The Ukrainian crisis has revealed a fundamental split between Russia and its Western partners, which has in recent years been transforming into a long-term opposition. Two years after the crisis has begun, one can observe a dramatic change in both international contacts and Russia's political image. On the basis of interviews, public speeches and analytical materials, the author of the article describes and classifies the main viewpoints existing within the European and American expert society as concerns the internal political climate in the Federation, its place in the current world order and perspectives of partnership. The article is structured for the reader to see, firstly, how the perception of political image can influence personal attitudes, which key factors can be used for these purposes, and secondly, to classify experts according to their stance on the origins of the Russia–West crisis. Among political psychological factors the author highlights: stereotypes, images of distinguished personalities, belief system, bounded rationality, personal perceptions, focus of attention, emotions. The main parameters of expert society classification include: career line, party affiliation, nationality, Cold War experience, education and the main research topic (if an expert is a professional Sovietologist/Russianist), personal attitude to the object (Russia). All experts mentioned in the article are divided in three categories. The first one includes the realist-pragmatists – those who do not want to reideologize relations with Russia and tend to seek ways to new normality. The second are the regime change supporters – those who believe that the current political system is the source of crisis. The third are the containment policy revival supporters – those who think that any means, including military, are good to confront the Russian aggression, which, to their opinion, lies in the core political and psychological basis of the Russia's nature as a successor of the USSR and the Empire. Today, foreign experts are more interested in Moscow's ambitions at large than in dynamics of the Ukrainian crisis, which dramatically harms relations between Russia and the West. The course on isolation in the long run is much more dangerous than it seems to be, as it impedes a global coordination of joint projects between Russia, the European Union and the United States. Track II diplomacy is a very efficient tool to normalize mutual relations, especially when there is little political will on every side.