This textual analysis examines online mainstream media coverage during Hillary Clinton’s 2015/16 presidential campaign. Previous research on female political candidates indicates that there are both subtle and unsubtle ways the media reinforces masculinity in the political realm. The results of the study provide a commentary on the internet as a cultural text and Feminist Communication Studies, suggesting that there may be a decrease in the institutionalized sexism in the reporting of mainstream online media. Although encompassing only a small snapshot of the 2015/16 presidential race, the results also suggest that media seemed to lack a category for Clinton – she is both an inside and outsider, sitting at the cusp of a transformative historical event.