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Dozens of pirate and corsair attacks against Spain were launched from Cartagena de Indias, in Colombia's Caribbean coast, between 1813 and 1815. To the best of my knowledge, no historian has yet provided a systematic account of these events. Based on documents scattered throughout the Atlantic world (Colombia, Cuba, Jamaica, France, Spain and the United States), my paper will offer an analysis of the social world behind this late chapter of piracy in the Americas. I will explore the social origins of the sailors in the service of Cartagena, as well as something of their political culture and their connections to various revolutionary events, traditions and enclaves. This exploration, in turn, casts light on the life of Cartagena as an independent State lasting from 1811 to 1815, the first one in the region to break with the monarchical power of Spain. Most of the sailors turned anti-Spanish privateers came from the “masterless Caribbean,” a world of maritime runaways and free people of color who enjoyed autonomy at sea through their work in coastal boats and sailing ships. Their experiences seem to reveal new connections between the Haitian Revolution and the South American Independence movements.