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This critical discourse analysis examined whiteness in a white Jewish middle school social studies class, during an antiracist-inspired unit on enslavement in American history. The researcher analyzed classroom conversation during a lesson that was challenging for the teacher, as well as post-lesson teacher reflections. Through the lenses of critical whiteness studies and discourse studies of whiteness, the researcher found that whiteness (e.g. entitlement, emotionality, silence) and other classroom factors worked together to shape participants’ discourse. This study demonstrated how whiteness is propped up and perpetuated by broader classroom dynamics and highlights the need for aspiring antiracist teachers to closely examine and deconstruct the complex network of factors that reproduce systems of racial oppression in daily classroom discussions.