This essay makes a strategically provisional attempt to trace some vari- ously relevant genealogies and itineraries of a song and a site whose vari- ous constructions, deconstructions, and deployments, both discursive and practical, point to a postnational (and perhaps less imperial) American future.1 The song, “Guantanamera,” may be familiar to many of us in one particular manifestation as a quasi-officially Cuban cultural and national artifact, though in fact its history of composition, performance, and recording reveals it to be a remarkably unstable and fluid text. It is still undergoing significant and strategic forms of expressive, critical resignification in a bracing variety of contexts and venues. The site, the U.S. naval base situated on Guantánamo Bay, on the island of Cuba, though perhaps politically and legally not “on Cuban ground,” continues to this day to challenge political and legal theorists in particular to worry the limits of what is (currently) politically thinkable and doable. Together, as I will argue from various angles below, these two decidedly “local” institutions have drawn into themselves an impressive procession of pub- lic figures and equally public figurations. They represent the complex and simultaneous careers of the nation, the transnation, and the postnation in ways that belie their origination in any one locality, and in ways that resist their definitive reduction to the terms, and the claims, of any one nation. The procession includes, in no order that can respect the demands of either chronological or geographical logics, such historical figures as the Cuban national hero José Martí, the Cuban-exile salsera queen Celia Cruz, the Haitian American hip-hop impresario Wyclef Jean, and some notable literary writers, such as the Cuban American poet Rafael Campo and novelist Cristina García, as well as the Guatemalan American nov- elist and journalist Hector Tóbar. I hope to implicate in this discussion whole populations that bear no simple or even coherent relationship with any of the more available categories (national, racial, cultural) accord- ing to whose terms we conventionally organize ourselves and others. Through such a gathering I hope, in turn, to demonstrate what can come not only from the kind of critically engaged postnational American stud- ies represented here by the authors of the two epigraphs, but also from a postnational Latino studies that understands its own organizing category as exclusively but emphatically historical, contextual, and critical.