This critical ethnographic qualitative case study uses a critical theory lens to discover the implications of academic tracking in a southeastern secondary school and to explore detracking English education for historically underserved students with critical literacy practices and multi-year placement. The purpose of the study was to determine the ways in which academic tracking affects standard and advanced classrooms, and to discover how detracking with critical literacy practices and multi-year placement might alter student engagement. In Vivo coding was used to analyze the data that included observations, field notes, interviews, and student artifacts, and was collected from 2015-2017. The findings indicated the district's academic tracking practices structure inequality and division in the school system; and, detracking 9th and 10th grade English education with critical literacy practices and multi-year placement engages historically underserved students. These findings support Freire’s notion of critical theory (1970), that argues for the amelioration of the oppressed through liberating practices aimed toward transforming the oppressive state. While similar studies have analyzed tracking, detracking, and critical literacy practices, they have not analyzed all three components in one study, from the teacher-researcher’s point of view, and in conjunction with the implementation of multi-year placement. This research provides insight into 1) a multi-year teaching approach in a secondary setting; often the studies focus on primary levels; 2) practical classroom applications of critical literacy practices from the teacher-researcher's point of view; often the studies explore theoretical assumptions; and, finally, 3) the entire detracking process. While many studies offer suggestions for detracking, very few explore what happens during or after classrooms are detracked.