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Bulger’s New Prison Will Be No Match For Time On Alcatraz

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Whitey Bulger, seen here with his girlfriend, as they visited Alcatraz while being on the run from federal authorities.(CBS/WBZ)

Whitey Bulger, seen here with his girlfriend, as they visited Alcatraz while being on the run from federal authorities.(CBS/WBZ)

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SAN FRANCISCO (CBS SF) – James “Whitey” Bulger is headed back to prison following his conviction on a series of crimes, including 11 killings. The former Boston mob boss won’t get his wish to live out his final days in the prison with “the best view from any prison in the world.”

The 83-year-old Bulger faces life in prison after being convicted Monday of committing or playing a role in the killings during the 1970s and ’80s while he led the Winter Hill Gang, Boston’s Irish mob.

But before Bulger rose to power in Boston, he was once an inmate at San Francisco’s notorious Alcatraz prison more than five decades ago.

Bulger was shipped to “The Rock” from a federal prison, where he was doing time for bank robbery, when he refused to snitch on a guard who was helping him in 1959.

“He arrived here basically in November of 1959 and he stayed here until April of 1962,” said Alcatraz historian Michael Esslinger, who has written two books about the prison, which is now a major tourist attraction. (Editor’s note: Ironically, it turns out that Bulger visited Alcatraz many years later as tourist while he was on the run as a fugitive – see photo on left.)

Two years ago, Esslinger wrote Bulger asking him to share his memories of Alcatraz. By then, Bulger was back in jail facing the murder trial following his 2011 arrest. Bulger’s response was more than he had hoped for.

“I probably have well over a thousand pages,” Esslinger told CBS News, before reading excerpts from the letters.

“I came over to Alcatraz on the Warden Johnston boat and was bolted in for security purposes,” read one letter. “While I didn’t know some of the earlier residents like Al Capone…I have a good idea of what thoughts he had while serving time on Alcatraz. We read from the same library, we worked some of the same jobs, and we were counted by some of the same guards…We were all part of a unique band of brothers.”

Bulger reminisced about how he used to take in the San Francisco skyline from the steps of the prison yard.

“I’d stand there and look out at the sail boats on the Bay, and at the Golden Gate Bridge. It was such a wonderful full view of the Bay from Alcatraz…It was the best view from any prison in the world.”

Once his sentence was up, he returned to Boston in 1965, where he worked his way up the notorious Winter Hill gang.

But as Bulger faces a life spent behind bars, he still has memories of his time on The Rock.

“If I could choose my epitaph on my tombstone, it would be ‘I’d rather be in Alcatraz,’” reads one of the letters. “All that remains on Alcatraz today are our ghosts.”

Bulger’s 16 years on the run exposed the FBI’s corrupt relationship with its underworld informants. he was found guilty Monday of counts including racketeering, racketeering conspiracy, extortion, money laundering, narcotics distribution conspiracy, and illegal firearms charges. He had been charged in 19 killings and an array of other crimes.

Bulger was found guilty of racketeering acts including the killings of of Deborah Hussey, John McIntyre, Arthur Bucky Barrett, John Callahan, Michael Donahue, Brian Halloran, Roger Wheeler, Richard Castucci, Thomas King, Edward Connors, and Paul McGonigle.

During the two-month trial, prosecution witnesses portrayed Bulger as a hands-on crime boss who killed some of the gang’s targets himself and orchestrated other killings.

Defense lawyers say three once-loyal Bulger cohorts got reduced prison terms in exchange for testifying against Bulger.

(Copyright 2013 by CBS San Francisco and CBS Interactive. All rights reserved. This material may not be published, broadcast, rewritten or redistributed.)

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