Chaffey Rising Scholars Alum Emerges from Prison as a Celebrated Artist, Mentor

Photos: Above, Kenneth Webb poses with his artwork. Below, "Blood in the Soil," 2023; "Floriography," 2024; and "Purifying Jihad," 2024. All images courtesy of the artist and Huma Gallery.

Kenneth Webb was just 19-years-old when a judge sentenced him to life in prison.

He stood in a Los Angeles courtroom and heard the words, but they didn’t register.

“I don’t remember the judge saying these things,” he said. “All I could think was how am I supposed to do 50 years in prison? What does that even mean?”

Webb, now 35 and a New York Times-featured artist, survived the horrors of prison violence, and turned his dark fate into a light that shines on himself and others. He credits Chaffey College with giving him the confidence to envision a life beyond prison walls.

“It showed me that I can study, turn in my assignments and get grades based on my work,” he said. “It allowed me to choose what I wanted to be in the future.”

Webb, a native of west Los Angeles, has considered art a focus in his life since childhood. He competed with dance crews, and sketched Spongebob and other characters on the backs of books. He would fill empty water bottles with paint from school to practice his craft at home.

But he admits he also made poor decisions leading to his incarceration.

“When I was a senior in high school, if I asked you who was the most creative, the answer would have been me. And if I asked who was the most likely to get in trouble, it would also be me,” he said.

His association with party crews – groups that organized underground parties in the early 2000s in Los Angeles – led to fistfights. Then he began to carry a handgun. As someone from the street, Webb said he was raised to meet violence with violence.

On Jan. 12, 2008, he shot an 18-year-old man in an alleyway after he thought he saw a gun, he says. The man died at the scene and Webb was arrested.

Due to the severity of his crime, prosecutors tried Webb as an adult even though he was 17 years old. After receiving his sentence, authorities transferred him to Salinas Valley Prison, documented as one of the most dangerous facilities in the state.

“Six people died within 90 days of me being there,” he said.

But the constant violence in the prison also led to frequent lockdowns. That kept Webb out of trouble, and gave him time to practice his art.

“Most people would spend time reading or writing essays, but I spent most of my time drawing and expressing myself through that lens.”

He initially focused on “tattoo art” – symbols and figures ranging from hearts to skulls. Eventually he received a transfer to the lower-security California State Prison in Lancaster, which was closer to his family and had a community of likeminded inmates with a passion for art, as well as an art studio.

Webb created pieces focusing on institutional issues facing people of color, and other themes. His painting “Khalifah’s Awareness” won top honors at the Antelope Valley Fair Art Exhibition in 2019. Since then, his work has been featured in various galleries, including the Frieze Exhibition in Los Angeles and his debut solo exhibition “Hymns from the Cave” at Los Angeles’ Huma Gallery. 

While at the California Institution for Men in Chino, Webb earned a high school diploma and took classes with Chaffey College in the communication studies and business programs. He recalls some of the earliest feedback he received from Professor of English Charmaine Phipps on a poetry assignment.

“She took those writings and critiqued them in such a beautiful way. She treated me human, like a peer I would say,” he said.

Phipps described Webb as a student who expressed vulnerability, thoughtfulness and encouragement of others.

“In his poem, ‘Inside the Inevitable,’ he wrote ‘I speak hope in spaces that oppose the life force that causes it to be’ and I’ve shared that line with other classes, asking students to ‘speak hope’ in their writing,” she said.

While in prison, Webb created a series of artwork called “My Black Thoughts are Not Contraband,” of which six pieces were sold. He eventually used the funds to hire an attorney that helped him regain his freedom. 

In 2024, he was re-sentenced to 21 years, and with time served and good behavior, he walked out of prison for good.

Webb now gives back to his community as a manager for the Bigg Dogg Gang and Violence Prevention Academy. He was named a 2026 ambassador for the nonprofit Represent Justice, and is currently producing a short film called “The Weaver in a Haystack” about a formerly incarcerated artist learning to navigate life in his old neighborhood.

In January, he accompanied several formerly-incarcerated Muslims to Saudi Arabia as a representative of Link Outside. He has also established a studio practice called Creative Currency to produce his own work and empower other artists.