With Life in Prison on the Table, Whitey Bulger Faces Judge Wednesday

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(CNN) — James “Whitey” Bulger, the convicted Boston mobster whose rise and fall was as convoluted as any Hollywood script, goes before a judge Wednesday with prosecutors calling for him to be locked away for life.
filephoto whitey bulger

James “Whitey” Bulger’s case was a scandal for the FBI, which had used him as an informant. (Credit: United States Marshal Service)

The 84-year-old Bulger was found guilty of racketeering, extortion and money laundering in August after a rancorous two-month trial, with a federal jury linking him to 11 killings. Federal prosecutors have urged District Judge Denise Casper to hand down a life sentence for the longtime fugitive, calling him one of the city’s “most violent and despicable criminals.”

“Presiding over a massive criminal enterprise, Bulger extorted dozens of individuals, flooded South Boston with cocaine, shot innocent people, strangled women, murdered his competitors, corrupted FBI agents, and then ran away and hid for 16 years,” U.S. Attorney Carmen Ortiz wrote in a November 7 sentencing memorandum.

“There are no mitigating factors, and defendant Bulger has no redeeming qualities which would justify any sentence below the one called for by the U.S. Sentencing Guidelines and the applicable case law and statutes,” she added.

Bulger didn’t testify in his trial, complaining the proceedings were “a sham.”

Bulger was captured in California in 2011, a decade and a half after skipping town ahead of a pending indictment. After he fled, investigators learned that the longtime head of south Boston’s Winter Hill Gang had been an FBI informant and that Bulger’s FBI handler had not only tipped him off to the charges, but also gave up another informant, who was later killed.

Meanwhile, Bulger’s brother William had risen from the family’s blue-collar Irish neighborhood to become president of the state Senate and head of the University of Massachusetts. But in 2003, he was forced to resign the school’s presidency after admitting to a congressional committee that he had spoken to his brother while Whitey was on the run, though he denied any knowledge of his whereabouts or alleged criminal activity.

Bulger denied being an informant even as he insisted that he’d had an immunity deal with the former head of the Justice Department’s Organized Crime Strike Force in New England. Prosecutors countered that with a 700-page file outlining how Bulger provided information on murders, drug deals, armed robberies and criminal fugitives that led to several arrests.

The tale became the basis for the Oscar-winning film “The Departed,” which starred Jack Nicholson as a character modeled on Bulger.

At the trial, Bulger snarled, hissed and scowled at prosecutors and witnesses. At one point, he and onetime enforcer Kevin Weeks shouted obscenities at each other when Weeks called Bulger a “rat” during his testimony.

But Weeks told CNN after the verdict that the Bulger who sat at the defense table was a shadow of the underworld legend he’d once known.

“He wasn’t the same guy I knew,” Weeks said. “I mean, he’s a lot older, but he had no life in his eyes. He was subdued. He had changed. He just kind of lost his spark.”

CNN’s Greg Botelho and Deborah Feyerick contributed to this report.

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