Growth mixture modeling was used to identify distinct trajectories of externalizing behavior for youth (N = 647) across the period 10 to 16 years of age. Four trajectory classes were identified: Low-Stable, Mid-Increasing, Borderline-Stable, and Chronic-High. Relations of the identified trajectories with parental incarceration, parent–child relationships, trauma, and parenting as well as future substance use and criminality were then examined. Children of incarcerated parents were underrepresented in the Low-Stable trajectory and overrepresented in the Mid-Increasing group. However, nearly 60% of the children of incarcerated parents were best represented by the low-risk trajectory. The trajectory classes differed significantly on many of the preadolescent measures, such as parent–child relationships and trauma, as well as on adolescent delinquency, adult criminality, and substance use. The Mid-Increasing, Borderline-Stable, and Chronic-High trajectory groups showed significantly higher levels of early risk factors and problematic outcomes than the Low-Stable trajectory group. Implications for practice are discussed.