After 1999, Ukraine and Russia both slid toward autocracy. As Leonid Kuchma’s autocracy made him a less fit partner for the West, he moved closer to Russia, and Ukraine’s 2004 presidential election looked set to solidify Russia’s position in Ukraine. The overturning of that rigged election via the Orange Revolution shocked the Russian leadership. In addition to snatching defeat from the jaws of victory in Ukraine, revolution now appeared to threaten the Putin regime. By merging the Ukraine–Russia conflict with the growing Russia–West conflict, this episode made both harder to solve.

The 1997 Russia–Ukraine Friendship Treaty appeared to confirm Ukraine’s borders and to settle the status of the Black Sea Fleet and Sevastopol, but many leading Russian politicians opposed it. Ukraine balanced its fear of Russia by becoming a leading participant in NATO’s Partnership for Peace. Meanwhile, the war in Yugoslavia exposed the tension between the western insistence on “European norms” and Russia’s insistence on its prerogatives as a traditional great power. By 1999, Russia was furious at NATO over expansion and Kosovo, and still sought to reintegrate Ukraine. However, the question of Ukraine remained largely distinct from Russia’s broader relationship with the West.

After 1999, Ukraine and Russia both slid toward autocracy. As Leonid Kuchma’s autocracy made him a less fit partner for the West, he moved closer to Russia, and Ukraine’s 2004 presidential election looked set to solidify Russia’s position in Ukraine. The overturning of that rigged election via the Orange Revolution shocked the Russian leadership. In addition to snatching defeat from the jaws of victory in Ukraine, revolution now appeared to threaten the Putin regime. By merging the Ukraine-Russia conflict with the growing Russia-West conflict, this episode made both harder to solve.