This paper applies the Foucauldian premise of governmentality and the analytics of government framework to demonstrate how exclusive modalities of power – of the European Union (EU) and Russia – and their competing rationalities relate, intersect and become, counter-intuitively, inextricable in their exercise of governance over the eastern neighbourhood. This particular approach focuses on power as a process to gauge the prospects for compatibility and cohabitation between the EU and Russia. Using original primary evidence, this paper contends that cohabitation between these two exclusive power modalities is possible and even inevitable, if they were to legitimise their influence over the contested eastern region. It also exposes a fundamental flaw in the existing power systems, as demonstrated so vividly in the case of Ukraine – that is, a neglect for the essential value of freedom in fostering subjection to one’s authority, and the role of ‘the other’ in shaping the EU–Russian power relations in the contested region.