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In The Senses of Walden, Stanley Cavell provocatively states that “America [has] never expressed itself philosophically,” save “in the metaphysical riot of its greatest literature”. A similar insight has prompted Richard Rorty to proclaim that philosophy can no longer sustain its old territorial claims, and that its sole remaining purpose is to supervise the “conversation” between non-philosophical discourses and forms of knowledge. Cavell counters this argument by pointing out that philosophy actually comes into its own when it loses its traditional privileges : if the mission of philosophical conversation is to question the legitimacy of territorial appropriation in the name of a common quest for justice, as it has been since Plato’s Republic, then American literature may be better equipped to carry it out than academic philosophy, with its recognized “field” and carefully guarded boundaries. This article seeks to test Cavell’s conclusions by examining Willa Cather’s 1913 novel O Pioneers !, which deals with what he calls “speculation in territory” while deliberately eschewing the conventional forms of philosophical rhetoric. It turns out that Cather’s narrative indeed stages a loving conversation between the main characters and the surrounding world: the correct combination of proximity and distance allows the protagonist and the land to gaze at each other; this gives rise to an intermingling of voices which in turn guarantees the possibility of genuine knowledge. Thus, while the novel is ostensibly about farming, it can also be read as a constructive critique of academic institutions, as it draws the reader’s attention to the broader context which alone permits teaching and research to carry out their true purpose.