Although the democratic role of journalism in new democracies is heavily debated, systematic empirical analysis is scarce. This paper studies how the performance of the watchdog and civic journalism role in Chilean newspapers develops during 22 years of democratic transition. We challenge the homogenization-thesis, which has often characterized thinking about the role of the media in democratic transition, assuming an automatic unidirectional trend toward more critical professionalism, where reporters increasingly act as watchdogs by taking the side of ordinary citizens against the political and economic elite. We argue that a rise in critical professionalism is often limited to a brief honeymoon period after the return to democracy. We furthermore argue that to understand changing role performance during democratic transition, one needs to look at specific developments of the media (press freedom, journalism education, advertisement income, and circulation) and developments in the political context, in particular the degree of political conflict. These hypotheses are tested with a unique data set consisting of a content analysis of 20,201 news articles, which make up representative yearly samples of newspaper coverage in Chile between 1990 and 2011. We find no trend toward more watchdog and civic journalism, and limited influences of developments of the media. At least for the performance of these two journalistic roles in Chile, changes in journalism during democratic transition can best be explained by the honeymoon hypothesis and the degree of political conflict. The generalizability of these findings to other transitional democracies is discussed.