This inquiry concerns the cultural history of the chess-player. It takes as its premise the idea that the chess-player has become a fragmented collection of images, underpinned by challenges to, and confirmations of, chess’s status as an intellectually-superior and socially-useful game, particularly since the medieval period. Yet, the chess-player is an understudied figure. No previous work has shone a light on the chess-player itself. Increasingly, chess-histories have retreated into tidy consensus. This work aspires to a novel reading of the figure as both a flickering beacon of reason and a sign of monstrosity. To this end, this book, utilising a wide range of sources, including newspapers, periodicals, detective novels, science-fiction, and comic-books, is underpinned by the idea that the chess-player is a pluralistic subject used to articulate a number of anxieties pertaining to themes of mind, machine, and monster.