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Finally he said, “Whitey owes me a letter.”Īn undated photo of Mr. DeMasi sat on his bed, trying to remember something. But on this August afternoon last year, Mr. The two men also exchanged yearly Christmas cards. Fellow Bank Robbers, not ‘Organized Crime’ guys. Felt like I was hearing from friends way back in the Az years. “Thanks for writing and I really enjoyed your letter. In another, he evoked his time in Alcatraz: DeMasi sell these notes they might be worth something. In one letter, written in slanted, nearly inscrutable script, Mr. DeMasi sent him a letter - a message, really - that he summarized as: “Whatever transpired between us, it didn’t kowtow me or make me any less of a man.”įrom this a pen-pal friendship grew.

Bulger was captured, convicted and sentenced to prison forever, Mr. DeMasi several times in the drive-by killing of another target. They often closed with “A friend always” and “With love,” and were signed by public enemies named Bobo, and Gerard, and even Jim, as in James Bulger, the murderous former fugitive better known as Whitey.įunny story: More than 40 years ago, Mr.

These letters, which he slept beside, were the coded missives of criminals, swapping family updates, sharing gun-rap loopholes. He kept more memories in boxes of correspondence arranged lengthwise on his bed, the dates of every receipt and reply recorded in his shaky scrawl. “So the pictures kind of keep me up to - you know.”

“You forget people, like, as you go along,” he said. …”īut he struggled to summon this mobster’s name from his mind’s darker recesses. “And the one on the right, he’s a wiseguy out of New York. DeMasi said, motioning to a photo of a vicious Mafioso from Rhode Island, long dead. Call 1-800-NYTIMES, or email to purchase copies. This story will be available as a special print section on Sunday, June 4.

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