A century on from the height of John Dewey's educational writings and the reputation of the Gary Schools Plan as a model of progressive education, the paper reappraises two key matters: the relationship between John Dewey and William Wirt, the first superintendent of the Gary Schools in Gary Indiana, and the coherence between John Dewey's progressive pedagogies and the early years of the Gary Schools Plan. Through drawing on a range of primary and secondary sources of information, the paper analyses the connections between John Dewey, William Wirt and the Gary Schools Plan in their shared quest to extend progressive education into new urban and industrial schooling contexts. The paper highlights areas where existing assumptions require review and the extent to which the relationship and connections between Dewey and Wirt's work were mutually beneficial. The paper ends by calling for further related research based on the archival material available.