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The aim of the paper is to reveal how T.W. Adorno’s and W. Benjamin’s criticisms of the Hegelian dialectic lead directly to two divergent accounts of history which also imply different answers as to whether the hope for a better world might still exist. Both Adorno’s and Benjamin’s starting points have been the criticism of the Hegelian philosophy of history, the motto of which is the famous Cunning of Reason. According to that, violence and antagonisms are always aufgehoben, that is, ‘converted’ into an instrument of historical reason, contributing thereby, to the overall harmony of historical progress. However, although Adorno remains loyal to the Hegelian negativity and tries to correct its ‘closure’ by means of its own method, namely that of immanent critique, Benjamin subverts it by developing his concept of the ‘now-time.’ Although the Adornian insights on the ‘totally administered world’ can hardly signify the hope for the possibility of a better world, yet his Negative Dialectics, as the effort to disclose and ‘correct’ the inconsistency of the Hegelian dialectics by insisting on its open, never-ending and hence, subversive character, becomes the exercise of hope par excellence. By identifying itself however with the never-ending work of consciousness’s critical self-reflection which unmasks the false harmony of the Hegelian system, Adorno’s hope becomes an intellectual exercise. Benjamin’s critique of Hegel on the contrary, leads to his materialist historiography of the dialectical images according to which historical fragments are removed from a context in which they were recorded as insignificant and constitute a constellation i.e. an image suggesting a new interpretation. The political synonym of the dialectical image which at the same is the historical token of hope is his idea of revolution interpreted in terms of ‘Divine Violence.’