This dissertation studies freedom under a series of emancipations in the colony of Santo Domingo that were variously unrecorded, impotent, planned, and successful. It explains how revolutionary ideology, custom, and the emerging state influenced the freedom, enslavement, and labor of ostensibly-free people of African descent from 1768-1844. The dissertation expands what is considered an emancipation to include events in 1795, 1801, 1805, and 1822, all key moments when the future of slavery came into question. These emancipations arose as the Spanish colony fell under the political and military control of first the French Republic and later, Haiti. The dissertation shows that the colony's first three multiple emancipations descended unevenly and transformed slave-holding rather than ending it. Freedom's meaning also changed under these emancipations, as slave owners amplified racial differences to draw free and freed people of African descent back into slavery. Esclavos que fueron, those who were slaves, is how one parish priest identified freed people in the decade after the colony's final emancipation during Unification with neighboring Haiti. The experience of former enslavement in Santo Domingo marked men and women as racially different at a time when elites circulated myths of racial harmony.