James 'Whitey' Bulger

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.

Deadly Alliance

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 Cream Story.

Whitey Bulger, young

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.

FBI Special Agent John
Connolly

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.

Lewisburg Penitentiary, PA

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."

Alcatraz Island

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 years.

Leavenworth Prison

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."

Howie Winter

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.