The Black antislavery theorist Quobna Ottobah Cugoano (c.1757–c.1791) is increasingly recognized as a noteworthy figure in the history of philosophy. Born in present-day Ghana, Cugoano was enslaved at the age of 13 and shipped to Grenada, before being taken onwards to England, where the 1772 Somerset court ruling in effect freed him. His Thoughts and Sentiments on the Evil of Slavery [1787/1791] broke new ground by demanding the immediate end of the slave-trade and of slavery itself, without any compensation to (...) slaveholders. Notwithstanding this, Cugoano endorsed the legitimacy of penal enslavement on principled grounds – like many other abolitionists writing in late eighteenth-century Britain. “Every free community might keep slaves, or criminal prisoners in bondage” – and even sell them. Amidst the growing literature exploring Cugoano’s abolitionism, his paradoxical justification of penal slavery has bewildered commentators. Far from an offhand inconsistency, I argue that this justification is deeply embedded within his moral and legal philosophy; constraining his antislavery arguments while simultaneously serving retaliatory aims. His two-pronged principle of just punishment – the lex talionis (‘eye for an eye, bondage for bondage’) as tempered by mercy – sometimes demands penally enslaving colonial slaveholders and slave-traders in turn. Throughout, I compare Cugoano’s justification of penal enslavement with those of other early modern philosophers, especially Locke and Kant. This helps me position Cugoano within the history of philosophy, thus making his views more accessible to a wider philosophical audience. It also indicates just how deeply theories of punishment shaped philosophical thinking about penal bondage in the period. (shrink)