Want to be cunning? You might wish you were more clever, more flexible, able to cut a few corners without getting caught, to dive now and again into iniquity and surface clutching a prize. You might want to roll your eyes at those slaves of duty who play by the rules. Or you might think there’s something sleazy about that stance, even if it does seem to pay off. Does that make you a chump? With pointedly mischievous prose, Don Herzog explores what’s alluring and what’s revolting in cunning. He draws on a colorful range of sources: tales of Odysseus; texts from Machiavelli; pamphlets from early modern England; salesmen’s newsletters; Christian apologetics; plays; sermons; philosophical treatises; detective novels; famous, infamous, and obscure historical cases; and more. The book is in three parts, bookended by two murderous churchmen. “Dilemmas” explores some canonical moments of cunning and introduces the distinction between knaves and fools as a “time-honored but radically deficient scheme.” “Appearances” assails conventional approaches to unmasking. Surveying ignorance and self-deception, “Despair?” deepens the case that we ought to be cunning–and then sees what we might say in response. Throughout this beguiling book, Herzog refines our sense of what’s troubling in this terrain. He shows that rationality, social roles, and morality are tangled together–and trickier than we thought.