This study presents the prisoner and prison staff ideographic experiences of an English initiative which aimed to use sport as a way of engaging young men in identifying and meeting their reentry (or "resettlement") needs in the transition from prison custody to the community. Young men aged between 18 to 21 years old (N = 79) participated in the prison-based sporting "academies" and the qualitative findings demonstrated how the initiative led to perceived benefits in terms of a positive impact on prison life and culture, preparation for release, improved attitudes, thinking and behavior, and in promoting desistance from crime. The results help to delineate how and why sports based interventions can motivate imprisoned young offenders in reentry programs, with the ultimate aim of reducing reoffending.