Arts interview

Seeking salvation through sketching: an artistic journey beginning in solitary confinement

Jake Pilsbury discovers his passion for drawing while surviving harsh prison conditions

Some quotes have been lightly edited for clarity and length. Content warning: violence, self-harm.

“My name is Jake Pilsbury. I am 29. Sorry, I had to think about that. I’ve spent basically half my life in prison — 12 years.” 

March 2021. Pilsbury sits across from me, albeit in Zoom world, for our interview. Beneath the sleeves of his brown uniform, his arms are decorated with intricate tattoos, many of which he gave himself. A picture-perfect skull and clown duo peek out on his forearm. Pilsbury sits in what looks like a typical classroom with round tables and aging plastic chairs, except instead of sitting in a school, Pilsbury speaks from a correctional facility where he is finishing a substance rehabilitation program while taking college courses to obtain his entrepreneurship degree. 

Pilsbury is a self-taught artist who discovered his talent while in solitary confinement. He spent over three years inside a supermax cell, which he described as a prison inside a maximum security prison itself. “The best way I can describe the supermax is they put you inside a hole and throw away the hole. It was during this dark time when I watched those around me slowly lose touch with reality, which is not that uncommon in that environment. Imagine staying inside a concrete box for years at a time with literally nothing to occupy your mind but your own anxieties.”

Besides mealtimes when guards placed trays of food in his cell door’s slot, Pilsbury did not have contact with anyone. Throughout his three years in supermax, he made a single phone call and went outside only once. Pilsbury said his time there was extremely lonely, dehumanizing, and painful.

“If you treat people like animals, what will eventually happen? They will start to act like animals. I do not understand why people treat each other like this and expect them to become rehabilitated. Sadly, that is not the worst of my trials in my life. I often wonder how I am not worse off than I am.”

His barren cell had no windows and only contained state-issued flip flops, a thin green mat to sleep on, an itchy wool blanket, and the boxers on his body. To pass the time, Pilsbury slept as much as possible. Like many supermax inmates, at times Pilsbury resorted to self-harm. “You spend so long desensitized with no contact with anyone that you eventually welcome any feeling at all, like injury, to remind yourself you are still alive. The pain stings, but it reminds you of what a feeling feels like again. I was aware I needed to find something to occupy my own mind, or I would lose it.”

Pilsbury’s life changed when an officer surprised him by breaking the rules to give him paper and a rubber flex pen (designed so it cannot be used as a weapon). Pilsbury admits that when he began drawing, his sketches were very much amateur. He recalls that his first drawing was biomechanically inspired, weaving together bolts and blades with human bones and tendons. “I would draw and draw until I had calloused fingers. Finally, after what seemed like an eternity, I was released from supermax into the general prison population. Once I was released, I was able to show people my drawings, and surprisingly, people loved my art; I truly thought I sucked.”

Through our email exchanges, Pilsbury showed me a gallery’s worth of his captivating drawings, which can also be viewed on his online portfolio. Although he only had simple supplies like pencil and pen to draw with in prison, his powerful pieces are shaded deeply and jump off the page. Blades, eyes, and the Holy Cross are common themes in his artwork, most of which he drew without actually seeing any reference. He signed each piece with his initials and a four-leaf clover, as homage to his Irish heritage. “From an outside perspective, most of my stuff looks evil, but really it’s just whatever strikes me at the moment. I learned to draw during a very dark time in my life. Having a way to express those emotions helped ease my anxieties, and eventually drawing evolved into a passion.”

Shortly after leaving the supermax, Pilsbury taught himself a different art form — tattooing. “The limited resources we have as prisoners mean that having ingenuity is a must for comfortable survival in an extremely uncomfortable environment.” For ink, Pilsbury burnt hair grease like pomade and used the soot mixed with water and instant coffee. He engineered his own tattoo gun by using the rotary motor of a CD player paired with a needle made from either a guitar string or the spring from a pen straightened out. According to Pilsbury, these tattoos last just as long, if not longer, than tattoos done on the outside. 

Known as one of the best tattoo artists in the Department of Corrections where he resides, Pilsbury had a never-ending list of clients waiting for tattoos, for which he was often compensated with instant ramen and honey buns. Such is the currency of a place without cash. Tattooing also offered Pilsbury the opportunity to interact with inmates beyond the strong racial divides that exist within prisons. “You’re shunned if you don’t get with the program and just deal with your own people, but I've had the free pass to interact with everybody because of my tattoo skills.” 

Pilsbury dreams of opening his own tattoo shop and becoming a freelance graphic designer once he leaves prison. Unlike supermax, Jake said that his correctional facility focused more on rehabilitation than penalization. He took classes through the MIT Educational Justice Institute (TEJI) run by Professor Lee Perlman. As a part of TEJI, the Prison Education Initiative (PEI) offers hybrid classes, where prisoners and MIT students can take courses together at the correctional facility. Due to the pandemic, these classes currently take place over Zoom. “The Nonviolence as a Way of Life course was a turning point, completely changing my perspective. I was getting in trouble here and on my way to get shipped back to supermax. But once I started taking that course, there was a lot of self-reflection. It gave me a purpose in here and something to look forward to twice a week. At first, it was a little weird because I was like, ‘Having classes with MIT students, they’re going to be smarter than me! They're going to judge me because I’m in prison.’ But by the end of the class, we all became friends.”

“Lee has been extremely helpful and supportive in helping me achieve my goals as an artist.” Today, Pilsbury is teaching himself graphic design. He has designed logos for PEI courses which are featured on their website. He also started his own clothing brand, Freedom Wear, where clothing and accessories adorned with his designs are available for order for the general public. The goal of the Freedom Wear brand is to spread awareness about struggles such as recidivism, mental health, and addiction. Pilsbury will use the sales revenue to help pay for his future education. Pilsbury also took courses at a community college to obtain a graphic design certification. After leaving prison, he plans to attend school in Boston to further his education journey. “This time, I’ve got a lot of good things going for me. I’m not getting out to a bad situation. I have goals, a positive living environment, and a good support network.”

“Overall, there have been years of my life inside a cell locked down. All I needed to mentally escape my physical confinement was simply a pencil and paper. Most people do not look at a pencil and piece of paper the same way I do. I look back and often wonder where my life would be if that officer never slipped me a pen and paper inside the supermax.”

If you would like to purchase Jake Pilsbury’s apparel, visit Check out Pilsbury’s art portfolio at and contact him through the site for graphic design, tattoos, or artwork commissions. Pilsbury has been released from the correctional facility.