Many researchers, educators, administrators, policymakers and members of the general public doubt the prevalence of high-achieving African-American males in urban high schools capable of excelling in mathematics. As part of a larger study, the current study explored the educational experiences of four high-achieving African-American males attending an urban high school with particular emphasis placed on their mathematical experiences, which have been largely understudied in the educational research literature. Specifically, using African-centered worldview as the theoretical framework and phenomenological qualitative methods, the researchers examined participants' lived experiences and how said experiences shaped their meaning of mathematics. Findings indicated teacher influence, peer influence, achieving success through sports and economic mobility were the most influential factors impacting mathematics meaning-making. Implications for educational researchers and mathematics teachers are discussed.