Today, the countries bordering the Red Sea are riven with instability. Why are the region’s contemporary problems so persistent and interlinked? Through the stories of three compelling characters, 2014 IDRF Fellow Nicholas W. Stephenson Smith’s Colonial Chaos sheds light on the unfurling of anarchy and violence during the colonial era. A noble Somali sultan, a cunning Yemeni militia leader, and a Machiavellian French merchant ran amok in the southern Red Sea in the nineteenth and twentieth century. In response to colonial hostility and gunboat diplomacy, they attacked shipwrecks, launched piratical attacks, and traded arms, slaves, and drugs. Their actions contributed to the transformation of the region’s international relations, redrew the political map, upended its diplomatic culture, and remodelled its traditions of maritime law, sowing the seeds of future unrest. Colonisation created chaos in the southern Red Sea. Colonial Chaos offers an interdisciplinary approach to understanding the relationship between the region’s colonial past and its contemporary instability.