Kevin Cullen

The prince of the city

By Kevin Cullen
Globe Columnist / June 28, 2011

E-mail this article

Invalid E-mail address
Invalid E-mail address

Sending your article

Your article has been sent.

Text size +

Whitey Bulger has been regaling his captors with tales of crossing the border at Tijuana to get cut-rate medicine in Mexico, making furtive visits home to Boston to settle scores, and living large in Vegas.

Actually, Whitey’s Mexican shopping trips merely confirm something we already knew: For a guy worth millions, he’s cheap.

As for talking wise with G-men, Whitey always considered cops bit players in a movie that’s all about him. Years ago, when he discovered a bug federal drug agents planted in his car, the DEA men rushed in to retrieve the expensive device.

Whitey tried to put the red-faced DEA agents at ease, reminding them they were all good guys.

“You’re the good good guys,’’ he said, “and I’m the good bad guy.’’

That’s the self-serving and completely bogus portrait Whitey and his apologists liked to paint, a benevolent gangster who hurt only the people who had it coming.

Whitey telling the feds about filling his prescriptions in Mexico and going home to Boston is a taunt: I was the most wanted man in America and I went anywhere I wanted, and you clowns didn’t catch me.

Whitey likes to remind you he’s the smartest guy in the room. Before last week, it was hard to argue with that.

With ol’ chatterbox already talking, everybody seems sure he’s going to talk some people right into jail.

There are at least a half-dozen retired FBI agents who have been accused by Whitey cohorts Steve Flemmi, Johnny Martorano, and Kevin Weeks of accepting cash or gifts. Weeks says they bribed 20 Boston cops. Maybe Dick Schneiderhan wasn’t the only state cop corrupted by the Bulger crew.

But what if Whitey is determined not to put somebody in jail but to get someone out?

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.’’

Whitey’s back, and he’s not crippled. He knows he’s going to die in custody. But he can make deals on other matters.

He used to have the FBI in his pocket. Now the only thing in his pocket is revenge. Just like old times.

And it’s beyond Machiavellian.

It’s so Southie.

Kevin Cullen is a Globe columnist. He can be reached at