Skip Navigation

Rethinking Criminal Justice (Part 2): An Interview with Skye Williamson

Image via Skye Williamson

Clifton “Skye” Williamson is a co-founder of Transforming Lives. Williamson has expressed his skill and passion for the arts by developing and directing educational, theater, and trauma-related rehabilitation programs for incarcerated individuals. Previously an associate at the Novogratz Family’s philanthropic foundation, Galaxy Gives, Williamson is now a project manager at the REFORM Alliance, a parole and probation reform advocacy organization. While incarcerated, he earned a BA in Mathematics from Bard College. His undergraduate studies focused on artificial intelligence (AI), algorithms, and machine learning. Williamson’s lived experience and ongoing research form the cornerstone of his passion to identify the most effective ways to leverage information technology and AI to support the criminal legal system reform movement.

Sam Trachtenberg: I’m curious about your experience with the New York prison system, and how, if at all, that system addresses the immense trauma that many incarcerated folks bring in with them?

Skye Williamson: I’m disinclined to talk about it through the lens of how the system addresses the problem. I’m also not inclined to talk about how the system is failing either. I can go into that, and I’m happy to do so, but I would rather talk about the culture of the institution and what it is fostering. Because if you understand that, then you can have a better sense of what the system is capable of producing. We can see the things that it’s failing to do and the harms that it’s causing. 

So I’ll go a little anecdotal here: I consider myself an advocate only because when you go into institutions, you see what they make available. Within the confines of the carceral system, at any given time you’re in one of three spaces: a yard, the recreational space (which includes the school and the library), and the visit room. There’s a place that’s reserved for the library, which you have limited access to. There’s a place reserved for school which you also have limited access to. 

I’m a data guy—I want to sort out the percentage of where you spend most of your time. You spend about 80 percent of the time in a cell; 15, maybe 18 percent of the time in the yard; and about 2 to 5 percent of your time in the visitation area. The visit room is your connection to your family, your community. 5 percent of your time there would be a lot. That would mean you got love, you got a lot of family, and you probably also got a lawyer who’s going to see you regularly. It would also probably mean you don’t have a lot of time inside the prison because the more time you have in prison, the less people come to see you. People die on you, your case is resolved, there are no more lawyer visits, and your relationships have been strained to the point that they don’t exist anymore. 

For the most part, you are in a cage and your effort is to get out of the cage just to get to the yard. So the question I’m asking is: What’s being fostered within that cage? How much time in your day do you have access to the places where you can be exposed to rehabilitative engagement, practice learning? Per day, you got about two hours of that. So most of the time that you’re in prison, you’re not actually invested in rehabilitation, institutionally. 

ST: What you’re describing sounds like a pretty solitary experience. What are the interactions with others like?

What I want to bring focus into is the culture that persists behind that wall. It affects us as incarcerated people and those who are corrections officers, medical staff, educational staff, and professionals like maintenance staff, industry workers, vocational teachers. 

It’s not the case that officers see themselves as role models. Quite frankly, officers see themselves as agents of control and management. So, when it comes to using your tongue to explain a situation, they say, “shut up,” “don’t talk,” “just listen.” Instead of telling you to shut up, officers could say, “I do want you to talk. Talk to me, tell me what you thought you were going to achieve in this controlled environment where there are clear rules that you stepped over. Let’s delineate those rules you stepped over, and let’s talk about the types of punishment or treatment or compensation for what you’ve done that makes sense to you. And then we’ll let you know how it makes sense to us, as an institution running this place and working on your rehabilitation.” That’s a conversation that just doesn’t happen. The culture of the institution is “shut up.” 

The people engaging in violence behind the prison walls are often committed gang members. They are often committed to drug use. They are often individuals who simply do not want to be controlled because they do not know how to cope with incarceration. But everybody gets treated the same way inside––the variation in human behavior isn’t really acknowledged, and that is a part of the culture. Prison officers don’t acknowledge that you are more reasonable than the violent gang member. They don’t acknowledge that you are someone who wants to be accountable. 

ST: Not acknowledging you as an individual at all, really.

SW: No, not at all. 

ST: What about the rest of the folks who work in prison?

SW: The medical staff, the educational staff, the maintenance staff, they come in as professionals. Before they came into prison, they worked in a community, or were educators, or went to college to learn how to help people. They think, “This is a group of people that deserves education, deserves healthcare, deserves to have these opportunities to learn skills.”

But then when they get into prison, the prison officers tell them “We control everything. I don’t like how you’re talking to that inmate. You’re talking too nice. Watch how you talk to them.” Some people say, “I’m not a correctional officer. I’m not a part of this culture. I’m here as a professional. I’m gonna give this guy medical treatment. He’s clearly bleeding profusely. He clearly is dealing with some mental health problems. You yelling at him is not helping his situation. He needs some other treatment.” Those people are told, “Stand down. You’re gonna find out that he’s injured in a way that we really don’t want to talk about, and we’re not gonna have this mess because of you. We run our institution the way we run it.” 

I was indoctrinated by this culture to some degree. I’d say, “Dude, you’re a little too nice, man. Just relax. Don’t smile so much. And don’t call me, ‘sir’ when officers come around.” I really was an agent of my own oppression because I wanted to look out for the guys working in the prison. Eventually, if you don’t succumb, the culture is gonna pound you into submission. When a guy is like, “Hey, I got a reasonable explanation,” the response is, “Turn around and put your hands on the wall. I told you to comply so now you’re being pummeled.” 

ST: How are the officers affected by this culture?

SW: The officers who work in prisons leave stressed as hell. They take the job because they need the money or the benefits. The data shows people stay correction officers because of the benefits, not because it’s a gratifying job. Inmates are harassing them every day. The culture kills them. 

ST: Many people would look at you and say, “Look, aren’t you living proof that the criminal justice system is working as it should? That people who try to rehabilitate themselves can do it.”

SW: The fact I’m showing up as I am now has everything to do with Transforming Lives. It has everything to do with the fact that I’ve had the benefit of having people who aren’t in prison care about me. The successes that come out of the system are often successes of families, the ones who have had to pay for phone calls that they can’t afford for years. Because when we lose connection to the world, what else are we living for? Prison isn’t giving you something else to live for. It isn’t going to inspire you to get back to the world. It’s really just holding you hostage. And that’s why a lot of people go from mentally well to mentally ill behind bars. There’s not enough awareness about how mental illness is an outcome of incarceration. Success has to do with family first. 

Beyond families, success comes from exposure to the people who work within the system: teachers and medical staff. Behind closed doors the medical staff is like, “Hey, I know how [the correctional officer] is talking to you is wrong, but I see you. I’m gonna try to give you everything that I can give you.” It’s in that moment, that human healing moment, that you think, “Okay, I can keep myself together because I’m getting the care that I want. I know I can’t expect anything from the system’s actors but in this moment a human being saw me, looked me in the eyes and spoke directly to me, the person, not the object. They saw me as a person, a human being.” And so that’s the next layer: There are people in the system that are operating with intention.

Finally, there are educators. Volunteers are the lifeblood because my family is my family. They’re my folks. The medical staff person is someone who’s here and has a certain professional distance; you’re never gonna get closer. The volunteer educators are coming in from universities. They’re strangers who we would never have gotten to interact with. Those human encounters make us say, “Whoa, wait. I’m not what everybody here is telling me. I deserve more than just the grace of the nurse whispering in my face when she’s trying to help me.” Our volunteers are our continuity to the real world. It’s a blessing to meet the people who come in and go. 

I went five years without meeting a stranger. Think about that. When you walk down the street and meet a stranger, you can have a candid conversation. I’m enjoying myself now. I travel. The joy of my travels is just to talk to someone randomly. My family is like, “Yo, dude, you talk to too many people, man.” But for me, I just got out of a place where there were no randomly-started conversations. You can spark a random conversation in prison, but just largely go back to the very basic things that we all dwell on: fate, conspiracy theories, harm, abuse, things of that nature. So I am me not because of the system, I am me because there have been people all along the way who’ve held out humanity to me.

S1: What are you most proud of in your life?

SW: I have to take a big breath and exhale. For a long time, I was a foster child, so my beginnings are complicated. And the only detail that I’ll air out in this interview is that anyone who has been in foster care knows identity crisis from the beginning. You don’t see people who are like you, walk like you, talk like you. You don’t see yourself evolving into them, which is what you see when you are with your family and your kin––even if it’s not your parents, you see your uncle or a cousin. 

So, it’s been hard to locate identity in this world. In some ways that has been very liberating to me. I do my own thing, and I’m okay with it. I don’t need to fit in. I’m not someone who aspires to fitting in or showing up like other people. But I will say that when it comes to being proud of oneself, this is a question where I recognize that I went to prison at 18, and I’ve spent almost 26 years in prison. I came out on February 1, 2021, so I’m still putting my life back together. What I had for a long time was a constant projected fantasy: My dream aspiration during my time of incarceration was to not to die in prison, to be able to have a child, and to have a life and live it on my own terms. I wanted the ability to find my purpose and to make a contribution. So, what would make me fundamentally proud of myself? I think any of those things would. For most people, they’re pretty basic. But I’m on a delayed track. 

I’m happy that I’m free. I love myself. I see my potential and my mom always says, “You’re alive. You are what you are now and that’s enough.” I struggle with being proud of myself because I’ve been in for a long time waiting for that ability to be activated. After two years and a few months of freedom, I do not feel like I am yet in a place to be settled and to understand that the freedom I have is a basis for being proud of myself in the ultimate way.

I am still living that out. I have reason to celebrate and be happy and hopeful. I am proud that I am someone who people see as valuable, having lived under the conditions where I was valueless no matter what I did. 

*This interview has been edited for length and clarity