This Article addresses the deviance of interracial sexuality acknowledged in testamentary documents. The language of wills calls into question the authority of probate and family law by forcing issues of deviance into the public realm. Will dramas, settled in or out of court, publicly unearth insecurities about family. Many objections to the stated intent of the testator generate from social prejudices toward certain kinds of interpersonal relationships: nonmarital, homosexual, and/or interracial. When pitted against an issue of a moral or social transgression, testamentary intent often fails. In order for these attacks on testamentary validity to succeed, they must be situated within an existing juridical framework that supports and adheres to the hegemony of denial that refuses to legitimate the wishes of the testator. Disinherited white relatives of white testators regularly challenged wills disposing a majority of an estate to paramours and children of African descent. In the nineteenth century, testators who eschewed traditional devises to spouses, relatives, and institutions in favor of mistresses, slaves, or both often incited will contests of testamentary incapacity, undue influence, or fraud. This Article is a case study of In Re Remley, an antebellum will contest between disinherited white collateral heirs and the intended black and mulatto devisees. It retains timeless value in its demonstration of the incompatibility of testamentary freedom and social deviance. I conclude that subjective conceptions of kinship, in particular those unpopular relationships that defy social norms, prevent the idea of testamentary freedom from reaching diverse articulations of family.