This article focuses on Mr. Kurt, a white, first-year English teacher in an all-white context who has chosen to teach his students about whiteness, white supremacy, white privilege, and the many ways institutionalized racism is enacted in daily life. I center this article on classroom scenarios that highlight the challenges embedded in dealing with race and whiteness in curriculum and classroom discussion. I conclude with a discussion of how possibilities for antiracist and social justice pedagogies in English education rely on the field's willingness to embrace a more nuanced conversation, and I offer implications for classroom practice at the K-12 and teacher education levels.