The Orthodox Church is a complex geopolitical reality, and it does not constitute a homogenous block. On the contrary, the rise of irredentism during the 19th century has created the basis for constant territorial fragmentation throughout the 20th century. Surprisingly, the worldwide Orthodox population continues to increase. The convergence of these two phenomena is a starting point for a reinvestigation of Orthodox power in international affairs, as well as a profound strategic change affecting the communion of the fourteen local Orthodox Churches. This article examines how Orthodoxy, through the process of convening a Holy and Great Council, has responded to geopolitics by developing new approaches and new Orthodoxy identities; how the territorial changes affected their strategies in the Diaspora; what was their role in new international conflicts. The first part of the article deals with an epistemological approach to place Orthodoxy in the context of geopolitical studies, while the second part highlights the persistence of a bipolar paradigm opposing the Patriarchates of Constantinople and Moscow. Finally, the paper considers geopolitical challenges for Orthodoxy created by today’s politico-religious crisis in Syria.