This paper is an effort to de-construct the two opposite ideas of hope and despair in Ahmed Ali's Twilight in Delhi and Khushwant Singh's Delhi. The comparative points of view regarding Delhi by Singh and Ali serve to construct the ideological, political and ontological framing of Delhi. The paper explores the significance of Delhi as a symbol of political energy which distributes power or snatches it as an active agent of power-history. The paper exhibits the socio-political, economic and communal structures portrayed by Ali and Singh. The study is an effort to detect the system of representation in the metaphor of Delhi in the context of power-resistance and failure of the struggle against the Raj. The paper tries to show that both Ali and Singh see Delhi with a difference of outlook and literary approach to manifest hope and despair.