In this paper we look to the Italian border city of Trieste—at various points in its past, a cosmopolitan port, Austria's urbs europeissima, but also a battleground for competing understandings of territoriality, identity, and belonging and a paragon of the violent application of an ethnoterritorial logic to a plurinational, plurilingual urban context; a paragon of the violence of modern borders. At the same time—and precisely by virtue of its border condition—Trieste has often found itself within the cracks of European modernity, rendering it a unique site for the rearticulation and reappropriation of that which Walter Mignolo terms “global designs”. In our analysis, we ask what lessons the experience of a city like Trieste in ‘inhabiting the border’ can hold for Mignolo's notion of “border thinking” and for the elaboration of alternative geopolitical imaginaries.