In the mid-nineteenth century, Frederick Douglass changed his opinion on the proslavery character of the U.S. Constitution. Most scholarship seeks to locate the core of Douglass’s politics in the critical patriotism of his post-change of opinion oratorical and literary output. However, if we keep the occasion for Douglass’s change of opinion firmly in view, that is, his critical engagement with the question of the pro- or antislavery character of the Constitution, there is a possibility not only of appreciating an experience of crucial significance to the development of his politics, but also of relocating the core of his politics in an ongoing ambivalence about the “moral power” of the United States. This chapter situates Douglass as a political thinker participating in a transatlantic paradigm shift in the rhetoric of sociopolitical change, a shift that gave rise to a new modern dilemma as to which form of change, reform or revolution, best suited one’s problem-solving needs.