Various cross-textual readings have been attempted between the Christian Bible and Chinese literature. Using cross-textual hermeneutics, this study centers on the political wisdom of Ecclesiastes and the Analects, and its goal is to demonstrate that both texts offer wisdom pointers for human survival amid uncertain sociopolitical realities. Chapter 1 introduces the vibrant interaction of biblical wisdom literature within the ancient Near East and highlights some of its political connections. The openness of wisdom literature is then proposed to support this present effort of cross-textual research. Chapter 2 offers readings of eight passages that communicate Qoheleth’s political wisdom in Ecclesiastes. Chapter 3 centers on the Analects and on some notable passages that relate to Confucius’ political ideas. Chapter 4 seeks to demonstrate the dialogical dynamics between the two works by exploring specific hermeneutical connections. In conclusion, readers will come to understand the distinctive and collective political insights of both wisdom texts. That is, this study suggests contextualized ideas for living wisely from within both a faith tradition and a native tradition.