Abstract: Inukai Tsuyoshi (1855–1932) was an influential party politician who quite famously served as Prime Minister during the Manchurian Incident, before being gunned down by radical military officers. His life story carries multiple historical legacies, both domestically and internationally. Here in Japan, he is best remembered as a champion of representative government whose death marked the end of party cabinets—at least until defeat in war; and in China, he is remembered as a loyal patron of Chinese expatriate leaders, particularly Sun Yat-sen. In retrospect, however, it is easy to overlook the importance of Inukai’s relationship with reformer and Confucian scholar Kang Youwei (1858–1927) and Kang’s competing constitutional reform movement. This paper will return to the years 1898–99 when these two political leaders met, discussed the fate of East Asia, and saw a good deal of themselves in the other. Using the previously unexamined text by Kang Youwei Mutangji (木堂記), this paper will consider the historical context and political potentials of their unfulfilled vision of alliance between China and Japan—one founded not on revolution and republicanism, but shared Confucian values and reform.