The Annapolis Police Athletic League (PAL) was established as an initiative to prevent juvenile delinquency by fostering positive relationships between at-risk youth and law enforcement. The study explored the effectiveness of the PAL program using a generic qualitative research approach informed by the CIPP evaluation model. Semi-structured interviews with police officers and volunteer mentors involved in the program provided insight into the program’s implementation, outcomes, and its influence on youth crime prevention in the Annapolis community. The findings from this study contribute to a deeper understanding of community-based crime prevention and the role of law enforcement in promoting pro-social attitudes among at-risk youth. This research addressed gaps in evaluating juvenile crime prevention programs and offers a framework for assessing the long-term impact of police-youth engagement on delinquency rates.