In the United States, a growing disparity exists between the racial composition of teachers and the students they teach. In 2006, 43.1% of K–12 public school students were reported as non-White—in 1990, 32.4% (U.S. Department of Education, 2008). Teachers, however, are predominantly White, 83.3% (U.S. Department of Education, 2007a). Exacerbating this disparity, it has been noted that fewer African Americans are choosing education as a profession (see, e.g., Irvine, 1989; Ladson-Billings, 1994). This growing disparity motivates a crucial question: Can White teachers be successful with “other people’s children” (Delpit, 1995)? This study explores this question by examining the life histories of four White mathematics teachers who have experienced success with other people’s children, specifically, with African American children. The purpose of the study was to better understand what led each of the participants to teach African American children, and what factors may have led to her or his success as a White teacher of African American students. A qualitative, collective case study methodology (Stake, 1995) was employed. Data were collected through semi-structured interviews and analyzed using an eclectic theoretical framework (Stinson, 2009) which included critical theory, critical race theory, and Whiteness studies. Analysis of the data revealed the participants incorporated into their own teaching many of the same characteristics of culturally relevant pedagogy identified by Ladson-Billings (1994). Nevertheless, three strategies were identified as being essential to the teachers’ success with African American students: (a) forming meaningful relationships with students, (b) engaging students in racial conversations, and (c) reflecting both individually and with colleagues. The findings suggest a need for “spaces” in which pre-service teachers, in-service teachers, and teacher educators can discuss and openly debate issues of race, and challenge racial hierarchies found in schools and society at large. The findings also suggest developing a sharp focus on multicultural anti-racist education in teacher preparation programs as well as incorporating it into professional development plans for in-service teachers. Moreover, the findings highlight a need for school districts to provide teachers with professional development in three “How to” areas: (a) build teacher–student relationships, (b) connect to the local community, and (c) develop as reflective practitioners.