This essay interprets Machiavelli’s famous letter to Francesco Vettori in terms of a play-element that runs across his works. The letter to Vettori is a masterpiece of epistolary form, but beyond its most memorable passage, where Machiavelli recounts his evening in study, it has not received much scholarly attention. Reading the letter in its entirety is to discover Machiavelli’s account of an eclectic political education and the pleasures of playing with others. Machiavelli’s letter speaks to a basic ludicity in his (...) political thinking, in which play is not opposed to the serious, and diverse play forms can be thought together. Hans-George Gadamer’s Truth and Method, Johan Huizinga’s Homo Ludens, and Roger Caillois’s Man, Play, and Games provide resources for reconstructing this play-element in Machiavelli’s thought. (shrink)