Between 1889 and 1890, John Wilson and his family were among nearly three thousand African American settlers to enter Oklahoma Territory, where Wilson's two daughters first attended an integrated school. The Wilson family was undoubtedly drawn by the educational and economic opportunities that were present in the fluid space--opportunities that did not always exist elsewhere in the country. Yet the territorial legislature sought to narrow those opportunities, which it did by segregating the schools. Wilson and his family did not accept this limitation and fought back through both the courts and active resistance. This article examines that first legal challenge to the segregated school system: "Territory ex rel. Wilson v. Marion et al." This case informs not only our understanding of the durability of racism in an actively contested western space but also the forms of African American resistance to the reactivation of racial hierarchy.