Ethnographic case studies of three African American student achievers attending desegregated urban high schools are analyzed in terms of theories in the new cultural pluralism in educational anthropology. The achievers are described as they sought to transform their “multiple selves” as Black persons, as women and men, and as members of social classes in transition between the “multiple worlds” of their families, schooling, and peers. They accomplished their self-transformations through the use of contrasting strategies of self-negation, self-fragmentation, and self-synthesis that were adapted in response to conflicting cultural expectations. This investigation offers crucial insights into the nature and consequences of the identity work of African American youths in urban educational contexts.