The article discusses three literary characters inspired by historical Estonian politician Aleksander Kesküla, found in the novels „Tõde ja õigus” III (Truth and Justice III, 2009 ) by Anton Hansen Tammsaare, „Dr. H. Rejsende i revolution” (Dr. H. Traveler in Revolution, 1986) by Tørk Haxthausen, and „Volta annab kaeblikku vilet” (The Plaintive Whistle of the Volta Factory, 2001) by Aarne Ruben. In all three novels, Kesküla is a secondary character, yet fulfills a significant role in the context of the author’s more general ambitions. The depiction of Kesküla, stressing mysteriousness as his main characteristic trait, is relatively realistic in the sense that it remains faithful to the memoirs and historical sources used by the authors. Nevertheless, this mysterious character functions quite differently in the different novels. Notably, Tammsaare uses him as an anti-hero opposing the protagonist, Haxthausen places him in the background thus contextualizing the activities of the main character, while Ruben makes him an epitome of the rest of the novel.