Background: This study is based on the emerging contradiction regarding trust in journalism studies. Initially, trust is the main source of legitimacy that cannot be negotiated for news media. In contrast, this has limited the media’s commercial operating space to sustain its organizational economics. The closest example is local media, which has been trying to strengthen trust to maintain its legitimacy. Purpose: This study analyzes how actors at Radio Suara Surabaya construct and negotiate trust through metajournalistic discourse, along with its implications for journalistic legitimacy and the organization’s economic sustainability. Methods: This research used a qualitative approach, employing a discursive case study design that positions Radio Suara Surabaya as a reflective case. Primary data were obtained through focus group discussions (FGDs) involving editorial and managerial actors, and supplemented by the organization’s historical documents and previous research. Results: For the actors, trust is built through a lengthy institutional process that serves as a moral compass for journalistic practices. However, trust also creates pressure from rising public expectations, and devising strategies to increase revenue within monetization limits could compromise trust. This is where the paradox lies: media legitimacy is obtained through trust, but it does not guarantee economic gains amid an increasingly platformized media ecosystem. Conclusion: This study introduces the concept of the “paradox of trust” to explain how trust can simultaneously serve as a source of legitimacy and a constraint on the monetization of local media. Implications: The findings of this study expand the research landscape on trust, showing that the sustainability of local media is also linked to the discourse on which values should be upheld and which changes are considered legitimate. Thus, it is not solely related to business and technology.