When family-school engagement models operate on the beliefs of engagement and disengagement, it leads to hierarchical understandings of leadership and practices of partnership with racialized populations. Drawing on the analytic framework of race-conscious transformative leadership, this self-study of a former bilingual school administrator excavates his recollections of working with immigrant communities in a large California high school. The article underscores the relational practices of leadership between school and parent leaders in deconstructing the systematic negation of immigrant students, reconstructing leadership practices that affirm the college-going expectations of immigrant families, and breaking the educational racial contract. This article illuminates immigrant families' commitment to equity and intervention on behalf of their children in the face of school-based injustices. This article calls upon leaders to address the educational racial contract that subjugates immigrant students and their families to low expectations at the intersections of immigration and education.