Amidst political challenges to Freedmen citizenship in the Five Tribes, Freedmen communities in Oklahoma struggle to prove their identities. This ethnographic and ethnohistorical work examines Freedmen identities through the study of two Freedmen activist organizations and two rural, historic Freedmen communities in Oklahoma. While bridging the gaps in twentieth century Freedmen history, this study examines the ways in which race and history have shaped Freedmen communities and identities. Everyday experiences within specific communities including segregation, land loss, cultural life, and racial integration have had important effects on Freedmen communities in the twentieth century, leading to the ultimate disintegration of some communities, and the virtual creation of others. Consequently, Freedmen identities today have been shaped by diverse histories and shifting racial structures. Despite differences in community histories and identities across Oklahoma however, Freedmen are tied together through their common experiences in asserting multiracial understandings of identities, in confronting everyday assumptions about race and history, and in overcoming the loss of their histories. Their common experiences within Oklahoma's racial structure have left many searching for the foundations of their own identities.