Schadenfreude and sympathy are often experienced at the intergroup level; however, little research has been conducted to examine their role in one of the most prominent and emotionally evocative intergroup contexts: the political arena. In this study, we assessed a sample of 506 Americans’ (Age M = 41.69 years, SD = 13.94; 57% women) schadenfreude and sympathy (and related cognitions) in response to then-President Trump’s COVID-19 diagnosis (a salient misfortune of a contentious political figure), and how their schadenfreude, sympathy, and related cognitions were associated with shifts in voting intentions (own and public’s) in the 2020 Presidential Election. We also examined trends in, and associations between, these variables by political affiliation (focusing on Democrats and Republicans) and gender (focusing on men and women). Unsurprisingly, compared to Republicans, Democrats expressed more schadenfreude and less sympathy. Contrary to previous research, however, Democrats’ experiences of schadenfreude were tempered and were primarily driven by deservingness beliefs rather than intergroup competition or malice). Amongst Republicans only, men experienced stronger schadenfreude than women. Regarding voting intentions, participants were more likely to report that the diagnosis would impact shifts in the public’s voting than their own voting, primarily in favor of the Democratic Party. Feelings of schadenfreude and sympathy were not significantly associated with anticipated shifts—rather, those who believed then-President Trump’s diagnosis was deserved (cognition strongly associated with schadenfreude) were four times more likely to believe the public would change their vote to the Democratic Party. These findings are discussed in relation to research at the intersection of psychology and political science and have implications for politicians and psychologists who aim to understand emotions underlying partisanship and voting behavior.