This article addresses an apparent contradiction in American teacher education that results in conflicting goals for educators. It asks: How do we prepare teachers to interrogate their inherited professional roles in the surveillance and disciplining of youth? How might teacher education inspire pre-service teachers to care more about youth who belong to populations that have been deemed “undesirable” and expendable? We critically examine the role of teacher education in contributing to the criminalization of certain youth in urban communities and the resulting school-to-prison pipeline crisis that leads too many students from the schoolhouse to the jailhouse.