Since the geopolitical breakthrough accomplished by Peter the Great, Russia has been a major part of the European “balance of power” system, engaging in various military alliances and partaking in every major European war. The nature of this military-strategic connection changed less radically that could have been expected after the revolutions of 1917, but was profoundly transformed in the course of the Cold War. The new Russian state that emerged in 1991 abandoned most of the crucial geopolitical positions in Central Europe (with the exception of Kaliningrad) and curtailed most of its military connections with Europe, compensating that with building ties of different types. The explosion of the Ukraine crisis has turned Russia into a major challenge for the European security system, and that signifies a new quality and intensity of the military-security connections between Russia and Europe. While in economic and cultural terms, Russia has essentially separated itself from Europe, in military terms, the interaction has become of pivotal importance, so despite all the talk in Moscow about “pivoting to China”, in reality, the Western theatre demands a massive concentration of military resources and political attention. The nature of this interaction continues to evolve, and the key issue presently is stabilization of confrontation and prevention of escalation.