The article analyses global and regional factors which determined post-Soviet Russia’s and Turkey’s policy toward Transcaucasia, on the one hand, and volatile reaction of the local high authorities thereto. As the author argues, the Kremlin’s strategy evolved from almost total detachment caused by weakness of the state lost in liberal reverie to the grasping of its own geopolitical interests in the Caucasus to be adequately translated into a much more assertive international behavior. As for Ankara’s policy in the region its evolution took place just in the opposite direction, i. e. from the euphoric desire to fill the Transcaucasian «power vacuum» to a sober reassessments of the viability of the course aimed at political and economic confrontation with Russia given her enormous military potential. This resulted in a formation of a blueprint for a long-term compromise capable to secure the framework for constructive partnership between Moscow and Ankara in Caucasian affairs.