Child maltreatment is strongly associated with adolescent psychopathology and substance abuse and dependence. However, developmental processes unfolding from childhood into adolescence that delineate this trajectory are not well understood. The current study used path analysis in a structural equation modeling framework to examine multiple mediator models, including ego control, ego resiliency, and internalizing and externalizing symptoms to investigate this developmental process. Participants were 415 children, assessed across 3 waves of data, (i.e., at ages 7 to 9, 10 to 12, and 13 to 15). The sample included maltreated (n = 259) and nonmaltreated (n = 156) children; groups were comparable in sociodemographic characteristics. Findings support an transactional-ecological model by revealing a developmental sequence in which severity of early childhood maltreatment potentiates less adaptive childhood personality functioning, followed by externalizing problems in preadolescence, and ultimately adolescent cannabis abuse and dependence symptoms. A developmental pathway from child maltreatment to adolescent cannabis abuse and dependence symptoms via personality and preadolescent internalizing problems was not supported. Understanding developmental pathways by which maltreatment experiences increase risk for substance abuse and dependence symptoms in youth has far-reaching implications for the treatment and prevention of substance use disorders.