Latinos labeled "English learners" by the school system face social and systemic barriers that limit their access to postsecondary opportunities. Using a multilevel model of intersectionality, this collaborative case study contextualizes influences that impacted the educational trajectories of two Latino students who came to the United States from El Salvador as young teenagers. Despite their many similarities, the data reveal salient differences about factors that affect opportunities and outcomes for these students. Findings for this study reveal the role of identity and social interactions at the meso- and macro-level, meritocracy and the American dream, and the barriers of immigration status.