The scholarly narrative of spoken Chinese studies in Tokugawa Japan is dominated by Ogyū Sorai, who founded a translation society in 1711 and urged Japanese intellectuals to learn contemporary spoken Chinese in order to draw closer to the language of the Chinese classics. This article explores the decades prior to this, when Sorai served the powerful daimyo Yanagisawa Yoshiyasu. By investigating Yoshiyasu's contact with Chinese monks and the surprising but previously untested claim that he could understand spoken Chinese, I explore the cultivation of spoken Chinese learning and the patronage of Chinese émigrés by members of Japan’s warrior elite in the late seventeenth and early eighteenth centuries. Prior to the scholarly interest in vernacular Chinese and the popularity of Ming and Qing literature in Japan from the Kyōhō period (1716–35) onwards, Chinese orality served as a tangible link to the Chinese tradition for Yoshiyasu and other powerful daimyo, functioning as a sign of their fitness for power in East Asia.