Studies of predictors of development of young men of color have been primarily focused on factors that impede positive development rather than factors that promote it. There are also few examples of longitudinal studies of positive development of this population and few that consider multiple protective factors simultaneously. Little is also known about how such positive outcomes might relate to prediction of problematic functioning. This study tests a developmental–ecological framework of positive and risky development among a sample of young men of color growing up in high-risk urban environments. African American and Latino adolescent males (148 African American, 193 Latino) were followed from early to late adolescence. Stress in early adolescence was related to school engagement and prosocial values as well as depressive symptoms and problems assessed 2 years later. The role of family and individual protective factors as direct effects and as mitigating the stress–outcome relation were also tested. Stress predicted problem outcomes but not positive functioning. Early engagement in prosocial activities and coping skills did predict positive outcomes. In contrast, problem outcomes were predicted directly by stress, with some indication of interaction with some protective factors for both such outcomes. Overall results suggest value in focusing on positive outcomes along with negative outcomes, as they are not the antithesis and have some shared but some different predictors. Implications for supporting positive development are presented.