Families facing significant stressors may be particularly vulnerable to less adaptive adolescent-caregiver communication, which can foster adolescent oppositional defiant behaviors (ODB). Black adolescents with high body weights (i.e., Body Mass Index [BMI] ≥ 95th percentile) face a myriad of intrapersonal and interpersonal stressors. However, the developmental assets model suggests that adolescent assets (i.e., positive characteristics and resources) may disrupt negative associations between risk factors and negative outcomes. The present study uses a strengths-based approach to assess whether adolescent assets strengthen or weaken the relation between adolescent ODB and adolescent-caregiver communication among Black adolescents with high body weights. Black youth aged 11–17 years and one of their primary caregivers (N = 64, 32 adolescent–caregiver dyads) were recruited from a healthy lifestyle clinic at a Midsouth pediatric hospital. Youth completed in-person interviews, while caregivers completed questionnaires assessing adolescent ODB, adolescent assets, and adolescent–caregiver communication. Two moderation models were conducted to examine associations between ODB and communication, with adolescent assets as a moderator, based on adolescent- and caregiver-report, respectively. The adolescent moderation model was significant, and the interaction between ODB and assets was significantly associated with communication. In the caregiver moderation model, the interaction effect was nonsignificant. Overall, assets were associated with adaptive adolescent–caregiver communication and acted as a buffer among Black adolescents with high body weights. Study findings highlight the potential value of strengths-based interventions among adolescent–caregiver dyads in which challenging communication or behavior exist.