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In this article, I develop a view of psychoanalytic freedom that draws heavily on traditions of the Anishinaabe/Ojibway First Nation Peoples as explicated by John Borrows, one of Canada’s preeminent legal scholars and a global leader in the field of Indigenous legal traditions and Aboriginal rights. Freedom will be understood to be a dynamic process that is lived, a process that is thoroughly relational and contextual. The recognition of our interpenetration and interdependency with both the human and non-human world will bring forth an ethics of relational accountability that will serve as a guiding framework for elucidating a conception of freedom consistent with the dialogic complexity systems sensibility informing my clinical psychoanalytic practice. The latter view of psychoanalytic freedom will be contrasted to Freud’s conception whereby the restoration of freedom to the ego will be understood to be an individualist masquerade for the restoration of White male power and privilege. The article concludes with a caveat that the full realization of freedom in this troubled world requires a willingness by (predominantly White mento give up some of their privilege.