For decades the Indian Mascot issue has fostered controversy across the land. Middle schools, high schools, colleges and universities and professional athletic organizations have wrestled with the issue. Port Townsend High School in Washington State is one of the schools coming to grips with its mascot name “the Redskins.” The community is in conflict about retaining or retiring the mascot name. Newly appointed Superintendent David Engle is no stranger to the conflict, having seen the same issue in the Edmonds School District where his children attended school. The Port Townsend School Board is determined to create “a fair, mature and respectful process for dealing with the sensitive issue.” This three part case explores the process of attempting to move the discussion of this issue from black and white, toward a deeper understanding of all sides. The case can be used as an interrupted case where each part is read and discussed separately or as a single session case.