In this article we try to describe and explain the nature of possessor doubling constructions, as we call structures containing both external and internal possessors, in Russian spontaneous oral speech. Drawing from the data extracted from the “One Speech Day” corpus of oral vernacular Russian we try to single out the reasons for using such constructions which are generally believed to be semantically redundant. We demonstrate that this redundancy is in many respects imaginary and claim that the two separate parts of this construction do not convey the same possessive meaning and their pragmatic orientation is quite different. The external possessor may in fact lack possessive semantics at all, being just the way of encoding the discursively central entity or the bearer of the local point of view, while the internal possessor may be overt or covert depending on its saliency and secondary meanings. This difference allows these constructions to appear in the same utterance simultaneously.