This paper reconsiders the possibility of freedom in the Soviet Union, generally regarded as a police state, through analysis of the texts of Yuri Lotman (1922–93), the leading scholar of Soviet semiotics. It is often said that Soviet society in the era of “stagnation” was rigorously divided into the overwhelming official sphere and a smaller space for private, occasionally dissident activities. This categorical division between the policing and the policed was questioned by Lotman, who endeavored to augment freedom within the official sphere. Although sympathizing with the dissidents, he persisted in publishing in officially sanctioned media. Lotman’s analysis of the theatrical culture of the Russian nobles can be interpreted as an implicit illustration of his ambivalent strategy toward this goal. When perestroika unexpectedly (“explosively,” in Lotman’s terminology) brought about freedom, he turned attention to the indivisible relationship between freedom (chance) and determinacy, warning against the extreme destructiveness to which an explosion of freedom may lead. Thus, Lotman’s pursuit of freedom always avoided simple opposition between the policing and the policed, illuminating the possibility of a route combining the two.