This article places the labor contracts signed in Tennessee by landowners and freedmen at the center of a study of a paradox of freedom in the United States. The text argues that freedmen’s health – which included medical care, sustenance, and physical protection – was negotiated during and after the Civil War with the goal of subjugating the interests of blacks, the state, and landowners to an ideal of social relations of production governed by freedom, law, and the market. Through an examination of labor contracts and their medical clauses, the article revisits the medical-political approach that has repeatedly led historians to the failure of Reconstruction. It also places the black family in the process of emancipation and production through contracts and a rereading of the “culture of dissemblance” proposed by historian Darlene Clark Hine over thirty years ago. Finally, the article moves away from a reading that reduces contracts to the oppression blacks faced after the Civil War. As additional input, the article invites an examination of the debates over citizenship that followed the ratification of the Thirteenth Amendment.