The chapter explores intersections and divergences in the thought of Rahul Sankrityayan and B.R. Ambedkar, two significant public figures in twentieth-century India. Though growing out of a primary interest in Sankrityayan, a neglected and utterly fascinating figure of polymathic reach, with a personal trajectory of extraordinary variety, the chapter expands the scope to consider how he helps us reconfigure our understanding of a well-known figure such as Ambedkar. It considers their life trajectories as personal and public quests at a formative juncture of the emergent Indian nation’s history. Sankrityayan and Ambedkar’s complementary and contradictory engagements with the categories of modernity and tradition, spiritual and material, nation and world, caste and class, occupy the chapter in the main. Buddha and Marx—two figures whose reception and reinvention in the Indian milieu have a narrative that intersects with that of these two individuals—help frame the chapter as these contemporaries engage with Buddhism and Marxism as key conceptual beacons and historical precedents in the pursuit of human freedom, negotiating spaces national and international, and times past and present, as they help shape the future of a new India.