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The aim of this article is to recover and reevaluate the American tradition of constitutional skepticism. Part I consists of a brief history of skepticism running from before the founding to the modern period. My aim here is not to provide anything like a complete description of the historical actors, texts, and events that I discuss. Instead, I link together familiar episodes and arguments that stretch across our history so as to demonstrate that they are part of a common narrative that has been crucial to our self-identity. Part II disentangles the various strands of skeptical argument. I argue that the various strands share a common core. At base, all forms of constitutional skepticism rest on doubts about whether moral and political disagreement can be bridged by a legal text. Those doubts, in turn, are grounded on a rejection of global moral skepticism and on deep strands of American thought that emphasize the possibility of moral knowledge. In Part III, I very briefly suggest some preliminary conclusions about how we should view constitutional skepticism. I argue that there are reasons to think that a dose constitutional skepticism might mitigate some of our current political dysfunction.