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Since 2003, the Russian-Georgian and the Russian-Ukrainian relations became worse because of pro-European policies of Georgia and Ukraine. Russia has had policy options of so-called “stick and carrots” for these two countries. In the case of Ukraine, the tensions between Russia and Ukraine has reached the peak when Russia annexed Crimea in 2014 after the collapse of the Yanukovich regime. This paper tried to prove that the selection of Yanukovich as a pro-Russian presidential candidate was a deep cause of “Orange Revolution” and “Euromaidan Revolution” and, consequently, the current conflicts between Ukraine and Russia. As a contrast to this, Ivanishvili’s active participation in Georgian politics has contributed to reverse Georgia’s pro-European policy and, consequently, a peaceful relations with Russia after the South Ossetian war. It also contributed to stabilize the domestic politics since 2012. This shows that the selection of political leaders and Russia’s support for them in these two countries is as important as other policy options. The comparison of personal background, education, economic ambition, the use of financial resources, corruption of Yanukovich and Ivanishvili presents a striking contrast. This has led to a completely different political fates of both leaders and different relations with Russia. In conclusion, more than any other means, the selection and support of political leaders in near-abroad countries has a critical meaning in defining the interests of Russia in this region.