Community violence negatively impacts the educational, social, and emotional needs of youth, particularly those living in under-resourced communities. Social and environmental influences can help youth develop resilience to this pervasive, destructive cycle of community violence. A particularly effective approach is programming that fosters positive youth development (PYD), which prepares youth to successfully adapt and function in the midst of ongoing stress and adversity such as community violence. This study examined Exploring Our Strengths and Our Future, a sport-based PYD programme empowering middle school youth to engage in their own strength-based, holistic development through sport, with a particular focus on education and career exploration and development. The purpose of this study was to examine connections between participant outcomes and programme implementation of this sport-based PYD programme, which used the Teaching Personal and Social Responsibility (TPSR) model. This programme was evaluated through multiple methods, including observational field notes, interviews, and written reflections that were analysed with deductive and inductive analysis strategies. Results suggested that meaningful life skills were learned and transferred to other domains. This was accomplished through an intentional programme climate (e.g., youth-centred philosophy, and task-oriented climate), effective leader and mentor strategies (e.g., relationships and engagement), and valuable campus visits.