Preparing European-American preservice teachers for diverse urban school settings pose multiple challenges. Of primary concern are the differences in race, culture, and community between teachers and students. Because new teachers prefer to work where they grew up, most preservice teachers want to teach students who are like themselves in familiar settings, and they are often uncomfortable interacting with families from ethnic and language minorities. Despite these challenges, preservice teachers need more knowledge of and experience with culturally diverse ideas and settings to be more effectively prepared to work in schools, particularly culturally diverse urban schools. This article describes a field experience activity, set in a culturally diverse urban middle school, that examined the culturally charged historical event, the "Amistad" uprising. In this article, the authors explore what the experience revealed about pre-service teachers' understandings (and perhaps misunderstandings) of the diverse populations of urban middle schools.