Criminal punishment practices in the United States have varied greatly in severity and purpose throughout their history. Nonetheless, prison practices have retained their basis in the theories of retribution and deterrence, theories that emphasize an offender’s rational choice to commit crime and to be punished legitimately for transgressions. This criminal corrections framework is designed mainly to address and punish criminal behavior. A purely castigatory approach, however, does not sufficiently address criminal identity. Using high recidivism rates as a springboard for the case that the American criminal justice system is not effectively reforming criminals, this thesis investigates desistance from criminal activity as a process that is heavily dependent on an individual criminal’s will to change. The strength of this transformational impetus then amalgamates external factors such as accessibility of legitimate work and strength of social bonds and internal factors such as perception and identity as an offender or non-offender.