Anna J. Cooper, Mary Church Terrell, and Eva B. Dykes shaped the educational landscape in Washington, D.C., in the late nineteenth and early twentieth centuries. These three pioneer educators serve as examples to describe the societal circles they were involved in. The many facets of their educational achievements are analyzed in the context of the educational elite of Washington. Cooper, Terrell, and Dykes not only had to live with race discrimination but also with gender discrimination. Unpublished archive material is used to illustrate how they interacted and how they treated each other.