After Wittgenstein, the most immediately visible – though by no means the only – philosopher addressed in Wallace’s work is the neopragmatist Richard Rorty, whose book Philosophy and the Mirror of Nature provided the title for one of Wallace’s later stories, a narrative concerned with the nature and revelation of truth. Indeed, the pragmatic concept that truth is a matter of vocabulary became one of the central pillars of Wallace’s own philosophy, as critics, including Hayes-Brady and Tracey, have shown. This chapter offers some context for reading the pragmatic strain that animates especially Wallace’s later works, including treatment of the liberal ironist and the question of the constituted other. Opening with an introduction to the history of the American pragmatic tradition, we move on to consider its direct and implicit presences in Wallace’s work, concluding with the proposal of a pragmatic model for reading Wallace’s writing in both thematic and structural frames.