This essay explores Eugenio María de Hostos’s and Ramón E. Betances’s notions of modern subjectivities, in the context of Romantic narratives, to index the fractures of collective and communal nationalist imaginaries within the Caribbean Confederation. Hostos and Betances were champions of the Antillean Confederation’s idea, but one must wonder why two modern political thinkers recur to the representation of unsuccessful heroes in their fictional texts. Through literary rhetoric, Betances and Hostos proposed a modern subjectivity that could promote national unity and collective political solidarities. Yet, surprisingly, their literary characters are instead inserted in a discourse that verges on a rhetoric of failure that contradicts the positive modern impulse of national/regional constructions.

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