The relationship between S. I. Gessen and V. V. Zenkovsky, representatives of Russian philosophical, psychological, pedagogical and social thought, is considered as an episode of the intellectual history of the Russian diaspora. It is argued that the image of S. I. Gessen, formed in the scientific works and memoirs of a famous teacher, complements the idea of his personality, of the position S. I. Gessen held in the scientific, pedagogical and social life of the emigration. An analysis of the relationship between two thinkers over a quarter of a century is presented. The conclusion is drawn about the “internal dialogue” between them, which developed on the pages of emigre periodicals, was recorded in correspondence with like-minded people and became the subject of reflection and self-reflection in scientific works. The author pays special attention to assessments of the theoretical contribution of S. I. Gessen to Russian and European philosophical and pedagogical thought, which are given in reviews and surveys, the essay “Russian Pedagogy in the XX century” and “History of Russian Philosophy”. It is shown that in this context, the responses to the death of S. I. Gessen and memories of him, which make it possible to determine the attitude of V. V. Zenkovsky not only to S. I. Gessen the thinker, but also to man, acquire great importance.