The US has one of the most inequitably funded school systems and the largest prison population in the industrialized world. These two factors help to construct what is known as the school to prison pipeline. The past 30 years has included punitive policies within schools and the criminal justice system that have resulted in a disproportionate number of Latino and African-American youth being suspended from school, dropping out, and/or incarcerated. In this article, the lived experiences of incarcerated youth framed by institutional policies within prisons and schools are discussed. In total, fifteen interviews with incarcerated youth who spontaneously discussed drug trafficking were analyzed using criminological theory. A key theme for many youth was how a lack of educational opportunity and success shifted their focus to attaining economic opportunities through drug trafficking. Policy implications are discussed relating to school and corrections funding along with the costs to society.