The Egyptian media system shows a stark paradox: Despite its long history and pioneering position in the Arab media landscape, under the current authoritarian trends today the media system has extremely blocked potentials for the possibility of independent media and journalism. Analyzing the current situation in Egypt does not disclose its status as a country with 200 years of history in journalism in the region, which has been marked by struggles and paradoxes. Reviewing the history of the Egyptian media system shows that three elements have influenced the evolution of the country’s media system. These include the geo-political position that made possible an early contact to the colonial French expedition which introduced the print press technologies and the restrictive political role of all subsequent rulers, whether foreign or Egyptian, in regulating and shaping possible media outlets as well as Egypt’s close connections to the evolution of global communication technologies. The political and legal framework has been dominated by mainly illiberal phases, with brief intermittent phases of liberalization that led to short-lived flourished media landscapes. The state engages in methods that apply legal authoritarianism to convey an impression of observing the rule of law, while in fact restricting freedoms and, in addition, controlling the political economy through indirect state capitalism, where media ownership stays within the state or the loyalist business elite, in particularly the popular audio-visual media. Amid the global journalism crisis, Egypt’s media system struggles for its financial survival, professional quality and recognition among young generations. Experts speak openly of “death of journalism”. Investments in the media are not on the current political agenda. On the contrary, they are viewed by the rulers as adversaries. Instead of making them powerful, the current credo is to weaken the media, as their loyalty and public influence are not guaranteed. The serious economic crisis and the lack of public credibility in media institutions only make struggles for professional independence harder. Coupled with brain drain trends and self-exile of oppositional journalists, forces to renew the profession seem to be distant under current circumstances. The article takes a nuanced position in the debate on the liberalizing role of the media in relation to the Arab Spring debate. The relevance of new digital media in Egypt had increased in the past 15 years. Many scholars and commentators attribute the Tahrir Revolution in 2011 directly to the rise of the Internet, as it was widely called Facebook Revolution. However, the article maintains that this is a simplified view of the events and interactions between media, politics and the online sphere. While the semi-liberal phase in the mid-2000s and the new technologies led to a vibrant blogosphere and opened up online spaces for otherwise marginalized voices, it took real grievances and real activism on the ground that interacted together. Since 2015, there are increasing signs of controlling the Internet: zero toleration policies towards dissent and criticism have marked the years through increased police control and imprisoning journalists, as well as takeover of all semi-independent media outlets and use of online surveillance technologies. Currently, more than 500 websites and news media are banned within Egypt. Therefore, despite growing numbers of Internet users and high Facebook penetration we cannot expect a simple linear mobilization effect. On the contrary, a strong backlash awaits any attempts for challenging the current regime. Situated within the persistent socio-economic problems that caused the Tahrir Revolution in the first place, the political system fears a potential opening of the media system and attempts at keeping a fragile stabilization at any cost. Clinging to the national security concerns and harboring stability at any cost, encouraged by the current global rise of right-wing authoritarianism, suspends any pressures towards reforms as previous US governments pursued. In addition to the restrictions, the professional media scene faces numerous crises: one of which is the erosion of the economic viability of media in times of a massive journalism crisis. Another crisis is the declining professionalism and reproduction of loyalist and propagandistic practices due to self-censorship and clientelist practices within a highly restrictive environment. These developments fragment the professional community of journalists across numerous political camps and weakens unionizing efforts. Finally, the audiences are increasingly pushed away from politics. Based on the analysis and challenges, the Egyptian media are heading into the unknown: “death of journalism”, extreme depoliticization of the public sphere and restrictive media environment weaken the media system. Under the current circumstances—and unlike former President Mubarak’s policies—no politician will push for progress and investments in the media sector. The Supreme Media Regulatory Council announced an ambitious digitization plan of the media; no clear agenda is seen, except tightening control and advancing loyalist media. In the current globally interconnected world, this is a serious challenge for the power holders. The current weakened and stifled media system has many potentials if given the chance to grow autonomously: a strong legacy, unused economic assets, talented journalists and a big market. These unused resources for now make it unlikely for Egypt’s media system to witness another golden time soon. Having said that, the situation is extremely unpredictable on the mid- to long term. Therefore, in case of a political opening, whether through reforms from above or a system forced to respond by a renewed public upheaval, potential for transformation is there, if given the necessary freedoms of expression.