We explore the paradox of why high-achieving black Americans, as measured by education, still exhibit large racial health disparities. Educational attainment matters within race group, but we find that blacks are not protected by socioeconomic status in the same way that whites are: for instance, the black/white disparity in health risk increases for those with a bachelor’s degree compared to those with fewer years of education. We explore how the potential physical and psychological costs of stigma and, ironically, of exerting individual agency in the context of a racist or stigmatizing environment, may explain the limited role of education and income as protective health factors for blacks relative to whites.