This article analyzes the possibility of development of liberal constitutionalism in the Russian Empire during the post-reform period in the late 19th – early 20th century within the context of European history, of which Russia was an integral component. It argues that the Russian autocracy had the potential to transform itself into a constitutional monarchy during the period that followed the Great Reforms of the 1860s (1861–1881) and, second, during the Revolution of 1905–1906 and in its aftermath. This promising evolutionary process was cut short by World War I and rejected by the Soviet period of Russian history that followed. Obstacles to constitutional government were mostly objective in character, but perhaps the most significant problem was the fragmentation and insufficient development of Russian political culture, or better said, cultures that failed to produce the consensus required for effective creation and functioning of a constitutional regime. This failure was further exacerbated by an evolutionary radicalization of revolutions in modern European history that culminated in October 1917. The author concludes that the events of the late 1980s and the Revolution of 1991 changed the character of the Russian historical landscape and provided the potential for renewed development of a pluralistic political system and a strong civil society that is its precondition.