The strained relationship between W.E.B. Du Bois and Booker T. Washington would define the bipolar intra-race debate about means, methods, and ideology in fighting discrimination throughout the 20th century. Du Bois' insistence on the Talented Tenth and organized protest contrasted Washington's insistence on economic autonomy, industrial education, and accommodation on issues of social segregation. This ideological divide, however, was fueled by a personal feud that would continue throughout their relationship, which stemmed from what Du Bois saw as a betrayal in 1900 by Washington in a recommendation dispute over a school superintendence position in Washington, DC. Although their relationship was problematic prior to the superintendence issue, the Du Bois -Washington rift was exacerbated by the formation of the National Negro Business League, Du Bois' review of Up From Slavery, the Boston Riot of 1903, and the publication of The Souls of Black Folk. This paper examines the strains between Du Bois and Washington, emphasizing Washington's early time in Boston and the Alabama controversy between them regarding William E. Benson's Kowaliga Academic and Industrial Institute in 1898, and provides insight and understanding about these two major leaders in the Black community during the era of Jim Crow.