This article aims to present an overview of the Moldovan media system, beginning from the 1990s. The paper maps the country’s media market and ownership structure, print press, broadcasting media, and journalistic culture. The findings are based primarily on 52 semi-structured interviews conducted in Moldova in 2006 and 2011 with journalists, media analysts, academics, and media owners, and on recent literature and some scholarship on the media system in Moldova. This article seeks to discuss the following questions: What forces have influenced media development and journalistic profession in Moldova over the past 20 years? Why has the critical situation of Moldovan media in the early years of democratization become the norm expression nowadays?