Recent studies of Indigenous educational leadership have contributed instructive conceptual insights to decolonize public schools. Building on these theoretical insights, we investigate the organizational and policy constraints leaders face when attempting to enact decolonial strategies. Combining “safety zone theory” and Critical Policy Analysis, we examine how one Apsáalooke educational leader, Cummins negotiated and challenged institutionalized practices delimiting “safe Indian-ness.” These include: (a) transactional, policy inscribed relations between schools and Native communities; and (b) tepid district implementation of pro-Native legislation, such as policies expressing a commitment to preserving Native American cultures. We convey how Cummins made, unmade, and remade new policy meanings through local leadership practices, such as creating more humanizing Apsáalooke-defined spaces for community-school engagements and orchestrating local pressure to move district leadership to fulfill policy commitments to serve Native students. Data includes 18 interviews with Apsáalooke tribal members, education policy texts, and collaborative auto-ethnographic memos. Based on these findings, we develop the notion of dangerous leadership: a decolonial leadership praxis that challenges settler–colonial conceptions of safety and negotiates material, communal, and personal threats that such acts of subversion tend to provoke. We conclude by discussing implications for dangerous leadership amid nonideal and constantly shifting settler-colonial school contexts.