‘Sing Sing is a war zone.’

I lay on my bunk after breakfast, eyes barely closed, when I hear, “Sheffield! Sheffield!”  

The sound echoes inside the empty cell. I open my eyes. A CO is standing at the bars.  

“You ready?” he says.

“Yeah, how long?” I ask.  

“Ten minutes.”

 Sullivan Correctional Facility is closing. I’m getting transferred today.

I learn I’m headed to Sing Sing. Disgust interrupts my sleep. I’m 67, and I’ve been in prison for the past 42 years. I’m a few semesters shy of earning my bachelor’s degree.  Considering my age, I’d hoped to get sent to a smaller, quieter prison with a better quality of life. Sing Sing is a war zone.

Cuffed, shackled, and chained, 19 of us make the hour-and-a-half trip to Ossining, New York. An Italian guy, Johnny Burke, sits next to me. He was in the B-block riot at Sing Sing in 1983. He asks me if I’d been there before. I nod. I didn’t want to talk. He recognized my need for space and left me alone.

The Sing Sing Correctional Facility, completed in 1828, is the second oldest prison in New York State. Its name comes from the Native American people who lived there—the Sintsink. A single wall remains from the first building. The facility overlooks the Hudson River, 30 miles north of New York City—it’s where the phrase “up the river” comes from. The two larger cell blocks, A and B, along with a few smaller buildings, rest atop a hill. Vocational training programs occupy the Death House, which sits right on the riverbank.

The bus arrives during count time, and we wait outside the gate until it clears. The heavy green gate grumbles open, and we roll inside. Soon we’re unchained and directed to a holding pen for processing. Guys pepper the draft porters with questions. 

“Yo, is seven still here?”  

“Yeah, he’s in A-block.”  

“What up with T-Guns?”  

“He’s sturdy. He’s a porter in 5 building.” 

Messages are sent, questions answered.

Sing Sing has changed since I was here 37 years ago. Gangs now run the prison. Everyone’s on alert. The tension feels like a rope stretched tight. Wary eyes analyze the slightest movement as a threat assessment. 

Noise greets us as we enter B-block. The block holds 68 cells in tiers that stretch five stories high. People yell over the sounds of TVs, rap, reggae, and reggaeton blaring from cell radios. Dirt, dust, and grime coat the white brick walls. There’s chicken wire on the tiers so guys aren’t thrown off them. Light filters in through opaque windows. The block glows a sickly yellow.  Weed smoke drifts through the air.

The block utility man, Big Dog, gives us the rundown. I’m in the back. I turn my head and see a female CO straight out of a “Dark and Lovely” shampoo commercial. Her straight, relaxed hair shines like polished onyx and perfectly frames her oval face. She’s stunning. Catching myself staring, I focus my attention elsewhere.

“You guys with 19, 20, 22, and 24 numbers,” another female CO says. “Listen to the old-timers, and you’ll make it.”

She gives out cell locations. When it’s my turn, she says, “We’ve been scoping you out since you got here.”

“Really, for what?” I ask.

“Your number.”  

My department identification number starts with the year I started my sentence. I’ve been down since 1982. We smile at one another, and I head to my cell for the night.

In the morning, on the way to breakfast, a young man’s face is slashed. They call it getting shot.  I haven’t been here 24 hours. Two COs walk down the tier checking hands. When they get to my cell and see the grey hair, they wave their hands in dismissal. 

“He’s not involved,” they say. 

I decide to stay in for the day. The next day, another slashing happens in the gallery below me. COs swarm, searching for weapons. I need to use the phone. I stay in again.

I wait another day before I venture out. The dirt yard I remember from years ago is now cemented over. The phones are inside a long, narrow cage. It’s not the place to get caught slipping. The line is long, so I head to the basketball court to watch the pick-up game. I walk by a guy slinging deuce—(K2 chemicals, sprayed on paper, clipped into small pieces, and smoked in a roll-up cigarette) in the middle of the yard. 

When I reach an area with several tables, there’s an empty one close to the action. I sit. But I’ve messed up. A young man walks over. I saw him the moment he started moving.  He asks if I’m from Brooklyn. 

“No,” I reply.  

He tells me I’m sitting at the Blood table. I get up to leave. 

“No, no, O.G. You can sit here.”  

I thank him. But I get up and move on.

I walk across the yard to the TVs. Michigan is crushing Purdue. I ask if they’re watching a game.  

“Who are you?” an older West Indian guy asks.

I give him my handle.  

“You can’t be here.” It’s the West Indian area.  

I move on. I’m a loner by nature. I need to learn names, the players, and the no-fly zones. Looking at the young men here, I’m saddened. I don’t understand their way of thinking, turning gangsterism into a virtue. During my bid, I’ve always felt safe and secure. Life moves a little too fast for me now that I’m older. I feel like a relic.

When I tell people how much time I’ve done, they wince, shake their heads, and frown in disgust.  

That’s too much time, they all say.  

I see the unasked question in their eyes: How do you do it?  

I’ve always followed the advice an old-timer gave me 42 years ago. Just keep waking up.

James Sheffield is a prison writer serving time at Sing Sing Correctional Facility in Ossining, New York.

ICYMI—From The Appeal

Federal prosecutors have charged at least three separate people around the U.S. with allegedly damaging Tesla property.

In January, prison staff abruptly stopped giving hormone therapy to Alishea Sophia Kingdom, a transgender woman. She became hopeless and suicidal.

Earlier this year, the U.S. Supreme Court said Brenda Andrew, who was convicted of killing her husband in 2004, should possibly get a new trial after prosecutors sex-shamed her.