The Shoeshine Exemption
by Millard Halftruth 

Life on the inside was tough. “The inside,” that was what we call the penitentiary. I had been on the “inside” for nearly forty years. I was forty-four. That’s more than half a man’s life spent repaying a debt to society. What kind of debt takes that long to repay? What did I get out of it? A house? That’s the kind of debt we’re talking about. House-size.

You had two kinds of people in the joint: The guys who took what life dealt them and the ones who didn’t. I was one of those guys who took what life dealt them. It was a pair of eights, a five, a four, and a two. Almost like it could be a decent hand, but not quite, enh, you know? I’m not complaining. And then there was Timmy.

Timmy was the kind of guy who didn’t take what life dealt them. He was always thinking there was a way out, that there was more to life than slaving away making license plates to keep your mind off doing the time, and avoiding sodomy in the shower room. There was successfully avoiding sodomy in the shower room, and so much more. Timmy was always thinking big.

There were two kinds of guys who didn’t accept the cards life dealt them: The kind who got angry, got mean, and turned it all against the prison. Bigot Deuceballs was like that, the meanest man the “inside” had ever seen. He would rip you a new asshole just as soon as look at you—some of them men he ripped a new asshole for didn’t even want it, but he did it anyway. And the other kind of guy who didn’t accept the cards life dealt them was the kind who dreamt of getting out, by any means necessary. That was Timmy.

There were two things Timmy was good at: Shoeshine and something else I probably shouldn’t mention. But he was good. Man, he was incredible with that one talent. But he also shined a decent shoe. And on the “inside,” that was his ticket to an easier life.

The warden made Timmy the personal bootblack to every officer in the prison. Sometimes the governor would visit and Timmy would give him the ol’ spit-shine. Then after that he would shine his shoes, and the governor loved the look of his big ol’ white bald head in that shoe, yes sir. It was better than the horrid demon face that popped up sometimes and scared him to loosin’ his bowels. The governor was insane, you see, I might have mentioned that earlier.

Being the penitentiary pet and having the respect of the governor, that was good enough for most of us on the inside. But Timmy always dreamt bigger and bigger. There are two kinds of guys who always dreamt bigger and bigger: The guys who nobody believed were ever going to do anything, and the kind who would actually do something. Timmy was the second kind, but we all thought he was the first kind. He kept talking of busting out.

“I’m going over the wall tonight,” Timmy told me one night, whispering down the cell block. For the sake of this story let’s say I could hear him.

“Ain’t no wall so much as a fence, Timmy,” I replied.

“Fine, then I’m going under the wall. You going with me or not?”

When you’re a young man, escape seems like it’s possible. It seems all you got to do is pick your moment and run, and keep running until you get somewhere better. Then you get to be a forty-four year-old convict like myself and start to doubt you ever knew how to run in the first place. I tried to tell Timmy not do to it—but there was nothing you could teach Timmy about the world. He had a learning disability.

For more of this great story, buy Millard Halftruth’s
The Shoeshine Exemption Study Hall Hood: A Hatty Pearst, Teen Detective Mystery
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Harvey Potluck and the Sophomore Slump
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