This study applies content and text sentiment analysis to the Twitter timelines of US Presidential candidates throughout the 2016 primary season. The two central questions examined in this analysis are the sentiment differences displayed by insurgent and establishment candidates and which of these sentiment traits are more likely to make tweets go viral. Tweet sentiment variables examined in this study include affective processes, drives, and gender references. Our evidence suggests insurgent candidates are more likely to exhibit both affective emotion and gender references while establishment candidates are more likely to demonstrate affiliation. Trump and Clinton were found to be strong representations of the insurgent and establishment candidates, respectively, with the main differentiator being Clinton’s propensity to reference females. The strongest sentiment traits linked to retweetability were negative emotion and female references.