This research focuses on the controversy surrounding the exhibition and media publication of Brett Murray’s painting, The Spear of the Nation (May 2012). It takes the form of a qualitative Critical Discourse Analysis (CDA), underpinned by Fairclough’s (1995) three-dimensional approach, to investigate how the contesting discourses articulated by the ruling political party (the ANC) and the news media have been negotiated in the City Press coverage in response to the painting. While the contestation was fought ostensibly on constitutional grounds, it arguably serves as an illustrative moment of the deeply ideological debate occurring in South Africa between the government and the national media industry regarding media diversity, transformation and democracy. It points to the lines of fracture in the broader political and social space. Informed by Foucault’s conceptualisation of discourse and the role of power in the production of knowledge and ‘truth’, this study aims to expose the discourses articulated and contested in order to make inferences about the various ‘truths’ the ANC and the media make of the democratic role of the press in a contemporary South Africa. The sample consists of five reports intended to represent the media’s responses and four articles that prominently articulate the ANC’s responses. The analysis, which draws on strategies from within critical linguists and media studies, is confined to these nine purposively sampled from the City Press online newspaper texts published between 13 May 2012 and 13 June 2012. Findings suggest the ANC legitimise expectations for the media to engage in a collaborative role in order to serve the ‘national interest’. Conversely, the media advocate for a monitorial press to justify serving the ‘public interest’. This research is envisioned to be valuable for both sets of stakeholders in developing richer understandings relevant to issues of any regulation to be debated. It forms part of a larger project on Media Policy and Democracy which seeks to contribute to media diversity and transformation, and to develop the quality of democracy in South Africa.