In this article, Dyrness and Sepúlveda argue that in El Salvador, young people are participants in a diasporic social imaginary that connects them with Salvadorans and other Latinos in the United States--before they have ever left the country. The authors explore how this transnational relationship manifests in two school communities in San Salvador: a private school long recognized as a gateway to the elite and a public school serving one of the most violent and impoverished urban marginalized communities in San Salvador. Focusing on two different contexts of socialization--"homeboy" expressive culture and school-based English instruction--they argue that both groups of students were experiencing contradictory forces of cultural socialization that are characteristic of the diaspora.