I use discourse analysis to investigate the white press of the original Rainbow Coalition, founded by the Illinois Chapter of the Black Panther Party, to dissect how radical media is used as a platform to build coalitions, and debate the role of allies. Borrowing from Viraj Patel’s intersectional approach to allyship, which suggests that one’s cross-cutting identities creates situationally-specific roles for allies, I add a communicative perspective to understand how allies can effectively represent and practice allyship using mass communication. In doing so, I break down how whiteness is represented in radical media to understand if it’s an inherently negative concept.