AbstractAlthough Japan is generally considered a liberal democracy with a free press, concerns about media independence have repeatedly been raised. The World Press Freedom Index ranks Japan last among G7 nations. One of the major reasons for its performance lies in a deep-rooted entanglement of the mainstream media with the political establishment, which is said to promote a climate of self-censorship and impede courageous, critical journalism. While the government-approved reporters’ clubs (“kisha clubs”) are often cited as lying at the heart of the problem, there are other relevant structural and historically grown factors hindering the improvement of press freedom: Despite theoretical constitutional protection, media governance in Japan does not provide an adequate framework for journalistic independence; furthermore, revolving door politics, editorial interventions and informal arrangements are well-established practices inside the sphere of media and politics. Nevertheless, there have been those critical moments when the mainstream media, in fact, influenced the course of politics. Setting out from the present condition of media democracy in Japan, this article traces back the historical roots of the seemingly firmly ingrained relationship between journalism and the state. Thereby, it portrays the ambivalent interdependence between the media and politics, and the dilemmatic tension between journalistic integrity, economic interests, and political influence. Finally, it explains why the current hegemony of the legacy media in the public sphere may eventually face a silent, but profound transformation in light of digitization and advancements in artificial intelligence.