Abstract: The article is devoted to the analysis of the last poem by the bright representative of the Silver Age of Russian poetry Sergey Yesenin. The poem "The Black Man" is not only and not so much the poet's confession before his death, but the result of the poet's work, the logical, albeit tragic, completion of his artistic and life searches. The article examines the key images and motifs of the Yesenin poem in trans-literary and trans-cultural aspects, including references to medieval mysticism, mediated by the Russian literary tradition of the XIX-early XX century. The reception of mystical experience in the artistic world of Yesenin takes place through a rethinking of the traditions of Orthodox spirituality, the European Christian worldview and the romantic picture of the world.