Drawing upon the authors' experiences working in schools as teachers, teacher educators, researchers, and community members, this study utilizes a Critical Race Theory of education in examining the school-to-prison pipeline for black male students. In doing so, the authors highlight the particular role educators play in the school-to-prison pipeline, focusing particularly on how dispositions toward black males influence educator practices. Recommendations and future directions are provided on how education preparation programs can play a critical role in the transformation of black male schooling.