A Look Back At ‘Whitey’ Bulger

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His mother called him Sonny, and he is Jimmy to his friends and siblings, but everyone else knows him as Whitey. James “Whitey” Bulger, Boston’s most notorious gangster, was arrested Wednesday after a 16-year manhunt. Once the head of the Winter Hill Gang, as well as a top FBI informant, Bulger will now finally face charges related to 19 murders and a host of other crimes. And while the 81-year-old’s long criminal career effectively ended while on the run in Santa Monica, Calif., it began, and will forever be linked to, South Boston.

The Bulgers were among the first residents of The Old Harbor Housing Project, the second housing project built in the United States, according to a thorough 1988 Boston Globe investigation of Whitey and his younger brother, William Bulger, who would go on to become the powerful president of the Massachusetts state Senate. The Bulgers moved to Old Harbor from Dorchester, Mass., in 1938. James Joseph Bulger, the brothers’ father, had lost part of his arm after a railroad yard accident when he was young and, as a result, had a hard time finding work throughout his life.

It apparently did not take long for young Jimmy Bulger to develop a violent side and, with it, a reputation. Close to the Bulger’s home was Mercer Street, a hang out for local gangs. From the Globe:

Whitey Bulger was as tough as any of them. While he was not a bully, it did not take much to cross him. He was a ferocious fighter with fast hands and a hair-trigger temper. Around Old Harbor, he was given a wide berth when he strolled the project, asking younger kids to punch him in his washboard stomach so he could laugh about it.

Bulger never went to high school, and by the early 1950s he had already faced and been acquitted on several minor larceny charges. He then graduated to a string of bank robberies in Massachusetts, Rhode Island and Indiana. Wednesday was not the first time the FBI has nabbed a fugitive Whitey Bulger. In 1956, FBI agents surrounded a nightclub in Revere, Mass., and apprehended Bulger in connection with the robberies. He was sentenced to 10 years in prison.

During the first part of his sentence, Bulger did time at a penitentiary in Atlanta, Ga., where, in exchange for a small reduction in his sentence, he participated in a CIA experiment on the effects of LSD. In November 1959, he was transfered to Alcatraz.

“Whitey was very quiet,” Teddy Green, a former bank robber who spent time at Alcatraz with Bulger, told the Globe in 1988. “A very gentle person. I never found nothing bad about him. He never got in no trouble. He was just a nice quiet guy.”

That quiet apparently continued through the first few years after his release. Bulger spent the second half of the 1960s living with his mother in South Boston and “tipping his hat to neighbors.” His brother William got him a job as a courthouse janitor. But it wouldn’t last.

By the early 1970s, Bulger had built a reputation as a fierce enforcer for local mobsters, and was working with the Winter Hill Gang, then headed by Howie Winter. And in 1975, he was recruited as an FBI informant by John Connolly, an agent who Bulger knew from childhood back in Southie. Bulger and an associate, Stephen Flemmi, helped the agency build a case against the Italian Mafia, in exchange, apparently for tips and protection from prosecution. When federal agents arrested Winter in the late 1970s, Bulger was able to ascend to the highest level of Boston organized crime.

Well before the details of his alleged crimes came out, Bulger had a reputation as a killer. The details were gruesome. From The Christian Science Monitor:

One victim was shot between the eyes in a parking lot at his country club in Oklahoma. Another was gunned down in broad daylight on a South Boston street to prevent him from talking about the killing in Oklahoma. Others were taken out for running afoul of Bulger’s alleged gambling enterprises.

On Thursday, Steve Kornacki at Salon highlighted one particularly horrid alleged murder, of 26-year-old Deborah Hussey in 1985. Flemmi had sexually abused Hussey when she was a teenager. From court documents:

They murdered her in much the same way they murdered their other victims, by luring her into a house and strangling her. Here again, Bulger grabbed Deborah Hussey from behind and scissored her neck between his forearms to crush her windpipe. Hussey fought desperately for her life and knocked Bulger over. When the two fell to the floor, Bulger jack-knifed his body to work his legs around Hussey’s body to crush her torso. The Court infers Hussey lost consciousness from asphyxiation and died within a few minutes.

One of Bulger’s strangest alleged schemes occurred in 1991, when a man named Michael Linskey purchased what ended up being a $14.3 million-winning lottery ticket at a store owned by the gangster. An FBI affidavit later alleged that Bulger and two associates paid $2 million for half of the winnings.

In the early 1990s, Bulger’s relationship with the feds soured. But he was tipped of by Connolly, the agent who had recruited him, and fled just before being indicted on federal racketeering charges in 1995.

According to a 1998 Globe story, Bulger had an alias ready to go when he had to flee. Bulger began using the alias Thomas F. Baxter while the real Baxter, who lived in Woburn, Mass., was still alive. After Baxter died, in 1979, Bulger got hold of a driver’s license with his picture but Baxter’s name, birth date and Social Security number.

Until Wednesday, Bulger’s whereabouts had been the subject of much speculation. He’d been spotted all over the country, and even the globe, and had made a few friends under his false identities. On Thursday, the property manager of the building where Bulger was arrested told The Los Angeles Times that Bulger and his girlfriend, Catherine Greig, had lived there for 14 years. They were known as Charles and Carol Gasko.

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