This chapter seeks to integrate the concept of the trickster into scandalogy research to explore how such disruptive, transgressive, and subversive strategies align with the commercial interests of modern media organizations This chapter serves as a starting point for developing a conceptual framework for making sense of media societies in which scandals are normalized and accepted as part of popular culture. Arguably, it is critical to understand how the role of the trickster influences the dynamics of today’s media environment, as well as the objectives of media companies that provide tricksters with a bully pulpit during times of transition and uncertainty.