Ernst Bloch is a philosopher of hope, of this there can be no doubt. It is the fidelity to the proposition that a better world is possible that undergirds Bloch’s work. Yet, the hopeful tenor of Bloch’s philosophy, as I argue here, is accompanied by a second, more subterranean strand: a concern with the phenomenon of disappointment. Bloch has an interest in what happens after hope fails; those moments when the desire for utopia confronts the impossibility of its realisation. By considering Bloch’s philosophical history of the defeat of the chiliastic movements of the medieval moment alongside his ontology of not-yet-being, the claim is made that disappointment has a constitutive role in the philosophy of hope, such that the dream of a new world is mediated through the history of its failures. Hope and disappointment are entangled, the power of the former indexed to the act of confronting the latter.