This paper explores two previously unstudied court challenges brought by black settlers in the territorial and early statehood period of Oklahoma (1889-1907). Oklahoma Territorial courts heard more challenges to segregated schools than in any state as these black pioneers challenged new legislation that segregated previously integrated territorial schools. These families sought the protective wing of the nascent courts whose judges were federal appointees, making Constitutional claims more viable. This was a time of unique confluence of law, public education, and defining African American citizenship. The paper asks: would schools be the gateway to full civic and economic participation? Or would schools be a gatekeeper, denying access to some in order to maintain dominance for others? Territorial courts tackled these questions.