In this article, the authors explore the generative possibilities of risk-taking in the Catholic school English classroom. They associate pedagogical risk with what Deborah Britzman (1998) has called "difficult knowledge"--content that causes students to consider social trauma. Incorporating difficult knowledge meaningfully requires English teachers to take significant pedagogical risks, especially in the Catholic school classroom. Drawing on critical theology and Cormac McCarthy's novel "The Road" (2006) as a difficult text, the authors employ a case study looking at how the traumatic difficulty of the novel could be fruitfully taught at a Catholic school. How might students reckon with "The Road" in a way that recognizes the terrible difficulty of its subjects? How might this difficulty help them to better understand their schools, their communities, and themselves? In engaging these questions, the authors provide new possibilities for class discussion, student engagement, and assessment.