THE BULGER MYSTIQUE|
As two brothers begin to flex their muscles, busing enters the
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
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
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
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
"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
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
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
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,
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
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
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
"The community has a message for you, Commissioner," Bill Bulger said. ''Go
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
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."
This story ran on page 1 of the Boston Globe on 9/19/1988.
© Copyright 1988 Globe Newspaper Company.