This essay examines English Renaissance chess manuals in order to understand why chess, a game that encourages subterfuge and stratagem, was nonetheless figured as the paradigmatic example of a virtuous pastime. Particular attention is given to da Odenara Damiano’s The Pleasaunt and Wittie Playe of the Cheasts (1564), Arthur Saul’s The Famous Game of Chess Play (1614), and Greco’s The Royall Game of Chess Play (1656).