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Research has confirmed the significance of the parent-child relationship quality in mitigating adolescents’ delinquent behavior; however, there is a dearth of studies examining the impact of multi-generational relationship quality on behavior. This study investigates the extent to which the quality of the relationship between grandparents (G1) and parents (G2) affects the delinquent behavior of the child (G3). Employing three metrics of parent-to-child relationship quality (RQ)—namely, mother-child closeness, identity support, and coercive parenting—this research explores the intergenerational influence of RQ on behavioral outcomes. Utilizing data from the Toledo Adolescent Relationships Study, we analyzed parent-adolescent relationship quality between G1-G2 and G2-G3 to determine whether these associations are predictive of G3 delinquent behavior.