In Democracy and Education, in the midst of the pivotal chapter on “The Democratic Conception in Education,” Dewey juxtaposes his educational aims with those of Plato, Rousseau, Fichte and Hegel. Perhaps Dewey believed that an account of their views would help elucidate his own, or he intended to suggest that his own ideas rivaled or bested theirs. I argue that Dewey’s discussion of historical philosophers’ aims of education was also designed to critique his contemporaries subtly and by analogy. My analysis of Dewey’s critique supports a second argument: one of the reasons Dewey’s legacy has been long debated (particularly his relationship to pedagogical progressivism) derives from his reluctance to criticize his contemporaries explicitly and directly. Had Dewey critiqued his fellow American progressives in the same way he did historical European philosophers of the past, his readers would have better understood his relationship to progressive American educational ideas and practices. Yet Dewey’s subtle approach also accounts for the creation of a work that genuinely warrants being called a classic – it rises above the educational debates of the early twentieth century to enter into a conversation with its educational ancestry, a conversation that Dewey propelled forward.