This paper is dedicated to the investigation of an important, but not particularly well known, connection between the work of Hegel and Dewey's early educational ideas. A brief exposition of Hegel's position in the "Philosophy of Right" is offered, with a particular focus on Hegel's idea of absolute freedom. This exposition is followed by an analysis of one of Dewey's earliest books, "Outlines of a Critical Theory of Ethics". Hegelian notions of absolute freedom are shown to be present in the "Outlines". Textual evidence is then presented which links the theoretical framework of the "Outlines" to Dewey's early educational thought.