This essay attempts to explain why philosophers, philosophers of education, and scholars of democracy should keep coming back to John Dewey for insights and inspiration on issues related to democracy and education. Mordechai Gordon argues that there are four major reasons that contribute to scholars' need to keep returning to Dewey for inspiration and guidance. First, is Dewey's pragmatic educational approach that seeks to maintain quality and stability in schools while rejecting the tendency to implement extreme changes in education based on the shifting winds of time. Second, Dewey's works contain both modern and postmodern elements and as such, it is difficult to label him as a member of one particular school of thought. Third, is the fact that Dewey's body of research represents a wide range of topics and interests from art to politics and from philosophy to the nature and purpose of education. Indeed, many of Dewey's essays and books can be viewed as a dialog between modern and postmodern ideas. Finally, and perhaps most important, Dewey's vision of democracy challenges us to recreate our global communities and our systems of education to meet the changing circumstances of history in such a way that all citizens (not just the wealthy or the powerful) can benefit.