Just Up the River

“Bring only your identification and your car keys,” the email said.

I couldn’t help but marvel at the contrast between the beautiful Westchester estates I’d passed on the way and the gorgeous views across the Hudson River on one hand, and the turreted guard towers and the expansive, hundred-year-old buildings that make up Sing Sing on the other. Copious amounts of barbed wire are meant to intimidate — and they do.

A friend had invited me to go with her on a tour with The Frederick Douglass Project for Justice, which brings small groups of “outsiders” to spend the afternoon with some of the most engaged incarcerated individuals (“IIs”). Our group was led by Marc Howard, the Project’s founder, and by Jon-Adrian (“JJ”) Velazquez, who was kind of the star.

JJ, with his tailored suit and Air Jordans, had a huge smile and was hugging several people warmly as we waited to get in. He was incarcerated for 23 years, most of them at Sing Sing, for a crime he did not commit. He got out in 2021 when he was granted clemency and was later exonerated. JJ explained that we would see the Honors Block, where he spent the last 8 years. While he was in, he co-created a program called “Voices from Within”, which helps IIs develop self-awareness and connects them with young people in the community. He goes back every Tuesday to work with the men who are still inside.

First, we met with the warden, a middle-aged woman with a kind face, who led the tour. Each small section of the hallway or staircase was surrounded by floor-to-ceiling black iron bars. We’d crowd into one section and wait for them to lock the gate behind us, and then to open the gate in front of us. The building was dingy, dark, and dank. Yet, as we got to the Honors Block, our first stop, I saw a man doing yoga with perfect form next to the stairwell. The ceiling was two stories high, with unlocked cells on each floor. I was amazed to see that one II had a keyboard inside his cell. A few men wearing dark green khaki pants and regular tops were playing chess and talking with each other. They showed us their kitchen where they cooked for themselves. JJ showed us his old room. He told us that when he was there, the wait to get to the honors block was about 3 years long – now it is nearly 6 years. You could understand why – it was prison, to be sure, but there was a sense of community. One disciplinary infraction and an II would be kicked back with the regular population.

Then we walked through A Block, a stark contrast. There, in one huge, long corridor, 88 cells wide and 4 or 5 stories high, were 640 men, each in his own tiny cell. The din was loud. As we passed through, I noticed that each cell had just enough space to hold a toilet, sink, a cot-sized bed, and a desk – about 4 feet by 8 feet. Some had medical supplies stacked up, and some had food. Some put towels or blankets over the front, but there was basically no privacy. All of the men in this section were wearing green sweatshirts atop their green pants. I thought of horse stables. I didn’t understand how anyone got any rest.

“How many hours a day do they spend in their cells?” I asked. It depended on which programs they were in. A guard would let them out for meals, or for meetings, or for school. If they went out to the yard, they had to stay for 2 hours. They each had to be in their cells 3 times a day for “the count.”

We finally got to the school area, which looked more familiar. The classrooms were separated by glass walls and held desks, blackboards, books, and notebooks. They were brightly lit.

About 15 IIs from Voices From Within were waiting for us. There were about 15 of us “outsiders,” too. We shook hands, then did an ice breaker in the large group and broke into groups of 6, each with 3 insiders and 3 outsiders.

“What made you interested in coming here?” Jamal[*] asked as we started our small group discussion. We shared different reasons. And we asked them, “What do you do all day? What programs are you in?” Angel was getting an Associate’s Degree from Mercy College. Malik was getting a Master’s from Union Theological Seminary. There were GED classes and Spanish lessons, and theater classes. The atmosphere there was loving and hopeful and very warm. “Can you stay in touch with your families?” we asked. “Yes,” they told us. “Now we all have free phone calls. They give us each a tablet and free wifi.”

“But,” they told us. “Everything shut down last year during the strike.” The corrections officers went on strike to protest unsafe working conditions in February 2025, which resulted in over 2,000 resigning or getting fired. That’s when they brought in the National Guard to fill in. And they shut down everything – all of the programs and the schools. They stopped these visits. It still isn’t back to normal.” “What did you do all day?” I asked. They looked at me with blank stares.

“How do you keep your humanity in a place that is designed to strip it?” I asked. “How can you guys be so relaxed and so warm?” “If I don’t keep my spirit, if I don’t keep remembering who I am, I have nothing,” Jamal said. “I’ve seen really tough men break down and call for their mamas,” Angel said, “The key here is being resilient. I’ve changed a lot since being part of Voices from Within. When I was growing up, my only role models were gang leaders. I didn’t know any different. I have new role models now.”

We asked if they had jobs. Yes, they said. Working in the kitchen or counseling others. How much did they get paid? 16 cents an hour. 16 cents!!!!

After too short a while, it was time for the wrap-up circle. I noticed now that some of the IIs had on regular shirts and some wore green sweatshirts – meaning some lived in the Honors Section and some were on the regular Block.

“I didn’t think anyone would care besides my family,” Angel said to the large group. “I won’t forget this day. It’s amazing to know that there are people on the outside who care about us.” Behind him, outside the glass wall, I saw 3 National Guard men joking with each other as they walked through.

And then it was over. We hugged goodbye and exited. In the van going back to the entrance, I asked JJ if the IIs were going back to their cells now. “Yes,” he said. “They’re probably back there already.”

It was a day I won’t forget, either. If you would like to do a prison visit, go to https://www.douglassproject.org/.