The centennial anniversary of John Dewey's "Democracy and Education" has been celebrated this year in a reconstructive and utility-based spirit. The article considers this spirit and the need to complement it with a critical-deconstructive and "use-less" prism that will reveal shortcomings in Dewey's and our own political pedagogies. Gleanings from Dewey's book allow us to begin with what most educational theorists today treat as strong points of Dewey's politics and then to explore how such points appear or disappear when Dewey's ideas travel and how they relate to colonial and developmentalist elements in Dewey's pragmatism. The article reveals how such elements operate in one of Dewey's educational policy writings and in his related travel narratives. The main aim of the article is to indicate that we often require a "learning by undoing" to obtain a heightened view on the stakes and challenges of old and current progressive pedagogies.