This article focuses on the symbolic use of dragons in several works by J. R. R. Tolkien and The Golden Legend, a popular compilation of saints’ lives by Jacobus de Voragine. In the medieval tradition, as recounted by Voragine, dragons serve as symbols of powerful evil through which the inherent weakness of postlapsarian (“after the Fall”) humans can be emphasized. The sudden, miraculous defeat of dragons also illustrates what is possible through faith and the grace of God, anticipating Tolkien’s notion of eucatastrophe, the unexpected reversal in fortune that characterizes the best fairy tales, which is now recognized as a key component of his own approach to mythopoeia.