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At first glance, John Dewey appears to be an outlier among Progressive educational and political thinkers. His radically democratic account of pedagogy and of political action—which both center on personal experience—contrasts with Woodrow Wilson’s ambition for an administrative training for an expert civil service capable of enacting sound policy above partisan strife. But Dewey’s immanent experientialism is in service of a sweeping ambition to unleash the potential of human beings’ desires, which he assumes not to be subject to challenge by reason and to be fundamentally benevolent if brought to self-understanding. Such a transformative project will require enlightened teachers of the people, both in the classroom and in the bully pulpit, who may become a political elite in turn. Wilson assumes that reason is objective and instrumental, and that the ends of political reason are set by the popular will, resulting in an elite that is in the service of a democratic project. Both men reject the classical tradition in education, which seeks to bring reason to bear on human desires and direct them to better ends. In contrast to classical pedagogy’s aristocratic ambition, Progressive pedagogy in both Wilsonian and Deweyan modes tends toward technocracy. This paper uses the two protagonists’ institutional educational work to flesh out their philosophical projects as given in Democracy and Education and “The Study of Administration,” examining Wilson’s founding of the Graduate College at Princeton and Dewey’s formative influence on Teacher’s College at Columbia.