As a long-term advocate for, and practitioner of, both Paulo Freire's theory of "liberatory education" and bell hooks's "engaged pedagogy," the author subscribes to their principles of encouraging freedom of thought through active dialogue and the dialogic in an attempt to empower students by making the classroom a space that opens up to radical possibilities. Although these tenets are ideal in theory, they are not necessarily idealized in practice. The article is about a teachable moment that might have gone unnoticed and sour, when high school students came ill prepared for class one day, had it not been for two young men in the class. This article details the critical incident, illuminates the teacher's reaction and action, and discusses how students responded and then became agents of classroom change. This case study details how the incident transformed the students personally and collectively and details the teacher's growth, expanding humility, and transformation as an educator.