As students’ racial and cultural diversity increases and researchers emphasize the benefits of having Black teachers, the number of Black teachers remains relatively small compared to their White peers, especially in AP English courses. When considering other Black populations from the diaspora, such as Caribbeans, teacher numbers are even lower. Simultaneously, advanced English courses remain particularly entrenched in Eurocentric, canonical curricula. Yet, the idea of veracity in curricula has taken a backseat to White hegemony which is detrimental to all students. Furthermore, though historical depictions of Black teachers exist, research describing the teaching experiences of twenty-first-century Caribbean Black Immigrant (CBI) high school advanced course English teachers remains relatively scarce. Drawing on theories of Afrocentricity and research documenting the mis-education of Black youth, this qualitative research study sought to understand CBI teachers’ past experiences with Black and minoritized students in advanced English courses. The study employed heuristic and narrative inquiry paired with narrative analysis within a naturalistic research design. Specific tools included semi-structured interviewing, journaling, a Kitchen-Table-Talk, and document analysis. Understanding CBI twenty-first-century teachers’ past experiences teaching Advanced Placement English courses – especially in a sociopolitical climate where discussing race and racism are under attack – offered the field a lesser-known and critical perspective that may have implications for increasing teacher diversity, addressing cultural irrelevance, and curricula violence for Black students.