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The protection of journalists' free press rights is often seen as necessary for ensuring the accountability of public officials. However, our research shows that judges' protection of these rights varies depending on judges' own institutional interests, those endogenous interests that arise from the institutions that judges themselves control. We analyze 659 free press cases and qualitative materials from journalists or media organizations who litigated their cases in high courts from Australia, Canada, Colombia, Germany, India, Norway, South Africa, the United States, and the European Court of Human Rights. Our study reveals that judges tend to grant journalists more protection when they report on bureaucratic and elected officials, but less protection when they cover judges or legal proceedings. We also use sentiment analysis to determine that judges' varied support cannot be explained by the tone of the underlying articles. Moreover, we use Annotation for Transparent Inquiry (ATI) to enable readers to assess the underlying qualitative evidence directly. Our findings suggest that courts play an important role as democratic safeguards for journalists. However, these safeguards are often reduced when judges perceive their interests to be implicated.