This study presents a portrait of a White high school English teacher in an effort to understand the relationship between her White racial identity and her teaching about racism within a unit on "A Raisin in the Sun" in a predominantly White teaching context. The author argues that the teacher's ambivalent White racial identity contributed to lack of clarity and conviction in terms of purpose, which presented a pedagogical dilemma that ultimately undermined her practice. Acknowledging ambivalent identity and compensating for ambivalence in practice could provide pedagogical support for English teachers when they strive to teach about racism in secondary English classrooms.