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This paper considers the "work" that is performed by particular inclusions and exclusions in the study of diasporic Puerto Rican literature in Puerto Rico, by focusing on the popular author Esmeralda Santiago. The historical value to island contexts of Santiago's first widely taught memoir When I Was Puerto Rican (1993), is explored for how its entanglement with jíbaro discourses supports current historicizing of the Muñoz era (Díaz Quiñones 1993, 2000, Moreno 2012), though it ultimately reinscribes the era's populism while simultaneously lamenting its rupturing effects. While her memoirs may usefully challenge essentialist views of the diaspora by insisting on different ways of being diasporic, the celebration of her work in Puerto Rico and the US mainstream an uplift narrative that problematically reifies the "rags to riches" story of Horatio Alger from early twentieth US literary history. As a counterpoint, Aurora Levins Morales' autobiographical essays and poetry, as well as her visionary revisionist history in Remedios (1998), eschews romantic tropes of diasporic longing, and defies paternalistic national and jíbaro discourses, while summoning traditions rooted to the land, and to Caribbean working class women's survival and endurance.