This essay makes two key arguments. The first is that preemptive politics often rely on strategies of rhetorical irony to cultivate perceptions of reasonableness, humility, and dialectical transcendence. As such, I expand the rhetorical conception of Stephen Skowronek’s “political time” thesis to reveal its dimensions as a Burkean “ironic development.” The second argument is that Barack Obama’s rhetorical strategy more directly fits the typology of preemptive presidents than that of reconstructive presidents, making him far more comparable in “political time” with Richard Nixon than with Ronald Reagan. I proceed to analyze the two presidential candidates’ rhetoric in their first winning campaigns for the presidency to discern the extent of these parallels and reveal the applicability of an ironist political style in preemptive electoral situations. The essay concludes by examining the trajectory of liberalism in political time and the implications of this analysis for preemptive “wild cards” in presidential rhetoric.