The polarization of American political debate reaches far into the academy. Yet such polarization plays out among historians far differently from how it does within the broader public realm. In the civic sphere, everyone has access to a wide variety of viewpoints, even if pundits bemoan the bubbling of America within an increasingly concentrated media landscape. In contrast, a great a majority of influential history departments have a mere handful—if any—conservative voices (or voters). The result: a crucial loss of intellectual dialogue as well as a failure to model complex civil conversation within the civic sphere. So how to bring together the liberal/leftist perspectives prevalent in the academy with conservative historical viewpoints? Through an exploration of both right-wing and left-wing historiography and present-day public commentary on progressivism and the Progressive Era, I point toward a path that highlights the value of respectful, as well as critically sophisticated, reaching across even extreme ideological divides.