This essay explores the language of social protest in two geographic and diasporic locations in the Caribbean (Puerto Rico and the Dominican Republic) with long and ongoing histories of colonialism and imperialism. We analyze social media and digital mobilizing to examine how, in the midst of social protest, linguistic and semiotic tools indexed historicity, contemporaneity, and futurity through relational strategies that are not just textual and discursive, but also historical, social, and political. Throughout this essay, we share examples of intertextual and interdiscursive strategies that marked particular moments of protest as articulations of historical precedents, imperial and colonial presents, and alternative futures. These examples reveal how collective identities (i.e. el pueblo) are mobilized in social protest to generate counternarratives that address structures and systems rather than locate social critiques in particular individuals and political parties. In shedding light on the intra-Caribbean solidarities that emerge over time, this analysis also points to a need to examine the erasures (Gal and Irvine 2019) performed through claims to unity and collective organizing.