Public education is modeled from the values and needs of society as perceived by those in power to make decisions – the educational leaders. Inequity and imbalance in education is a significant multi-faceted challenge within the Inuit homelands. And addressing these challenges is a foundational task of educational leadership. However, within Inuit Nunangat, which is divided by four different regional governments, as well as separated from the rest of country through Federal policy governed by land claims, most educational leadership positions are held by non- Inuit. Through an ArcticNet sponsored grant between (2019-2023) we attempted to examine this puzzle: why in Inuit population dominant areas, were there so few Inuit leaders in education? The answer to this question, derived from interviews with approximately 60 Inuit educators pointed to a series of complex entanglements related to multiple identities, personal, cultural and community. The intention of much of the literature related to Inuit education to date has been to situate education within the colonial society and engage in identifying and undoing the dominant and assimilative practices as a pathway to reconciliation. This work has both practical and theoretical value for education, however within this talk guided by postcolonial theory and Inuit Qaujimajatuqangit we will discuss the complexity of leadership entanglements for Inuit educators, that reaches far beyond the obvious and requires rigorous societal and personal reflexivity.