This study examined the association between perceived family economic stress, quality of father–son relationships, and depressive symptoms among African American adolescent fathers. Data were collected during pregnancy from 65 African American adolescents who were first-time fathers, ages 14–19. Results from multiple regression analyses indicated that higher paternal relationship satisfaction was associated with fewer depressive symptoms among adolescent fathers. Additionally, depressive symptoms were higher among adolescent fathers who reported experiencing higher levels of conflict with their fathers. Further, paternal conflict moderated the effect of perceived family economic stress on depressive symptoms. That is, among adolescent fathers experiencing low levels of conflict with their fathers, high perceived family economic stress was associated with more depressive symptoms. Study findings suggest that the risk for depressive symptoms is highest among adolescent fathers experiencing low family economic stress and highly conflictual relations with their fathers. These results highlight the complexities of paternal relationships and perceived economic stressors on depressive symptoms during pregnancy for African American adolescent fathers. The importance of expanding research on influential familial relationships and economic stressors on adolescent African American fathers is discussed.