The article deals with the two main ways of interpreting freedom in the Russian philosophical culture of the 20th century: 1) through the conceptualization of the positive content of freedom, as a result of which it turns into a concept, an element of a philosophical doctrine; 2) through the negation of any positive content, which led to the identification of freedom with necessity. The thesis is proved that both of these ways of considering freedom made it impossible for the real problem of freedom to be under the philosophical research in Russia. By means of analyzing the concepts of freedom created by both religious and Soviet philosophers, the author shows that despite the fundamental difference in their positions, they all tried to do the same, that is to interpret freedom as a necessity. This is explained, in the author’s opinion, by the fact that both the religious-Orthodox and the Marxist-Soviet philosophical traditions in Russia focused on creating generalizing discourses, the structure of which initially excludes the possibility of grasping freedom.