Abstract Purpose: Early exposure to multiple risk factors is known to predict involvement in criminal offending. The purpose of this study was to examine the processes responsible for this association. Specifically, the focus was on the capacity of adolescent educational experience to mediate the effect of childhood cumulative risk (CCR) on criminal offending, net of expected continuity in antisocial propensity, and behavior. Methods: Data from the Northern Finland Birth Cohort Study 1986 (n = 5743) were used to estimate a structural equation model to examine the hypothesized pathways. The educational pathway was captured by a latent variable (educational marginalization) consisting of indicators of low academic performance, weak school attachment, and low educational aspirations. Results: CCR had a strong positive relation with educational marginalization, which, in turn, emerged as a statistically significant predictor of having criminal record by age 19. Although continuity in antisocial behavior accounted for most of the total effect of CCR on criminal offending, one-third of it was mediated by educational marginalization. Conclusions: The results highlight the adolescent educational experience as a promising target of intervention in efforts to curb criminal careers among children at risk.