The aim of this article is to determine the features of the genre and the moral-philosophical perspective of Vsevolod Ivanov’s portrait essays of the 1920s – early 1930s published in Vladivostok non-Bolshevik newspapers (Russkiy krai, Russkaya armiya, Vechernyaya gazeta), in Harbin émigré periodicals (newspapers Svet, Gun-Bao, the magazine Rubezh). To achieve this aim, using a semantic-cognitive approach, the author of the article studied archival materials of periodicals of the Russian Far East and Far Eastern emigration and introduced into academic discourse new unexplored factual material contributing to filling gaps in the history of Russian literature and journalism of the 20th century. Ivanov’s portrait essays are analyzed in the context of the sociopolitical and cultural life of the Far Eastern Republic (FER) that existed in the Russian Far East and the large-scale emigration of Russians to China. The author considers the dynamics of Ivanov’s portrait essay genre development. It acquires elements of the memorial and obituary essay, the genre of the literary portrait as a reflection of the progress of the national historical-literary process in the mother country and in the diaspora caused by the spiritual-moral confrontation of the political forces of Russia, the ideological split in the national culture of Russia due to the events of October 1917. The author of the article relies on historically significant material: the memorial essay with the conceptual title “Justified Avvakum” actualizes the problem of a reasonable and balanced attitude to changes, the correlation of evolutionary and revolutionary principles in the development of society. Ivanov raises the question of personal, moral, and civil responsibility for the fate of his country in the essay “The Blood of the Tsar”, which recreates the tragic events of the execution of the family of the Russian Tsar Nicholas II by Bolsheviks. In the analysis of obituary portrait essays about the tragic losses of Russian literature of the Silver Age (“Conversant with Secret (In Memory of A. Blok)”, “In Petrograd the Bolsheviks shot the poet Nikolay Gumilev”), the author of the article concludes about the originality of the creative potential of Ivanov, who, using elements of the genre of the literary portrait, demonstrates the synthesis of scientific, literary, and journalistic writing. The portrait essays of Ivanov’s prominent contemporaries, figures of politics and culture (“Admiral Kolchak”, “Semenovshchina “, “Prof. D.V. Boldyrev”, “Vasiliy Fedorovich Ivanov”) complement the complex picture of the sociocultural context of the era with relevant axiological aspects identified in the essays. The author of the article considers Ivanov’s reference to the iconic figures of the turning epochs in the fate of Russia as a peculiarity of his journalistic position in relation to history as a criterion of truth and moral value of a person.