The chapter explores Dr B. R. Ambedkar’s account of the relationship between Buddhism and Marxism. It holds that post-Ambedkarian readings of Buddhism have taken him away from radicalism to a more spiritual or psychological version of Buddhism, whereas the conservative trend in the scholarship has always fanned tension between Buddhism and Marxism. At the other end of the spectrum, the rigid reduction of Buddhism to a Marxist essence has been a contentious issue within left-leaning scholarship in contemporary India. It is in this discursive domain that an attempt is made to locate Ambedkar’s response to both Buddhism and Marxism. The chapter is divided into three parts. The first discusses the moral and political/philosophical significance of the debate on Ambedkar’s version of Buddhism and the Indian version of Marxism. The second part explores the possibility of discovering the epistemic deficiencies in the Marxian understanding of social reality. The third part explores Ambedkar’s inversion of the famous Marxist architectural metaphor of base–superstructure to unravel a conversation on the relationship between Marxism and Buddhism. It shows that the alienation of the shudra cannot be reduced to that of the proletariat for Ambedkar.