This article examines Sai On's understanding of language and its correspondence with reality within the context of Confucianism, Buddhism, and the politics of eighteenth-century Ryukyu. Well aware of the limitations of language in conveying profound metaphysical truths, Sai On criticized Buddhists for their alleged erudition while displaying considerable rhetorical skill and erudition himself. Though a critic of Buddhism, Sai On,s writings suggest a strong Zen influence. Like most other Confucians, he accepted the Buddhist-inspired understanding of a material world whose basis was constant change and sought to create a stable society by mastering the principles of change. The ambivalence in Sai On's critique of language use and Buddhism is in part a reflection of a broader problem many Confucians experienced in dealing with foundations and change, and in reconciling Buddhist and Confucian truths.