A key element of a liberal education is engagement with "classic" texts, texts that often present views in conflict with our commitment to diversity and inclusion. This article will ask, although not necessarily answer, a number of important questions: Do classic texts perpetuate long-refuted and harmful ideas? Can a racist, sexist, homophobic, or otherwise problematic text still be considered a "Great Book?" To what extent does the inclusion of a text in a syllabus imply endorsement by the professor? Should students have the right to refuse to engage with texts they find offensive? How should professors address student resistance? In this article, Matt Hlinak presents three cases that illustrate the best practices for dealing with problematic texts.