This lecture draws on my experience of teaching a course on the History of American Conservatism almost every year since 2010, the year the Tea Party Movement made its momentary splash on the American political stage. Each year I have made slight changes to the course in response to new issues that have emerged on the political scene. The election of 2016, however, forced me to dramatically rethink how I approached this class. Topics in the history of American Conservatism that I had once considered fairly marginal (like the history of America First isolationism or the John Birch Society, to take just two examples) now appeared to have played a far more important role in shaping the nation’s political culture. As Trump’s opponents in both the Republican and Democratic parties made ever more strenuous arguments in defense of longstanding institutions like the press, the courts, regulatory agencies, international alliances, and the intelligence community, it made me reconsider whether it even made sense to use the term “conservative” to describe the current Republican administration. Were contemporary progressives and moderates the ones most eagerly seeking to conserve the nation’s political traditions and institutions, and were they thus the true inheritors of the American conservative tradition? And if that was the case, how do we explain why most Americans who called themselves “conservative” voted for Donald Trump? Amidst all of this terminological confusion, we are left to wonder what words like progressive, moderate, and conservative even mean, in both a contemporary and a historical sense. This talk will discuss how the scholarship on the history of American conservatism has evolved since the early 1990s when the field first emerged. It will also offer some thoughts on how the present shapes the ways historians view the past, both as scholars and as teachers.