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This essay utilizes chess to ventilate and then re-inter a sustaining premise of Western thought: the belief that practically all phenomena are susceptible to rational calculation, and that even the most aleatory cultural processes can be captured within a matrix of formal procedures. Although this tendency toward mathematical operationalization—the re-inscription of culture into algorithms—is often depicted as emerging alongside computers, my study of chess demonstrates that algorithms have a much longer history within the European cultural imaginary, particularly where Europeans have imagined the culture of the Other. Computers and computation, I argue, must be considered as only one narrow part, albeit a vigorous part, of this older and broader historical project. To begin, I show how algorithms aided European philologists who traced chess back to its origins in India; next, I use this philological history to contextualize subsequent debates in the prominent Artificial Intelligence subfield of computer chess. For computer scientists as well as textual scientists, chess's internal mechanisms become a locus for validating judgments and actions that far exceed the confines of the chessboard itself. Reading AI within the shadow of European philology discloses a critical history of computation, broaching the impingements that computers place upon critical scholars in the present. If today's culture is indeed a digital culture, then it is incumbent upon us, as humanists, to investigate, study, and critique the digital aspects of that culture. But this means seeking digital problems and digital objects where they actually are, rather than imagining them where they are convenient. A postcolonial account of chess forges one—but only one—new trailhead for this spatio-temporal re-mapping of our so-called digital culture.