Democracy is in crisis around the globe, especially in the United States due to the results of the presidential election in 2016; it is now a bitterly divided society. In this context, this article reviews the democratic conception in education presented by John Dewey as his "Democracy and Education" celebrated its centenary also in 2016. A few key concepts of Dewey's ideas and structural features of democratic schooling were combined to develop a conceptual framework to analyze democratic schooling. Then, two U.S. democratic schools were comparatively analyzed using the conceptual framework, including participation in a small diverse community. This study concluded that democratic schooling has enormous potential to educate citizens who can become the effective agents of change desperately needed in the larger society, although the number of schools which systematically implement it is limited due to various obstacles. Lessons for Japan include the idea that giving students the authority to decide what to learn and how to learn it can lead them to take responsibility for their own education. There is anecdotal evidence that many graduates of the first democratic school examined here work in service and social justice professions, so further research is needed to pursue this theme along with others.