This article considers the relationship between historical and fictional accounts of piracy, and relates them to contemporary issues about the legitimacy of states and global business. I begin by showing how privateers were gradually distinguished into pirates and navies. At the same time, the pirate becomes a character in the popular imagination, a 'trickster' figure on the side of the people, and against authority.The second main section of the paper moves from 'histor y' to 'representation' and shows how the image of the pirate moved from a wild character on the edge of the world, to a stock cliché for Hollywood swashbucklers. I then investigate the legacy of radical histories and representations of piracy, focusing particularly on the idea of alternative organization on the ship and the pirate utopias on the land. The final section pulls together the historical figure, the stock character and the radical rogue in order to suggest that the pirate can mean what we want him (or to her) to mean. Nonetheless, the biggest historical irony is that the golden age pirate emerges at the beginnings of international business, and is only wiped out when the state and the businessman strike an alliance that lasts to the present day.