This essay ties together some key elements of a maritime existence – indulgence, mercy, pretence, prerogative, plunder, homicide – and contrasts them with the growing importance among commercial societies of contract, justice, rights, the legal alienation of goods, and the punishment of those who take what is not theirs. And then it measures Defoe’s adherence on the one side to what amounts to a state of war, and on the other to a state of civil society. It comes as a surprise to find that Defoe, author of The Compleat English Tradesman, entertains opinions about sovereignty that are far from being commercially orthodox. The moment when the pirate Bob Singleton becomes aware that he can exercise the prerogative either of absolute power, and kill his captives, or of mercy, letting them live and even healing their wounds, marks the end of his feelings of guilt and uselessness, and the access of an ecstatic kind of self-discovery, a sort of sublime caprice.