Recent advances in positive youth development theory and research explicate complex associations between adaptive functioning and risk behavior, acknowledging that high levels of both co-occur in the lives of some adolescents. However, evidence on nuanced overlapping developmental trajectories of adaptive functioning and risk has been limited to 1 sample of youth and a single conceptualization of adaptive functioning. We build on prior work by utilizing a nationally representative sample of U.S. adolescents (N = 1,665) followed from 7th grade until after high school and using a measure of adaptive functioning that was validated in a secondary sample of older adolescents (N = 93). In using dual trajectory growth mixture modeling to investigate links between developmental trajectories of adaptive functioning and delinquency and substance use, respectively, results provided evidence of heterogeneity in the overlap between adaptive functioning and risk trajectories. Males were more likely to be in the highest adaptive functioning group as well as the most at-risk delinquency class. The magnitude of negative associations between adaptive functioning and both risk behaviors decreased at Wave 3, indicating a decoupling of adaptive functioning and risk as youth aged. These findings converge in underscoring the need to generate a cohesive theory that specifies factors that promote adaptive functioning and risk in concert.