In 1989, former Major League Baseball (MLB) player John Young created the Reviving Baseball in Inner Cities (RBI) program as a way to increase the number of African Americans becoming involved with the game of baseball. Along with this program, MLB created the Urban Youth Academy (UYA) in 2006 as a way to not only teach the game but also provide life skills to youth and adults. However, MLB continues to struggle in developing relationships and increasing involvement of African Americans. Therefore, the purpose of this study was to understand why African Americans are not interested or involved in MLB. Corporate social responsibility and relationship management theory were used as the frameworks for this study. Eleven RBI and UYA program managers were interviewed to determine the challenges they face in getting African Americans involved in the game. Results from this study indicated four themes regarding MLB program managers’ challenges: inconsistency in measuring success, lack of parental involvement, and lack of trust. A discussion, implications, and future directions are addressed.