Intergenerational risk within families, stemming from familial history of mental health problems and encompassing exposure to childhood adversity, poses challenges to adolescent adjustment. However, it is important to recognize that negative developmental outcomes associated with intergenerational risk are not inevitable. To better understand resilience in this context, there is a need for studies that systematically compare different models of resilience. Further, few studies have estimated what level of adjustment should be expected for youth with high intergenerational risk but also a diverse set of strengths and competencies. Here, an intergenerational risk pathway and compensatory and protective resilience models were evaluated in the Future of Families and Child Wellbeing Study (N = 4,897, 52% female, 49% non-Hispanic Black at the age 15 assessment). The link between history of mental health problems in maternal grandparents and adolescent maladjustment (depressive symptoms, substance use, delinquent behavior, and troubles at school) was serially mediated through maternal mental health problems and its association with children's exposure to adversity. Data-driven trajectory analyses identified participants characterized by increased exposure to multiple types of adversity across childhood. Chronic exposure to multiple adversities, in turn, predicted increased adolescent maladjustment. Yet, resilience factors, including childhood social skills, perseverance, and connectedness at school, effectively offset intergenerational risks. Adolescents with high intergenerational risk who experienced high levels of these childhood assets demonstrated adjustment that was comparable to their average-risk and low-risk peers. These findings advance our understanding of pathways of intergenerational risk and provide new evidence for a compensatory model over a protective model of resilience. (PsycInfo Database Record (c) 2025 APA, all rights reserved).