This paper examines the changes of the language of liberty from Plessy v. Ferguson(1896) to Brown v. Board of Education of Topeka (1954). The language changed from the formalist liberty between the socially constructed "blocs"-the white and the black-to the individualist liberty based on "sociological" examinations of the racial discrimination. During the change, the equality of condition, one of the intrinsic and necessary principles for the establishment of the "separate but equal" doctrine, was effectively attacked in a series of "victories" by the NAACP. The Brown decision furnished the egalitarian and integrationist forces but failed to enshrine the inspiring "color-blind" vision of Justice John Marshall Harlan in Plessy. In a profound global paradigm shift regarding racial equality, the Warren Court failed to inherit a relentless criticism on deep-seated de facto white supremacy from Justice Harlan, although he expressed his opposition to any kind of social equality between races. The Supreme Court`s desegregation decision was based on the white-centered assimilationist notion of African-American inferiority. The NAACP also failed to present a more sophisticated attacks on the "separate but equal" doctrine in Brown by ignoring the voices of the "separatists" such as W.E.B. Du Bois. After 1950, the NAACP did not pay a scrupulous attention to the differences between separation and discrimination in reality by rigidly identifying separation with inequality. The Brown decision was a product of assimilationist white supremacy and a result of long-planned integrationist strategy of the NAACP on the basis of the new discourse of racial equality.