Tsunesaburo Makiguchi (1871–1944) was a geographer, elementary school teacher and principal, and educational reformer, who was active in the early-to-mid 1900s in Japan. As a school leader and scholar-practitioner guided by a passion for supporting teachers and improving education for the happiness of children, Makiguchi scrutinized pedagogy as a science and proposed a number of reforms of the Japanese education system, key elements of which, he believed, were failing teachers and students alike. His proposals included, among many: the establishment of standards of competency expected of school principals as well as a system of examination to uphold these standards; the abolition of a government-led school inspection system that pressured and restricted teachers from freely conducting teaching activities; and the establishment of an “education research institute” and an organization for the training of teachers. The growing number of modern educational scholars and practitioners paying attention to Makiguchi’s work and philosophy find his ideas not only valid and applicable to education in the 21st century but also remarkably innovative and insightful. His proposal for school leadership was still but a voice in the wilderness in the 1930s. It was also a bold and audacious attempt for him, especially at the time of the militarist regime. Makiguchi is often compared with his contemporary John Dewey (1859–1952). Evidently, Makiguchi and Dewey were both visionaries, passionate school leaders, and fearless reformers. Bearing this in mind, Makiguchi deserves much more attention than he has received thus far—at least as much as Dewey, if we are to balance the historical account of progressive education as a transnational phenomenon.