This study 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. The formation of these images has been underpinned by challenges to, and confirmations of, chess’s status as an intellectually-superior and socially-useful game, particularly since rule changes five centuries ago. Yet, the chess-player is an understudied figure, whose many faces have frequently been obscured. No previous work has shone a light on the chess-player itself. Increasingly, chess-histories have retreated into tidy consensus. This work takes aim at the kaleidoscopic chess-player. It aspires to a novel reading of the figure as both a flickering beacon of reason and a sign of monstrosity, one looking forwards and backwards, lurking out of reach at the heart of modernity. 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 whose identity is used to articulate a number of anxieties pertaining to themes of mind, machine, and monster. Covering a wide variety of locations and individuals including Bobby Fischer, Garry Kasparov, the Automaton Chess-Player, and moving from Victorian Paris to the neo-Gothic castles of twenty-first-century New York, this work is aimed at students and researchers in the fields of cultural history, leisure and sport, and monster theory, as well as those interested in the intersection between human and machine.