Kevin Cullen

Whitey Bulger’s wily ways

Is Whitey Bulger crazy?

Or just crazy like a fox?

When it comes to Whitey, I always think it’s the latter. But, hey, easy for me to say. I’m not 83 years old, locked up in a tiny cell, 23 hours a day, talking to myself.


Whitey was always the most sociable of reputed gangsters, so maybe being confined in such a small space, cut off from human contact, is really cracking him up. Maybe that’s what made him such a chatty Cathy last September when his brother Jack visited him at the jail in Plymouth.

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Now, Whitey’s many things, but he’s no dummy. He knows that his conversations with visitors are going to be recorded. So he had to know that when he insisted to Jack that he wasn’t an informant for the FBI, it was more or less for eventual public consumption.

The problem for Whitey is not just that his laugh-out-loud claim to Jack is undermined by a sizeable public record. His outlandish claim also undermines his own outlandish defense, which is that he was granted immunity by a conveniently dead federal prosecutor to engage in any and all crimes, including those 19 murders he is charged with.

If he wasn’t working for the feds, why would they grant him immunity?

Now, don’t get me wrong. I have a certain level of sympathy for Whitey’s reality-challenged defense. The FBI went out of its way not only to ignore Whitey’s penchant for violence, as it ludicrously gave him credit for helping them take down the Mafia, but its agents also thwarted the efforts of honest cops to charge Whitey with killings in Oklahoma, Florida, and right here in Boston.


If I were Whitey, I would think I had immunity, too. Whitey’s problem is the immunity was in his head, not on a piece of paper.

When Whitey got pinched in Santa Monica back in June 2011, those who believe his longtime FBI handler John Connolly is innocent were convinced that Whitey would help exonerate Connolly. Instead, Whitey used his jailhouse conversation with brother Jack to throw Connolly under the bus, implying that he bribed Connolly and explicitly accusing Connolly of filing phony reports that credited Whitey with giving him information about assorted and sundry criminals.

“I never told them a [expletive] thing,” Whitey insisted. “I bought [expletive] information. I didn’t sell it.”

Just for giggles, I went through Whitey’s 900-plus page informant file. Some of my favorite entries are the ones in which Connolly notes that Whitey gave him information about other criminals, including both rivals and friends.

One of the reports has Whitey saying that two of his partners in the Winter Hill Gang, Joe McDonald and Jimmy Sims, were coming into town to resolve a beef. Given that they were fugitives at the time, that was probably not a wise or collegial thing to share with an FBI agent.


But Whitey would have you believe that Connolly made the whole thing up. Connolly does the right thing by Whitey, tips him off so Whitey can take off, and this is the thanks he gets? Whitey spent 16 blissful years on the run, living three blocks from the Pacific Ocean, while Connolly has been doing hard time for the last 15 years. And now Whitey says he’s a corrupt, congenital liar.

If that’s what passes for loyalty in Southie these days, thanks, but I’ll pass.

On Thursday, federal judge Richard Stearns told Whitey and his lawyer, Jay Carney, that they had to put up or shut up next Wednesday. They’re going to have to offer some proof that Whitey had been given immunity by the late prosecutor Jeremiah O’Sullivan if they want to put that forward at Whitey’s trial in June.

If they can’t, then Whitey’s thin defense gets even thinner.

Kevin Cullen is a Globe columnist. He can be reached at Follow him on Twitter @GlobeCullen.