Rhetorical studies has long worried about its identity as a critical discipline and a practical art. Since the Great Recession of 2008, a myriad of social and political forces has provoked a discourse about the vitality of the liberal arts, which brings this identity crisis to the fore. Defenders of the liberal arts have deployed a negative critical stance, positing the liberal arts as external to liberalism as a public culture. This stance limits criticism’s political potential because it ignores the productive role of liberal cultural constraints in forming social bonds and creating self-understandings. As the liberal arts grapple with an evolving liberty to learn, so too might the rhetorical arts commit to the productive possibilities of simulation and judgment. This path would respond to the needs of students, who find themselves between structural constraints and contingent possibilities for change.