Drawing on data from a historical-ethnographic study of the cultural politics of school desegregation in Seattle, USA, the author explores suffering as a recurring theme in the narratives of four black leaders, educators and activists involved in the struggle for black educational opportunity in that city during the post-Civil Rights Era. As these black subjects reflect on the historical trajectory of racial desegregation policies and practices, they offer us a unique view of the confluence of racial melancholia, a heavy, deeply-felt awareness of the history and persistence of racial disregard and subjugation, and school malaise, a form of what Pierre Bourdieu has called la petite misère, or ordinary suffering. The author’s analysis of these narratives highlights how these school and community leaders reflect on the meaning of black suffering in schools, what they understand as the source of that suffering, and how they imagine that suffering might be alleviated. The article concludes with recommendations for research at the nexus of race, education and social suffering.