The article investigates the fate of Freedom of Speech, one of the basic democratic values, amid the monopolization of the digital market and information space by large IT companies (the Big Tech “digital dictatorship”). The author relates the history of the Freedom of Speech principle, considers its connection with the new category of “informational freedom”, touches upon the term “informational violence” (which includes censorship). An important aspect of Freedom of Speech is its relative character, as it must not infringe on other agents’ rights or lead to state (social) security concerns. This provides a great opportunity for various interpretations and hence manipulations of this principle. Under conditions of “digital dictatorship”, Freedom of Speech appears to be limited by censorship on the part of the digital market owners who veil their political bias by worshiping the ideals of democracy. A detailed analysis of IT giants’ activities in the digital market reveals their monopolistic nature, which has economic, legal and socio-political consequences: the digital market submission to the terms set by the dominant companies, the violation of personal data confidentiality laws, the restriction of democratic rights and freedoms (primarily, the right to privacy and the Freedom of Speech). The antitrust campaign against four of the five Big Tech companies launched by the U.S. Congress in 2019, has not been successful. Regarding rights and freedoms violation, the IT giants also remain elusive, given the lack of effective legal practices for the settlement of such conflicts in information space. The situation is worsened by the politics of digitalization itself, which delivers additional controls to the monopolists. Having taken on the roles of censors, law-makers (defining the terms of service) and even policemen (blocking and deleting accounts in social networks), the Big Tech bunch has become a self-sufficient political actor. From a geopolitical perspective, the competitive struggle also takes place in the digital technologies arena, which complicates the maintenance of states’ political independence from the digital monopolists. All this creates conditions for an unlimited “digital dictatorship” of the big IT companies against untrusted users and even states.