This study investigated the impact middle school tracking has on outcomes in high school and the factors associated with those outcomes. Utilizing data from a large, diverse school district, this quantitative study investigated the relationships between middle school and high school English course enrollment among 4,503 middle school students. The conceptual framework of the Ouroboros, combining the theories of Lucas's effectively maintained inequality (EMI) and Merton's self-fulfilling prophecy (SFP), was used to examine and challenge the status quo of educational tracking systems. We identified three major findings from the study. First, chi-square analysis indicated a statistically significant difference between enrollment rates in accelerated or AP English courses between students who came from tracked and detracked middle school English programs. Second, logistic regression models indicated socioeconomic status, race/ethnicity, GATE-identification, gender, and eighth-grade English course enrollment were significant predictors of student enrollment in an accelerated or AP English class in high school. Third, chi-square analysis indicated that there was a significant association between a student's eighth-grade English course label and their high school English course enrollment choices. Findings of this study suggest that detracking English classes at the middle school level represents an important stride forward in closing gaps in education.