The relation between being out of school and participating in criminal economies is widely documented in the literature on youth delinquency. However, the complex connection between these two phenomena has not yet been fully unpacked. This paper draws from two studies that we, the authors, conducted separately to explore the role educational experiences play in shaping the delinquent trajectories of male youth who participate in the drug business in urban centers located in Mexico and Colombia. The first consists of in-depth interviews and surveys conducted in Ciudad Juárez, Mexico, while the second is based on long-term ethnographic engagement in Medellín, Colombia. We provide unique insights into the educational experiences of this hard-to-reach population and find that economic hardship does not wholly explain why these young people leave school and engage in delinquent activities. These youth do not "drop out" of school in search of money; rather, they are "pushed out" by a vicious cycle of stigmatization, segregation, punishment, and exclusion. By exploring these dynamics in two cities that have waged long drug wars, this article furthers understanding of the nexus between crime-related violence and educational experiences, thus making an important contribution to the field of education in emergencies.