Why did the relationship between Russia and the West collapse so dramatically with the onset of the Ukraine crisis in early 2014? Answers to this question have focused on the role of the enlargement of Euro-Atlantic institutions — the European Union and NATO — in this process. The debate has been divided between those who blame the crisis on enlargement of Euro-Atlantic institutions and claim that Western encroachment precipitated Russia’s moves, and those who argue that enlargement cemented democratic gains in post-communist Europe and protected vulnerable states from Russian aggression. The former group calls for an end to enlargement to resolve the crisis; the latter proposes granting full institutional integration to Ukraine, Georgia, and any other interested Russian neighbor. This talk will address the fundamental issue missed by both sides of the debate: whether the conflict we have today is a function of immutable structural factors, or contingency and path dependency.