Originating from the linguistically diverse Caribbean, Jamaicans come from a diglossic sociolinguistic context where standard Jamaican English (SJE) co-exists with Jamaican Creole (JC), locally termed “patois” or patwa. While JC is a significant cultural identity symbol for Jamaicans, it also acts as a class marker and is at times stigmatized. When teaching in an English language teaching (ELT) context outside of Jamaica, like Japan, Jamaican English as a foreign language (EFL) instructors also grapple with the perception that their English variety, which is often contrasted with the more “prestigious” American variety, is “non-native.” Nevertheless, they attempt to carve out implementational spaces (Hornberger, 2002) to champion multilingualism by introducing students to JC. By conducting in-depth, semi-structured interviews with ten (10) Jamaican educators across educational school contexts in Japan, this study aims to gauge their perspectives on exposing students to JC within the EFL environment, examining power dynamics “within” language classrooms and institutions and how certain varieties might be given precedence over others. Additionally, the study addresses the power dynamics “for” the classroom, considering how implementational spaces for multilingual TESOL are adopted by teachers in innovative ways, but then at the same time closed due to individual ambivalence, curricular constraints, and linguistic discrimination.