During the 20th Century, Latin American theories of liberation moved allegorically from Shakespeare’s Ariel, The Tempest’s personification of hope, to the character of Caliban, the play’s foolish and violent brute. In so doing, theories of liberation not only replaced Ariel’s hopefulness with Caliban’s resistance, struggle and ‘freedom now,’ but also with a sense of despair. This paper examines the temporal and spatial nature of Ariel and Caliban’s respective signifying systems. Then it attempts to describe a Chicana-feminist configuration of hope by reading Gloria Anzaldúa’s Borderlands/La Frontera: The New Mestiza within the debate in Latin American intellectual history that draws on Shakespeare’s tempestuous figures. Though the essay Ariel has been critiqued and dismissed, through a closer reading we can see how José Enrique Rodó’s essay complicated conventional notions of hope, in particular, its relation with despair. In Rodó’s discussion of hope, despair becomes inspiring and knowledge producing. The paper then reconnects Caliban with Ariel, and by allegorical extension, with hope. Finally, through this reappraisal of Latin American intellectual history, the paper describes how Anzaldúa’s Chicana feminism further complicates Caliban’s spatial representation, thereby enabling a reconfiguration of hope as a form of knowledge.