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A letter to Whitey Bulger

(Editor’s Note: Just a heads up to those of a more delacate nature: This article contains adult language. If you are offended by that sort of thing, you might want to stop reading.)

Dear Whitey,

I bet you watched a lot of TV in the years you were on the run. Please tell me you watched The Sopranos. Remember in the third season, when the great Burt Young makes an appearance as Bobby Baccala’s retired hitman father? Uncle Junior is on trial and is doing whatever he can to win it, while fighting cancer at the same time – as is Burt Young’s character. So in the episode they are all at a funeral. Burt Young goes over to say hello to Tony and sees Uncle Junior on the sidewalk. Burt Young, while coughing and hacking up blood, looks at Junior and says something along the lines of “You cagey fuck, you got’em all fooled,” while smiling with blood in his teeth.

You, Whitey, are a cagey fuck. And right now Boston is in your face smiling at you with blood in its teeth. You had us all fooled. Some thought you were dead; others figured you were on some island somewhere. Some people said Ireland; other said you were hiding in Southie dressed as an old woman. One thing nobody questions is your intelligence. You are a brilliant motherfucker. You always thought around corners. Personally, I figure you have something up your sleeve. I think you might get on the stand and tell the story that most people are dying to hear while still others would kill you to keep quiet.

Did you give yourself up because somebody high up in the government who knew all about you retired, or died, and you felt it was safe to come in out of the cold? Do you have some health issue that makes it only a matter of time before you pass and you want to tie up loose ends? Did Catherine finally wear you down? By the way, when it comes to her, I gotta ask: What the fuck were you thinking when you took her with you? Don’t you know when you run, you’re supposed to run alone? Didn’t you ever see Heat with Pacino and De Niro? Never have anything you can’t drop in seconds when it’s time to go.

I also think you should thank Howie Carr, and that in return he should get on his knees for you. You made him into what he is today. You made him a rich man and he turned you into a legend. You can’t buy the kind of publicity. You know he will be at your trial every day with a big shit eating grin on his face, like when they called your brother Billy into the Senate. Carr raked Billy over the coals for the shit you and he pulled. Oh, by the way, there is not a single person in Boston who doubts that he was watching your back all these years. People here want to see Billy crucified just as much as they do you.

I think this is all great, I can’t wait for your trial. I want to hear your secrets and get the truth that only you can provide. You have become a superstar. The last old school gangster, the last of the Mohicans. They broke the mold after you. Even though you are a degenerate piece of shit, I have this weird respect for you. You put on a magic act that most criminals could never even come close to. You got away. You made the greatest law enforcement system in the world look like assholes. Jesus Christ, Whitey – I gotta hand it to you.

I’ll say this: Motherfucker, I personally figured you were dead. I figured that somebody with the means, whether law enforcement or the criminal element, (doesn’t really matter which since you fucked with both) tracked you down in some corner of the rock we all live on and left you where you fell. How wrong I was. Hell, there is still time. The people you hurt (and there are too many of them to count) have been waiting years for a chance to make things right, they can wait a little longer. Enjoy your rides in Coast Guard helicopters and the security details that normally are reserved for heads of state. It could still come. Someday when the trial is over and you are doing time, some crackhead might decide to make a name for himself by stabbing the great Whitey Bulger. And you have done time Whitey, so you know it won’t be pretty. Most guys in prison, when they stab somebody, have a technique not unlike that of a teenage boy fucking. Think on that one, my friend.

Anyway, I hope you’re settling in. I just wanted to drop you a quick line to say “What up.”

Be well,

Dave Wahlman