The British, French and Italians carved the Red Sea into spheres of influence during the imperial era, which set the stage for the rise of a host of smugglers, outlaws and rogues who the colonial powers lumped together as 'pirates.' The pirates occupied what the imperialists – and later scholars – described as extra-territorial space, where no single power was sovereign. While the imperialists characterised extra-territorial, maritime space as anarchic, contrasting it with orderly, sovereign space, I argue the division is artificial. The pirates fostered commercial disorder and inter-imperial rivalries over extra-territorial space to defy the imperialists' attempts to regulate the sea. The pirates took imperial patronage but used it to create networks, which they in turn integrated, with varying success, into the international order. I examine this link between piracy and sovereignty through the careers of four pirate entrepreneurs; Yusuf 'Ali, a renegade sultan from northeastern Somalia; the Naib of Arkikko, a renegade Ottoman-Egyptian governor in Eritrea; Henry de Monfreid, a French merchant and adventurer; and Ahmed Fetini, a Yemeni tribal elder and the leader of a network of smugglers and pirates in the Tihama. Their careers fall consecutively through the years 1860-1930 and offer a window onto the evolving political economy of imperial conquest in the southern Red Sea.