On the surface, this book seems to be in the genre of cultural history, the history of an idea (Machiavellian maneuvering). But wait a minute! Isn’t Machiavellian maneuvering a timeless fact of life for us humans? Isn’t the idea of a history of cunning as odd as the idea of a history of sexuality? There’s the rub. It turns out that how we think about cheats and scoundrels has a history, and one can’t quite view it in the same way again once this comes to light. More: not only do our assumptions about scoundrelhood reflect a history, but they don’t stand up to critical scrutiny (the author’s beautiful final story of the gulled murderer at the end illustrates this, but I don’t want to spoil it for you by explaining it here). More: dubious assumptions about scoundrelhood are lurking in the deep background of how slews of people today think about rational choice, philosophy of social science, and the nature of morality, and though the author does not lean heavily on this point, if the reader is aware of what, say, economists think rational self-interest is, the implications of the critical history of scoundrelhood for all kinds of projects is quietly devastating. This agenda, if it is his agenda, sneaks up on you in the course of what you might think is just a really fun sequence of anecdota, revealing him as a stealth philosopher. The stealth philosopher seems also revealed in the very quiet undercurrent of insistence that we rethink our assumptions about morality, selfishness and deceit, and acknowledge them, and human life more generally, as the cussedly complex, theory-defying things that they are. Yet this touches the reader on a more intimate level–are you sure you are a good person? How do we draw the boundaries between dupe and knave? Can we? The author provides no answers, only lots of really uncomfortable questions. Last but not least, all of this is presented in one of the most delightfully wicked, jazzy, clever, fun prose styles I have ever encountered. There is a kind of brilliantly improvisational quality to the book which makes it a joy to read. The better to sneak up on you with its deeper concerns, sowing seeds of doubt that we know what rationality and irrationality, honesty and deceit, good and evil, really are. How very cunning.