This dissertation argues the South’s system of Jim Crow segregation, exploitation, disfranchisement, and violence was both embedded in and evolved through the successive reorganizations of the region’s forests. In turn, it tells a three-hundred-year history of black resistance and resilience in the forests of the Deep South. In the longleaf pine and bottomland hardwood forests along the Gulf of Mexico, water proved just as important as soil in determining the contours of the colonial and antebellum plantation regimes. This project follows the water to show how African Americans drew on deep environmental knowledge to form maroon communities in the colonial era, create a free, politically engaged Afro-Creole culture in the antebellum period, and build successful farming communities after Emancipation. From New Orleans to Mobile, African Americans deployed skills in shipbuilding, sailing, agriculture, and cattle herding to engage in trade that brought them to ports like Havana and Tampico. These economic relationships created enduring patterns of black land ownership on the coast. The deep history of African American autonomy along the forests of the Louisiana and Mississippi Gulf Coast – an area I define as the Piney Woods Littoral – makes the region an opportune space in which to analyze the ways in which environmental relationships inflected the economic, legal, and political history Jim Crow. While this study shows how white supremacy hastened the collapse of the Deep South’s forests just as reforestation perpetuated Jim Crow, it also broadens our understanding of the connections between human domination and environmental change. Some of the most important battles over race and the rights of citizenship in the South, from the 1875 and 1890 Mississippi Plans to Plessy v. Ferguson (1896), were part of broader contests over land and access to resources between white and black farmers, planters, and industrialists. Twentieth century efforts to transform Gulf Coast politics and modernize its economy helped break the environmental connections that had long supported African American self-determination. In turn, they inscribed patterns of inequality on the landscape that persisted well beyond the passage of the Civil Rights Act of 1964.