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Rethinking Criminal Justice (Part 1): An Interview with Skye Williamson

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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: You started Transforming Lives while still behind bars. Can you tell me a little about how the organization began?

Skye Williamson: Transforming Lives is a nonprofit organization that I co-founded with a friend, Alex Duran, who was also incarcerated, and Cynthia King, who volunteered for an education program from Bard College. That program also had Brown students in it too, just for the record! [laughter] 

Alex, who was one of our co-founders, had gotten into some conflicts. He was an ex-gang member and had prominence in his gang, but decided to just step away from it––what they call “dropping the flag”––and focus on himself and his family. He had a son. He wanted to get an education and get his life together. And given his politics inside the prison, some unfortunate events happened. 

Cynthia was someone who just volunteered from the community and wanted to help people who are incarcerated succeed in education. So one day, she found out that Alex was in solitary and it was just a very unjust situation. And so she was like, “Well, how can we help?” 

It was her effort that helped pull him out of solitary confinement for what was going to be upward of three to five years. She wasn’t supposed to get involved like that, but she made a choice to break the contract that she signed by choosing to care enough about Alex to intervene. From there, Cynthia was like, “I’m not the only person out here who cares and wants to make a difference outside the restraints of the institution, right?” And so, we just said, “Let’s start this organization.” 

We started a program called Transforming Lives, which connects people from the public who care, like Cynthia and others, who want to support incarcerated artists or writers. We’re not there to hang out with people just because they’re incarcerated. Transforming Lives is about saying, “Let’s take one of the best things in your life and let’s help you hone that.” We take the approach of what Brian Stevenson calls “getting proximate.” I’m the biggest fan of that approach. It made a lot of difference in my life. 

ST: After starting Transforming Lives, you began working with Galaxy Gives. What led you to work in the philanthropic space?

SW: Galaxy Gives is a family foundation started by Michael and Suki Novogratz. They have a Bitcoin investment bank, Galaxy Digital, and a family foundation, Galaxy Gives. We create impact. The giving is focused on mental health, democracy, criminal justice reform, and we’re currently working on mental health and wellness. We engage in a giving process that goes beyond grant giving. We do a lot of work through our fellowship program. Galaxy’s Philanthropy Fellowship is focused on directly-impacted people, specifically those who otherwise would not have the structure or the experience to win a lot of the grants that are heavily competitive. 

For me, it’s really important to recognize that part of the issue that we’re trying to resolve with criminal justice reform is the legacy of enslaving people in this country, promising they will be released, but not really doing so and instead allowing legal and other structural impediments to be imposed upon them that aren’t as apparent as chains on their bodies. Then it is normalized to blame the African American community for not coming into economic stability, for not having education, for not having good health outcomes. These are consequences of systemic choices, but are projected back on us as if they’re personal subjective choices––like if we just get focused, we can overcome them. And that is just false. It is an illusion. 

Galaxy recognizes that until we give ourselves and our people an opportunity, they’ll never develop those skills. They’ll never develop the skills to be the best nonprofit organization leader if they’re never given the opportunity. The idea is to support organizations that are working to create change in their own communities, but haven’t had mentorship or leadership training, and who don’t know how to really manage groups, but have nonetheless done the work with just their passion. They’ve assembled themselves with what they’ve had. They deserve resources, and those resources shouldn’t be contingent on how well they present themselves. Instead, we’re going to look at the work that they’re doing and the impact it has had.

We know that when we just throw money at the African American community it doesn’t circulate in our community. It goes back out into the infrastructure that has excluded us. And so you don’t just throw money at this generational problem. You have to invest money into it but also then bring leadership and mentorship development skills. So, we bring the mentors to our fellows, we bring them into trainings, we expose them to a network of people who do have resources. A lot of people are successful, not because they’ve pulled themselves up by their bootstraps, but because they’re part of networks with people who are successful and offer them opportunities. A lot of what we see as success is often being in the right room with the right people. So we create a space where people can intermingle, and have their work known by others who are making decisions and have the abilities to provide support. 

And also we’re looking at building power for communities not just through agency, but self-determination. We’re really looking to give grants to people who are clustered, inclined to collaborate with each other, and doing work that actually has longevity to it. I feel that Galaxy’s giving is innovative and unique. Transforming Lives is about addressing the public perception about the lives of incarcerated people by bringing people together. Galaxy understands that once those people are recognized and well-positioned, they still need support to develop and cultivate their skillset to create change at an organizational level in their communities. 

ST: While incarcerated, you were able to get a degree through Bard. How common is that?

SW: People think education doesn’t belong behind the wall and low enrollment numbers reflect that mentality. I was among the fortunate 3 to 5 percent of incarcerated people who get entry to college programs. That is a small percentage, but even still, there is pushback. One prison that I was in was the flagship for Bard’s program and had nearly 10 percent of people enrolled. There was pushback. Even 10 percent of the population being in a program for education, for improving themselves, made people frustrated, angry. Like, “What do you think this is? You guys are forgetting that you’re prisoners.” Actually, we’re not forgetting because we’re not living lives like free people––we’re just pursuing education. 

ST: The mentality you’re describing, the belief that incarcerated people don’t deserve opportunities, seems pretty pervasive in the system still. Can you talk about the work REFORM Alliance does to change this culture?

SW: While I was incarcerated I got an education, a very slim statistical thing to be able to achieve. I got my BA in Mathematics. I worked around some machine learning, some natural language processing algorithms, and network systems. I just really enjoyed and appreciated that. AI is a thing that I love. Blockchain is a thing that makes a lot of sense to me. And I already cared about criminal justice reform. It’s my issue. It’s been the defining aspect of my life. And information science, data analysis, and technology are all things that I feel like we need to be leveraging for criminal justice reform. 

REFORM Alliance is at the front line, working on a very specific issue: parole and probation reform. We want to keep people from going back in. REFORM is doing this work at a bipartisan level. We’re even bringing in the other side who built the prison industrial complex, and working with them to try to change the system. There are decriers in our space, just to be candid and frank. But the truth is that those who decry working with the other side happen to be the extreme. And those who feel the same on the other side, they’re also the extreme. Most Americans are in the middle. I’m delighted to be working with an organization that’s working towards the middle and not polarizing itself when we’re trying to solve an American dilemma, a problem that’s affecting all of our quality of lives. 

There’s legitimacy coming from both sides of the conversation. However, the reality is that you’re not going to be able to work with the other side every time. In my experience here at REFORM, working under Robert Rooks, bipartisanship isn’t a goal. The goal is the right solution, but we’re willing to find the right solution through bipartisan efforts. We’ll also make a unilateral decision when we have to make it because we do our own metrics internally. We have a research implementation department. So we follow the data, follow the information. And if the information tells us that something is gonna help more people, again, we’re looking at the solution. We’re driven by the solution, not by the political posturing and representation of what it looks like to work with both sides. 

We have an amazing board made up of individuals who are committed to that as well. It’s a joy to see the face of our organization be a bipartisan face––people who you would not expect to be in the room together. And we have people like myself. I don’t have a token position, which is really critical. I’m not just a directly impacted person who’s been brought in because it’s the right thing to do. That’s not why I’m here. REFORM understands that if someone’s not giving you an opportunity, you won’t build the capacity for opportunity acquisition. And so REFORM is more than willing to give you that opportunity, but once you’re there, you stay based on your work, because that’s how it is in the world. 

Some people stay because it’s their space. But whether you stay or not is not a statement about you. Some people come and say, “I had a great experience, but I’m actually committed to doing something else.” It still matters that they were here. 

I’m here in the office as a project manager, and I’m working on our CourtWatch app, which has me psyched out. I can’t sleep. I wake up at five in the morning anyway to do my exercise. But sometimes I’m in flux between whether I’m gonna actually work out or just continue researching on solving this thing that I’m working on. 

As an organization, we’re driven by policy change. We build relationships up on Capitol Hill, work across the aisle, and Jessica [Jackson] gets it done. Policy change is the lifeblood of this organization. Change at the government level makes an impact that no individual organization could. To go back to Mike Novogratz, even with all of his capital he can never create the change that the government can do with just the pen. 

ST: How do programs like the job fairs and the court watch app fit into REFORM’s policy change goals?

SW: The job fairs we have been running represent an understanding that policy change is dependent upon the relationship that we have with the communities we are operating in. Most policy battles are protracted and require three to five years of building relationships with people. But we care about what’s happening to people while they’re waiting for policy to be implemented. I’m really excited to be here at REFORM and working on those things. 

When we talk about incarceration, we often talk about the people who are actually physically incarcerated, which was around 2.3 million people at some point. But what we don’t often talk about are the people who aren’t incarcerated, but are still bound up with the system. It’s like if we talked about slavery but not about Jim Crow and all the other ways we have been restrained even after being taken out of shackles.

There are around seven million people who are impacted by the larger criminal justice system, which includes post-release supervision. People on post-release supervision are being constantly punished, even once they’re outside of a cage, for what they’ve done in the past even though their punishment was just supposed to be their separation from society. So we’re really fighting the good fight here by making sure that people actually can move on. And it’s personal to me. I wanna move on. I did 26 years, damn it. I wanna move on. 

So, I started with Transforming Lives while I was still in prison, and then at Galaxy, I had this exposure to strategic giving and learned how to create impact. Now I’m at REFORM doing the quintessential things, policy and law. But I’m also realizing we gotta support that policy and law with some teeth, with some monitoring. And now I’m in a sweet spot because that’s what I love: machine learning, AI, and algorithms. 

For most of the criminal justice reform movement, the success has been policy or law about a very specific thing, right? But the Achilles heel of getting a law passed is that even after a five-year protracted fight it becomes an issue of implementation and enforcement. To do effective court-watching, you have to wake up in the morning, go to a courtroom, hang out until the case gets called, collect the information, take it, package it, deliver it, and go home. That’s your whole day. The only people who are doing that are the people who fought for the legislation in the first place because the quality of their life is on the line.

We live in a digital age, the information age. How can we make use of that? We want to keep bringing more people into court-watching locally, but also open court-watching up as a national thing. We want to let the efforts of those in Arkansas be of benefit to those in California. How can we build that bridge? How can we convene and bring court-watching to another generation? Next-generation court-watching, what does that look like? It looks like something with a digital interface. And so that’s what this project is about. 

The CourtWatch app has the ability to say, “you don’t have to fight alone” when it comes to overseeing the implementation and enforcement of legislation. We want to turn court-watching from a 12-hour to a 4-hour thing. By lessening the time it takes to court-watch we are bringing in a whole new demographic of people who say, “Hey, I don’t have 12 hours because I have a job, a life, a family, but I can give you a few hours on that app to make a difference.” We’re getting the government to be accountable in the ways that we can, and we’re hoping that this app adds value to the field. 

ST: I want to thank you for giving that great explanation of your work. What you said about REFORM hit the nail on the head for me. Like that’s what brought me here: We care about results. We don’t care about posturing or who we work with; we just want to get stuff done. And that’s part of the reason I think I was drawn to REFORM over other places because we certainly dream big, but we’re still focused on concrete actions that we can take now. As I think of the dreamers in the criminal justice space, so to speak, one of the topics I was curious about your thoughts on is the movement to abolish prisons. What are your thoughts on those efforts?

SW: Let me start by asking this: What’s the criminal justice budget? What’s the law enforcement budget? What’s the military budget? What’s Housing and Urban Development’s budget? What a nation invests in an institution is an indicator of that institution’s capacity to persist. The criminal justice reform budget is one of the biggest budgets—it’s larger than education, food assistance, and housing budgets. I definitely would love a conversation about abolition. But abolitionists must understand that they’re trying to abolish the thing that we’ve invested in the most. 

That doesn’t mean we shouldn’t aspire to it. There has to be a space where we hold the ultimate vision for where we’re trying to go and I think abolition is that place. Small reforms to the system aren’t really what we wanna be doing. We’d much rather be straight cutting the thing off and replacing it with something else.

Decarceration means that we’re just going to pull people out every time we get a chance. But we would much rather open the damn door. Abolition is the manifestation of the larger consciousness in this movement that has to exist. There has to be a conversation about abolition because it’s where we’re trying to go. 

I also have to speak more broadly about revolutions. Frantz Fanon, who was writing about the Algerian Revolution against the French, wrote an essay called “The Pitfalls of National Consciousness” in which he argued that people were working to supplant something because the conditions compelled them to do so, but they failed to envision what would replace the thing that they wanted to oust. The Algerian people occupied the government that was already in existence. But that system was conducive to colonialism, to oppression, to the extraction of resources from the Algerian people. You can’t go occupy that. You have to redesign that. You have to re-envision that. And so, for me, the abolition movement, the abolition discourse is about re-envisioning a system.

People ask the question, “If we get rid of prisons where would all the bad guys go?” I think that’s a really myopic way to think about something that’s a really large problem. ” Instead, we should be asking where do bad guys come from? How do bad guys get to be bad guys? We have 5 percent of the world’s population and 25 percent of the world’s incarcerated population. Why is that?

*This interview has been edited for length and clarity