In Madison, Wisconsin, a member of a typically marginalized community challenged the status quo with the proposal for a charter school dedicated to Black youth. A year of debate ensued in mainstream news organizations and social media. Calling on critical race theory, this research compares the legitimation strategies of journalists to school officials, activists, and others writing online. Using textual analysis and in-depth interviews, the evidence demonstrated that even as journalists and others worked to reinforce the status quo by drawing from dominant institutions and principal storylines, the digital work of authentication and grassroots organizing of African-Americans and other supporters of the charter school forced an alternative discourse to developone centered on experiences of inequities. The article also shows how organizational constraints stymie well-meaning reporters when trying to story-tell about issues of race, and how all of these strategies from both Blacks and Whites come from a place of identity construction and maintenance.