Situating ethnographic methods within a framework of engaged research we offer a window into the adoption, implementation, and sociopolitical dilemmas of 15 African American males participating in a program designed to maintain diversity at one of Chicagos most successful and elite public high schools. The article presents a four-year study (20072011) of an explicitly class-based and implicitly race-based attempt to engage the new politics of desegregation and the microprocesses of integration. Promoted as reaching across geographic, race, and class boundaries, the Black Male Achievement Initiative (BMAI) at Selective Preparatory Academy (SPA) is just one of many attempts to satisfy stakeholders in a political environment that promotes school choice and voluntary initiatives to desegregate schools. Situated within the local context of Chicago school reform, the BMAI provides opportunities and builds relationships even as it raises questions about racial formation, the appropriation of space, the meaning of diversity, and how such educational programs are part of the broader processes of gentrification.