This chapter considers how advocacy of press freedom necessarily implicates contested political questions about desirable structures of governance and social interaction. Professor Magarian discusses two political oppositions that strongly influence how the free press functions: objectivity vs. subjectivity and institutionalism vs. populism. First, the chapter describes the late-twentieth-century news media’s heightened commitment to objective reporting. That commitment has strong political resonance with our era’s anxiety about submergence of objective truth in political debates. At the same time, the news media’s push toward objectivity fostered a stultifying homogeneity that prompted dynamic efforts, embodied imperfectly in the Fairness Doctrine, to complicate hegemonic narratives. Present advocates for press freedom must assess which truths the press should propound and which positions it should interrogate. Second, the chapter juxtaposes the institutionalized character of dominant late-twentieth-century news media with the populist fragmentation of news sources in the age of online communication. Institutionalized mass media have inculcated valuable journalistic norms of professionalism and ethics that contemporary online news sources often elide. However, populist mass media present a wider, more diverse range of voices than institutionalized media support. Present advocates for press freedom need to pursue the optimal balance between these opposing virtues.