Based on an ethnographic study at a middle school in a Midwestern city, this article examines the difficulty in creating anti-racist educational spaces, even in schools with a stated desire to do so. The school's curriculum was mainly based on teachers' abstract ideas of social justice and was not grounded in students' everyday realities. It failed to connect students to larger histories and stories of oppression and resistance, the central tenets of culturally relevant approaches. The school also failed in its attempts to shift its culture around discipline that disproportionately impacted Black students. The school's failure to implement culturally relevant and anti-racist curriculum and disciplinary practices illuminates various barriers to such implementation, including a lack of racial and experiential diversity among teachers, a focus on individual behavior rather than classroom and school culture, and a focus on maintaining enrollment as a charter school.