This article conducts a negative reading of Weber’s ideal type of charismatic authority, seeking to anticipate and discern hidden social interactants that are implicated in his descriptions of charismatic social processes. In so doing, this article advances the “charismatic counter-role” as an umbrella term that captures the performative bearing of a variety of actors on processes of charismatic interaction. Specifically, in addition to devoted followers (already much discussed in the literature), this typology contains unworthy challengers (competitors who fall short when judged by the new terms of legitimacy that the charismatic leader creatively establishes); and colossal players (interlocutors that are appropriately “to scale” for highlighting the extraordinary missions to which the charismatic leader aspires). Together, these charismatic counter-roles interact in ways that comprise a charismatic social system that gives a better account than has heretofore been available for the unstoppable momentum of charismatic challenges. Using the “Trump phenomenon” of 2015–2016 as its empirical source, and employing analytical tools from symbolic interactionist and performative approaches to social theory, this article has implications for future studies of how charisma destabilizes traditional and/or rational-legal social orders.