This dissertation argues that, beginning with the Generation of the Thirties, twentieth century brown and black Puerto Rican poets were conditionally incorporated into an exclusionary literary canon as ambassadors for class and racial otherness, acting as self-translators, making aspects of their experience legible according to the standards set by a criollo intelligentsia. Additionally, that they pushed against the discourse that sought to incorporate theme, with varying degrees of success. Mulatez, was both held up, through individual examples, in order to cement the myth of mulataje, and constantly monitored for its proximity to blackness. Chapter 1, “The Promise and Betrayal of Brownness in the Work of Julia de Burgos,” posits the poet Julia de Burgos as a as a model for a poetic self-translation practice, as she was one of the first Puerto Rican poets to translate her brownness for a criollo audience. It examines De Burgos’ own anti-blackness and argues that the particularity of her position as a mulata with aspirations for class ascension led to her inclusion in literary circles that allowed for a kind of brownness that translated blackness into a whiter register. Chapter 2, “The Spector of Crip Queerness and the Construction of Post-War Masculinity in the Poetry of Sotero Rivera Avilés,” takes a close look at the work of Rivera Avilés, a poet from the Generation of the Fifties, and his fraught relationship with his own working-class background. His writing served as a prosthesis through which he negotiated a relationship to his cripness and marks the intersection of colonial, racial, and economic trauma. Chapter 3, “The Book as an Open Womb: The Radical Vulnerability of Loss in Fierce and Tender Animal (Animal fiero y tierno),” shows how Dávila’s book points at processes of collective loss that led to the formation of affective bonds. Like Rivera Avilés, her work is a testament to a lifetime of self-translation, the cost of class mobility and the persistent contradictions posed by the cultural nationalist liberation model. The final portion of the dissertation is composed of translations of Rivera Aviles’ unpublished work and Dávila’s Fierce and Tender Animal.