The article analyzes the semantics of the image of the holy fool in V. A. Nikiforov-Volgin’s short stories “Holy Fool” and “Glebushka the Holy Fool.” The image of the holy fool in the author’s prose took shape under the influence of the Old Russian literary tradition, works of Fyodor Dostoevsky and Ivan Shmelev. Nomination of the holy fool in the prose writer’s works reflects the character’s childishness and soul purity, characteristic for this image. Glebushka the Holy Fool from the eponymous short story is a big child, and he is praying for forgiveness for his people, who are burdened with great sins. The holy fool in V. A. Nikiforov-Volgin’s short stories is a traveler, a pilgrim who lives outside the community. An encounter with him makes other characters rethink their lives, and offers an opportunity for repentance and life changes. Nikitushka (“Holy Fool”) is a messenger of the spiritual world; he appears to be reverend-like for one of the story’s characters. This hero appeals to the characters’ conscience without words, notations or rebukes; he relates to the motifs of spiritual transformation and enlightenment. The repentant bandit bows to the ground before the holy fool, thus pleading for forgiveness, and expressing humbleness and awe of the sanctitude. In this short story, Nikitushka the Holy Fool becomes the one who helps the wayward sinner reach God.The world of angels is close to the holy fool. V. A. Nikiforov-Volgin’s short stories present angels either as the holy fool’s interlocutors, or characters in the spiritual poems recited by the holy fool.The holy fool is an advocate not only for salvation for particular people, but for all of Russia.