This article examines four poems published by Cuban author Virgilio Piñera (1912–1979) in the official Revolutionary literary journal Casa de las Américas in 1961. The poems illustrate the depth of Piñera's optimism about the freedom of personal and artistic self-expression he believed Cuba's new government would allow. This attitude is evident in the fact that the texts dramatize personal acts of transcendence in the face of social repression. The speakers of the poems evidence a faith in the power of theatricality to allow the apprehension and revelation of an authentic self. The timing of the texts' publication is of poignant significance, given that later the same year, Piñera found himself the victim of the Revolution's intention to suppress both sexual and intellectual individuality.