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"America's Leftovers" by TaSin Sabir.

‘Art helped save my life’: Finding joy and survival behind prison walls

Jessie Milo knew art had found him as a little boy. On his rides with his mom to the Methadone clinic, his mother would throw him art magazines to read in the backseat while she went inside. Amidst scenes of drugs and gangs, art was there while his mother waited in line for her dose. Colorful patterns and flowers emerged from her highs when she took heroin, and his father would send him drawings from prison. Both his parents helped him fall in love. 

He began trying to draw in earnest when he was 10 or 11 years old. When his father got out of prison, he sat down to teach him drawing techniques. At 14, in juvenile hall, Milo drew pictures to impress his future son’s mother. She loved them, and he just wanted to make her smile. Art was an escape for Milo, to take his mind off things, a way to create, to bring joy. 

“Art helped save my life. Coming to prison with a life sentence was a weird mixture of wanting to die and live at the same time,” said Milo. 

A comic of an man in prison talking to his now incarcerated son.
(Original comic by Jessie Milo)

For incarcerated artists like 44-year-old Milo—who sports a neatly trimmed goatee, short haircut and sleeve tattoos—art is not just a way to reintegrate into society, or a way to pass time. It is a filter through which attitudes about a situation can change. It’s a survival mechanism. 

He remembers arriving at North Kern State Prison in shackles on the prison bus:

“The officers unshackled us and had us line up next to the bus, and said, ‘Take off all your clothes and your shoes and throw them in the bin on the way in.’  I can still feel the gravel beneath my bare feet as we walked naked in the sun into the processing area, where we then lined up naked in a holding cell. This was prison reception. When I got to my destination prison where I would serve my time, we were locked in the cell days and months on end. We couldn’t seek mental health treatment because the prison gangs determined that was weakness, and they would stab you. So to cope, I started to draw sitting on my bunk.” 

Years later, as he got out of gangs, Milo began counseling and attended mental health and behavioral theory classes where art served as a “safe space to meditate and change,” he said. 

“I would draw and replay all I was learning and question my beliefs. Changing is uncomfortable, but art helped me through it all. Art is more than just a coping skill. It’s proof that I have value, that I can bring joy instead of pain. I let go of the walls I built and the shame.”

—Jessie Milo

“I would draw and replay all I was learning and question my beliefs.Changing is uncomfortable, but art helped me through it all. Art is more than just a coping skill. It’s proof that I have value, that I can bring joy instead of pain. I let go of the walls I built and the shame. I learned to love myself again, if not for the first time. What people do to us as children is not our fault,” Milo said. 

For Donald Diggs, art was a way of processing the world around him after being released from Salinas Valley State Prison in 2022, where he had been incarcerated for 20 years. Post-release, he moved to a shelter and then a small studio apartment in Oakland, where he now takes classes at Laney College. 

Painting of a nude pregnant woman covering her breasts, with the African continent on her belly.
Drawing of a man with his hands on either side of his face.
Original artwork by Donald Diggs, formerly incarcerated at San Quentin. State Prison. (Courtesy Donald Diggs)

Diggs was incarcerated in late 1979. Ceramicists, artists, painters, woodworkers, poets and filmmakers from across the state came to his prison. Their classes were part of the William James Foundation Arts and Corrections Program’s collaboration with the California Department of Corrections and Rehabilitation. One day, Diggs decided to try his hand at it. He’d always appreciated art, but he never thought he could paint. 

“It wasn’t just drawing, it was ceramics, clay. So I [had] a little exposure to different things. We get a lot of lockdown cell time so they would give us pencil, paper, pads, and I just started doodling or trying to copy something I see,” said Diggs. “That’s how I started to draw, that’s how I worked into a technique, by watching everybody else and learning on my own.” 

As Diggs’s art developed, so did he. He developed his own style, cutting pieces of paper into shapes and using wax to bring out colors and baby oil to set and smear color on his canvas. Art made Diggs “feel himself again.” And, he kept learning to hone his mixed-media style from the creative ways he saw others in his program experiment with what materials they could find. 

Painting of three vases with flowers.
(Courtesy Donald Diggs)

His first time in the Emeryville Blick art store in February 2022, Diggs carefully selected the materials he needed; he didn’t have much money to spend yet. He fell in love with bristol board for the way it absorbs the baby oil and wax he still uses to mix colors. He gathered colored paper and colored pencils for drawing figures. His latest purchase, a set of five X-Acto knives, will allow him to shape paper figures more precisely and quickly make copies he stacks on top of one another to create a three-dimensional effect. As he gathers materials, he said he gathers inspiration and excitement for what is possible. 

Diggs, towering nearly 6 feet tall, likes to take walks on Laney’s campus and observe the trees twisting different directions, the ornate patterns on the wood. He marvels at how much things have changed in the 43 years he was behind bars. Change, and the trees, are inspirations for his next project. 

“I once believed I’d be confined behind bars for the rest of my life, but now I sense a profound renewal within me. The world has undergone significant transformations, constantly evolving. Although things have shifted, there’s an intriguing constancy amidst the change. Observing this aspect is what makes this experience so captivating and intriguing to me,” Diggs wrote in a message to AfroLA. 


During the pandemic, Milo’s parents got sick, he lost a cousin to suicide and his uncle was murdered by his nephew the same day his grandmother died. Amidst what seemed like insurmountable loss, Milo turned to drawing comics about his and other inmates’ struggles while incarcerated.

“Comic art is stress free and is a great way to have a voice! That’s important because we all need to be heard,” said Milo.

Comic panels depicting an incarcerated person trying to purchase items at the prison canteen. The second panel is a corrections officer telling an inmate wrapped in chains: "Right of the Incarcerated Shopper! Prison Economics: We'll reduce prisoner pay to $14.00 for 160 hours labor. We'll raise price of goods higher then grocery stores. They are in chains. They have to buy from us."
A commentary on prison canteen markups in a comic drawn by Jessie Milo, currently incarcerated at San Quentin State Prison. (Credit: Jessie Milo for AfroLA)

In addition to his personal art and drawing comics for both San Quentin News and All of Us or None, Milo works as a youth mentor and is a freelance journalist. “I feel a duty to participate in the conversation,” he said. 

Black power fist surrounded by ALL OF US OR NONE and its Spanish translation TODOS O NADIE.
All of Us or None Newspaper is a part of Legal Services for Prisoners with Children.

Art from both Milo and Diggs has appeared in All of Us or None Newspaper, a work of the grassroots group Legal Services for Prisoners with Children. Editor-in-chief TaSin Sabir said linking those who have been locked up to their families and allies. Part of this is ensuring that talents like art are uplifted, encouraged and supported. 

“It is important to our organization that incarcerated and formerly incarcerated people be heard in their own voices as writers, authors, poets and artists,” said Sabir.

“Even people not in San Quentin prison might feel like they live in a cage and are invisible, and they just want someone to see them,” said Milo. “Through my art or poetry or writing the world knows I’m alive, and that makes me feel alive.” 

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