Max Weber has typically been regarded as a central thinker in the liberal tradition of social analysis. At the same time, critics have long noted how his democratic commitments were compromised by his nationalism. Drawing on existing criticism, I discuss the importance of charismatic leadership in Weber’s thought and its implications for his understanding of the process of democratization. Reconstructing core concepts in Weber’s political thought, I analyze how Weber’s concept of plebiscitarian leadership unites charismatic domination with nationalism and skepticism concerning effective democratic politics. I show how Weber’s concept of plebiscitarian rule grew from deeply held political values and his engagement with German politics. I then generate propositions regarding the problem of democratization in regime transitions and apply them to contemporary charismatic leaders and ethno-nationalist mobilization in post-Communist transitions. I argue that as much as it anticipates the central dilemma of charismatic solutions to political crisis, Weber’s thought favors nationalist and plebiscitarian responses to democratization that have been largely discredited by historical experience.