This is a study of the losers in three major episodes in American political history and shows how their ideas ended up, at least partially, winning, in the long run. The authors consider the campaign of the anti-Federalists against the adoption of the Constitution; the failed presidency of Andrew Johnson; and the defeat of Barry Goldwater in 1964, as political losses that later heavily influenced American politics later. Sometimes the losers, because they articulate a vision of American government that resonates with some part of America, later contribute to a new political order. This is not an effort to explain winning or losing in American politics. Rather, it is intended to offer a new understanding of American political development as the product of a kind of dialectic between different political visions that have opposing ideas, particularly about the size and role of the federal government and about whether America is exclusively a liberal regime or one in which illiberal ideas on topics such as race, play an important role.