Isawa Shūji (1851-1917), a Japanese educator in the early Meiji period (1868-1912), dedicated his life to the profession of teaching. He was not only a key figure in establishing Japan’s modern educational system, but also a pioneer in modernizing schools in Japan’s first colony, Taiwan. In 1895 Isawa volunteered his services to the Japanese Government-General despite the turbulent state of affairs in the colony at that time. Isawa’s decision to become Taiwan’s first Director of the Bureau of Educational Affairs was strongly influenced by the education he received at Bridgewater Normal School in the United States. This paper focuses on the influence of Isawa’s American experience on his decision to go to Taiwan and on his approach to education there.