In this dissertation, I explore the some of the key shared conceptual questions that W.E.B. Du Bois and B.R. Ambedkar considered in their writings and their political efforts to fight untouchability, caste, white supremacy, patriarchy, class-exploitation, and empire over the course of their lives. This exploration will help lay a basis for a philosophical and historical sociological account of why the Black liberation struggle and the struggle against untouchability and caste were linked at their roots. I will make the case for the mutual imbrication of these struggles by arguing that each thinker’s articulation of a problem that they faced can be clarified and sharpened in light of the other’s conceptual approach to their own. The first chapter covers Du Bois’ approach to spiritual pedagogy in The Souls of Black Folk and how his experiences of space helped to inform his theory of how race operated. The second chapter discusses Ambedkar’s Waiting for a Visa to help us understand the centrality of the experience of untouchability to Ambedkar’s political philosophy. Untouchability was legally abolished in both the US and India by the early 1960s and yet systemic caste and racial violence against Dalits and Black people continued. The final chapter discusses Ambedkar’s and Du Bois’ philosophies of education and why the development of liberatory pedagogy remains a live, urgent question in casteist, racially hierarchical societies today.