The legal environment particularly the body of laws that regulate media operations are telling, yet underexplored, indicators of press freedom. Using the analytical concept of episodes of contention based on a reading of contentious politics, the article examines the ambivalent state of press freedom in the Philippines. The argument is that the protracted issues of media access and libel serve as two episodes of contention that identify extant and emerging sets of actors, mechanisms, and claims that collectively characterize the role of media law in the body politic. Drawing from interviews with journalists and review of the Supreme Court rulings about media access and libel, the hope is to underscore the potential and limits of the Court as an ally of the media in advancing press freedom. The decision of the Court does not at all times favor a liberal interpretation of press freedom but it deploys ways including dissenting opinions that can balance, if not outrightly oppose, the occasional negative view of the Court toward media-related cases.