Previous analyses of data from the 4-H Study of Positive Youth Development (PYD) have examined concurrent trajectories of positive development and risk/problem behaviors among adolescents, finding complex and not necessarily inverse relationships among them. In this article, we expand on prior research by employing a person-centered approach to modeling risk behaviors, assessing development from approximately 6th grade through 12th grade among 4,391 adolescents (59.9% female). Latent profiles involving the problematic behaviors of delinquency, depressive symptoms, substance use, sexual activity, disordered eating behaviors, and bullying were then assessed for concurrent relationships with the Five Cs of PYD: Competence, Confidence, Character, Caring, and Connection. We found six latent profiles, based primarily on mental health, aggression, and alcohol use, with significant differences in Confidence levels among many of the profiles, as well as some differences in the four other Cs. We discuss directions for future research and implications for application to youth policies and programs.