The article provides a semantic analysis of the theme of kitovras (centaur) in Russian medieval fine art. The author argues that in the system of relief decorations of Russian medi-eval cathedrals in Vladimir, the centaur is associated with the Jerusalemite kings David and Solomon and serves to accentuate the theme of a wise and righteous ruler. The study of kitovras images in Russian medieval art, traces the origins of this character back to apocry-phal literature or even further to ancient mythology, Talmudic tradition and biblical nar-ratives, which merged into a ‘Russian centaur’. The earliest kitovras images are found in Novgorod region in the 11th century. The typology of centaur images in Rus’, as well as the study of possible contexts for the use of these images in church decoration and in everyday life, make it possible to systematize the semantic and axiological connotations evoked by this figure of a man-beast. These connotations are associated with the ideas of (1) natural savagery, (2) demonic character, (3) duplicity, (4) wisdom, (5) architectural skills, (6) moral perfection, (7) saving pedagogy, (8) protection from evil and, finally, (9) religiously sanctioned author-ity. Since all these connotations are associated with the same character, the kitovras should be understood as a polyvalent symbol that reveals to viewers one or another of its aspects depending on a viewer’s semiotic code and on the visual and narrative contexts in which it is integrated. Russian churches open their facades into the surrounding urban environment and thereby saturate it with certain meanings, conveyed both by the outline of the churches and by their exterior decoration. Any figure, any scene and any character represented on external surfaces of the churches directly contributes to the semantics of the urban space, to its ideo-logical and cultural program, and functions as a means of informing both confessional and local identity. Such is also the function of kitovras images in the semantic structure of tradi-tional Russian cities.