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This is a study of the lived experiences of Black teachers who teach in white-majority schools in the Western Cape Province of South Africa. The main objective of this paper is to document the racial struggles and opportunities that Black teachers experience in these privileged schools. Informed by Critical Race Theory, a mixed methods research methodology was deployed to capture both quantitative and qualitative data on these teachers’ experiences. An emergent construct derived from the data is “emotional ambivalence” which points to the dichotomous lives of Black teachers in white-majority schools where racial struggles (negative) and professional opportunities (positive) both compose their lived experiences, an issue that has received little intellectual attention in research in post-apartheid South Africa.