Clinical experiences are crucial to the development of prospective teachers (PTs), especially the student teaching practicum. While the dynamics of schools are beginning to change in response to documented inequities for students, particularly students of color, the student teaching practicum remains largely unchanged and unchallenged with regard to addressing racism, oppression and white dominance. In this study, we explore PTs’ experiences and discourse in the context of student teaching in urban schools and the corresponding supervision of student teachers. Specifically, we examine the ways in which whiteness and racism obstruct the development of culturally relevant teachers. The data illuminate key insights into the ways in which PTs maneuver to avoid critical self-interrogation in relation to racism and inequities in schools. We conclude that clinical supervision experiences are opportunities to hide behind and/or challenge whiteness, and that the role of the supervisor is critical in facilitating the exposure to, and enactment of, culturally relevant pedagogy.