We are living through a historical moment that is marked by a protracted struggle for systemic changes in the United States as demanded by the broader Movement for Black Lives, as well as a visible increase in White supremacist violence. Although studying race and racism should have always been part of the kindergarten through twelfth-grade curriculum, it is seen as a more imperative need in our current climate. We argue that White students in particular, as the beneficiaries of White privilege, need opportunities to discuss racism in the classroom. Using Critical Whiteness Studies and antiracist teaching as analytical lenses, this article uses qualitative, ethnographic methods to analyze classroom discussions about racism in a predominantly White high school English/history class in a suburban, private school. Our findings describe the ways the (White) teacher explicitly encouraged White students to interrogate the sources of their discomfort when talking about race and racism, as well as intentionally disrupted White epistemologies through his choice of texts and accompanying discussions. This work serves as an example of the ways Whiteness can be interrogated in literacy instruction, thus equipping White students with the tools to take antiracist action in their lives.