This article examines the ways teachers, students, and teacher educators interacted in a unit around Christopher Columbus and other historical figures that have been given places of privilege within the dominant society. The authors trace how color-evasiveness and explicit engagement with race in the classroom intermingle with the implementation of a Youth Participatory Action Research (YPAR) project. Findings reveal that differences in teacher comfort discussing race shaped how students imagined monuments that might take the place of a local statue of Christopher Columbus to represent community values and needs. This study contributes to the body of scholarship about using YPAR as part of a larger endeavor to sustain inclusive learning environments where teachers teach about race and racism in their middle school classrooms.