Whitey Bulger: Boston’s ‘Prince of Darkness’ plots his revenge…

It’s worthwhile sticking with some of this Whitey Bulger stuff, partly because I’m enjoying Kevin Cullen’s sceptical, but never cynical journalism, and partly because of that politics and gangsterism crossover that Pete highlighted the other day. Here’s his latest thought provoking piece:

As for settling old scores, what if, holy moly, he decides to help the only lawman he believes kept his end of the bargain, his old FBI handler John Connolly?

Connolly, the Southie agent who worked the Southie gangster, is serving 40 years for helping the Bulger crew murder a Boston businessman named John Callahan in Florida. Connolly is one of the few lawmen who went to prison in this whole sordid mess, and he’s the only one still incarcerated. Connolly’s corrupt supervisor, John Morris, avoided prison by testifying against Connolly.

Connolly did something Whitey appreciated: He kept his mouth shut, even after he was convicted of racketeering, even after he was convicted of murder.

To get revenge by springing Connolly, Whitey would have to contradict his erstwhile partners in crime and be believed. There’s other evidence, not to mention Morris’s testimony, that corroborates Weeks, Flemmi, and Martorano. Two juries, one in Boston, one in Miami, weighed their credibility and convicted Connolly.

But the opportunity for Whitey to wreak legal havoc is huge.

“I’m not interested in preserving the status quo,’’ wrote one of Whitey’s favorite authors, Niccolo Machiavelli. “I want to overthrow it.’’

When he was doing time for bank robbery, Whitey sat around reading “The Prince’’ and “The Art of War.’’ Machiavelli believed powerful men were necessarily immoral men.

“People should be caressed or crushed,’’ Machiavelli wrote. “If you do them minor damage, they will get their revenge, but if you cripple them, there is nothing they can do.’’

It’s worth bookmarking Cullen’s column page

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  • pippakin

    Machiavelli, required reading for all politicians, crooks and of course bank managers.

    I understand several of the charges have been dropped in favour of the remaining nineteen

  • pippakin

    Sorry laptop being a pain, again the last sentence should read:

    nineteen murder victims. But for me the most interesting aspect is his age. He is eightyish and although I know we all want to live forever I wonder how afraid he is going to be of death or prison. I’m looking forward to the trial, if it ever happens.

  • Pippikin,

    That’s a big “if”. People that age can get real or imagined illnesses and delay proceedings indefinitely.

  • pippakin


    So, not that big an ‘if’ then? and eighty might even get bail. The legalities of it are fascinating, but I still think age is on his side…