This chapter describes the complex and sometimes contradictory nature of race and gender preferences among middle-class Black women. First, the author presents a case study of Tammy, a focus group respondent whose great-grandfather was involved in the Tuskegee Syphilis Study. Although her case illustrates underlying assumptions of the race concordance hypothesis (that Black patients want Black providers), her story also points to the persistence of structural discrimination and limits of using race concordance as a strategy to overcome it. Second, Tammy’s case is contrasted with women who complicated the underlying assumptions of the race concordance hypothesis by emphasizing the intersection of race, gender, and other identities (e.g., disability, age, sexual orientation) on the formulation of preferences and the futility of race concordance as a strategy to mitigate the effects of a rushed, impersonal, and neo-liberal healthcare environment.