Introduction. Unfortunately, at present, scientists have not given an adequate assessment of the political ideals of Russian thinkers, writers, and publicists of the XV – early XVII centuries, many of them are directly discredited, as they are manipulated into the scheme of “the initial commitment to autocracy», perceived as synonymous with absolutism. Serious scientific disagreements concern not one, not two, or even not three medieval thinkers, but all of them, especially the late Middle Ages, represented by such famous names as Joseph Volotskiy, Filofey Pskovskiy, I. S. Peresvetov, A. M. Kurbsky, Zinoviy Otenskiy, anonymous authors of the Valaam Conversation, etc. This galaxy is completed at the turn of the Middle Ages and the first quarter of Modern Times by the sovereign clerk Ivan Timofeyev. Methods. The authors, based on a systematic, historical, and comparative analysis of the works of these thinkers, offered their own viewpoint on the political ideals formulated by them. Results. The result of the study is presented by the following conclusions: researchers’ understanding of the political ideal of medieval thinkers depends on the assessment of both their works themselves and the historical conditions in which they were created; the preservation of some outdated schemes, many of which originated in the pre-revolutionary period which were uncritically perceived in Soviet historiography and remain up to nowadays, prevents the achievement of unity in the definition of the forms of government which were forming in different historical epochs and the assessment of the accompanying political and legal doctrines; in historical and especially historical and legal studies, it is always necessary to apply historical, rather than modern terminology in the analysis of key concepts used by medieval thinkers in characterizing existing (for them) historical conditions and in their proposed projects of state-legal transformations.