Research findings state that ELs (English Learners) are an ever growing population of learners in the American education system that continue struggle in school (Verdugo, 2006). This study is an interpretive biography of Juan, an EL student, and his journey in Southern American schooling. Chronicling his first days of elementary school and following him into high school, the research looks closely at Juan's state of illiteracy, both the successes and barriers he encountered. As Juan's tale unfolds in a narrative style, a stream of consciousness story-telling approach is used wherein the researcher looked not only at Juan's life, but takes a holistic research approach to Juan's education and schooling. Looking into various sociocultural aspects that influenced his past, the researcher interviewed Juan's parents, teachers, administrators, community members, and Juan himself. Data were collected over a six month span of time. Data from interviews and educational documents in Juan's past detail what teachers did when educating Juan. The research at times critically examines the politics of Southern culture, the small town mentality of immigration, and a school board influenced by that very same southern culture that seems to produce white flight. Touching on sensitive topics such as lingering racisms in the South, immigration, and illiteracy, this small scale study and its findings on Juan's issues in school, may point to large scale problems in U.S. education.