Russia’s annexation of Crimea in 2014 is widely framed as an outside-in process, not only enabled but also enacted by the Kremlin. Prevailing accounts privilege geopolitical analysis and place those developments in a broader narrative of tension and competition between the West and Russia. Such a narrative downplays the involvement of local actors and the importance of the choices they made prior to and during those events. This article revisits the period leading up to March 2014 through a focus on critical junctures, critical antecedents, a near miss, and the path not taken. It argues that a full account of Crimea’s incorporation into Russia – while acknowledging Moscow’s role – cannot ignore the local contingencies that preceded and shaped it. We understand the region’s annexation as a key moment of institutional change in Ukraine and focus our attention on explaining how that outcome was determined, identifying the path to such a political outcome. Yanukovych’s decision to “catapult” political-economic interest groups from Makeevka and Donetsk into the peninsula led to the marginalization of the local elite. Regime change in Kyiv and a slow and cumbersome response from the new authorities in February-March 2014 triggered, but did not cause, Crimea’s exit option.