One of the defining markers of Jamaican students’ academic success (for teachers and students) is their ability to speak Standard Jamaican English (SJE) fluently. However, SJE fluency is challenging for many majority-speaking Jamaican Creole (JC) boys who experience language conflicts within their social and educational contexts. Consequently, this study sought to investigate the impact of systemic negative perceptions of JC and its speakers on four inner-city adolescent boys (14-17 years old), who were dominant & JC-speaking—their perceptions of self, language ability, and attitudes toward English Language Learning (ELL). The study embraced a social constructivist approach, via use of multiple case studies, anchored within a narrative inquiry, over a period spanning three months. Within this period, the boys' lived language experiences were documented, through interviews, video diaries, and graphic novels. The study revealed that the boys experienced language complexities that left them feeling inadequate and disenfranchised, with systemic language practices that positioned them as deficit language learners. The study aimed to construct new knowledge to assist policymakers and educators in developing more inclusive language practices that can provide opportunities for all students to thrive.