The present study proposes and tests pathways by which racial discrimination might be positively related to bullying victimization among Black and White adolescents. Data were derived from the 2016 National Survey of Children’s Health, a national survey that provides data on children’s physical and mental health and their families. Data were collected from households with one or more children between June 2016 to February 2017. A letter was sent to randomly selected households, who were invited to participate in the survey. The caregivers consisted of 66.9% females and 33.1% males for the White sample, whose mean age was 47.51 (SD = 7.26), and 76.8% females and 23.2% males for the Black sample, whose mean age was 47.61 (SD = 9.71). In terms of the adolescents, 49.0% were females among the White sample, whose mean age was 14.73 (SD = 1.69). For Black adolescents, 47.9% were females and the mean age was 14.67(SD = 1.66). Measures for the study included bullying perpetration, racial discrimination, academic disengagement, and socio-demographic variables of the parent and child. Analyses included descriptive statistics, bivariate correlations, and structural path analyses. For adolescents in both racial groups, racial discrimination appears to be positively associated with depression, which was positively associated with bullying perpetration. For White adolescents, racial discrimination was positively associated with academic disengagement, which was also positively associated with bullying perpetration. For Black adolescents, although racial discrimination was not significantly associated with academic disengagement, academic disengagement was positively associated with bullying perpetration.