In contemporary South Africa, racism, economic exclusion, and spatial segregation remain trenchant features of everyday life 25 years after the end of apartheid. In this article, I show how therapeutic practices by black South Africans in one of the country’s largest townships address the ongoing legacies of this history. Rather than treat individual psyches, therapists’ practices are oriented toward the relational space between generations, a political therapeutic driven by the affective force of the therapists’ own history of struggle toward a different future for black youth, who continue to be marked by the legacies of colonialism and apartheid. In the process, I track how this political therapeutic confronts the normative demands of psychiatric knowledge. Overall, I argue that rather than solely focusing on the violence of care in clinical settings, we should interrogate political generation and embodied history as forms of expertise and their constitutive potentialities.