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Poised between violent repetitions of state power and hopes for poststate alternative futures, in our dual role as historical actors and historical narrators, what do we do with the past today, with which past(s) and for whom? This essay asks about the ethical/political stakes in reflecting on where we are speaking from, but also when we are speaking from, as a question of temporality and generational positioning. Caribbean theorists, writers, artists, and activists offer us productive theoretical interrogations of the convergent and divergent crossroads that constitute “now.” Imagining other times and possible futures, juxtaposing temporalities and ways of timekeeping, marking temporal breaks, returns, and ruptures, this work helps us ask, What time is it? Whose time is it?