Western political theory’s engagement with settler colonialism has tended to consistently focus on its capitalist-materialist aspects viz., ownership of territory, extraction of resources, and the resultant genocidal erasure of Indigenous peoples of the land. Insofar as radical Indigenous responses to settler domination move between the wholesale rejection of colonial relationship on the one hand and direct action against the colonial state (blockades, protests, etc.) on the other – this paper argues that until the socio-psychopathological aspect of settler colonialism is uncovered and addressed, reconciliation itself will remain impossible or primarily settler-mandated (hence, rejected). Using Canadian settler society as its case study, and further utilizing the recent turn towards understanding the thing-based nature of democratic polities, the paper follows Winnicottian object relations psychoanalysis to trace the logic of settler colonial attachment to land-as-object. It argues that the desire for and dependence on land as a transitional object turns into exceptional Oedipal psychopathology since the attachment not only fails to get decathected but instead ensures itself through the structural regulation and hegemonic domination of the Indigenous peoples.