This paper aims to comparatively, critically, and constructively engage with two major tendencies when it comes to (Eastern) Orthodox Christianity's approach to sociopolitical matters, namely, accommodationist and critical/prophetical stances. Whereas the academic engagement with political theology has only recently started to gain prominence among Orthodox theologians and scholars, particularly within the anglophone Orthodox academic milieu, and generate though provoking perspectives, Orthodox Churches have both a rich and tragic historical experience with the political, constantly swinging between the extremes of protest and criticism, to accommodation and privilege. In the context of contemporary political turmoil, the relationship between institutional Orthodox Churches, especially but not exclusively in countries where Orthodoxy is majoritarian, increasingly becomes an exponent of political agendas and interests. Given this tendency of Orthodox Christianity to side with sociopolitical institutions of power, of particular interest are the recent political theologies developed by Pantelis Kalaitzidis, Aristotle Papanikolaou, and Davor Džalto. The three theologians aim to construct distinctive political theologies in response to the challenges posed by contemporary (post)modern society and to scrutinise Orthodox Christianity's theological ossification and apparent inclination to align itself with a sociopolitical agenda, promoting it in an attempt to secure a privileged position in society and gain economic benefits. By engaging with concrete responses of Orthodox Churches to sociopolitical issues, as well as with the three aforementioned political theologies, this paper uncovers the ideological entanglement of Orthodox Christianity's attitudes to sociopolitics, as well as the strengths and shortcomings of contemporary theological responses by focusing on the political theologies of Kalaitzidis, Papanikolaou, and Džalto and their implications for the future.