This dissertation establishes a new analytic approach to understanding fundamental political ideas of other cultures and time periods and applies it to a study of ancient Greek and Indian conceptions of ruling. What I call a historical-comparative approach builds on continuing debates over how best to develop a cross-cultural perspective in political philosophy. Accordingly, I show how this approach enhances analytic rigor for both the history of political ideas and normative political philosophy while preventing culturally reductionist comparisons. Examining ancient Greek and Indian political thought ca. 1500--650 BCE provides an important test of this approach because ruling questions were central to both Greek and Indian cultures. This study focuses on Homer's Iliad and Odyssey, Hesiod's Theogony and Works and Days, and the Vedic Sam&dotbelow;hit as and Brahman&dotbelow;as. Ruling proves to be the most important political concept in each tradition, although each one develops a very different understanding of what it means to rule. I elucidate the earliest tradition of Indian political thought as one of stewardship and the Greek tradition as one of distinction. Using the Indian tradition as a cross-cultural vantage point provides critical leverage to better understand the emergence of self-possessed individuality in the Western tradition, further uncovering the earliest move towards a democratic way of thinking. Finally, I make a critical-normative move and draw upon the Indian understanding to challenge ancient and contemporary Western beliefs about ruling. I then formulate an alternative understanding of ruling predicated on an outwardly porous, polycentric conception of individuality that addresses contemporary issues of human-centrism, individualism, and communal interconnectedness.