This essay aims to demonstrate and explain how Russia’s evolution and positioning internationally has led, with the annexation of the Crimea and the war in Donbass, to a deterioration in its relations with the West unprecedented since the end of the cold war. It shows how multipolarity became the primary objective of Russia’s foreign policy as early as 1996 due to the expansion of Nato and subsequently became one of the main recurring factors leading to the current situation. It also highlights and compares the choices made in this context by the two Canadian governments elected since the crisis. It shows how and to what extent the current government’s stances and options have been influenced by past relations between Canada and Russia.