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This manuscript traces the ideas and experiences of the diverse peoples who moved between the Southeast and Mexico during the nineteenth century. Based on a corpus of documents drawn from U.S. and Mexican archives, I examine how poor and elite white Southerners, enslaved and free African Americans, and Mexicans of all classes engaged in contested processes of comparing, constructing, and challenging evolving hemispheric systems of racialized, unfree labor. By illuminating Southerners' visions of themselves as members of a transnational community, I show that Southerners' conceptualizations of race and labor were not limited to the categories of “black” and “white,” nor those of slavery and freedom. Southerners considered Mexico and Mexicans as providing alternative configurations of race and labor. Ultimately, I argue that such transnational visions worked simultaneously to stabilize and to undermine Southern U.S. racial and labor systems.