Artist and movement lawyer Tyler Whittenberg is using his brush to challenge the systems that criminalize and confine Black youth. His recent work, featured in the EJA Community Hub’s art residency, merges visual art, symbolism, and activism to reveal the deep structures of power that shape our education and justice systems.
Through a powerful series of paintings, Whittenberg invites viewers to imagine liberation, not as an abstract concept, but as a living, breathing possibility. Whittenberg’s dual identity as both a movement lawyer and painter informs every stroke of his work. He has spent years fighting to dismantle the school-to-prison pipeline, striving for a liberatory system of education rooted in Black self-determination. On canvas, these struggles take form through symbolism, contrast, and color theory, each layer building toward a deeper emotional and political atmosphere.
During the early 1900s, transient people in the United States developed a coded visual language—hobo signs—to communicate vital messages about danger and opportunity. Whittenberg reimagines this historical vernacular as a tool for contemporary resistance. In his hands, the hobo sign becomes a warning, a rallying cry, and a vision for transformation.
In “code of conduct” (30 x 30 inches, acrylic and oil on canvas), Whittenberg anchors the composition with the hobo symbol for “well-guarded home,” depicting a heavily policed school building. The piece contrasts this image with the sign for “dangerous neighborhood” in the lower right-hand corner, an unsettling reversal that mirrors how students are criminalized within institutions meant to protect them. Scattered across the canvas are other coded warnings: “beware of 12 dogs,” “hit the road quick,” “they will want to get rid of you,” and “there are thieves here.” Together, these marks speak to the ever-present threat of surveillance and punishment in spaces meant for growth and safety.
The painting “fair eastside high w/o the bat” continues this exploration, again invoking the symbols for “well-guarded home” and “dangerous neighborhood.” Here, however, they are met by a defiant Black body, amplified and alive. The figure confronts the visual metaphors of the pipeline head-on, embodying the resistance and resilience that communities cultivate in the face of institutional violence.
In “recess or recession,” Whittenberg shifts the tone toward empowerment. A Black figure stands surrounded by symbols of energy and amplification, an “amplifier,” “battery,” “electrolytic capacitor,” and “loudspeaker.” These symbols suggest collective power, echoing the belief that when people organize and educate themselves, they generate the energy needed to dismantle oppressive systems.
Through this series, Tyler Whittenberg bridges the historical and the present, the symbolic and the structural. His paintings critique our school systems while mapping out a better way forward. In reactivating the language of travelers from a century ago, he reminds us that we, too, are travelers on a shared journey toward freedom.
