How does a history of discrimination and marginalization affect Chicanos' perceptions of schooling? This article offers a brief analysis of the Treaty of Guadalupe Hidalgo as an instantiation of a historical metanarrative of colonialism. Using a critical theoretical framework, the article explores the destructive impact of this narrative on Chicano youth. Although it is clear that times change, certain essential elements of a colonial relationship remain; they are inescapable for Chicano youth and affect their view of schooling along with their school performance. Furthermore, students' critical examinations of these metanarratives can empower young people to disrupt predictable educational trajectories. The article concludes with suggestions for creating a caring school culture through a culturally relevant critical pedagogy that empowers students to develop a sense of hope, purpose, and positive identity.