
Whitey Bulger was just reestablishing himself in South Boston when his younger brother, Bill, decided that 10 years in the state House of Representatives was enough. He saw no future in the House. He was never on the leadership ladder, and he was unwilling to drink with the boys after work to position himself for advancement. Instead, when a hearing ended, Bulger headed home to a houseful of kids, or dashed off to court to handle a criminal case to augment his meager legislator’s salary.
The smaller body of the state Senate seemed to offer Bulger more opportunity, individuality, prestige. During the 1960s, the House was unwieldy and rudderless. Bulger built a reputation as the wittiest, most talented speaker in the House. When he approached the rostrum, the clamor, which made the House sound like a classroom after the teacher left the room, subsided. His colleagues listened to Bulger. In 1970, Joe Moakley, a childhood neighbor of the Bulgers, called one night to let Bulger know he was going to give up his state Senate seat to run for Congress. It was history repeating itself. Ten years earlier, Bulger had decided to run for the representative seat Moakley had vacated in his first unsuccessful bid for the Senate.
Joe Moakley’s phone call, like Joe DiCarlo’s fall from grace, are integral to Bulger’s political rise, a remarkable mixture of gumption and luck. It was, by his own account, a reluctant rise. He did not foresee himself as a career politician. He expected a short political career, followed by a longer one as a criminal lawyer. It was also a rise fueled by his upbringing.
“He’s the luckiest man in the world. He has two educations,” says John Jennings, a retired firefighter and longtime Bulger supporter from South Boston. “He’s got the education of the streets, in a housing project. And he’s got the education of academia, with the Jesuits.”
The streets taught Bill Bulger you give and get loyalty from your friends and you never take an insult. At the State House, these precepts became a credo. From the beginning he was his own man, voting against John (Iron Duke) Thompson in a leadership contest, despite tremendous pressure to stand by the speaker, a once-formidable leader who was in alcohol’s grip. Bulger only released his vote to Thompson when his candidate threw in the towel. He expected no favors from Thompson and got none. Bulger saw that the most successful pols kept score and did not forget.
Once inside the Senate, Bulger found that punishment was as much a part of the routine as debate. President Kevin Harrington had a difference with the Judiciary Committee chairman, Sen. Joseph Ward, and all of a sudden Bulger had the committee chair.
”He gave me the thing. I had never asked for it,” Bulger says. “He was being a little punitive to Ward. And I don’t think Joe Ward ever appreciated my taking the thing. He didn’t know that I had not gone looking for it.”
While Bulger generally tried to finesse thorny issues, he was not above open combat. In his first term, he took on the leadership when it reneged on a promise to give rent control at least a perfunctory hearing at the end of the 1971 session. Both Harrington and Ways and Means Committee Chairman James Kelly told him that the bill would be aired and, as the night wore on and Bulger saw there would be no time left, he took on all comers, bringing the Senate to a standstill with a filibuster. He had Kelly glaring at him from across the chamber and Harrington snapping at him from the rostrum. But Bulger had told some constituents he would at least get the issue aired, and so he did.
It was not a lasting rupture, however. By 1974, when Mario Umana left the majority leader post to become a judge, Sen. Joseph DiCarlo of Revere took his spot, opening the job of Senate whip. Harrington gave Bulger the job.
Even then, Bulger insists, he had no visions of landing what he calls “the gavel,” the Senate presidency.
“It just looked like a hundred years away from me,” he says. “I never had any great ambition for it. And even later, when I was majority leader, I would say to Harrington, ‘I think majority leader is a great job. I don’t have to make the hard decisions. Each one of us nods his head up the line further, and there’s only one person to whom the final nod goes.’ So I didn’t look forward to that. I always wondered, could I cope with that?”
But the Senate’s leadership would be decimated in the late 1970s by a series of scandals, with DiCarlo going to jail, Kelly convicted of extortion and Harrington resigning after accepting a dubious campaign contribution from the firm involved in bribing DiCarlo. When the smoke cleared, Bill Bulger was the only person with the stature to take the gavel and cope.
Bill Bulger has remained an implacable foe of court-ordered busing. To this day, the subject stirs him like no other. For him, it is like chewing tin foil. His legislative agenda still reflects his concern about what he views as the unfair burden placed on South Boston parents forced to send children to schools away from their home.
It has produced such things as bills to provide state aid to private schools, and, most recently, his proposal for open enrollment in suburban schools for Boston students. Neither bill has become law.
Busing was a searing emotional and political experience for the usually equable Bulger. He remembers going out to dinner with family friends with everyone vowing, “We’re not going to talk about it tonight.” But the deep- seated anger and dismay would force the matter up within minutes. Bulger never challenged the federal judge’s findings that Boston schools were egregiously segregated. He did, however, steadfastly oppose any remedy that would force students to travel out of their home district.
His intransigence pivoted on the principle of parental prerogatives, and it is as strongly held today as it was then.
“The strength that we had in that place was the stability of the family and the community. And a community can’t exist very long if its institutions, especially the schools, are being dismantled. As a parent, I felt it was the natural right of the parent to make these decisions,” Bulger says.
Even before busing, Bulger’s relationship with the press was cool. Although his colorful orations were “good copy,” he did not court the press, did not need the press to get elected in South Boston, nor did he seem at ease with reporters. Bulger thought many State House reporters were self-important, and believed the media had no business getting involved in setting the legislative agenda. The press coverage of busing -- which he says overemphasized the hateful diatribes of a few while virtually ignoring more thoughtful opposition -- convinced Bulger the media wanted to make, not just report on, public policy.
Rev. Thomas McDonnell, the pastor of St. Augustine’s Church in South Boston and a close friend of the Bulger family, sees Bulger’s Jesuit education as the underpinning for his views on the three legislative mainstays of Bulger’s career: busing, aid to private schools, and access to private beaches.
“He would take a typical scholastic approach to justice, one of the things being a just law must not put an undue burden on a small proportion of the population,” says McDonnell, who has walked a fine line in South Boston, criticizing those who would brand the neighborhood racist, while at the same time urging the acceptance of minorities. “That would explain his stand on busing. A just law demands an equal sharing of the burden.”
But if Bulger’s antipathy toward busing rested on principle, the realities of the street forced him to abandon a scholastic approach at least one time. Bulger acknowledges one of his worst moments occurred in 1974, when he confronted then Police Commissioner Robert diGrazia outside South Boston High School. Bulger thought the police had overreacted by arresting protesters outside the school.
“You don’t have to get this excited,” Bulger told diGrazia.
DiGrazia confirmed that the confrontation between the two turned ugly -- but only after Bulger called the assembled police officers “Gestapo.”
“If you had any guts,” diGrazia sneered at Bulger, “you’d tell those people to get their kids into school.”
Billy Bulger’s blood boiled. Here, standing on Dorchester Heights, in the neighborhood he had called home all his life, Bulger stood nose to nose with an outsider, someone he saw as a career guy on the make, some bureaucrat just passing through.
“The community has a message for you, Commissioner,” Bill Bulger said. ‘’Go expletive yourself.”
As he stomped off down G Street, Bulger regretted the remark before he got to the bottom of the hill.
“It was really self-demeaning,” he says now. “I shouldn’t have said it.”
As much as the confrontation with diGrazia stands out, Bulger says his darkest moment during the first year of busing in 1974 was watching federal authorities wearing helmets coming out of the Andrews school.
“I was standing there with all these people I knew, watching helplessly as these federal people ran in and out of the school I went to, wearing these war helmets. It was quite overwhelming. ‘Gosh, what are we ever going to do about this?’ I just had no answer for anyone, including for myself. It was a black day. There were worse days but none affected me so personally as that. It was my school as a kid.”
Unlike some of the hate-mongers who surfaced during the busing crisis, Bulger has a history of tolerance in the area of civil rights. In the 1960s, federal Judge David S. Nelson, who is black and knew Bulger from law school, was a guest of Bulger’s at St. Monica’s Church.
“On two occasions, Billy invited me to speak on interracial justice,” said Nelson, who at the time was a lawyer and member of the Catholic Interracial Council, a civil rights advocacy group. “I was well received. Billy thought it was important.”
But Bulger’s subsequent stand on busing disappointed Nelson. “I know he has loyalties, I know he has a strong sense of family. But I hold Billy responsible as a leader. He came to the conclusion that desegregation was a bad idea, that busing was an atrocious idea, so I can allow that on an intellectual basis. On the other hand, he really proferred no response to, ‘What then, if not busing? What then, if not desegregation?’
“Billy, in my view, had more power and influence than anyone to at least assuage, and ultimately do away with the kind of hatred and anger and regressiveness, by reason of his strength and leadership. I don’t think he did much to do that. . . .
“I’ve always thought of it as really funny, as ‘I’ve got my turf, I don’t want any more, I don’t want anybody to have to support it, I’m all set, just leave me alone.’ But it’s that kind of notion that can’t work. You can’t have a city or any large entity viewed as pockets, as separate countries. And yet anybody would be dead wrong to say I would call him a racist, because I don’t view him that way at all. It’s that curious sense of territory, that extraordinary, exaggerated care about protecting the family.”
While some may think Bill Bulger did not do enough to quell the hate that sprung from busing, what is not commonly known is that Whitey was a leading force, albeit behind the scenes, in keeping the unrest from escalating. Whitey did not, however, do his peacekeeping for altruistic reasons, according to law enforcement officials, diGrazia among them, and those who know Whitey. He opposed busing as vociferously as most of his neighbors. Whitey had a financial stake. He feared the prospect of a protracted, extensive presence by law enforcement in South Boston, and the heat it would generate.
“Do you think Whitey wanted the feds around?” asks a friend of Whitey’s. ‘’I mean, you’re running the whole operation in town and you don’t pay taxes. You want them looking at you? Asking you, ‘Where’d you get the car?’ You don’t want them for one minute to think you are involved in any of this, because all of a sudden they are going to try to find a way to put you away.”
And so Whitey put the word out: Knock it off.
And, for the most part, it was knocked off.
Despite the tumult caused by busing, and despite his growing rift with the media which fueled a growing negative image, Bill Bulger was able to rise to power. His election to Senate president in 1978, at a time when the busing controversy was still intense, and when it was common knowledge in South Boston and on Beacon Hill that his brother was a reputed gangster, is testimony to Bill Bulger’s rapport with his colleagues and constituents.
But while Whitey’s reputation had not prevented his brother’s ascendancy in politics, it clearly had exacted a personal toll on Bill Bulger, who cares deeply for his brother. It was a toll that lobbyist Judy Meredith got a glimpse of a few years back, when, during a meeting in the Senate president’s chambers, she told Bulger that she assumed he was a supporter of prison reform because of his brother’s experiences.
“I got the look. Whew!” she says. “Which anyone else would have assumed meant, ‘How dare anybody actually raise my brother’s name in my presence.’ But it wasn’t that. He was looking at me and said, ‘My father died while Whitey was in prison. My father never had a good day after that imprisonment. ‘ And I sat there speculating about the younger brother, who was the perfect son, who got good grades, went to Boston College and to law school and was the successful politician, and couldn’t make it up to his father.”