Current trends in disaffiliation and declining enrollment in Catholic schools raise difficult questions about the perceived value of Catholic education and the Catholic Intellectual Tradition (CIT). Following the work of theologian David Tracy, the author makes a case for engagement with Christian "classics" as a promising means not only for re-engaging a wider audience with the CIT but also for addressing the sense of fragmentation and lack of meaning experienced by many contemporary persons. The paper proceeds by presenting an analysis of the plurality and ambiguity of contemporary culture, an explication of Tracy's work on "classics," and finally a new approach to engaging students with Christian classics that has proven fruitful in undergraduate courses.