This study was designed to investigate the mathematical identity and achievement of one cohort of underrepresented male youth who participated in a pilot school intervention program in an urban middle school. Using counternarratives and a case study method, the experiences of four traditionally underserved high school students were investigated to explore their emerging mathematical identities. Results revealed the intervention program had very limited effect on the participants' mathematical identity. As engagement is prerequisite to student achievement, this study sought to understand what environmental factors (family, peers, teachers, self) affect student engagement and their developing mathematical identities. To explore the environmental factors, the Research Assessment Package for Schools (Institute for Research Reform in Education, 1998) was used to establish levels of engagement among family, peers, teachers, and self. Results indicated among the four environmental factors, family was most influential in their mathematical identity. Peers ranked second in terms of influence, self-engagement ranked third and teacher engagement ranked in the fourth position. To understand the impacts of race and culture on mathematical identity, the Multidimensional Inventory of Black Identity was administered to explore levels of race (cultural) centrality, and regard (public and private) as well as explore their identities as being members of their respective groups. A cross case analysis was conducted on the four participants to determine the impacts of race (cultural) centrality and regard (public and private) on their mathematical identity. Results revealed each member had a high race (cultural) centrality score and a high private regard score and a moderate public iii regard score. Participants were aware of stereotype and stereotype threat; however, it did not appear to affect mathematical identity. This model integrates racial and/or cultural identity and the engagement of family, peers, teachers and self to better understand the conditions that contribute to the mathematical identity of traditionally underserved young men. / Math & Science Education