Using Édouard Glissant’s assertion that the imagination is shaped by and expresses itself through the materiality of space, this essay focuses on a geopolitics of the figure of Caliban in Antillean theatre. No longer the incarnation of nativist claims of sovereignty, Caliban is precariously repositioned on the shoreline, which may or may not open him to new forms of dwelling and resistance. A spatial restaging of Caliban traces a trajectory from the frustrated rebel who winds up on the porous ever-shifting beach in Aimé Césaire’s psychodrama to the “marroneur” Toussaint, who liberates himself by transforming his prison into archipelagic space. While Césaire’s Caliban does not have the imaginative resources to transcend his island prison, Toussaint’s cell is transformed into unbounded liminal space. Poised on the quintessential site of revolutionary possibility, Caliban must choose between reductive insularity or the rhizomatic archipelago that destabilizes categories of near and far, inside and outside.