Studies of the institutional development of the presidency and popular leadership by presidents over time lead us to contrary expectations as to how a nineteenth-century president would react to a major political scandal. Scholarship on newspapers of the late 1800s is also unclear on how a quasipartisan media, with some outlets moving toward independence, would cover a White House scandal. I find that a close analysis of the case of President Ulysses S. Grant and the Whiskey Ring scandal forces us to reconsider what we assume to be firmly modern developments in both presidential studies and media history. Though a supposedly “premodern” president, Grant still mounted a concerted effort to mitigate the damage of the scandal. Further, although the president could get his version of events across in prominent newspapers, Republican newspaper coverage was hardly reliable. Newspapers also connected politicians’ character and psychology to mistakes made in office and made presidential strategies to shape public perception clear to their audiences—emphases on political gamesmanship considered hallmarks of the modern media environment.