The short-run deleterious effects of gang involvement during adolescence have been well researched. However, surprisingly little empirical attention has been devoted to understanding how gang involvement in adolescence influences life chances and criminal behavior in adulthood. Drawing on the life-course perspective, this study argues that gang involvement will lead to precocious transitions that, in turn, will have adverse consequences on the fulfillment of adulthood roles and statuses in the economic and family spheres. Moreover, problems fulfilling these conventional roles are hypothesized then to lead to sustained involvement in criminal behavior in adulthood. Using data from a sample of males from the Rochester Youth Development Study, results from structural equation models support the indirect link between gang membership and noncriminal and criminal outcomes in adulthood. Specifically, gang involvement leads to an increase in the number of precocious transitions experienced that result in both economic hardship and family problems in adulthood. These failures in the economic and family realms, in turn, contribute to involvement in street crime and/or arrest in adulthood. Implications for the criminal desistance process are discussed.