Through a review of interviews with West Indian, African American, and white teachers at a New York City high school with a large West Indian population (ages 14 to 18), in this paper I discuss the complicated nature of teacher-student matching, and its impact on student achievement. I find that West Indian teachers have strong points of connection with their West Indian students, and clearly serve as their advocates when cultural differences such as parental nonparticipation, lack of discipline, and avoidance of eye contact come up. Non-West Indian teachers, however, also connect with West Indian students. White teachers draw upon common experiences of immigration, and African American teachers draw upon common experiences of race prejudice and American race relations. The downside of strong identification with one group of students--in this case, West Indians--can sometimes lead to a distancing from others--in this case, African Americans. West Indian teachers sometimes identify strongly as West Indian in opposition to negative stereotypes of African Americans, possibly to the detriment of their African American students. Hence, although recruiting teachers of color to serve our increasingly diverse school population is important, teacher training must also spend time on diversity training and developing intercultural understandings.