The article presents the results of research on the expressive and stylistic load of graphemes in Ukrainian discourse from the end of the 19th century till today. Capital and lowercase letters are noticeably developing their expressive potential in modern Ukrainian discourse, becoming a significant means of text creation. At the same time, the issue of a capital letter going beyond the orthographic index of its own name (and the beginning of a sentence), transferring this function partly to a lowercase letter due to the ideological instructions of the speaker / speakers is on the fringes of scientific observations, while such use of these graphic signs was and is popular in the 20th–21st centuries. The purpose of our investigation is to trace the formation of the grapheme capital/lowercase letters as an ideologeme and to find out the productivity of this process at the current stage. During the research, it has been determined that capital and lowercase letters perform a crucial ideological function along with distinguishing names and appellatives. In general, Ukrainian spelling codes have been declaring a departure from the principle of “a capital letter is a proper name” for more than a century, giving these graphemes an expressive and evaluative meaning. The article traces the acquisition of a capital letter with the stylistic meaning of respectability, positive and evaluative connotations, and the reflection of this process in the spelling codes of the Ukrainian language. It has been also found that because of the intervention of the Soviet authorities in purely linguistic issues, expressions of contempt, insignificance, and pejorativeness, in general, were fixed in lowercase letters. The axiology of these graphemes is determined by extralinguistic factors, primarily the political situation and ideological guidelines of society, and is directly related to the evaluation of the referent of the corresponding lexical unit. The process of using capital/lowercase grapheme as an ideologeme is highly productive at the current stage of the development of the Ukrainian language. The powerful connotative potential of the lowercase letter became an indicator of the new linguistic thinking of Ukrainians and ideological resistance to Russian aggression. Despite the mass of “derogatory” spelling of proper names, one way or another connected with the Russian Federation, the issue of introducing a new spelling norm seems to be quite debatable.