Based on a theoretical perspective linking international actors with domestic elites, this article explores how Ukraine’s process of democratization in the 2000s should be understood in terms of international pressure from the European Union (EU) and Russia squeezing the domestic elites into two alternative roadmaps for Ukraine. Ukraine, as a “swing-state” of democratic progress and problems, is assumed to have great impact on the regional democratic landscape. The contemporary hybrid nature of Ukraine’s political regime is a consequence of Ukraine being located geopolitically between the authoritarian Russia and the democratic member states of the EU, leading to competing political elites with alternative visions for the future of Ukraine.