The subject of this paper is Taras Shevchenko’s attitude towards the key personalities – Mykhailo Shchepkin, Nicholas I, and Yekaterina Piunova – as reflected in his diary (also called “The Journal”). The goal is to focus on the author’s characteristics of these people, those that illuminate his own personality too. Although there are a number of studies on the poet’s contacts with them, quite a few important details still remain unclear and unexplained. Another pertinent issue is dubious theses and interpretations, which have become widespread in academic discourse. Thus, the article proposes possible answers to a number of problematic issues in the studies of Shevchenko’s biography. It covers the formation of an almost entirely positive image of Shchepkin, the expressions of the author’s respect and affection to him, that were misunderstood by researchers. The paper also emphasizes Shevchenko’s authorship of the bright expression “neudobozabyvaemyi Tormoz” [hardly-forgettable brake/slowpoke], the one attached to the most negative character of the diary, Tsar Nicholas I. It explains the accuracy of the author’s notes about the monarch’s influence on the architectural development of the cities in the Russian Empire. Particular attention is paid to the prospects of research of those events and plots that, for various reasons, were virtually never mentioned in “The Journal.” I propose an explanation for the fact why Shevchenko did not provide lengthier feedback on his train ride, this new experience for him. The article also talks about the most controversial figure in the diary, namely Piunova. I suggest an alternative reading and etymology for one of the epithets addressed to her, that speaks in favor of the poet’s linguistic competencies and creativity. The emerging result of the research is the clarification of a few episodes of the poet’s biography and his relationship with the mentioned persons. The article demonstrates the productivity of a comprehensive examination of the text both at its macro- and micro-levels. This novel approach combining “distant” and “close” reading can be successfully used for investigation of other Shevchenko contacts and personalities mentioned in his diary.