This paper will examine Kuo Pao Kun’s modern reiteration of the Zheng He theme in his 1995 Singaporean play titled Descendants of the Eunuch Admiral 郑和的后代. The memory of Zheng He and his legacy rooted in an anomalous series of sea expeditions makes him unique in Chinese history and speaks to contemporary issues of multiculturalism, ethnic hybridity, and the geopolitics of migration and diaspora. Kuo reappropriates the Zheng He theme to re-present the eunuch admiral as an ancient paradigm of the modern multicultural man in an increasingly transnational world. Scholars have noted the way Kuo uses storytelling to prompt people in Singapore to show a greater willingness to live together as a multiethnic, multicultural, and multilingual nation. However, I argue that the play’s text reveals more somber and personal undercurrents, where Kuo draws upon an intimate understanding of the classical Chinese Zheng He story to record shrewd observations and articulate concealed shafts of criticism about Singapore’s bureaucracy, intermingled with philosophical reflections addressing contemporary Sinophone lived reality.