The paper aims to describe the impact of judicial thinking on the style and imagery of L. Andreev’s prose. The research provides a theoretical interpretation of such central symbol-metaphors related to judicial issues as court, sentence, defence, and prosecution. The study draws parallels between the writer’s biography and the existential themes which L. Andreev reproduces in his writings by applying specialised terminology to metaphysical problems. To identify the above-mentioned parallels, traditional literary analysis is employed. It aims to generalise the writer’s aesthetic views on literature in the light of the judicial peculiarities of his thinking. Particular attention is directed to the influence of judicial stylistics on the poetics of L. Andreev’s writings. As a result, the application of linguostylistic analysis (aimed mainly at examining the lexical and syntactic structure of L. Andreev’s texts) enables the author of the paper to conclude that there is a sudden reorientation of the writer’s artistic strategy. L. Andreev replaced the rhetorical expressionist impact on the reader’s mind with the sharp, abrupt syntax of the story "The Seven Who Were Hanged". The form of judicial rhetoric manifestation also changed. The author substituted the deliberately monotonous stringing of "formulae-sentences" for the ornamental suggestion of the previously used techniques. The concise and compressed bare phrase became the method of conveying the author’s marked tendency that is indicative of the enormity of executions. The methods of statistical calculation and the linguostylistic analysis of excerpts from the short story "The Seven Who Were Hanged" were used to reinforce the derived conclusions. Additionally, theoretical material which helps to comprehend the specific features of courtroom prosecution speeches with regard to L. Andreev’s texts is analysed. The literary generalisations provided in the paper can be used in Russian language and literature lessons.