Hegel’s remarks on Africa in the Lectures on the Philosophy of World History are notorious among critics and defenders alike—in particular Hegel’s claim that the Atlantic slave trade, while unjust, was superior to native African slavery and thus should be abolished only gradually. Joining an ongoing conversation in black studies interrogating freedom’s status as a structuring desideratum of critical and political practice, I argue that for Hegel, the European enslavement of Africans was essentially an emancipatory project that would rescue the Negro from his impenetrability to world spirit and introduce him to the long dialectical march of world history. Specifically, I argue that Hegel’s distinction between Atlantic and African slavery reprises his distinction between good and bad infinity in his Science of Logic. As the case of slavery illustrates, however, neither distinction holds. Hegel could imagine no freedom for the Negro except in the form of infinitely more slavery—the slave labor of the negative through which the Negro would (never) become free. In such a project, freedom remains forever on the dark side of a middle passage. These conclusions challenge us to consider what radical politics without a concept of freedom would look like.