When explaining the trends and level of the three freedoms, the role of the rule of law with regards to governmental effectiveness, the control of corruption, and the compliance of public order with fundamental rights should be considered. Besides, there is the paradox of more information and less freedom and the paradox of more rules and less freedom. We also focused on economic freedom, freedom of religious association, freedom of movement, and improvement of protection of dignity because of the modernization of the judicial systems and the prisons. Moreover, the wave of technological development did not translate into an improvement of individual freedoms, especially for privacy protection, freedom to access information, and freedom of movement. The media and pluralism of information are considered critical in helping individuals to make conscious choices and ensuring the possibility of shedding light on rulers’ behaviour and filling the gap between the asymmetry of information that marks the hiatus between rulers and ruled. Despite the undeniable advantage of being provided with a potentially infinite range of information and being able to access a spectacular plurality of sources of information, citizens easily fall victim to what is now labelled as fake news. Overall, the Web is ill-prepared to cope with the risks of the biased information available on the Internet. Freedoms seem to be running the risk of being subverted by the overwhelming availability of data and information if a sound plural and institutionally embedded system of media pluralism is not in place.