This article examines instances of a U.S.-Mexican transnational youth honing his critical translingual literacy skills through his engagement with corridos, Mexican balladry in Spanish that often emphasizes injustice and border strife. The author relies on ethnographic classroom observations, the student's journals, and semistructured interviews to provide a glimpse into the complexities and sophistication of the bilingual youth's everyday language and literacy practices in an era of vehement anti-immigrant rhetoric. This inquiry asks, (a) What do literacy practices deeply rooted in corridos look like? (b) How does one youth read and engage with the Mexican musical genre of corridos to make sense of his social and political world? and (c) What are the environments and educational settings that supported this literacy development? Findings detail a transnational youth's "corridista" (balladeer) consciousness and its concomitant language and literacy practices that shape and are shaped by his participation in both his Tijuana communities of origin and his Los Angeles communities. Specifically, this study showcases a student's uses of literary devices, including allegory, to describe myriad forms of oppression and resistance found in corrido lyrics and throughout the lives of U.S.-Mexican transnational youths. Attention to literary genres that are often unsanctioned in traditional English-medium classrooms and recognizing the complex cognitive abilities of bilinguals can harvest critical insight about literacy education in and out of school. Implications from this study highlight meaningful learning contexts for transnational adolescents' literacies and how engagement of these literacies might be (re)conceptualized through an ethnic studies and Chicanx/Latinx Studies lens.