Although Nabokov dismissed Freud as a trivial and vulgar thinker and derided him at every turn, the presence of Freud and Freudianism is quite conspicuous in his works. With great vigilance, Nabokov anticipates and short-circuits potential Freudian interpretations of his work through parody, travesty, and psychoanalytic pastiche. Taking as points of departure Jenefer Shute's framing of Nabokov's conflict with Freud as an attempt to ensure hermeneutic control over his own texts and the cultural fields within which Nabokov's works were written and read, I analyze a literary mechanism within the 1966 text of Despair that both relies on and undermines a Freudian reading. I identify a set of objects whose Freudian valence could easily mislead the unwary reader into taking them symbolically, thus overlooking their function as important clues to events in the novel. I also posit that prevailing discourses, coupled with what might be called the “cultural competence” of the reader or scholar, are co-determinants of literary devices, semantic structures, and textual patterning in Nabokov's texts. In the case of the 1966 version of Despair, the resulting text is a palimpsest, as Nabokov adds, deletes, and reconfigures passages in translation, and the text itself is overwritten by discourses in the target culture. Moreover, by attending to cultural debates extant in mid-1930s émigré Berlin, where the Russian original was composed, it is possible to see within the canonical 1966 version vestiges of this originary text. While I do not tackle the larger question of the nature of Nabokov's reliance on Freud head on, my analysis provides some purchase on this fraught relationship, its literary manifestations, and what may be learned by pursuing a line of questioning that Nabokov himself sought to stymie.