This paper argues that transparency projects retain a political hue from the social-technological context from which they are created. Thus, radical transparency is considered as an opportunity to evolve both journalistic and democratic practices. Transparency in practice reveals diverse expectations of how journalists reporting should be used, and these expectations in turn, seem dependent on specific worldviews. This paper presents a comparative analysis of the effects of the current exemplar of radical journalism, WikiLeaks. It compares Wikileaks to its historical equivalents, including Hansard in the 18th century, and the reporting of open diplomacy in the early 20th century. This analysis shows how journalism evolves along with radical transparency projects, and how the current context of networked radical transparency can, and will, be made into news with specific political effects. In conclusion, this paper argues that practitioners should be aware of the political hues that new transparency mechanisms afford. Being cognizant of context and design choices can increase the degree to which new initiatives can have a deep systemic impact—as well as acknowledge the qualities and repercussions of that impact.