This article re-examines the history of NATO’s original post-Cold War enlargement to include the Visegrad states of Poland, Hungary, and the Czech Republic. It uses both published materials and the author’s new interviews with key US and Russian policymakers, and employs robust qualitative counterfactual methods to ask two questions: whether there were any realistic alternatives to NATO enlargement, and whether NATO enlargement was responsible for the downturn in Russian relations with the West. It concludes that domestic politics were the dominant factors explaining policy directions on both the US and Russian sides; that NATO enlargement was probably inevitable given US domestic political factors and West European acquiescence; that Russia’s turn against the West preceded the NATO expansion discussion in the US; that the tenor of the Russian turn is explained by status concerns rather than military threat perceptions, and that it was aggravated most by Western unilateral airstrikes rather than NATO’s geographical enlargement; and that the one policy initiative that might have realistically slowed NATO enlargement if it had been adopted differently, Partnership for Peace, did not affect those Russian status concerns and thus could not have redirected the relationship.