Greg Bolden
Greg Bolden Credit: Darrow Montgomery

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Greg Bolden was cleaning out his mother’s house in Clay Terrace 25 or 30 years ago when he came across an old school assignment she had saved. His drawing of a rubber duck, on old newsprint, transported him back to Ms. Charles’ first grade classroom.

“I was like the duck, man, that was the ultimate rubber ducky,” Bolden says.

Standing in front of his mother’s closet, Bolden, then about 16 or 17, didn’t think much more of the drawing and put it back in a box. His mother has since died, the house was renovated, and the drawing is lost to time.

It didn’t mean much to him back then—just another school assignment. But the moment stands out in his memory now as a crossroads of sorts. The drawing was a fleeting reminder to the teenage Bolden of his natural artistic ability that he was leaving behind.

In 2006, Bolden was arrested and charged with first-degree murder. He was convicted and sentenced in 2008, and went on to serve more than 16 years of a 31-year sentence. He was released in July 2022 under the Incarceration Reduction Amendment Act, which allows people sentenced to long prison terms for crimes committed before the age of 25 to ask a judge for a sentence reduction. Some successful motions result in the release of men who have been locked behind prison walls since they were teenagers. The law, initially approved in 2017, follows the growing understanding of how young brains develop and what that means for their culpability.

Illustration by Greg Bolden

During his 16 years as Inmate No. 03676-007, Bolden returned to the pastime where as a child he showed a natural ability. Behind bars, he studied other artists and honed his craft. He lists Jean-Michel Basquiat, Henri Matisse, and Harry Ellis, an incarcerated artist, as sources of inspiration.

Bolden says his journey to becoming an artist in prison started when a job in the art room opened up at FCI Bennettsville in South Carolina. He had been working as a janitor cleaning the showers, and when he got the job teaching in the art room, other prisoners and guards began to recognize his talent. Eventually they started asking if he took commissions.

At first, Bolden says, he accepted payment in the form of art supplies. He grew his collection with donations from guys who were getting transferred or released, and he soon had everything he needed—canvas, brushes, paint, pencils, pastels. Anything he could get his hands on.

But sometimes Bolden had to get creative in the way that living inside a prison requires. At FCI Bennettsville, Bolden was feeling inspired after reading about ancient Egypt and studying Basquiat and his depictions of ancient Egypt. He made his own primer using white latex paint and chalk that the prison used to line the athletic fields outside.

“So I mixed me a little concoction, and I primed a cardboard with that. And I had one of my buddies give me some paint, and a little brush and a small diamond paint knife like this one,” he says holding up a similar tool from his basement studio during a FaceTime interview with City Paper. “I just used that, man, and I went to work.”

The completed piece, about 40 by 30 inches, features two Eyes of Horus, lotus flowers to represent eternal life, and a sundial. It’s one of his favorites, he says. It represents resurrection and rebirth.

Soon, art became more than a pastime. It was his business (he would charge $50 to $85 for commissions depending on the size of the piece).

“Art was my freedom,” Bolden says.

“Instead of me always having my hand out for family members to support me, when I reached out, it wasn’t empty,” he adds. “I had something to contribute. And that was a blessing, man, to be able to do something that I love and get paid for it and not resort in violence, not having to take anything from anybody.”

That violence, Bolden says, was a fucked-up, everyday reality inside those walls.

“It was really not too far from the environments that we grew up in,” he says. Violence, guns and drugs were all around him as a kid on the outside. Inside, it came from other prisoners and from guards, and in the form of shake downs and lock downs. The brutality often fell along the fault lines of race, religion, and gang affiliation. Being Black in prison comes with its own unique set of burdens, he says.

“That shit is a lot to deal with even if you’re not a person who is involved in anything violent,” Bolden says. “Sometimes just going day to day, to commissary, just going through an average day in jail, it can end up bad. I’m talking about [even] the most pleasant individual in there, that shit tests you, and it calls you to be a certain type of way … and if you allow yourself to drown in it … you’ll find yourself in a worse situation than you were coming in.”

Surrounded by violence, Bolden started to realize the flaws in his own thinking. It exposed the images of success and masculinity that he had learned growing up as destructive and fraudulent: the flashy cars, the jewelry, and the women.

“We try to grasp and imitate and emulate these individuals we see in the streets, who we think are fly and [demonstrate] who we’re supposed to be as men,” he says. “But not seeing down the line that this person went to jail for that or died or got robbed.”

In that journey, art was also his refuge. It kept his mind and his hands busy. His work also earned him credibility with the officers. 

“These officers, they belittle you, they demean you,” he says. “They run up in your cell and totally demolish all your motherfuckin’ property regardless of what it is, [whether it has] sentimental value, just because they can do it and out of spite because that’s the type of shit that they’re on.”

Sometimes, he says, officers who didn’t know him—usually rookies—would come through his cell and destroy or confiscate his work. But eventually he started making a name for himself with his art. His work earned him respect.

“I always wanted them to look at me as I was,” he says. “I didn’t want you to look at me as no number or no inmate. … I saw myself as something different and something better, and the way I conducted myself, that’s the respect I wanted to demand from people.”

Since his release, Bolden has thrown himself into his craft. Once the product of a family broken by drugs and poverty, he now works as a security guard and has a family to take care of—he got married while he was in prison and his youngest daughter is 10. He’s currently in the middle of creating a mural for a public charter school in D.C. and is selling more of his work online. 

Bolden stays connected with other returning citizens (he was listening in on a meeting of the Free Minds Book Club when I interrupted him for our interview). Ten months after coming home, he’s still focusing most of his energy on building a new identity for himself.

“I’m just really really soaking up the job of being home, being free, and being in a really really good, healthy space in my spirit, in my mind, and with the people who I deal with and my family,” he says. “The things that I create in this new space, in my new element, they’ll be beyond the things I’ve created in the process of my incarceration.

“Every moment of the day, if I’m not sleeping or working, I’m strategizing, thinking about what I’m going to create,” he adds. “I’m comin’, Ryals.”