From 1816 to the 1830s, the islands of St. Eustatius, Saba, St. Thomas, St. Maarten, and St. Barts were actively engaged with illicit trade in ships, prize goods, and the transatlantic slave trade. Ships’ crews, governors, and merchants took advantage of the islands’ physical, political, and legal environments to effectively launder goods, ships, and people that were actively involved in these activities. St. Thomas stands out due to the longevity of its status as a regional and international hub for illicit trade at the end of Atlantic and Caribbean privateering and piracy. Within this social and political environment, this paper will unveil the tensions between international, regional, and local interests that drove merchants and colonial officials on St. Thomas to engage with illegal transatlantic slave traders, privateers, and pirates, during the early nineteenth century. Secondly, this paper will reveal the processes through which these relations occurred.