Donald Trump’s continual popularity since 2016 in the face of scandal after scandal has left social scientists to seek explanations for his political appeal. This paper extends one such explanation for his enduring support: that Trump has a charismatic appeal akin to a liturgical authority for his followers. Because much of Trump’s behavior appears repulsive, obscene, and socially unacceptable, theories of Trumpian charisma need to reconcile this apparently uncharismatic behavior with the enjoyability he creates. Trump’s charismatic appeal may appear to be something pre-ideological, some visceral enjoyment that goes beyond good and evil, but the construction of this affect needs more investigation. Drawing on the work of literary theorist Mikhail Bakhtin, this paper proposes Trump’s transgressive behavior becomes enjoyable through the aesthetic of grotesque. Like a medieval carnival, Trump’s supporters are enlisted into celebrations of disgust, ridicule, and mock divinization to challenge existing orthodoxies. These performances of obscenity and fantasy collectively mediate Trump as an intensely enjoyable and outrageous experience that his supporters can participate in.