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Life Inside

The Freak Accident That Deprived Me of a Great Prison Boss

In prison, tears are a form of weakness inviting retaliation. But he cried with me.
Illustration af John Lee

This article was published in collaboration with the Marshall Project.

I worked for the same boss for eight years, a long time for an inmate to hold a job in prison.

The day he hired me all those years ago—for a maintenance gig that paid barely $2.00 a day—he said, "If you don't show up bright-eyed and bushy-tailed every morning at precisely quarter till 7:00 Monday through Friday, don't bother showing up at all."


And when we worked on the roof, or used ladders, he'd say, "If you fall, you're fired before you hit the ground."

Like all the other staff in my prison, from wardens to case workers to nurses and maintenance people, my boss knew he was viewed a certain way by much of the inmate population: as a captor, an authority figure to be resented, blamed, vilified. I myself once saw prison staff this way—as cardboard figures in blue, clones of the policemen who had cuffed my hands behind my back and led me into the prison system in the first place and left me here to rot.

Yet even though my boss and I didn't quite get off to the right start, over the years I grew to respect him and see him more as a person and less as a badge. For one, he did not laugh at me when he caught me crying over the loss of my father, because he, too, had recently been in mourning.

In prison, tears are a form of weakness inviting retaliation. But he cried with me.

Check out our look at the nuts and bolts of solitary in an American jail.

A few months ago, my boss, his assistant, my co-worker, and I were assigned to a routine installation of a P.A. system atop the prison roof. Outside, with guards looking down on them, groups of inmates ran the yard in T-shirts and shorts—in January. Winter had decided to take the season off, though the forecast called for storms and wind.

We needed to work quickly. On the roof, the tar paper beneath our feet was already wet with a light mist. The skies above had become overcast, and the wind threatened to blow the tools from our grip.


From below, one of the prison's case workers noticed us and reminded us to be careful. My boss, in a flash of good humor, called back to her, "We wi-ll-ll-ll," like a child promising to do a chore. We found this to be hilarious.

The view from the rooftop of the prison has always been as close to freedom as I can get, at least in the past 11 years since I arrived here. From up above the fence line, above the razor wire, I can briefly convince myself that I am no longer confined to the blank white walls, the cracked concrete floors. I breathe deeper, will myself to take in every detail and think beyond the barriers of the prison.

When we were about done with the P.A. installation, my co-worker and I gathered the tools and materials, took a look back at the rolling countryside, and resigned ourselves to climbing back down into the yard.

The next few moments still replay in my mind every day.

My co-worker, my boss, and his assistant moved to cross a parapet wall, and as my boss, a man of 5'6" or so, climbed over, I looked down below the fence line. I could hear inmates shouting "Jump!" and saw them tossing rocks and batteries when they thought no one was watching.

I looked up just in time to see my boss cross over the wall, let out a short yell, and violently twist as his right foot hit a slick patch of wet tar paper. Trying to catch himself, his knee struck the ledge that ran the perimeter of the roof. He tottered.


My co-worker latched onto our boss's belt in an attempt to slow him. His assistant lurched at his feet. I, too, reached across to try to grab him.

My boss toppled over the wall. His belt pulled free of my co-worker's fingers; his assistant's attempt to snag his feet narrowly missed; and his foot, as it hung suspended in the air, slipped my grip.

My co-worker quickly yelled out for our boss's assistant to call in a medical emergency over the radio. I dropped to my knees in prayer and in shock.

After a minute, I willed myself to move over to the roof edge and look down upon the man who'd hired me and expected so much from me when I expected little from myself. He laid broken on the ground below, alive but gravely injured, with grossly distorted limbs and torn fingers where he'd tried to grasp the gutter pipes.

First responders responded; an ambulance arrived on the scene. We returned to the prison grounds below.

In prison, a medical emergency brings all inmate movement to a halt. Gates slam closed, wings lock down, and radio traffic ceases. There's not much to do.

So when my co-worker and I returned to our dorms, the questions came fast from our cellies and others:

"What happened?"

"My boss fell off the roof."

"Did you push him? Tell me you pushed him."

"He fell… I couldn't save him."

"Fuck that! He's one of them."

Then the taunts began. Word of my co-worker and me attempting to rescue one of them spread.


"Did they give you a pardon? Are they gonna set you free? Hell no!"

"You should have pissed on him," someone else said.

My boss survived the fall but ended up with multiple broken bones and can no longer work at the prison. He had been nothing but good to me.

"I would have done the same for you," was all I could say to my fellow inmates.

Prison changes everyone. Some folks lose hope, while some lose compassion altogether.

But sometimes prison offers us a vantage point on one another—on our humanity—a view that lifts us high enough above it all to see clear beyond the chain link, beyond the sharpened steel of the fence line.

Derek R. Trumbo Sr., 39, is incarcerated at the Northpoint Training Center in Burgin, Kentucky, where he is serving 25 years for charges stemming from the sexual abuse of a child. He has maintained his innocence in court. He is a two-time winner of PEN writing awards for his plays, which have been performed in Australia, New York City, and Louisville, Kentucky.