This article describes how one Latinx sibling pair, Sebastian and Sophia, negotiates dominant forms of family-school relations that permeate their experiences within a bilingual elementary program. I report on focal interactions that I, as an aspiring Latina school administrator, had with Sophia and Sebastian in fall semester 2021. In this narrative, Sophia and Sebastian resisted, reconfigured, and repurposed expected behaviors and routines in school spaces to engage in collective meaning-making and assert their sense of selves as family members. Despite deficit institutional labels about their language and literacy practices, these Latinx siblings connected their understandings of disciplinary concepts to their everyday experiences inside and outside of school. Sebastian's and Sophia's interactions demonstrate how creative, joy- and freedom-centered possibilities for learning, leading, and relationality are here because they have been born out of necessity within minoritized groups to resist and survive oppressive schooling structures and norms. Their portrait demonstrates the importance of educational leaders, researchers, and policy makers recognizing the brilliance, joy, and creativity of Latinx children as catalysts for reimagining education in a post-pandemic, heightened racially tense world.