A simplistic assumption of democracy and oppression would be that many regard them as antagonisms by association. This study seeks to explore whether the relation between the two concepts in fact is inevitable, if the concept as well as the theoretical application of the “ideal of democracy” is consistent with oppression. In order doing so, the concept of democracy is being broken down into its necessary and unavoidable features, which is found to be an ideal of freedom, equality and the majority rule. From these necessary ingredients, classic democratic theory is taken into account to explore the critical aspects of the principles and ideals. The controversies and inconsistencies are then placed against, however subjectively, a stipulated definition of oppression. The major results are that a hypothetical oppression is most likely to be part of the theoretical applications of democracy, that there is a constant underlying risk for oppression and in some extent, the oppression is indeed inevitable.