The stories of four mathematically successful middle schools African American boys are used to describe the roles, perceptions, and experiences of their parents. The parents of played multiple roles for their sons: (a) guardians of opportunities, (b) standard setters, (c) resources for mathematical knowledge, and (d) models of success. As guardians of opportunities, these parents were advocates, protectors, and supporters. As standards setter, parent placed high value on education and succeeding academically. As resource for mathematical knowledge, parents provided or served as a resource. As models of success, parents provided or served as roles models. Each of these roles shaped the mathematical experiences and contributed to the development of a mathematical identity that shaped the boys' understandings of and persistence with mathematics.