Born on the brink of emancipation, Coleman and Davis grew up watching their parents’ generation move from plantation to plantation, from country to town, using their newfound “freedom” to find, in Nell Painter’s words, “real freedom.” As adolescents, they witnessed the foreclosure of opportunities across the South and were attracted to nearby Indian Territory. The subsequent moment of African American participation in the appropriation of Indian Territory was tellingly short-lived, ending abruptly with Oklahoma statehood, Jim Crow segregation, and oil speculation. This paper narrates the post-emancipation migration and settlement of African Americans from the Deep South to Indian Territory and West Africa. That so many migrants attempted to move decisively beyond the borders of the United States following Oklahoma statehood underscores the notion that part of what attracted African Americans to Indian Territory in the first place was its momentary status as a political and economic space on the margins, if not beyond the bounds, of U.S. oversight.