The article is a trial of reconstructing one of the most important components of the culturalhistorical landscape of Russia at the 15–16th centuries, which is of paramount importance for understanding the essence of the ideas of monk of the Pskov Eleazar monastery Filofei, the author of the theory «Moscow as the Third Rome». According to the conventional opinion, relations between Russia and the West after the Ferraro-Florentine Council became irreconcilably hostile, and the perception of Catholicism, the «First Rome», was unequivocally negative. If cultural contacts persisted, it was only in spite of confessional differences. However, the situation of the late XV – early XVI centuries demonstrates a more flexible and pragmatic attitude of the Russian intellectual and political elite: society and the church remained faithful to Orthodox teaching, not inferior in dogmatic and canonical issues — such as filioque, communion with unleavened bread or the ecclesiastical supremacy of the pope, but were quite ready to assimilate Western experience. Even such prominent representatives of the church hierarchy as Avraamiy of Suzdal, Gennady of Novgorod and Metropolitan Makarius recognized that something could be learned from Catholics. Against this background, the position of Filofei, who considered everything emanating from the Western church to be the machinations of the devil, seems much more categorical and intolerant. According to the author of the article, this difference in the perception of the «First Rome» is one of the reasons for the weak interest of the Pskov elder’s contemporaries in the idea of the Third Rome. He sees the explanation of such a position of Filofei, on the one hand, in the specifics of the border position of Pskov, which is why the degree of hostility to the West was clearly higher here, and on the other hand, in the fact that the theory of the monk of the Eleazar Monastery was exclusively theological and had nothing to do with foreign policy, the structure of the Russian state or the perception of Western culture.