Most Indians inherit a rudimentary knowledge of the Ramayana and Mahabharata stories as part of their cultural DNA. Multiple literary versions thrive, as do oral narrations, at least as numerous as have been Indians themselves through history. Indian politics too uses the vocabulary of the epics — from ramarajya, to describe an ideal polity, to Kurukshetra, to metaphorically describe battlefields in electoral and ideological contexts — as well as stories and characters from the epics feature in polemics and analyses. The significance of the epics extends to all spheres of social life in India, particularly statecraft, since the protagonists were born into princely families and their alienation and accession to power were central elements of the plots of both epics. It is both interesting and useful, therefore, to ask: What was India’s ‘grand strategic thinking’ as revealed in the epics? In answering this question, this chapter explores several related ideas in the context of the Ramayana and the Mahabharata to illuminate the values, worldview and codes of their characters.