Max Weber was one of the first social scientists to give a critical analysis of the socialist experiment in Russia from 1917 to 1920. The fundamental importance of this segment of Weber’s heritage today is that Weber makes his interpretation of the 1917 Russian Revolution not only from a practical-polemical standpoint, but also from a theoretical-sociological one. The main focuses in the article are Weber’s analysis of the Russian revolution from the point of view of the practical results of Bolshevik policies, and his comparison of the policies of the Bolsheviks during the Russian Revolution and Civil War of 1917–1920 with the doctrinal propositions of Marxist socialism. The article also deals with Weber’s thesis of the unavoidable bureaucratization of socialist society, and with his comparative analysis of the market and the planned economy. In conclusion, we formulate the idea of the heuristic potential which Weber’s analysis of the experience of the practical implementation of socialism in Russia might have for contemporary studies of the history of Soviet society.