A strong link exists between exposure to violence and drug use, yet their simultaneous development is less understood. This study utilizes multi-trajectory modeling to investigate the dynamic relationship between violence exposure and drug use among justice-involved male adolescents. Using a sample from the Pathways to Desistance study ( n = 1,095), we identify five group trajectories of violence exposure and drug use; “Chronic Low” (39.2%), “Resisters” (17.6%), “Accelerators” (13.9%), “Desisters” (22.2%), and “At-risk” (7.1%). Multinomial logistic regression analysis examines individual, social, and environmental risk factors predicting trajectory group membership. Results highlight the need to address cumulative vulnerabilities shaping outcomes among high-risk adolescents. We conclude by discussing the importance of drug treatment and intervention strategies to foster positive outcomes for justice-involved youth.