In If on a Winter’s Night a Traveler, by showcasing “you” the Reader’s rite of passage from the outer world to the self-reflexive, self-referential inner world, one of fiction and fictionality, Italo Calvino puts across his own thoughts on Literature and its function in our society, which, according to us, is informed by a completely apolitical vision, divesting it of any critical or interventional agency. He reduces the acts of reading and writing to a mere aesthetic and formalist game, an isolated “play” of signifiers, detached from any existing material reality outside of these acts. Thus, Calvino is able to produce a perfect embodiment of the Derridean post-structuralist thought but, as a consequence, the vitality and vigor of his fiction suffers. Through a reading of the element of apolitical in the novel under consideration, we seek to establish the entrenchment of the aforementioned school of thought in Calvino’s fictional universe.