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More than twenty years after the collapse of the Soviet Union, Russia’s military intervention in the Syrian Civil War in September 2015 was perceived by many Western observers as the comeback of the “Russian bear” to the Middle-Eastern battleground. Despite having a long term diplomatic alliance with Russia, the Syrian republic is not a part of post-Soviet Russia’s “near abroad.” Therefore, the deployment of Russian airstrikes on the Syrian territory is strong evidence of the resurgence of Russia as a great power. It also demonstrates the Kremlin’s determination to once again include the Middle East in its sphere of influence. This paper provides a general overview of Russian, Soviet and post-Soviet involvement in the old and new “eastern question.” It also highlights, within a broader historical perspective, the major shifts of Russian multilateral diplomacy and the long-term underground strategy of the instrume­ntalization of minorities in the region from the mid-nineteenth century up until 2017.