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.A significant body of literature on the life outcomes of black males examines how school practices and policies file children out of educational environments and into the criminal justice system