This research poses two interrelated questions. How important is it for the formation of democratic ideas about educational leadership that the group or individual promoting those ideas is operating within a democratic political environment or, to the contrary, in the absence of one? And second, in the case of the latter, what are the available resources--historical, educational, philosophical, and transnational--for a countervailing vision of educational leadership, one rooted in precisely those democratic forms that have failed to find a hospitable environment in the home country: in the case of this research, feudal Japan in the 1930s and 1940s when a heightened form of militant fascism ruled the country. The strength of an idea, especially one that emerges in an inhospitable environment, that draws its strength from a kind of stress of opposites, and that survives the political machinations against it, may in selective cases be sufficient enough to overcome the structural limits of context. One such idea, the article argues, is 'Soka,' a Japanese term that translates as value creation. A fundamental critique of this philosophy is that 'education is unproductive,' not in the narrow economic sense of the term, but in the production of 'benefit, good, and beauty,' the building blocks of 'value creation,' a dynamic process of meaning-making within any given reality. The article demonstrates how an historical case from Japan can have broad contemporary use and significance for educational leadership and its preparation.