This article formulates an original account of the Enlightenment through an interpretation of C. L. R. James’s The Black Jacobins, a landmark work of transatlantic anti-colonial thought. It defends a dialectical account of the Enlightenment as a singular transatlantic historical process whose content and critical import changes across space and time. In The Black Jacobins, James shows the Enlightenment’s revolutionary and emancipatory political legacy by staging the dialectic of the Enlightenment in a colonial situation defined by a slave-plantation economy. James illustrates the Enlightenment’s political legacy as a “concrete universal” that has particular and singular aspects, each with its own unique contours. In doing so, the article considers other themes at the center of both historical and contemporary political theory such as how to best conceptualize colonialism; the traveling and misplacement of Enlightened ideas; and the critical importance of the dialectical legacy and critical theory in these efforts.