Engaging students in controversial issues provides numerous benefits for developing democratic citizenship. A wide variety of pathways and challenges exist to their discussion in classrooms, many of which are based upon societal and cultural context. This study explores the context of Guam and maps the issues of controversy within categories of identity, colonization, and the relationship with the U.S. military. This study provides multicultural and other contextual considerations for future curricular and instruction efforts directed toward the full release of controversial issue discussions in Guam classrooms. Findings from this research add to the growing body of literature documenting country-specific case studies of controversial issues education.