With data from the middle cohort of the Pittsburgh Youth Study, a prospective longitudinal study of inner-city boys, we examined whether Big Five agreeableness facets could be reliably recovered in this sample, and whether facets predicted educational, occupational, social, and antisocial life outcomes assessed a decade later. Caregivers described their adolescent boys’ personalities using the Common California Q-Set; twelve years later, participants were interviewed and court records were obtained. Factor analyses recovered two facets: compliance and compassion. Compliance predicted more schooling and lower risk of unemployment, teenage fatherhood, and crime; compassion related to longer committed relationships. Findings highlight the value of studying personality at the facet level.