This article challenges 20th century ways of conceptualizing bilingualism, arguing that they are no longer applicable to the linguistic heterogeneity of the 21st century. Using case studies of two small high schools in New York City, this article re-imagines the possibilities of bilingual education to more accurately reflect the realities of bilingual students. Rather than imposing a top-down process, these two schools, although very different demographically and pedagogically, attempt in different ways to create language education policy through a collaborative process that incorporates bilingual students' hybrid practices and gives students agency in negotiating their linguistic repertoires. These two schools provide a window into new and innovative ways of approaching bilingual education for the 21st century. (Contains 3 figures, 2 tables, and 7 footnotes.)