That Donald J. Trump won the US Presidential Election of 2016 defied the expectations of almost all seasoned observers of the US political system. Scholarly explanations stress structural factors that produced a substantial cohort of identity-vulnerable voters in tandem with Trump’s personal populist appeal. Trump benefitted from his political outsider status, celebrity familiarity, heteronormative masculinity, and unconventional rhetorical style including humour, all of which were amplified (and also mocked) by extensive mainstream news media coverage. Trump’s distinctive political use of the social media micro-blogging platform Twitter (now known as X) in engaging those cohorts has also been emphasized. The research presented here sits at the confluence of prior scholarly work on structural causes of identity vulnerability, on contestation involving humour, and on the enhanced political usage of Twitter. It examines the historical record of Trump’s tweets and re-tweets to see if and how the demarcation of his ‘humour brand’ affectively engaged his substantial Twitter followers and may thereby have contributed to his electoral success in 2016.