This chapter explores how an English as a Second Language (ESL) classroom in a US public high school addresses diversity through the implementation of critical pedagogy, examining the curriculum’s impact on student engagement and learning. An analysis of yearlong ethnographic data reveals that the physical setup of the class, the inclusion of historical fiction as compulsory reading, and a variety of thoughtfully designed activities collectively foster a culturally vibrant and intellectually stimulating learning environment. In addition to securing more opportunities to read and write in English, English learners start to understand intertwined sociopolitical realities by connecting course materials to their own experiences. Nonetheless, some learners struggle to grasp the rationale behind their teacher’s diverse intellectual exercises and find it challenging to immerse themselves in the curriculum. By unpacking these contradictory findings, this chapter discusses ways in which a diversity-oriented, critically informed educational initiative can bolster its efforts to decolonize diversity and maximize its transformative potential.