Political campaigns have a temporal nature, which means that the strategic environment shapes the nature of candidate communication, especially the stages of campaigning—from surfacing to the general election. As social media platforms have matured and political campaigns have normalized their use of those platforms in this decade, this study examines the 2016 and 2020 US presidential campaign communication on Facebook and Twitter using data from the Illuminating project at Syracuse University. Our objective is to explore how the stages of the campaign cycle shape political communication. We also explore social media platforms as additional factors. Moreover, given the distinct and anti-normative communication style of Donald Trump, we examine whether his communication is an outlier relative to his competition in the primaries and the general election, and while a challenger in 2016 and an incumbent in 2020. Our results suggest that campaign messaging changes over the stages of the campaign, with candidates more likely to advocate for themselves during the crowded primaries, and then engage in high volumes of calls to action in the general election. The 2016 posts were substantially more attack-focused than in 2020. There is some evidence to suggest that the global pandemic affected the ways in which campaigns used their social media accounts. Of note, campaigns seem to heavily rely on Facebook for all types of strategic communication, even as the academic community primarily analyzes Twitter. Finally, Trump’s sum-total of his discourse is less negative than Clinton’s in 2016 and more advocacy-focused, overall.