This chapter argues that Adam Smith's moral theory and political economy confront human ambivalence about risk, by now a permanent feature of the human condition. Smith's analysis of individuals, groups, institutions, and policies leads him to find that human beings have a risk-loving side, which drives them to take chances to pursue gain, but that they also clamor to secure themselves against possible loss. How well they balance these two impulses can, Smith argues, issue in productive or dangerous approaches to risk taking. Moreover, Smith's critique of monopolies and mercantile policies depends very much on his view that traders exploit risk badly, by redistributing or jettisoning loss. Smith argues that those who pursue highly uncertain profits by taking risks in the political economy must also be willing to brook loss.