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Whitey Bulger still milking his crowd

Whitey Bulger was apparently being treated like a celebrity behind bars.Handout

Just sitting here, after clearing the driveway for the fourth time in 24 hours, and trying to decide what’s more depressing: the incessant snow, or the idea that Whitey Bulger was being treated like a celebrity behind bars.

The thought that some 30-something prison psychologist lady took a shine to the octogenarian gangster from Southie is kind of creepy.

But what was it that Kevin Weeks, Whitey’s boy Friday, once said about him? If Whitey wanted you to like him, he wouldn’t stop until you liked him. Never has a sociopath been so concerned about what others think of him.

Call me naive, but I was hoping that once Whitey got shipped out to the federal penitentiary in Tucson, he’d either be shunned or not taken seriously. But then Whitey got lucky and got put in a section of the prison called the Dropout Unit, which housed mostly sex offenders and informants. Perverts and rats. Whitey’s kind of crowd.

When I was in Tucson last year, a guard told me inmates were lining up to have their photographs taken with Whitey. Apparently, the fact that Whitey ruined untold lives, put women and men in shallow graves, and flooded his own neighborhood with cocaine didn’t faze the losers in his midst. My colleague Shelley Murphy recently learned much more, that Whitey is shopping his own celebrity, and other inmates are buying it.


A judge who teaches a course on sex offenders at the University of Arizona told me she saw Whitey’s digs when she took a group of students on a prison tour last year. She said Whitey was in a two-man cell.

But that was never going to last. The first thing Whitey did when he got shipped to the Atlanta pen for bank robbery in the 1950s was to make believe he was going crazy so they’d put him in a single cell. He liked Alcatraz because it was all single cells. And so he prevailed upon his psychologist to get him a single cell in Tucson, too.


Serial killers need their space.

By hitting the psychologist up for favors, Whitey got her and himself in trouble. Of course, it was only a matter of time before Whitey’s overweening egocentrism got somebody else in a jam.

When he was on the run, he dragged his brother Jack into a conspiracy to obtain phony IDs. Against his better judgment, Jack Bulger helped his brother out, and in doing so walked himself into a felony and lost his pension from the Boston Juvenile Court.

Now that prison psychologist is the subject of an investigation that could result in her being disciplined or even criminally charged if she did favors at Whitey’s behest, including lobbying to get him approval to correspond with his girlfriend in a Minnesota prison.

It’s heartwarming to know that Whitey and the love of his life, Cathy Greig, were able to resume their prison correspondence, this time without resorting to having lawyers smuggle their letters. While Cathy no doubt took comfort from the letters, she should take further comfort knowing that Whitey is 1,200 miles away, where he can’t get her into any more trouble. Then again, he’ll probably figure out a way.

In the meantime, Whitey’s trying to make the best of his new digs at Coleman II, the federal prison in the middle of nowhere Florida.


Maybe, if he plays his cards right, he’ll get a chance to meet another Coleman II resident, Benjamin Arellano Felix, who’s doing a 25-year bit for leading the Tijuana Cartel, which brought tons of cocaine into the United States and killed more than 1,000 cops and civilians who got in their way. Felix was expert at bribing bent law enforcement types. I’m sure he and Whitey would have lots to talk about.

Whitey’s 85 now and his famously robust health is fading. He’s sometimes using a wheelchair these days. Think Lionel Barrymore as Mr. Potter in “It’s a Wonderful Life.” A guy with all the money in the world who’s miserable.


Even in prison, ‘Whitey’ Bulger is pushing boundaries

Kevin Cullen: In the end, everything has passed Whitey by

Photos: Whitey Bulger on trial

Whitey Bulger’s life in exile

Kevin Cullen is a Globe columnist. He can be reached at cullen@globe.com.