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Why does the existing debate about the Russian government’s decision to annex Crimea fail to explain why the annexation took place following Ukraine’s Euromaidan protests in 2014 and not following the Orange Revolution in 2004? This study examines the evolution of the Russian bureaucracy from 2002-2014 to demonstrate that bureaucratic willingness, enhanced by military successes derived from previous bureaucratic actions, was a necessary condition for the annexation to be justified and conducted. The existing theories place Putin as the sole decision-maker of Russia’s foreign policy, suggesting that all of the country’s actions derive from one man alone. This study aims to challenge this commonly accepted belief and instead suggests that the country’s foreign policy decisions are the product of a wide collection of individuals. The implications of this study suggest that Russia’s foreign policy may remain consistent beyond Putin’s presidency.