Advanced age affected the performance of mastery, and some slavers saw the declining fortunes of another as providing them with the opportunity to rise at their expense. Concerns with – and contests over – the authority of aged enslavers did not end at their death. Wealth generated by slaveholding needed to be passed on, and the quest for profit and status that animated southern enslavers saw ferocious disputes erupt over the transferal of property between generations. Contests over wills and inheritance help reveal the complex and contested relations between enslavers, intergenerational tension in the American South, and shifting social hierarchies shaped by the passage of time. Antebellum enslavers prized the presumption of authority and craved respect from family, kin, and community. And yet, in legal challenges to wills, deeds, and bills of sale recorded posthumously, antebellum southerners revealed the disregard they held for aged enslavers’ claims of dominion, and their willingness to trash the reputation of fellow “masters” both before and after death.