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Between 1854 and 1864, more than a hundred free African Americans in Virginia proposed to enslave themselves and, in some cases, their children. Ted Maris-Wolf explains this phenomenon as a response to state legislation that forced free African Americans to make a terrible choice: leave enslaved loved ones behind for freedom elsewhere or seek a way to remain in their communities, even by renouncing legal freedom. Maris-Wolf paints an intimate portrait of these people whose lives, liberty, and use of Virginia law offer new understandings of race and place in the upper South. Maris-Wolf shows how free African Americans quietly challenged prevailing notions of racial restriction and exclusion, weaving themselves into the social and economic fabric of their neighborhoods and claiming, through unconventional or counterintuitive means, certain basic rights of residency and family. Employing records from nearly every Virginia county, he pieces together the remarkable lives of Watkins Love, Jane Payne, and other African Americans who made themselves essential parts of their communities and, in some cases, gave up their legal freedom in order to maintain family and community ties.