This article draws from data in a larger qualitative study on the lives of black male teachers in US public urban schools. I examine their schooling experiences as black male youth. By coupling theories of social suffering with life history methodology, this research analyzes how three black male teachers experienced frustration, marginalization, and misery as students. For these participants, academic tracking was a site of social suffering. This suffering persisted into their adult lives as classroom teachers, as they witnessed and attempted to mitigate the struggles of their own black male students. The findings in this study have implications for further research on black male teachers as well as their recruitment and retention in US public schools.