In this chapter, I present narratives of two Black men who represent a population of people who are often talked about but seldom heard from in school-to-prison pipeline research. To analyze their stories, I employed a framework that centers on understanding human dignity and the conditions, circumstances, and experiences that threatened it. I found that their sense of self was eroded by moments of personal loss, disposal, and ways that even well-intentioned people marked them as "problems." I explore how their eroded sense of self led them to engage in disruptive and destructive behaviors. I conclude by discussing the importance of supplementing school-to-prison pipeline research with Black boys' and men's first-hand accounts of their own experiences as a way of humanizing the primary subjects of this burgeoning area of education research. [For the complete volume, "The School to Prison Pipeline: The Role of Culture and Discipline in School. Advances in Race and Ethnicity in Education. Volume 4," see ED661082.]