During the nineteenth century, the Gulf of Mexico fostered the movement of people, ideas, and news throughout the surrounding regions. Although each colony and state surrounding the basin had distinct cultures and traditions, they shared the legacy of slavery and emancipation. This study examines the transformation of labor that occurred for sugar planters in British Guiana and southern Louisiana during the age of emancipation. In this comparative project, I argue that in the 1830s planters from the British West Indies set the trajectory for solutions to the labor problem by curtailing the freedom of former slaves with Asian contract labor. Those in the sugar parishes of southern Louisiana followed this same framework in the 1860s yet it led to different outcomes. The nature of the circum-Caribbean provided opportunities for planters throughout the Gulf to observe the Asian indentured system and use a form of it in their distinct societies.