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Painted in 1582, Giacomo Vighi’s portrait of Carlo Emanuele of Savoy is unusual for showing an aristocratic youth with a dwarf attendant. The ten-year old son of Duke Filiberto Emanuele and his wife Duchess Marguerite de Valois, the princeling appears with his diminutive sidekick in a sparse interior with red and black tiled flooring. As this paper argues, the floor has been configured to evoke a chessboard with the two figures appearing as pieces in a game of “living chess.” While this conceit reflects the popularity of chess among the nobility in the Renaissance, it also pays homage to an important treatise on chess that presented the game as a metaphor for battle and for rulership. In the portrait the chess topos was thus used in the service of the duke’s military and royal pretensions, while duly acknowledging Marguerite’s French pedigree as the daughter and sister of French kings.