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Educators’ social identities influence their professional work. The present study examines how White medical educators understand race, racial identity, and racism. The author uses Critical Race Theory (CRT) as a framework to understand how educators both reproduce and disrupt contradictory understandings of racial identity and racial privilege. Analysis of semi-structured interviews with six medical educators suggests that faculty understand racial privilege in contradictory ways, that faculty view the experiences of people of color as legitimate, and that faculty are committed to learning how to overcome their own biases. These findings reveal that although White medical educators may have problematic understandings of racial identity and privilege, they are committed to improving the learning environment for their students.