This dissertation investigates the exegetical form, rhetorical function, and theological imagery of Paul's midrash on Exodus 34 in 2 Cor 3:7-18. Paul's pattern of biblical exegesis in this passage, which is unique among his letters, has given rise to numerous explanations. The contribution of this study is to read Paul's midrash through comparison with the forms and traditions of Hellenistic Jewish commentaries, particularly Philo of Alexandria's Allegorical Commentary.  Through a close textual evaluation, I suggest that Paul's midrash bears the closest formal similarity to a commentary pattern found in Philo's interpretation of secondary biblical lemmata in the Allegorical Commentary. Although Paul may have adopted this pattern from homiletic convention, it seems more likely that he has borrowed it directly from Jewish commentaries, which he could have known through his advanced Jewish education. A study of the reuse of Jewish and Platonic commentary traditions in various contemporary treatises and letters confirms this hypothesis. Such traditions were often incorporated as exegetical excursuses.  Reading Paul's midrash on Exodus 34 in light of other exegetical excursuses has several ramifications for the study of 2 Corinthians. First, it offers new evidence for the rhetorical unity of 2 Cor 2:14-4:6. Second, recognizing the presence of covenant renewal themes in both Paul's epistolary frame and in his midrashic excursus suggests that his opponents in 2 Corinthians were Hellenistic Jewish Christian missionaries. Third, paying attention to Paul's complex portrait of Moses, facilitated by his sequential commentary in the Exodus midrash, provides a window into his confrontation with these missionaries. Although he approves of their use of Moses as a model of Christian transformation, Paul wants to distinguish further between Christian and Hellenistic Jewish versions of this tradition. Shying away from the more traditional biblical locus used to promote Mosaic exemplarity in Hellenistic Judaism (Exodus 33), Paul focuses on Moses' role as a renewed covenant minister in Exodus 34. Drawing together central theological themes like covenant renewal, priestly tabernacle vision, and particularly parrhēsia, Paul aims to present Moses as both a foil and an exemplar of the Christian apostle, a figure whose glory should be viewed in light of the glory of Jesus Christ.