Academic failure and exclusionary discipline practices are key elements in what has been described as the "school to prison pipeline." While there exists a strong body of research on the risks for delinquency, few studies have addressed the variables within schools that exacerbate or counteract these risks. We examined the academic pathways in English/Language Arts (E/LA) of a group of students recommended for expulsion in one school district, including students with and without disabilities. We obtained the letter grades that students received and the statewide assessment (SWA) results from elementary through high school for 81 participants who were recommended for expulsion in high school. Multiple t tests demonstrated that overall, students’ performance decreased as they progressed through school and students’ SWA scores differed considerably from course performance grades in elementary school. We discuss the results in terms of implications and recommendations for improving the educational pathways of students at risk of school expulsion.