Umberto Eco’s philosophical project, which culminates in the development of a systematic and philosophically relevant semiotics, has a perplexing and problematic debt to and link with pragmatism in its many forms. Indeed, his apparent relation to pragmatism as such is in fact quite tangential if we ignore the pivotal role of Peirce in defining and supporting Eco’s explicit semiotic turn. But Eco claimed that John Dewey’s Art as Experience , the foundation of a distinctively pragmatist aesthetics, was a major factor in his early philosophical movement away from certain premises of the aesthetic tradition that held sway during his student days. Eco engages Dewey in surprising and enlightening ways in his early books, but the trail of Dewey is gradually ‘lost.’ It is this trail, wandering through different contexts, that I follow in this paper. I also indicate how Dewey’s work could have played a larger role in Eco’s mature aesthetic thought and that we should see the absence of Dewey to represent a lost opportunity for emphasizing and enriching the pragmatist side of a semiotic approach to aesthetics.