This paper examines the nature of contemporary bilingual Chicano poetry from the 1970s to the present, particularly in terms of the poetic use of bilingual wordplay and the questions it raises about the uses and possibilities of translation. Using Walter Benjamin ‘s essay The Task of the Translator as a touchstone, and positing a metaphorical link between translation and transfer, the paper looks at bilingual wordplays as a kind of bridging-over or translation of one language into the other, crossing and breaking down borders and hierarchies between the two languages. To illustrate this, cultural practices and uses of bilingualism are examined from both a sociolinguistic and a poetic point of view, with examples of how puns, (mis)pronunciations, slang, loanwords, and mixtures of Spanish and English are used in bilingual poetry for formal and polemical effect.