This article examines the fate of the well-known chess players of the middle of the 20th century - the “expatriate defector” Alexander Alekhine and the Soviet champion Mikhail Botvinnik - as one of the little-known stories related to the history of the contacts between the representatives of the Russian diaspora and the Soviet state of the Stalin era. The author examines the history of the failed match between these two outstanding chess masters in 1939-1940 and shows why the Alekhine-Botvinnik match, which had been initially approved at the highest party and state level, was not held, and find out what role the Soviet administrative apparatus played in this. The author comes to conclusion that under the conditions of strict authoritarian leadership, with the directives of V.M. Molotov, N.A. Bulganin and A.Ya. Vyshinsky, and possibly Joseph Stalin, the managers had a sufficient set of bureaucratic methods that allowed delaying the process of preparing the match up to a favourable occasion which led to the final breakdown in the negotiations. Such methods include precaution, prolonging pauses in interdepartmental communication, requesting for “instructions”, recalculating estimates, using rumours as arguments, using erroneous addresses and redirecting correspondence. The reason for the officials’ inactivity was the fear of personal responsibility for the defeat of the Soviet champion by the “expatriate defector”, especially in the situation when some leaders of the USSR chess movement were repressed. The author’s analysis provides insight into the problems of the functioning of the executive power in the conditions of the political regime established in the USSR by the beginning of the Second World War.