The Eunuch Sanbao's Voyage to the Western Ocean, a late sixteenth-century novel loosely based on the historical expeditions commanded by Zheng He (1371–1433), is a peculiar mixture of factual accounts of foreign lands and fantastic narrative. While previous studies have confirmed its historical value, evaluated its literary achievement as fantastic literature, or criticized its plagiarism, this article situates the novel within the context of the late-Ming publishing boom and expanding world knowledge and examines how its author negotiates cultural boundaries through refashioning historical accounts and classical allusions. The key questions explored are whether the broadened knowledge of the world beyond China brings about new ways to conceptualize and imagine cultural others, and how the novelist maneuvers between an enlarged understanding of the world and a long-standing Sinocentric discourse. The article demonstrates that the novel reveals much of the curiosity, ambivalence, and conflict at work during the early stages of global contact. Throughout the novel, its author oscillates between conflicting urges to differentiate or assimilate, to antagonize or empathize, and to emphasize Ming superiority or identify a common humanity. These oscillations give us a glimpse into the complex responses to a changing world and propel us to reflect more deeply on the conflicts and struggles experienced in the early stages of global contact.