Maxims, proverbs, and other forms of pithy sayings are sprinkled throughout ancient and medieval literature; polysemous and manipulable by nature, they serve as communicative tools whose precise meaning and function shifts from context to context. My dissertation explores how late antique and medieval Christians capitalized on the flexible forms of Greek and Latin aphorisms to negotiate and construct what it meant to be a Christian. Using theories and methods developed in the fields of folklore, linguistic anthropology, and ethno- and sociolinguistics, I investigate three examples in which Christians revised and reused wisdom in new contexts. First, I document the proverbial concept of gathering something useful from somewhere dangerous as expressed in sayings like “to pluck a rose from among thorns” and “to gather gold from shit,” charting how it originally went viral in the late fourth and early fifth centuries, remained in vogue well into the Middle Ages, and continued to evolve in meaning throughout its usage. I then analyze the Sentences of Sextus, a second-century collection of Greek maxims assembled from various Pythagorean aphorisms and sayings of Jesus. Whereas previous scholarship has focused on the authorship, content, and structure of the Sentences, I study the new meanings, functions, and forms the collection acquired as it underwent processes of translation, transcription, epitomization, excerption, and quotation. The text’s gnomic format and armchair morality contributed not only to its centuried popularity and widespread readership, but also to the dispersion of many of its individual sayings. In particular, I consider the extensive and unstudied reception of the Sentences of Sextus within the mid-ninth-century legal forgeries known as the Pseudo-Isidorian Decretals. I show that the Sextine elements reveal the presence of recurring textual units across the Decretals and offer new insights regarding Pseudo-Isidore’s compositional method—a method that, in many ways, parallels the Sentences’ recycling of Pythagorean and biblical material. Ultimately, my project models how wisdom-centered investigations of late antique and medieval literature lead to new understandings of the craftsmanship of individual authors as well as to deeper understandings of the time and its culture.