The purpose of this article is to investigate images of Polovtsians (Cumans) in the chronicles in terms of their direct perceptions by Russians—as enemies and neighbors, allies and relatives. Narratives and messages in the early chronicle tradition enable us to trace the formation of such images and the dynamics of their transformation. The study was conducted on the basis of reports and narratives in the Laurentian and Hypatian Chronicles that transmit events of the pre-Mongol period. The chroniclers describe the Polovtsians in terms of ethnic, religious, and, sometimes, geopolitical features. In some cases, they appear as a single entity and in others, as individuals. The latter includes contexts in which the Cuman act as allies of the Russian princes. Analysis of the chronicle material shows that the image of the Polovtsian is a complex and evolving phenomenon. As a general trend, it can be noted that there is a transformation from general references, which are not personalized, to images of Polovtsians either as individuals or as engaging in some kind of community-driven actions with understandable motives and goals. In the assessments of the chroniclers, negative or neutral impressions dominated, with special emphasis on confessional aspects of the Polovtsians they were describing.