My Trip to Sing Sing Correctional Facility

Sing Sing Correctional Facility Sing Sing Correctional Facility, housing close to 2,000 inmates, is located in Ossining, New York. || Source: Brett Weinstein

“The only thing that changes here is the number of the date. Everything else stays the same.” I’m sitting among a circle of chairs in an auditorium at Sing Sing Correctional Facility, listening to an inmate, who was convicted of second degree murder, describe to my Criminal Law classmates and I about what it’s like to spend years incarcerated in prison. How once you spend enough time in prison, eventually all you become to many of your family and friends is just a memory, and you’re all but forgotten. As he continues describing to us how the days blur together as the years pass, I can feel a weight press down on my chest. I look around the room and toward the windows, trying to imagine what it would be like to be trapped in this very same place, going through the motions of life. Every. Single. Day. For ten, twenty, more than fifty years…for life. I direct my attention back to the inmate telling his story, and think about how glad I am to have signed up to take this class, and how lucky I am to have had the opportunity to go on this field trip…


The morning of Thursday, March 9 started out just like any other morning of the year. The birds were chirping, the sun was shining, and the irony was not lost on me—I was spending the day with my Criminal Law class at Sing Sing—a maximum security prison in Ossining, New York. This visit to Sing Sing was made possible through the Youth Awareness Program (YAP), which is meant to make students conscious of the lives and backgrounds of the inmates who inhabit our nation’s prisons, as well as the nature of the American criminal justice system itself. The YAP is not meant to intimidate students, rather, it is meant to inform them of the realities of life in prison, and that all actions have consequences.

After I sat down on the school bus that was taking my class and I to Sing Sing, I really did not know what to expect for the day. As soon we arrived, I was greeted by the intimidating and ominous facade of the prison against the clear blue sky. The location overlooked beautiful views of the Hudson River, however marred by the chainlink fences and barbed wire that enveloped the prison. As we entered, the first thing I noticed was a framed photograph of Governor Andrew Cuomo under a sign that attested to the commitment to professionalism and honor of all of those who work within the correctional facility. However, after hearing in the news over the years about the nefarious activities of those who the inmates refer to as “dirty officers”, I started to wonder how much weight such a pledge truly holds.


After having our identifications checked, we were led to an auditorium where chairs were set up in a circle on the stage, and inmates participating in the YAP sat at intervals in between the students. When I was assigned my seat and realized I would be sitting next to one of the inmates, I felt my palms start to sweat and my heartbeat accelerate. They were seating us next to convicted murderers? I couldn’t believe it. However, as the inmates arrived and began to tell their stories, both my nerves and my preconceived notions of criminals—that they all were just simply remorseless, evil, uncivilized human beings—began to fade. The inmates described their realities of selling drugs and guns during their childhood (one commented that he started when he was twelve years old), joining gangs, robbing stores, and using violence as a means to an end. However, some of the inmates also spoke about the abuse they encountered from various family members at home as children, the struggles that some of their single parents endured in trying to provide for them, and the toxic criminal influences that they were surrounded by in the impoverished areas of New York City that they grew up in. They also described the constant peer pressure that they faced from others in their neighborhoods. The inmates then emphasized to us that we be extremely careful with who we associate ourselves with, and to make sure to surround ourselves with people in our lives who will respect us. I started to realize that in the criminal justice system, as in all facets of life, nothing is black and white. Each and every prisoner participating in the YAP had a story to tell, and despite the atrocious crimes they committed, they were all human beings, hoping for their voices to be heard.

Question and Answer

After the inmates finished telling their stories, they allowed us to ask questions, and said that no question was off limits. I raised my hand, and asked if based off of their experiences at Sing Sing, whether they thought the purpose of the prison system was to rehabilitate or to punish. I had been intrigued by this idea since the topic was broached in the first week of my Criminal Law class at school, and was curious to hear a response from a convicted criminal’s point of view. In his answer, one of the inmates told me that he thought the system’s purpose was to punish. He said many of the corrections officers don’t care about the prisoners, and with insufficient resources to help those with mental conditions and aggressive tendencies, their conditions only worsen. As the inmates were asked about their daily life in prison, it quickly became clear how virtually no privacy exists in their lives.

Other questions ranged from the characteristics of their trials to the years of their sentencings, and I was shocked to learn that one of the inmates had been in Sing Sing for 35 years—he described to us how his son was two years old when he was incarcerated, and that now his son is 37 and he has a two year old grandson. He also explained to us that once he is released from prison, he hopes to be there for his grandson in ways that he never was for his son. One of my classmates then asked what the rest of prisoners’ plans were once they were released from Sing Sing. At first the question was met with silence, but then one by one each inmate gave their response, each one more inspiring than the next.  One inmate described the pattern of criminal activity that exists in his family, and his hopes to work with his loved ones to change that upon his release. This sparked a conversation about the difficulties many ex-convicts have in acquiring jobs once they are released from prison, due to the prejudices held by many employers. Another explained how this June he would be completing his bachelor’s degree in behavioral sciences, and how once he is released he hopes to earn a master’s degree in social work so that he can help others. This response particularly inspired me; I am a firm believer that education is the key to success in the world, and thought it admirable that one of the inmates understood this and was working to change his life for the better.


After questions were answered, the corrections officer that was with our class took us on a tour of Sing Sing, along with the inmates. We passed the door behind which prisoners are kept in solitary confinement for 23 hours a day, and learned that some can stay in there from weeks to months on end. Remembering my question about rehabilitation in the prison system, one of the inmates shared with me his thoughts on how the aforesaid room’s purpose was to punish, because those he has known who have been in solitary confinement leave with mental conditions far worse than what they had when they entered. The same inmate explained to me how he felt he was lucky to be at Sing Sing, as opposed to Attica upstate and Rikers near New York City. When I asked him about Rikers, he said how the only two types of people in the island prison are wolves and sheep, and that each day there an inmate runs the risk of physical harm. This metaphor really shocked me, and made me wonder what role criminal justice reform (or a lack thereof) plays in the prison system.

We eventually made it to the cell block at Sing Sing, which is one of the largest in the world, and I was greeted by the loud noises of the corrections officers yelling unintelligible things at the inmates. I vividly remember stretching my neck to look up and see what seemed like never-ending rows of cells. I’m not usually one to feel claustrophobic, but at that moment I felt the walls pressing in on me, and could not begin to fathom how someone could live in a place like this every day of their life. Four of us at a time were then locked in a cell that was converted to hold phones, and feelings of claustrophobia again began to set in. It seemed unimaginable to me how a bed could fit in the cell, and how a person could manage to sleep there every night. I thought back to one of the inmates in the YAP saying how he never gets much sleep, because an officer is always walking by the cells flashing light into each one throughout the night. I begin to truly understand how little privacy people have in prison, and to me, the reality of the American prison system seems to be that the inmates’ civil liberties all but disappear.

Walking through the halls of the prison, the temperature seemed to drop and one of the inmates explained how freezing it is at night in the winters, and how swelteringly hot it is come summertime, especially since he is in the top row of cells in his cell block. The state provides one blanket, which the inmate explained is never enough, so it is up to those convicted to purchase any extra blankets they might want. However, many of the inmates come from poverty and have no money, which makes it impossible for them to do so. Next we were brought to the shower room, where the corrections officer described to us how fights break out daily, and that inmates usually form a buddy system in order to avoid being stabbed.

Lunchtime arrived and we made our way to the mess hall, where soup, salad, and frozen pizza were being served. The inmates in the YAP sat among us, and the one at my table spoke to us about our goals in life and what we wanted to pursue as careers. Many of my classmates around me didn’t know what they wanted to do once they graduated from college, and the inmate replied that we should “seize the day”. He advocated for us to use our time in college to figure out what we want to do with our lives, and to have a purpose, so that we can take advantage of all that life has to offer and not waste our time. His mantra was “no hope, no vision”, meaning that without any vision for what we wanted to do in our lives, there would be no hope for us to thrive and succeed.

Reconvening for Reflection

Toward the end of the afternoon, we reconvened in the auditorium to reflect upon the events of the day. The inmates in the YAP wanted to impress upon us the idea that although at some point we may do something in our lives that may not seem so bad, like lying, the little things that we do can worsen and lead to the committing of much worse things in the future. My Criminal Law teacher explained to my class that although we may have had a different, more privileged upbringing than many of the inmates at Sing Sing, these crimes can be committed by any of us, and that we could easily be in the inmates’ positions. Regardless of race, gender, and social class, we are all human beings, and actions will always have consequences. As the program came to a close and my classmates and I exited Sing Sing, we made our way toward the bus in the parking lot that would take us back to school. Looking back at the prison, a stark contrast to the beautiful weather outside, I was humbled. I realized that although these inmates are locked away, their voices are not, and their stories will last with me for the rest of my life.