The present study investigates the relationship between childhood placement in special education and adult well-being among 1,377 low-income, minority children participating in the Chicago Longitudinal Study. Roughly 16% of the sample received special education services in Grades 1 to 8. After accounting for sociodemographic factors and early academic achievement, children receiving special education services tended to have lower rates of high school completion and fewer years of education, as well as greater rates of incarceration, substance misuse, and depression. Eighth-grade academic achievement significantly mediated the association between childhood placement in special education and adult well-being outcomes. The study contributes to the literature by providing support for a pathway from childhood special education placement to adult outcomes among an inner-city minority cohort.