The current state of the relations between Russia and the ‘West’ presents curious similarities with the ’30s appeasement of Germany. These include the change in the international order, the (late) emergence of a system-challenger after an ‘intermediary’ period that followed the change, the conduct of the challenge and the reactions of the direct custodians of the system. Similarly in both cases, a cycle of escalation-empathy-appeasement defines the interactions between the system and its challenger, creates a centrifugal effect among third actors and deteriorates the system. The similarity necessitates a theoretical effort to define the phenomenon as to its genesis, processes and its end from a systemic perspective, through the comparison of the two cases yet beyond a purely historical angle that has been almost the only one in dealing with the appeasement. In other words, this article engages in two theory-developing case studies centred on the German Reich and contemporary Russia to understand the theoretical value of appeasement as a specific mode of interactions in international politics.