Abstract: Memories of the Tuskegee Syphilis Study persist in the minds of many in the African American community and informs both individual and group responses when exposed to the clinical gaze. However, the contemporary political value of diversity drives new forms of inclusion in both medical research projects and public health programs linking race, risk, and disease. This article is based in part on community-based participant observation and clinical fieldwork in Rochester, New York from 2008 to 2013. I provide an ethnographic narrative of one church’s Type 2 diabetes outreach efforts amid the diversity of the African American racial category in which the postcolonial subject is as embedded as the post-Jim Crow citizen. I examine the gendered problematics involved in establishing trust toward achieving robust outreach and recruitment goals within church spaces. This article aims to contribute to the literature on community health practices, the anthropology of trust, the sociology of knowledge, religion, and the study of race as a social category.