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This chapter traces a genealogy of the two predominant interpretations of African colonization—the anti-imperialist interpretation and the return-to-Africa interpretation—to the late eighteenth-century writings of Phillis Wheatley and Olaudah Equiano. It argues that African colonization was, at its black diasporan foundations, a site of more equivocal thought about how to live a free life in the Atlantic world than either interpretation grants. It then turns to the epistolary archive of common black settlers in order to show how their reflections on “return” and “the natives” offer a speculative body of thought about living unsettled lives. The archive shows that living free in Liberia could mean ongoing, improvised encounters with the legacies of chattel slavery; fragile and volatile interactions between settler and native; a life on the brink of death, as well as a death haunting life itself; and a future sought skeptically and critically.

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