During the 2016 US presidential campaign, historians and other scholars of fascism explored the question of whether the Trump phenomenon was fascist in nature. Following the election, Elizabeth Heineman developed a course to investigate these writings in tandem with a close inspection of historical fascism in the German case. The course coincided with the first months of the Trump presidency, inviting discussion not only of ideology and popular appeal, but also of specific developments in the young administration. Students were challenged to think critically about the uses of historical analogy in a politically charged setting. Presenting the voice of a student, William Simpson, “When History Meets Politics” highlights the importance of discussions that happen beyond the instructor’s hearing. Simpson’s account underscores the potentially transformative experience of well-structured debate among students with opposing viewpoints, each committed to deep reading and careful thought about both history and present-day politics.