Intergenerational transmission processes have long been of interest to demographers, but prior research on the intergenerational transmission of criminal justice contact is relatively sparse and limited by its lack of attention to the correlated “family troubles” and familial incarceration that predate criminal justice contact. In this article, we provide a test of the intergenerational transmission of criminal justice contact after adjusting extensively for these factors that predate such contact by linking longitudinal data from the Project on Human Development in Chicago Neighborhoods with official arrest histories from 1995 to 2020. The results provide support for three conclusions. First, parental criminal justice contact is associated with a shorter time to first arrest and a larger number of arrests even after rigorously accounting for selection. Second, robustness checks demonstrate that neither the magnitude nor the significance of the findings is sensitive to model choices. Third, associations are strongest among White individuals and inconsistently significant for African American and Hispanic individuals. Despite large recent crime declines, the results indicate that parental criminal justice contact elevates the criminal justice contact of the adult children of the prison boom, independent of the often-overlooked troubles that predate criminal justice contact, and that these associations are strongest among the White population.