This article seeks to dislocate Orientalism from its Anglo-French origin by investigating the problem of its theorization in the context of the Russian Empire. I frame Russian Orientalism through the representation of the Caucasus in the Russian imagination as a border space between Europe and Asia. Reading Russian narratives about the Caucasus alongside narratives by Muslim writers of the Caucasus, I challenge the ideologically constructed binaries of Self and Other, Europe and the Orient, as well as history and personal memory. More specifically, this article discusses the figure of the Circassian hero in Mikhail Lermontov’s poem “Beglets” (“The Deserter”) and the Adygea writer Sultan Kazy-Girei’s short story “Dolina Azhitugai” (The Azhitugai Valley). I illustrate how Kazy-Girei’s story places itself in dialogue with the Russian Orientalist trope of the Circassian hero embodied in Lermontov’s work. Kazy-Girei’s narrator represents his North Caucasian homeland in order to reveal his struggle to reconcile personal memory with his own self-conscious performance of this Orientalist trope. In so doing, I emphasize the geospatial and ideological location of these narratives on the threshold of the Russian Empire and discourses of Orientalism more broadly.