The present study was designed to shed light on specific risk mechanisms and protective factors in the relation between aggression in childhood and long-term unemployment in adulthood. Participants were drawn from the ongoing Jyväskylä Longitudinal Study of Personality and Social Development; data gathered at the ages of 8 (N = 369), 14, 27, and 36 years (n = 311) were used in the present study. Teacher-rated aggression at age 8 was related to subsequent long-term unemployment through a cycle of maladaptation. Specifically, childhood aggression predicted school maladjustment at age 14, which was both directly and indirectly (via problem drinking and lack of occupational alternatives at age 27) related to long-term unemployment. Child-centered parenting and prosocial tendencies in an aggressive child significantly lowered his or her probability of becoming long-term unemployed in adulthood.