• Whitey pens words of advice, regret in another jailhouse letter

    PLYMOUTH, Mass. (MyFoxBoston.com) -- It is, at times, a touching letter Mark Gallagher recently received, full of advice about staying on the right path.

    “I think about you a lot, Mark, and you want to benefit from past mistakes. Nothing is worth chance of losing your freedom. “

    Only this letter didn't come from a motivational speaker. It came from James “Whitey” Bulger, the convicted South Boston mob boss.

    Gallagher told FOX 25’s Bob Ward that he met Bulger at the Plymouth County House of Correction last year.

    When asked how he justified convicted murderer Bulger’s actions with the advice he was given, Gallagher was conflicted.

    “I can't almost. It's hard to take the advice knowing what he did,” Gallagher said. “But at the same time, I feel like, he did all that, and he's ok with himself. He's able not to shut down and feel like he's not worthy of talking to anybody else, and helping anybody else out. “

    Gallagher has written to Whitey, and Whitey has written back, usually urging Gallagher to stay out of prison.

    In one letter, Whitey writes, “If I knew this is how it would end for both of us, may have preferred a Bonnie and Clyde Barrow exit.”

    Bonnie and Clyde were killed in shootout with police.

    But once, Gallagher remembers a jailhouse conversation where a different Whitey surfaced.

    Gallagher asked Whitey about the murders he was on trial for committing.

    “I said, ‘So what's the deal, how many was it?’ He smirked and said, ‘Some people in this world deserve things that other people will never ever have to experience.’ I said, ‘What does that mean?’” Gallagher said. “It was definitely surreal.”

    But Gallagher’s letter from Whitey is mostly about doing the right thing.    

    “Whitey Bulger killed a lot of people and all that. I can't say he’s a great guy,” Gallagher said. “My experience, he was all right. He never stood me wrong. “

    The letter ends with Whitey telling Gallagher to “stay on the ball,” and wishing the “best of everything to you and your family.”

    He signed the letter “James Bulger.”

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