In this thesis, I work through the educational narratives of young Aboriginal women and men as I explore the relationship between cultural programming and student engagement. My analysis is structured through a collaborative Indigenous research project. My overarching task is to explore how a cultural support program, the Native Youth Advancement with Education Hamilton (NYA WEH) Program, offered at Sir John A. Macdonald Secondary School, located in Hamilton, Ontario, Canada, attempts to re-imagine Aboriginal education in ways that directly challenge the residential school legacy. In particular, I work to illuminate how particular forms of Aboriginal education are connected to the graduation rates of Aboriginal youth. I argue that the ways in which the NYA WEH Program navigates Native Studies curriculum, relationships, and notions of culture and tradition are significant to the engagement of Aboriginal youth. This research develops theoretical connections between the contemporary experience of Aboriginal social inequality and educational initiatives which attempt to reverse that legacy. By placing the NYA WEH Program narratives side-by-side with literature supporting Aboriginal education for Self-determination, I work to learn how to best support and encourage Aboriginal student engagement in secondary schools across Ontario.