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Meet Leo: The College’s first incarcerated professor

Everyone in Carcerality and Abolition, a course in the Anthropology Department, first met one of their professors through a screen. Leo Hylton, who co-teaches the class with professor Catherine Besteman, is incarcerated in Maine State Prison and Zooms into every class.

Hylton proves that the model can be successful. Just because he is on Zoom does not mean that he is any less involved or tuned into the class.

Rachel Hatheway `24 explains how the pandemic introduced Zoom to the classroom, so Hylton’s method of participation has been normalized.

“Obviously with the pandemic, lots of aspects of my academic experience have been virtual and I’ve been in classroom spaces that have been entirely on Zoom. Because of all of that, having Leo on Zoom isn’t necessarily new,” she said.

She explained that, even though he is on Zoom, he is as present as any other member of the class.

“The way he is able to participate in class as well as guide discussions, lead centering activities, and connect with us while he is physically apart from us is really amazing,” she said.

Hylton makes sure that his spatial distance does not stop him from connecting with students in the class. He ribs Besteman when she isn’t on screen enough, chats with students during downtime, and even has Zoom office hours every Sunday for two hours. He never hesitates to answer any questions about his life or what it is like to be incarcerated, creating a space of openness and community.

Hatheway points out that community is one of the most important things to him.

“Leo does a great job of setting the tone of community at the core of all of our learning, and he encourages all voices to be heard because he genuinely wants to hear our thoughts and opinions. This also allows for almost a deeper level of learning because you are fully committed to being present and engaged in class because you know that you as an individual are important in everyone’s learning,” she said.

When Hylton sat down with The Colby Echo, he explained that his teaching journey began when he was getting his bachelor’s.

“I served as a program facilitator for a number of years when I was getting my bachelor’s degree. A program facilitator is a teacher without a name. Within the system, an incarcerated person cannot be in a position to have power over the trajectory of another person’s life. So, a teacher can grade, and an incarcerated person cannot be a teacher and be able to grade another incarcerated person,” he said.  

While getting his bachelor’s and serving as a program facilitator, Hylton was also getting involved in activism. He originally served on the board of the National Association for the Advancement of Colored People (NAACP) as the executive secretary with the plan of becoming president after two years. After a year, he realized that the NAACP conflicted with what he learned as a restorative justice advocate.

“I started realizing that the adversarial approach wasn’t going to work. It hasn’t worked, and it’s not going to work. I was also growing as a restorative justice practitioner, and living through this restorative lens while working with an inherently adversarial organization. It was creating conflict within myself,” he said.

He had learned about restorative justice during his earlier studies.

“During my undergraduate years, I took a 300-level restorative justice course and that was coinciding with the same time that the prison was contracting with the Restorative Institute of Maine to explore how to introduce and initiate restorative practices within carceral spaces. My name kept coming up during listening circles as someone who the executive director needed to get in contact with, and so when the listening circle ended, she reached out to me, I joined, and next thing you know, we were doing a restorative practice steering committee. Still holding strong six years later,” he said.

While this was happening, Hylton was still focused on his education. He was working on his master’s degree when he started getting speaking engagements about his work. He knew an alum who connected him to Besteman while she was working on the Freedom and Captivity project. 

Through this connection, Hylton was able to do an Oak Institute talk about the reform of criminal justice on Oct. 27, 2021. 

Besteman, who was already in the beginnings of planning Carcerality and Abolition, heard this talk and knew she needed Hylton on board.

“I had arranged for Leo to give a lunch talk on campus through the Oak Institute, and after hearing the talk, I realized I wanted to invite him to co-teach a new course I was developing (Carcerality and Abolition). I first asked the Provost if it could even be possible, and when she said yes, I asked Leo if he’d be interested. He said yes, so I wrote to the Commissioner of Corrections to ask if there was any way he could see to make this possible. I had my answer within about 24 hours and it was a go! We were all pretty surprised that it was so easy since it was contrary to all sorts of policies,” she said. 

Hylton explained why it was so important that he was teaching at a college, and at the College.

“Being able to teach in the same country where I got arrested is an avenue of meaning and purpose for me. This is something I can directly contribute to cultivating healing in the same community where I caused so much harm. I didn’t realize how powerful that was going to be. Being able to hold space in the way that Catherine and I do, with this co-creation of space and the development of this community is just a really heartening, really fulfilling process,” he said.

The goal of Carcerality and Abolition is not to make every student an abolitionist but to explain the prison system in greater detail than many people know.

“Before working with Leo, I really had no idea how systems of incarceration worked. I had this image of bad guys going to prison, but the narrative that existed in my head had no nuance nor complexity and was not really informed by actual facts. Now I have a deeper understanding of the injustices of carceral systems, and imprisonment specifically,” Hatheway said.

Along with explaining how the current system works, the class talks about alternative systems, such as restorative justice. 

Hylton explains that restorative justice is “an avenue of meaningful accountability balanced with healing through repair, and through a reparative process. And repair for all parties involved. It’s an avenue for each person to be able to be heard and be able to gain an understanding of the impact of any interpersonal harm that occurred with the north star of accountability, repair, and healing.”

This system contrasts with the prison system that the United States uses.

“The current system is based on retribution and adversity. It perpetuates cycles of harm instead of interrupting them, whereas restorative justice interrupts harm. If we actually want to have safe communities, if we actually want to interrupt the levels of harm and the cycles that continue to persist, if we want to interrupt them then that’s where restorative justice comes in. When it stands on its own, then it is inherently transformative and can serve to cultivate community capacity and hold people accountable without ripping them out and punishing them. There is a massive difference between punishment and accountability. Punishment is a passive process where all you have to do is endure the system. Accountability is an active process where you actually need to participate in repairing the harm that you’ve caused,” he said.

Besteman explained what it was like working with Hylton these past two years.

“Working with him is wonderful. He brings a humanistic restorative approach into the classroom, rooted in vulnerability, honesty, openness, and exploration. He treats the classroom as a community-building space and not simply a place to develop and impart knowledge, which brings a very different vibe. We found that we worked really well together – I am more inclined to lean hard into the text and textual analysis, and he is more inclined to want to talk about why the text is relevant and how. It produces a nice balance,” she said.

This balance of Besteman and Hylton’s approaches has allowed the class to become tight-knit and engaged, learning about the topics at hand while connecting with each other on a personal level.

Hatheway spoke about how the class and working with Hylton have changed her view.

“Having someone who is so wonderful and kind, who also happens to be incarcerated, and teaching your class puts a face to this imagined image of an incarcerated person, giving humanity back to how you imagine people who are incarcerated,” she said.

Along with being a professor at the College, Hylton is in the process of getting his Doctor of Philosophy degree (Ph.D.) and continues to fight to reform the justice system. 


~ Mairead Levitt `25

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