Philo of Alexandria and Gregory of Nyssa each composed a two-volume work entitled the Life of Moses. While a few scholarly treatments have been written on how these two treatises have retold the story of Moses as depicted in scripture, a full analysis has yet to appear that investigates how they use the art of ancient paraphrase to reshape scripture. By performing a comparative literary analysis of the two Lives of Moses, both externally with the LXX and internally between episodes within each Life, this study sets out to examine how paraphrase serves a mediatorial role in the interpretation of scripture in the hands of Philo and Gregory. Building on scholarship in the fields of ancient rhetoric and biblical hermeneutics, I argue that paraphrase serves as an interpretive mode somewhere between the literal and allegorical. Both authors use it as a kind of interpretive bridge that mediates between the LXX and, ultimately, the reader. In the body of this study, I analyze episodes that appear twice in the two Lives. By examining such episodes, we are able not only to determine how Philo and Gregory recast the LXX depiction of Moses, but also how their initial paraphrase of events relates to the second version of the same episode. In this way, we study how paraphrase mediates externally between the LXX and each Life and how it mediates internally within the text itself. Moreover, by performing such an analysis on both Lives, we are able to determine the influence that Philo’s treatise and his method had on Gregory’s own Life. This study has implications well beyond a better understanding of each individual Life. In addition, the results of the inquiry provide a better understanding for how biblical hermeneutics operate in the ancient world. While paraphrase is often perceived as a literal form of exegesis, I demonstrate that the paraphrase actually stands between the literal and the allegorical as it mediates between reader and text.