African American (AA) adolescent girls are at heightened risk for HIV and sexually transmitted infections (STIs), and thus knowledge of factors related to risky sexual behavior in this population is crucial. Using Social Learning Theory (Bandura, 1977), this paper examines pathways from female caregivers' risky sexual behavior and substance use to adolescent girls' risky sexual behavior and substance use in a sample of 214 low-income, urban AA female caregivers and daughters recruited from outpatient mental health clinics in Chicago. Structural equation modeling (SEM) revealed that sexual risk reported by female caregivers was associated with adolescent sexual risk, and illicit drug use reported by female caregivers was related to adolescent-reported substance use, which was in turn associated with adolescent-reported sexual risk behavior. These findings suggest that female caregivers' sexual behavior and substance use both relate to girls' sexual risk. Thus, results emphasize the role of female caregivers in transmitting risk. (Contains 3 tables and 2 figures.)