Center for New York City Affairs

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Returning to Rikers On a Bridge of Memories


I would imagine every bridge has a story. You know, a tale that gets told over the years and grows with each telling. In New York City, the bridge leading to the infamous Rikers Island jail has a terrifying story that grows with the passing of time among the unlucky souls still going across it.  

My part of that story began 30 years ago – and picks up again now.  

As a young adult, the people who had the most influence on me were considered criminals, and the one thing they talked about with a moth-to- the-flame fascination was Rikers. Rikers had a reputation for being an environment where manhood was tested in the most brutal and violent ways. Men who passed that test were seen as men above men.  

By the time I was 17, I had heard all kinds of horror stories as well as stories of triumph. The stories I heard about the bridge to Rikers told of potholes, a broken-down Department of Corrections bus, and people shackled to each other.  

I remember that when I was being outfitted with chains and handcuffs for my first trip to Rikers, I associated what I was feeling to my ancestors being enslaved. On that bus were human beings who wore despair, pain, sorrow, anger, and dread like a second skin. 

The bus we rode in had about 15 rows split down the middle with four men per row. The men who had visited Rikers before talked, seemingly to distract themselves, while everyone else just listened or pretended to listen. I’ll never forget the advice I got on that bus. “Don’t gamble. Don’t do drugs. Mind your business. Your word is your life.”  

Every horror story I had heard came to the forefront of my memory. I was afraid of the unknown but dared not show any hint of it. When I looked in the face of the other men, I could see most of them were thinking the same thing I was: Shit’s hit the fanI’m going to Rikers Island. The bus felt like a tin can, and every time the driver hit a targeted pothole it sent us reluctant passengers flying.  

As the bus driver pulled up to the building where we would be detained, he announced: “Listen up. This is the world-famous Rikers Island. If there is any bitch in you, Rikers will bring it out.” Then he escorted us off the bus and into the building.  

It took 30 years for me to go back across that bridge. This time I am not shackled, I am not riding in a Corrections bus, and I am not traveling against my will. I work for one of a number of organizations contracted by the Mayor’s Office to help with the current staff shortage crisis on Rikers Island. However, we do not police the detainees in any way. My colleagues and I help process social services requests and provide transitional programs. The commissioner of the New York City Department of Corrections, Vincent Schiraldi, has implemented a program where each detainee gets a tablet to use for education, entertainment, and to request social services.  

When trying to prepare to go back on Rikers, I found myself reliving the sound of the gates closing behind me, the smell, and the noise of jail or prison. What I had forgotten was the bridge.  

I was fine until we got to the last checkpoint before crossing the bridge. Then my palms got sweaty and I had sumo-wrestling butterflies dancing around in my stomach. At one point it was surreal. 

There were people with us who were new to the job; others were veterans. And just like on my first trip to Rikers, the vets were giving last-minute advice. “Don’t promise anything. Don’t go on the unit without second officer to cover you. Don’t argue with staff no matter how much they might trigger you.” All good advice.  

As I had on my first bus to Rikers, I looked at those around me. On their faces I saw the same determination and wonder that I felt going back to Rikers for the first time. The ride over the bridge was a little rocky but smooth for the most part, because our driver was avoiding the potholes. Those potholes were still there.  

Going across the bridge to Rikers Island is always going to be a potential trauma point for me. The first time I ever existed in an atmosphere of pure misery was that first trip across that bridge. And I found out that even the people giving out advice then were simply looking for someone naive enough to believe that all they wanted was to help you get through this horrible time.  

Now, the advice I get comes from a place of actual concern for my safety, and for the people we came to help. Also, I am not alone. I am joined by a team of dedicated professionals whom I trust.  

When my actions first forced me to endure the bridge, I would not have gone if I had a choice. Today, I choose to endure the bridge and all its memories to bring reminders of humanity to a place where man’s cruelty to man is par for the course.  


Cincere Wilson is a program facilitator for a non-profit organization, Exodus Transitional Community Inc., where he is part of a team that goes to Rikers to bring transitional programs to the detainees and to make them aware of the community resources available once released. He was formerly on the staff of the Institute for Transformative Mentoring at the Center for New York City Affairs at The New School.

Photo by: Cincere Wilson