I argue that early reformers viewed prisons as institutions that complimented processes of emancipation. My paper traces the concurrent development of emancipation and incarceration, highlighting the overlap of penal reform and early abolitionism, demonstrating that prison was central to reformers’ vision of a free-labor society, and suggesting that historical understandings of black freedom in the early republic need to incorporate structural unfreedoms such as the penitentiary that accompanied abolition in New York. I then discuss the broader New York context in which white European immigration and the policing of black communities conspired to institutionalize black economic marginality and widespread incarceration. Finally, I compare the denial of mobility inherent in incarceration with diasporic geographies discernable in the lives of Newgate’s black inmates. The presence of black cosmopolitans from the Caribbean, Africa, Europe, Canada, and the U.S. South suggests that black New Yorkers’ understanding of freedom was more sophisticated and diasporic than is generally understood. In closing, I ask whether “freedom,” as we have come to understand and theorize this term, adequately characterizes the exigencies of black mobility, political identity, and the complicated transition from slavery to a free-labor society.