Presented by royal engineer Wolfgang von Kempelen, “The Turk” was a chess-playing automaton that debuted in the court of Maria Theresa in 1770 and defied skeptics of the illusion for decades. This article contends that, viewed in terms of the specific time and place of its creation, the automaton serves as a nexus of mixed nostalgic and fearful associations with the Ottoman world. On the one hand, the Turk’s stereotypical—yet, in that period, stylish—appearance and von Kempelen’s playful presentations of the automaton reflected evolving perceptions of the Ottomans that had developed during the relative peace after the 1739 Treaty of Belgrade. On the other hand, the automaton would also have invoked equally powerful associations of Turks as warlike and inscrutable, drawing on memories of a series of bloody conflicts. Beyond the fantasy of winning lost battles and regaining lost territories, the chess-playing Turk also offers a template for understanding nostalgia more generally: as an inherently unwinnable scenario that seeks to recapture a golden past.