That education is empowering is one of the U.S.'s most sacred tenets; however, for many Indigenous students, schooling has been intentionally damaging. Drawing on semi-structured interviews, in this article I highlight tribal education leaders' sensemaking about the paradoxes and promises of their work in education, as they navigate the antinomical ideas that education can be both empowering and damaging. Rooting analysis in Tribal Critical Race Theory (TribalCrit) (Brayboy, 2005), I connect tribal nation-building with various Indigenous educational efforts, including opportunities provided by the charter school movement. Findings highlight values that Indigenous leaders hold for their students' education, including cultural and linguistic sustenance, cultural congruity, and self-determination. Using mathematics as a lens to examine some of the contours of Native education, analysis illuminates complexities inherent in Indigenous education and tribal nation-building.