This ethnographic case study examined the experiences of African American students within an urban school detracking reform initiative, which was intended to replace tracking practices through the institution of small schools. Over the course of a year, the researchers interviewed administrators, teachers, and students while gathering observational data from classrooms to explore the political nature of the reform and its impact on how students were viewed and treated by their teachers. Although this school reorganization aimed to expand opportunities for African American students, ultimately the data illustrated that restructuring efforts failed to change teachers’ attitudes and academic expectations, thereby denying students equitable educations. We found colorblindness to be a key factor that informed teachers’ persistent low expectations for students of color that reproduced tracking practices and inequitable opportunity structures in the smaller schools, thereby reinforcing the former stereotypes of low achievement for those students. This study calls for educators to challenge the racial ideologies of academic achievement, vis-a-vis teachers’ colorblind expectations, through political, normative, and technical dimensions of change to actualize educational equity in urban schools.