Connections between the philosophies of Machiavelli and the Daodejing have been ignored in the comparative literature for far too long. Despite their many differences, these philosophies revolve around the concern for survival, both of the ruler and the state. This should not be surprising as each philosophy arose out of historical circumstances, Warring States China and the Italian Renaissance, that were violent and tumultuous. Further, each philosophy posits a worldview that is driven by a fundamental concept—the Dao or Fortune—which while different, are similar in significant ways. In order to successfully navigate the world (driven by either principle), each philosophy encourages a ruler to thoroughly manage their desires and the desires of the people. Not only do properly controlled desires prevent personal vice, corruption, and social instability, but restrained desire is the foundation for the key to success: flexibility of thought and action, as epitomized in the image of the dragon, associated with Laozi through his biography in the Records of the Historian, and the image of the centaur employed by Machiavelli in The Prince. Despite promising indefinite success, each philosophy has its limitations. The Daodejing allows for maximum flexibility through offering a path to cultivating a state of mind characterized by emptiness, but it’s political ideals are unlikely to work in a large state or one that is technologically advanced, and is noticeably silent on the idea of succession in leadership. Machiavelli’s philosophy, in contrast, is intended for large states, deals with succession through transforming a principality into a republic, and recognizes the need to remain flexible, but is unable to conceive of a way to achieve the state of emptiness that makes such flexibility possible.