Early prison days honed criminal skills

Flashy young gangster left more mature

By Andrew Ryan and Stephanie Ebbert
Globe Staff / June 24, 2011

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Young James J. “Whitey’’ Bulger spent some of his most formative years in California, locked in Alcatraz Prison serving time for bank robbery.

Bulger passed the time there and at other federal prisons in the late 1950s and early 1960s in the library, studying World War II military history and honing the fierce discipline that would later define his violent grip on Boston. He had arrived in prison a flashy gangster in his late 20s from Southie’s Old Harbor projects, known for wild car chases and what a biographer described as Jimmy Cagney flair.

But Bulger left his cell nine years later a mature criminal, a violent man who shunned the flamboyance of his youth. He became an exercise fanatic, rarely drank or smoked, and lived for years with his mother in Old Harbor.

“I think he came out of prison different,’’ said Dick Lehr, coauthor of the book “Black Mass’’ and former Globe staffer. “He came out a much more disciplined guy, determined never to go back to prison.’’

When authorities arrested him Wednesday, Bulger had become more myth than man: a notorious mobster wanted by the FBI in 19 slayings who at one time had a higher bounty on his head than anyone but Osama bin Laden. He was a power player who had once imposed twisted order on the streets of Southie while his brother, William ruled the corridors of Beacon Hill as Senate president.

The man who surfaced in Santa Monica Wednesday was 81 and weakened, ready to surrender to the government he had long eluded. His 16 years on the run fueled Hollywood lore of a gangster too smart to be caught. But the cache of firearms police said they found in his apartment served as a brutal reminder of the truth.

“Until I was knee deep in [his] prosecution, I would say I and many others did not appreciate the level of violence,’’ said Donald K. Stern, the former US attorney who was preparing a case against Bulger when he fled in late 1994. “If murders can be themselves characterized by severity and horror, a number of the murders that Bulger is alleged to have participated in or orchestrated are shocking.’’

James Bulger is the oldest of six children who was nicknamed Whitey because of his blond hair. His father had lost part of his arm in a railroad yard accident, and could not hold a full-time job. He moved the family to Old Harbor, the first public housing project in New England, when it opened in 1938.

While some of his siblings excelled in school, James Bulger thrived on the streets. He was a petty thief who ran with gangs, a high school dropout with a penchant for pranks, like driving his car off the street and onto streetcar tracks.

At age 14, he joined Barnum & Bailey Circus as a laborer. That year he also earned his first larceny charge. He would join the US Air Force, but his taste grew for more serious crime. In his 20s, he went on a bank robbery spree that ended when the FBI surrounded a Revere nightclub.

While James Bulger was in federal prison in 1960, his younger brother, William M. Bulger, entered politics. William Bulger would become the longest-serving president in the history of the state Senate, his tenure overlapping with his brother’s reign as a mobster.

Extorting money from drug dealers and bookies, Bulger ruled by brutality. His sidekick, Stephen “The Rifleman’’ Flemmi, testified two years ago that in the early 1980s, he watched Bulger strangle Flemmi’s girlfriend, as well as a woman that Flemmi had raised like a stepdaughter.

But Bulger also cultivated a Robin Hood-like image in South Boston, famously giving away turkeys to low-income families for Thanksgiving. Bulger perpetuated the neighborhood myth that he shunned the drug trade while profiting from it. He frowned on drinking, but was his neighborhood’s biggest liquor supplier.

Bulger’s most significant coup came in the 1970s, when he began working as an FBI informant against the local mafia. FBI agents helped protect Bulger while his criminal enterprise flourished and his alleged death toll mounted.

His principal guardian became John J. Connolly Jr., the FBI agent who tipped Bulger off that an indictment on racketeering charges was finally imminent. He fled in 1994.

“It’s the biggest crime story in our lifetime,’’ Lehr said yesterday. “He’s part of the biggest informant scandal in FBI history that left many people dead and lives ruined.’’

Ultimately, Bulger was charged with killing 19 people, many of them whom were killed while he was working as an FBI informant. While Bulger was on the run, the fallout grew. Connolly, the FBI handler, was convicted of tipping off Bulger and leaking information that led to the killing of a potential informant.

John “Jackie’’ Bulger, the youngest of the brothers, served as a juvenile court clerk magistrate until retiring. But John Bulger kept in touch with his fugitive brother and lost his pension after a conviction for lying to a grand jury about his contact with James Bulger.

William Bulger kept his political power even after his brother fled. He left the state Senate and became president of the University of Massachusetts. But his admission under oath that he had spoken to his fugitive brother in 1995 — and did not urge him to turn himself in — led William Bulger to be called before a Congressional committee and ultimately to resign under sustained political pressure from Governor Mitt Romney.

“I do have an honest loyalty to my brother, and I care about him,’’ William Bulger said in his 2001 testimony before a federal grand jury, according to a transcript obtained by the Globe. “It’s my hope that I’m never helpful to anyone against him.’’

Andrew Ryan can be reached at; Stephanie Ebbert at

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