To understand how jokes have functioned as part of U.S. presidents’ strategic communication, this project examined every available White House Correspondents’ Dinner (WHCD) speech over the last century, documenting various presidents’ approaches to humor. I argue that the ability to talk about difficult or taboo subjects through jokes’ deeply enthymematic ways of communicating has offered presidents expanded rhetorical spaces during crises, providing insights into why they started using humor with such routine frequency. Working with multiple factors shaping the modern presidency, presidents have used the elastic and inventive nature of enthymematic joking in attempts to move pressing issues outside immediate lines of criticism. The use of jokes in presidential communication is charted through three periods of WHCD. Several implications are drawn from this analysis, including the risks of humor as a rhetorical strategy.