This chapter argues that the first two cantos of Childe Harold and the Turkish Tales can be read as a sustained critique and questioning of a teleological history, or a history impelled by the acts of great men and heroes. It suggests that these poems engage with the intellectual crisis precipitated by the Napoleonic wars and a devastated Europe in different ways, representing a broad alienation from the meaningful progress of history both within and beyond European borders. Understanding Byron’s distinctive romanticism as primarily political rather than ontological, the chapter reads this group of poems as being charged with a late-enlightenment scepticism representative of a new freedom of thought in which there are no structural possibilities for history, and through which heroic acts are rendered ever more remote from civilisation’s improvement.