A parent-researcher examines two adolescent immigrants' educational journey to success through the analysis of positioning theory and negotiated identities. Through the boys' direct voices about their schooling experiences with a particular focus on the middle and high school years in the United States, this article reports on the complexities of their identity negotiation and the process of their self-positioning and interactive positioning. This longitudinal study suggests that, rather than a single focus on language or culture, the immigrant students' critical awareness of identity, negotiated identities, and external confirmation of unique abilities enable them to construct and reconstruct the context that contributes to their success. This study aims to help educators reframe the dialogue on immigrant students to include a new voice, from their own perspectives, of how they have been able to be successful in the U.S. social and educational systems.