This article presents case studies of two long-time English language teachers: a California English as a second language instructor originally from Brazil, and a Chilean English as a foreign language teacher who worked for many years in the United States before returning home. Based on interview and classroom observation data, this research explores teachers' perspectives on the connections between their transnational life experiences and their development of intercultural competence, how they define their own (inter)cultural identities; and how they approach cultural issues with their English language learners. Although both women self-identify as bicultural, they were observed to have somewhat different approaches to teaching cultural issues: The California teacher emphasizes subjective comparisons between the many national cultures represented in her classroom, but the teacher in Chile focuses more on the cultural changes that she and her students have experienced as a result of globalization. Whereas previous studies of teacher identity in TESOL have focused primarily on the dichotomy between native- and nonnative-English-speaking teachers, this article argues that the profession needs to put more value on the pedagogical resources that transnational and intercultural teachers bring to English language teaching. I end with implications for educating intercultural teachers. (Contains 9 footnotes.)