This chapter offers a possibility of tracing a radical political theology in the Indian thinker Dr. B.R. Ambedkar’s writings by exploring two of his most significant intellectual inheritances—American Pragmatist thought and Buddhist philosophy. Its ideological concern is derived from Professor Clayton Crockett’s project of a radical political theology for our contemporary political world where institutionalized religions get conveniently aligned with a majoritarian political worldview to facilitate a neo-liberal, aggressively consumerist, and capitalist economy. This ideological concern is manifested through this chapter’s concerted effort to underscore how both Buddhism and American pragmatism, through Dr. Ambedkar’s writings, could offer us a template for critiquing modernity without getting entrapped by the temptations of the Right-wing politics or an easy framework of liberal, secular, and modern electoral democracy. This chapter is speculative as well as a textually embedded reading of Amedkarite thinking to come up with the arduous task of arriving at a radical political theology at the limits of ‘liberal modernity’. While doing this, I bring in some of Jacques Derrida’s ideas to form a framework of speculative philosophy that would connect these dots: American Pragmatism, Buddhism, and Ambedkar’s writings.