In letters, Whitey Bulger fondly recalled the old days, Alcatraz

This photo taken by Urban Culture Auctions in West Palm Beach, Fla., leave a hand-written letter by the late gangster James “Whitey” Bulger, an envelope and a holiday greetings card decorated with his 1959 Alcatraz mugshot, that Bulger mail from the federal prison in Coleman, Fla., in 2015. The items are among those that are offered by the auction house for the auction on Sunday, feb. 24, 2019. Bulger was found dead in a wheelchair on Oct. 30, 2018, killed by the prisoners within hours of his transfer to a prison in hazelton, W. V. He was 89. (Darin Rone/Urban Culture Auctions via AP)

BOSTON – Imprisoned for life after 16 years on the run, murderous Boston gang boss James “Whitey” Bulger couldn’t stand how much the world around him had changed.

The prison was nothing like his days on the island of Alcatraz, with its “beautiful view” and clear rules, Bulger said. And the former Irish Catholic stronghold of South Boston, he once terrorized was now filled with “rich college kids living in expensive flats.”

“The world has changed … everything is different, even around,” Bulger wrote to a friend he met in the lockup in newly public letters.

The letters, which will be auctioned Sunday, offer a glimpse into the once mighty and feared gangster everyday life behind bars before he was beaten to death by fellow inmates last year. Bulger wrote about the small excitement of prison life — “tonight we had an ice cream!” and his treatment by other prisoners.

“Almost every time I go anywhere guys ask “hey old timer, do you want a push” … or simply just handles and begin to push it,” Bulger wrote in a letter postmarked in February 2015. “One advantage is that we can go in the front of the chow line when in the wheelchair.”

The authorities said two Massachusetts gangsters are under investigation for 89-year-old Bulger killing, but no one has brought. His death hours after he was transferred to a troubled West Virginia in the prison has raised questions about the reason why the well-known “snitch” was placed in the general population, instead of more protective enclosure.

Bulger ratted on the New England mob to the FBI, authorities said, though he insisted during his trial that he was not an informant, but was actually in the pay of the FBI for the scoop on his enemies.

The auction received the letters of a man who says that he became friends with Bulger when the geriatric gangster was briefly held in a federal lockup in Brooklyn after his conviction in 2013 of participating in 11 murders, among other crimes.

That man, Timothy Glass, said he took Bulger in his wings, and they tied about their criminal past. Glass recalled how Bulger would sign autographs for the inmates who asked, but had a tendency to give a “death stare” guys he didn’t like.

“I was like, ‘this man is a hardened killer as 80 years old.” It was wild, Glass, 55, told The Associated Press.

Glass was locked up on robbery and other charges, when he met Bulger after more than a decade in the state of New York jail for separate crimes, he said. The prisoners were not allowed to write to one another, so after Bulger was transferred to a different prison, Bulger would send the letters to a friend on the outside, who would get them on the Glass, ” he said.

In the letters, Bulger complained about the cost of books (“$32 for the book!”), the cold weather (“the liberals, as vice president Gore made a fortune with his frighten people with talk of a “planet warming”‘) and the media, which he called “a part of the particles of the corruption instead of the society ‘watchdogs.'”

He grumbled about the process, slammed the prosecutors for deals that they made with his former friends, and promised his appeal would create quite a stir.” He also bemoaned what he saw as the unfair treatment of his ex-girlfriend Catherine Grieg, who was sentenced to eight years for helping Bulger avoid capture.

“I played a rough game and accepted the rough treatment. But the feeling Catherine was treated to hard,” Bulger wrote.

He told enthusiastically about his time on “The Rock” — Alcatraz — where the rules are ‘clear and understandable’ and the prisoners were allowed at Christmas time to buy chocolate, which she likes to share with prisoners who were not supposed to have candy.

‘Here, ‘they’, the ‘prisoners’ would you sell chocolate! When no one was looking to make a profit on another prisoner,” he wrote. “I look back on those years and the place with nostalgia. It’s all gone.”

Hidden in some of the letters were pictures of Bulger as a young man, or Alcatraz. On the back of one of the photos in a mugshot taken in 1965, the year Bulger was released from prison and returned to South-Boston — he scribbled: “the good old days.”

With a different letter, Bulger included a holiday card that he apparently made in 2015 with the message in gold script: “I wish you peace and courage in the New Year.” In addition to the cheerful greeting Bulger’s Alcatraz mugshot, his eyes piercing blue eyes narrowed and furrowed eyebrows.


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