Developed at the end of the 1900s, largely in his short-lived Laboratory School at the University of Chicago, John Dewey's vision of democratic education has remained influential for over a century. Yet, as he grew older Dewey himself increasingly lost faith in the ability of schools, alone, to create a more democratic society. Drawing on data available from the Laboratory School, this paper expands upon Dewey's concerns. Ultimately, I argue that Dewey's educational approach failed to equip students to act effectively in the world as it was (and still is), and, further, that Dewey's model of democracy, while extremely useful, is nonetheless inadequate to serve the varied needs of a diverse and contentious society.