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In this case study, I propose interview analyses to examine why and how people engage in criminal behaviors or desist from committing crimes. By analyzing the experiences of four male subjects coming from different backgrounds of Southern Italy, I identify several turning points and transitions that reveal the main causes that led them to commit crimes or desist from any kind of illegal activity. Among the main reasons behind the criminal engagement are family problems, peer influence, and other utilitarian reasons, while the motivation behind the desistance from criminal activities are the beginning of a romantic relationship, the approach to Catholic religion and church, enrollment at a university, the focus on a new job, and many other life events. This study was conducted to contribute to the researcher's completion of her Master's Degree requirements in Criminology and Justice at St. John's University in New York City.