Early modern authors, often by recourse to the game’s allegorical associations, frequently figured chess as an ethical pastime—indeed, very often as a pastime unique in the degree of its ethical valences. The allegorical dimensions of chess have their uses, but early modern chess writing presents to its readers a remarkably more complex network of ethical figurations— both, internally, to the details of gameplay and, externally, to the social setting of the gaming table itself—that aims to explore the inherently fraught relationship between virtue and stratagem. By way of illustration, we may turn to Baldassare Castiglione and Thomas More, who provide a window into this broader range of the ethical registers of chess. In The Book of the Courtier, for example, Castiglione relates the story of a chess-playing monkey who held a match with his master before the King of Portugal. After the monkey wins and the master, in an unexpected outburst, strikes him, a second match can only be arranged after much cajoling. In that contest, the monkey, “seeing that it was going to be able to checkmate the gentleman … conceived a clever way to keep from being struck again: without revealing what it was about, it quietly put its right paw under the gentleman’s left elbow (which was fastidiously resting on a taffeta cushion) and, in the same moment that with its left hand it checkmated him with a pawn, with its right it quickly snatched the cushion and held it over its head as a protection against the blows.” Castiglione has the various courtiers declare the monkey “wise, wary, and discreet” and indeed a very “doctor among monkeys.” In a less humorous and decidedly more didactic vein, Thomas More also surprises his readers with a sudden turn to chess in his Utopia. Describing the Utopians’ recreation, More relates how they “play two games not unlike our own chess.” One “is a game in which the vices fight a battle against the virtues.” The game is designed, explains More, “to show how the vices oppose one another, yet readily combine against the virtues; then, what vices oppose what virtues, how they try to assault them openly or undermine them insidiously; how the virtues can break the strength of vices or turn their purposes to good; and finally, by what means one side or the other gains the victory.”