The prospective relations between perceived racial discrimination (PRD), assessed at 4 different time periods from childhood through adolescence, along with assessments of PRD from the police ("hassling"), and self-reports of arrest and incarceration at a mean age of 24.5 years, were examined in a sample of 889 African Americans from the Family and Community Health Study. Multiple covariates were included in the analyses (e.g., academic orientation, socioeconomic status, self-control). Structural equation modeling revealed relations between PRD, especially that assessed in childhood, and both arrest and incarceration reported in adulthood. Mediators of these relations included deviant affiliation and self-reports of both substance use and illegal behavior. PRD from the police directly predicted subsequent illegal behavior. Racial pride moderated reactions to both types of PRD: Persons high in racial pride reported more illegal behavior after PRD from police but less illegal behavior in the absence of perceived police discrimination and less illegal behavior overall. Finally, childhood PRD, but not adolescent PRD, directly predicted incarceration that occurred up to 14 years later, and it did so when controlling for arrest, self-reported illegal behavior, and other covariates. The importance of childhood PRD experiences and possible avenues of intervention suggested by the pattern of results are discussed. (PsycInfo Database Record (c) 2020 APA, all rights reserved).