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Approximately 6 million African Americans left the South and relocated to either the Northeast, Midwest, or West in what was called the Great Migration. Many articles and books have documented them Great Migration; however, there is less awareness regarding the experiences and perspectives of educators who participated in this migration. This study centers the experiences of retired teachers and administrators in a Midwestern industrial city. Qualitative research approaches are utilized to capture their experiences with segregation, migration, and education. Data was collected mainly by semi-structured interviews. Findings indicated that these educators dealt with different boundaries, sought to create community, and continued a long-standing legacy of enhanced education for liberation.