Our reflection on the work of Andrew Stables begins by considering the distinctive approach, informed by literary criticism, that he brought to the study of education. His acute sense of the significance of the reader’s relation to the text, inspired in large part by Coleridge, led him to a robust appreciation of the importance of critical reading. This sensitivity led him in turn to the more obviously philosophical consideration of the nature of meaning and the relation between language and thought. In exploring these matters he drew somewhat eclectically on the writings of Wittgenstein, Derrida, and Lyotard. In due course he came to think of poststructuralism as too relativistic in tendency, but he had greater hopes for Wittgenstein. In tandem with a burgeoning interest in Peirce, he came to the view that Wittgenstein’s work might contribute to a fully semiotic perspective. As is well known, semiotics was to define the theoretical territory within which Stables’ later thinking unfolded. It was surely through his deepening knowledge of Peirce that his philosophy developed its fullest expression. His ambitions were large, and many have been drawn by his enthusiasm and commitment. Our discussion sets out to acknowledge these achievements and to show appreciation for the insights that Stables brought to educational debate, but also to question the basis for his turning away from some of those earlier influences and to take issue in some ways with the philosophical stance that he came to espouse.