It is in the context of ideas of “new Middle Ages” that the author is carrying out his analysis of post-Communist transformations of Russian society. He reads into the “Middle Ages” notion – following J.Jacobs – first of all, a philosophical and culturological meaning of a universal historical buffer separating the dying-away of one civilization from the generation of another – at the same place. The author analyses the processes of “evolution of the chaos” of the post-Communist period, the opportunities and dangers Russia faces today and is yet about to face.