The Six Day War of June 1967 transformed the political and physical landscape of the Middle East. The war established Israel as a major regional power in the region, while the Israeli territorial acquisitions resulting from the war have permanently marred Israel’s relationship with its Arab neighbors. The May crisis that preceded the war quickly spiraled out of control, leading many to believe that the war was unavoidable. In this paper, I construct three counterfactuals that consider how May and June 1967 might have unfolded differently if a particular event or person in the May crisis had been different. Ultimately, the counterfactuals show that war could have been avoided in three different ways, demonstrating that the Six Day War was certainly avoidable. In the latter half of the paper, I construct a framework to compare the effectiveness of multiple counterfactual. Thus, the objective of this paper is twofold: first, to determine whether war was unavoidable given the political climate and set of relations present in May and June 1967 and second, to create a framework with which one can compare the relative persuasiveness of multiple counterfactuals.