The intention of this research is to bring us to Worcester, Massachusetts, New England's second largest city, to critically investigate the punitive patterns that exist in the "second chance" opportunity structure experienced by young people who have been dropped-out of schools. The conceptual framework I've constructed pulls from developed theories on the relationship between structural processes, institutional practices and lived experiences of marginalization. There is a need to understand how the process of school leaving, the label of "dropout," and the pursuit of second-chance opportunity are connected and exercise forms of punishment that have clear messages about the worth of these young men's aspirations and the value in fostering support for their opportunities. This critical ethnography introduces the narratives of four young men, marginalized by race and class, whose pursuits of alternative education pathways in Worcester, MA lead them towards constructing an inclusive opportunity on one's own terms. My assertion here is that the social issue is not exclusively about "dropouts," but about the relationships our schools, neighborhoods and society at large have on creating the enabling conditions of opportunity for our most marginalized students.