From the northern middle-class household to the southern slave market, historians of the antebellum United States have broken through the ideological walls dividing the public and private spheres, revealing the inseparability of home and market. Less attention has been paid to the ways that elite Southern men espoused the values of paternalism and domesticity while defying them in practice through their creation and maintenance of interracial households. This article analyzes the culture of inheritance within the Simons family of Charleston, South Carolina, during the early republican period. These five Ashkenazic Jewish brothers moved from England to the Low Country in the years surrounding the American Revolution and became wealthy merchants, land speculators, and slave owners. Like the planters they emulated, they had sexual liaisons with enslaved and free women of color and kept close ties with their mixed-race children. Through the power of testamentary freedom, the Simons men openly recorded their own definition of legitimacy and expected the state to support their wishes. Their choices triggered three court battles through which African American women, slaveholding siblings, cousins, and illegitimate children battled for their share of the fortune, using ideas about dependency, racial identity, and religious affiliation to shape their appeals to the community and the courts. These cases tested the limits of property rights as a marker of kinship, legitimacy, and freedom.