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This single case study explores the pedagogical decision making of an “outsider” U.S. history teacher and relative newcomer to his rural community. I begin by analyzing this teacher’s pedagogical thinking and community perceptions. Next, using a portraiture methodology, I compare his thinking with that of other community members. From comparison, I found that this teacher’s sense of widespread community conservatism, Latine marginalization, and fear of political disclosure were all well-founded. However, his perceived lack of community development and fear of addressing contentious topics deviated from many community perspectives. Findings highlight the importance of intentional place-based teacher preparation for rural social studies teachers and suggest a continued need for research exploring political disclosure, controversial issues, and hard histories in rural contexts.