Pauline scholarship has gone through fundamental changes during the last decades. Old assumptions and premises have been questioned, debated and reformulated through the so-called New Perspective on Paul (NPP). A more recent variant is known as the Radical New Perspective on Paul (RNPP; also known as Paul within Judaism), whose adherents go even further in rejecting the negative sentiment against Jews or Judaism on the part of Paul. Certain key passages have been at the heart of the debate and almost all of them are found in two of the Pauline letters: Romans and Galatians. This paper focuses on another passage in light of the current debate. In 2 Corinthians 3, the apostle compares himself, as a minister of the new covenant, to Moses, the minister of the old covenant. The passage has several features that makes it important for the discussion of Paul and Judaism and, yet, it has largely been neglected, in particular by representatives of the RNPP. The purpose of this paper is to demonstrate how 2 Cor 3 has been neglected in previous debate and argue that it should play a more prominent role. The paper explores three aspects of the passage: 1) The comparison of the two covenants (2 Cor 3:7–11); 2) Paul’s comparison of his own ministry to that of Moses (2 Cor 3:12–13); and, 3) The apostle’s comments regarding the Jewish people, both the wilderness generation at Sinai (2 Cor 3:7, 13) and the generation contemporary to Paul (2 Cor 3:14–15).