Theoretical approaches traditionally applied in mental health and criminal justice interventions fail to address the historical and structural context that partially explains health disparities. Community Wise was developed to address this gap. It is a 12week group intervention informed by Critical Consciousness Theory and designed to prevent substance abuse, related health risk behaviors, psychological distress, and reoffending among individuals with a history of incarceration and substance abuse. This paper reports findings from the first implementation and pilot evaluation of Community Wise in two community-based organizations. This pre-posttest evaluation pilot-tested Community Wise and used findings to improve the intervention. Twenty-six participants completed a phone and clinical screening, baseline, 6- and 12-week follow-ups, and a focus group at the end of the intervention. Measures assessed participants' demographic information, psychological distress, substance use, criminal offending, HIV risk behaviors, community cohesion, community support, civic engagement, critical consciousness, ethnic identification, group cohesion, client satisfaction, and acquired treatment skills. Research methods were found to be feasible and useful in assessing the intervention. Results indicated that while Community Wise is a promising intervention, several changes need to be made in order to enhance the intervention. Community Wise is a new approach where oppressed individuals join in critical dialogue, tap into existing community resources, and devise, implement and evaluate their own community solutions to structural barriers.