My paper examines the economic, ecological, and social aspects of northern entrepreneurs in Florida’s convict lease system. In the first decades of the twentieth century, Florida leased nearly all prisoners to turpentine companies—industries that relied on the exploitation of the longleaf pine to produce valuable commodities. Moreover, many of these laborers were African Americans arrested on trumped-up charges and their only crime had been being black in the Jim Crow South. Northern investors funded many of these businesses in a system that profited public and private coffers, while heavily exploiting land and labor across the southern coastal plain. Convict camps were generally dreadful and turpentine operations pushed the longleaf pine to the brink of extinction by the late twentieth century. By examining the intersections of race, ecology, and capital, I hope to show the degree to which tensions wrought by southern industrialization took advantage of subsidized African American labor in the name of profit.