This essay is an analysis of educational philosophy and ideals in Japan. Japan’s recent educational reforms have been criticized as a “return to imperialism” or as “undemocratic.” In order to clarify the content of ideas/ideologies like “imperialist education” and “democratic education,” this essay examines the relationship between Japan’s imperialist philosophy of education, as articulated in the Cardinal Principles of Japan’s National Polity (1937), and democratic education, as represented by John Dewey’s Democracy and Education (1916). Usually, these two are considered to be opposed, with the former prevailing during Japan’s imperialist expansion, and the latter prevailing after Japan’s fall. However, this essay argues that while there are key differences between these imperialist and democratic philosophies of education, they do have their points of continuity. Thus, in order to pursue democratic education, it is necessary to criticize imperialist education without going overboard and criticizing the moral elements shared by both democracy and imperialism. This issue is relevant not only to Japan but to all Asian countries—like the Philippines—that are struggling to build their own forms of democracy.