Like legendary gangster Benjamin "Bugsy" Seigel, James "Whitey" Bulger hates his nickname, and those who
know him know better than to call him by that name. He prefers "Jimmy." He received the nickname as a child
because of his natural white-blond hair color. The oldest of six children, he was brought up in the Old Harbor
housing projects in South Boston. Even as a young man, he ran rampant through the streets of Southie, building
a reputation for mischief and mayhem. Young Whitey fulfilled every little boy's dream of running away and
joining the circus, returning to Southie after a few weeks with vivid tales of his big-top adventures.
According to Ralph Ranalli in his book Deadly Alliance, when Whitey was a teenager, he kept a pet
ocelot named Lancelot and "dated a much older burlesque dancer" named "Tiger Lil." Ironically, every morning he
and his studious little brother, Billy, would leave the projects together and go their separate ways - Billy to
school and Whitey to the streets.
To this day, many Southie residents speak of Whitey with misty-eyed nostalgia, portraying him as their own
Irish-American Robin Hood, recalling how he would buy groceries for widows and distribute free turkeys to the
poor at Thanksgiving. One story in particular has been repeated so often, it's almost become legend: The Ice
As the story goes, 19-year-old Whitey walked into an ice-cream parlor and spotted three 8-year-old boys
standing at the counter. Feeling magnanimous, Whitey offered to buy them all ice-cream cones, but one of the
boys balked, saying that his parents told him never to take gifts from strangers.
Bulger allegedly picked up the boy, sat him down on the counter, and looked him in the eye. "Hey, kid,"
Bulger said, "I'm no stranger. Your mother and father are from Ireland. My mother and father are from Ireland.
What kind of ice cream do you want?"
The little boy, who knew of Bulger's reputation as a street tough, was instantly won over. "Vanilla," he
said with a smile.
That little boy was the young John Connolly, who would grow up to become an FBI Special Agent and Whitey
Bulger's handler in the Top Echelon Program. Connolly told the story often, citing it as the beginning of a
trusting and beneficial relationship with the gangster, but author Ralph Ranalli doubts the veracity of a lot
of Connolly's colorful stories, including this one. As an FBI agent, Connolly told a lot of stories about
Bulger, most notably his embellished accounts of Whitey's supposedly invaluable help in providing inside
information about the Mafia.
In his early twenties, Bulger graduated from street tough to career criminal, getting involved in bank
robberies and truck hijackings. In 1956, he was arrested at a nightclub in Revere, Massachusetts, his blond
hair dyed black. The police charged him with a series of bank robberies in Massachusetts, Rhode Island, and
Indiana. He was convicted in federal court and sent to the federal penitentiary at Lewisburg, Pennsylvania.
When guards discovered that Bulger was planning a breakout, he was transferred to Alcatraz, the infamous
maximum-security facility on an island in San Francisco Bay. His defiant attitude there earned him several
stays in solitary confinement. According to author Ralph Ranalli, at Alcatraz, "unruly inmates were thrown into
unheated steel boxes in just their underwear," but Bulger "developed a technique where he would crouch for
hours on the metal floor, with his entire body weight resting on his elbows, knees, and toes - putting the
smallest skin area possible in contact with the frigid, body-heat-sapping steel."
When Alcatraz was shut down in 1963, Bulger was sent to Leavenworth Prison in Kansas, where he volunteered
to take LSD as part of a CIA-sponsored experiment called MK-Ultra. He was paroled in 1965 after serving nine
After returning to Boston, he eventually hooked up with the Winter Hill Gang, which was led by gangster
Howie Winter. His old friend Stephen Flemmi was also a member of the gang. Flemmi preferred Hill's Irish gang
over the Italian-American Mafia which had actively courted him for induction into their ranks. Bulger and
Flemmi were an effective team, working as enforcers for Howie Winter. Bulger's hair-trigger temper and
proclivity for violence became so feared in the Boston area that sometimes the mere suggestion of a visit from
Whitey would prompt deadbeats to pay their outstanding debts. According to Eddie MacKenzie, who worked for
Bulger as an enforcer, "Whitey was as evil as Lucifer."
One of the Winter Hill Gang's most lucrative rackets was fixing horse races up and down the east coast,
paying off jockeys to throw races. They had a good run with it until a jockey in Atlantic City came forward and
started talking to the New Jersey State Police. As a result, Howie Winter's chief fixer, "Fat Tony" Ciulla, was
convicted and sentenced to four to six years in prison. But Ciulla soon sought to cut a deal, promising to
testify against the Winter Hill Gang if the authorities would get him out of prison and put him in witness
protection. According to Boston Globe reporters Dick Lehr and Gerard O'Neill in Black
Mass, when Ciulla testified for the government in a 1978 trial targeting crooked jockeys, the judge
demanded that Fat Tony identify those who led the race-fixing racket. Reluctantly, he named Howie Winter,
Stephen Flemmi, and Whitey Bulger, among others.
In the meantime, the FBI in Boston was putting together its own case against the Winter Hill Gang for
race-fixing. But when indictments were handed down in 1979, neither Bulger nor Flemmi were charged because both
men had been working secretly as informants for the Boston office of the FBI for years. Whitey and Stevie had
friends in high places.