Contemporary political discourse often centers on a shared set of normative commitments: freedom, toleration, and limited government. This dissertation examines the theoretical basis for these commitments, through a comparative study of two eminent skeptics: Michel de Montaigne and Zhuangzi. Both develop forms of skepticism that are rooted in analyses of the phenomena of diversity and disagreement. They contend that our inability to reach convergence on central philosophical questions demonstrates the fundamental limitations of human knowledge. I argue that both offer novel and powerful arguments connecting these skeptical epistemological theses with the relevant normative commitments. In particular, both take skepticism to advance human fr...