Discourses on democracy in Africa often revolve around the relevance of Western democracy to African nations given the region's peculiar socioeconomic and cultural conditions (Ezeani, 2013). In many African countries, evidence abounds of the absence of democratic dividends, an indicator of the apparent failure of liberal democracy in the region. The media as the fourth estate of the realm is often seen, albeit idealistically, as being positioned to rise above democratic failures and, in its watchdog roles, to work towards the enthronement of good governance. Unfortunately, in Nigeria, the environment within which the media operates vis-àvis the ownership structures has continuously posed stoic challenges to its expected roles. The result is continuous dilemmatic practices, whereby the media's position as bastion of democracy is consistently negotiated. This article, with exemplars from the Nigerian media scene over the years, x-rays the stoic challenges which media ownership poses to Nigerian society as the nation works towards development through good governance. It argues that ownership patterns, pressures and politics continue to challenge the consistent and committed role of the media in deepening our march towards good democratic governance. The article, however, concludes that rather than heaping the blame on the media, one could more safely return a verdict of collective responsibility-viewing the failings of the media within the larger context of the failings of the social system in which the media are embedded. Such thinking invariably points to the fact that various stakeholders other than the media have a role to play in enthroning good governance in the Nigerian polity.