The proponents of postwar democracy in Japan have focused on defending its tradition against rising post-postwar trends such as neo-nationalism, neo-conservatism, and historical revisionism. Yet their attempts to reassert it as representative of a timeless universal spirit and progressive values often obfuscates the historicity of its foundation and the deeper roots of the current democratic crisis in Japan. My article problematizes such perspectives by focusing on the case of a repeatedly published educational text on postwar democracy entitled The Primer of Democracy. Jointly produced by the U.S. occupation personnel, Japanese intellectuals, and the Ministry of Education, and published in 1948 and 1949, The Primer of Democracy was Japan’s first postwar textbook on democracy used in both formal middle and high-school and social education. More importantly, the textbook has been repeatedly brought back to public attention throughout the postwar and post-postwar eras by Japanese progressive intellectuals who view it as a canonical text on democracy. My study situates its production at the intersection of the defeat in the Asia Pacific War, de-imperialization, and the formation of the Cold War liberal order and it considers the premises and characteristics of the specific idea of democracy presented in the textbook as deeply embedded in such a historical context. By so doing, I propose to reconsider the recurrent understanding of Japan’s postwar democracy as a form of Cold War liberalism. This approach, instead of insisting on preserving the postwar liberal order at all costs, opens up the possibility to reassess the accomplishments and limitations of postwar democracy within the specific historical circumstance of the long Cold War in Asia.