This chapter presents the seminal work of chief counsellor Kautilya, Arthaśāstra. Arthaśāstra has been unanimously accepted not only as one of the most precious works of Sanskrit literature, but also as an ancient Indian compendium of principles and policies related to political science. The chapter begins by unfolding the ‘philosophical foundation’ of Kautilya’s Arthaśāstra. A systematic study of this foundation clarifies the moral footing of Kautilya’s political theory. The chapter then unpacks the structural and functional outlook of Kautilya’s Arthaśāstra, demonstrating how Kautilya’s political theory is eclectic. It fuses the allegedly conflicting rational/prudential and abstract/ideal concerns in politics, thereby outdoing the prescriptions of Eurocentric realpolitik. Finally, the chapter inspects the position of gender and caste in Kautilya’s political theory. In so doing, it probes the gaps between Kautilya’s theoretical plan and its practical performance.