The study examines reflections on freedom in the thinking of two important representatives of the democratizing changes in Czechoslovakia in the 1960s. Both Miroslav Kusý and Milan Hamada were among the original thinkers who dealt with the issue of the institutional and power determination of man and his freedom. Despite their different philosophical perspectives, both focused on seeking answers to questions about defining the conditions for the development of individual freedom, which was combined with an interest in the humanistic interpretation of Marxist philosophy. In this context, Kusý’s thinking concentrated on the practical problem of social democratization, which he defined using the term “institutional revolution.” In contrast to this perspective, the thinking of Milan Hamada was inspired by an interest in the issue of power interference in the creation of a space of personal freedom, which he interpreted from an existential-phenomenological point of view. The study will detail how both thinkers reflected on possible solutions to the struggle for freedom and human dignity, which is determined by the risk of a homogenising political power.