Most of the existing sociological and epidemiological literature has focused on the protective effects of high socioeconomic status (SES) on population health through reducing exposure to risk factors and increasing human and material resources that can mitigate adversities. Recent studies, however, have documented poor mental health of high SES Blacks, particularly African American males and Caribbean Black females. The literature also shows a link between perceived discrimination and poor mental health. To better understand the extra costs of upward social mobility for minority populations, this study explored ethnic by gender variations in the associations between SES indicators and perceived discrimination in an ethnically diverse national sample of Black youth. This study included 810 African American and 360 Caribbean Black youth who were sampled in the National Survey of American Life-Adolescent supplement (NSAL-A). Three SES indicators (financial hardship, family income, and income to needs ratio) were the independent variables. The dependent variable was perceived (daily) discrimination. Age was the covariate. Ethnicity and gender were the focal moderators. Linear regressions were used for data analysis in the pooled sample and also based on the intersection of ethnicity and gender. Considerable gender by ethnicity variations were found in the patterns of the associations between SES indicators and perceived discrimination. Financial hardship was a risk factor for perceived discrimination in African American males only. High family income and income to needs ratio were associated with high (but not low) perceived discrimination in African American males and Caribbean Black females. SES indicators were not associated with perceived discrimination for African American females or Caribbean Black males. When it comes to Black youth, high SES is not always protective. Whether SES reduces or increases perceived discrimination among Black youth depends on the intersection of ethnicity by gender. Additional research is needed to understand why and how high SES increases exposure and vulnerability to discrimination for some groups of Black youth.