We examine how an assistant coach's race and the race of his supervisor (the head coach) interact to affect future job quality. While past research argues that homophily is beneficial to job mobility, we find differential effects based on the race. OLS and OLR regression analyses on the quality of one's first head coaching job in NCAA men's basketball indicate that black assistant coaches working under black head coaches (black homophily) are significantly disadvantaged compared to all other racial combinations: white assistants with white supervisors (white homophily), white assistants with black supervisors (white heterophily), and black assistants with white supervisors (black heterophily). In contrast, there is no significant difference in job quality among the latter three groups: white homophily, white heterophily, and black heterophily. This indicates that while homophily is neither advantageous nor disadvantageous for whites, it is disadvantageous for black job candidates. This racially based disadvantage makes it difficult for minority job candidates to break through the glass ceiling and has real-world financial implications.