In this paper, the authors explore—within an eclectic theoretical framework of critical theory, critical race theory, and Whiteness studies—the life experiences of four White high school mathematics teachers who were “successful” with Black students. The data were collected through three, semi-structured interviews, conducted over a 5-month time period. Through a cross-case analysis of the data, three commonalities among the teachers were identified as being significant contributors to their success in teaching Black students. Two commonalities the participants themselves felt strongly about, and a third became apparent during the cross-case analysis: (a) forming meaningful relationships with students, (b) engaging students in racial conversations, and (c) reflecting both individually and collectively with colleagues on issues of race and racism. Implications for classroom practice and teacher education are discussed.