Once democratic elections are installed in a liberalizing political regime, what determines the quality of media performance in a new democracy? The literature from academia and free press advocacy groups suggests a number of hypotheses, but the political ideologies and journalistic norms of newsroom leaders often are downplayed or even missed. Based on a comparison of Latin American newspapers known for bringing assertive, diverse, and autonomous news coverage to their countries, the central finding of this study is that, once a threshold of political liberalization is passed, the organizational dynamic matters most. Given enough slack in the environment, the political ideologies and journalistic norms of media owners and decision-making editors acting within hierarchical news organizations determine the fate of ”democratic” journalism. This finding demonstrates the need for comparative journalism studies to pay more attention to organizational and institutional dynamics as media systems are transformed.