One of the debates about Paul vis-a-vis Judaism and the Law is how Luke’s picture of Paul in Acts relates to the discussion. Some argue that the Lucan Paul is far more positive about the Law than Paul himself is in his letters. Others say, no, Luke is right, and Paul himself was Torah-observant and his default setting even if he did flex a bit to fit with his audience as he says in 1 Cor 9:20-23.
See for instance this passage from Acts 21:20-25
Then they said to Paul: “You see, brother, how many thousands of Jews have believed, and all of them are zealous for the law. They have been informed that you teach all the Jews who live among the Gentiles to turn away from Moses, telling them not to circumcise their children or live according to our customs. What shall we do? They will certainly hear that you have come, so do what we tell you. There are four men with us who have made a vow. Take these men, join in their purification rites and pay their expenses, so that they can have their heads shaved. Then everyone will know there is no truth in these reports about you, but that you yourself are living in obedience to the law. As for the Gentile believers, we have written to them our decision that they should abstain from food sacrificed to idols, from blood, from the meat of strangled animals and from sexual immorality.”
At the 2019 SBL, there was a good session on this topic, and one of the papers by Josh Jipp has now been published:
Joshua W. Jipp, “The Paul of Acts: Proclaimer of the Hope of Israel or Teacher of Apostasy from Moses?” NovT 62 (2020): 60-78.
Here’s the blurb:
The question of the relationship between “Judaism” and “Christianity” in the Acts of the Apostles has been marked by two contradictory interpretive traditions. One tradition emphasizes conflict and rupture, whereas the other sees continuity and a positive treatment of Judaism. These interpretive traditions both find significant textual support from Acts. There is an internal tension within Luke’s characterization of Paul that does not fit neatly into easy dichotomies and is representative of Luke’s broader two-volume work. The present author argues that the significance of God’s history within Israel centers upon Paul’s central conviction that Israel’s Davidic Messiah, resurrected and enthroned at God’s right hand, is the singular dispenser of salvation for Israel and the pagan nations. This messianic conviction results in a re-evaluation (not rejection) of Israel’s primary identity markers that will only be embraced if one grants Paul’s claim that the hope of Israel is identified with Jesus the resurrected Messiah.
Jipp also concludes:
The Paul of Acts does not criticize his fellow Jews for failed observance of the Torah, for legalism, for hypocritical judgment of others, or for national pride. In short, Paul is not a critic of, let alone one who rejects or abandons, his Jewish ancestral heritage (cf Rom 3:1; 7:7, 12; 9:4; 11:1). The Lukan Paul, thus, stands as a witness against supersessionist forms of Christian theology that have dispensed with the ongoing significance and of God’s election of Israel, which view Christianity or the church as replacing Judaism, and which denigrate Judaism as particularistic and now superseded by the universal gospel of Paul. On the other hand, one cannot ignore the historical consequence of Pau’s emphatic definition of Israel’s history (Acts 13:13-41) and Israel’s hope (Acts 22-28) as centering upon the crucified Jesus of Nazareth, resurrection from the dead, enthroned at God’s right hand, and responsible for pouring out God’s Spirit on Jewish and gentile believers in Jesus. Thus, Paul’s foundational commitment to Jesus as the risen Messiah results in a totlaizing and hegemonic appropriation of Israel’s ancestral heritage, customs, and Scriptures. Gods’ election of Israel finds its significance, for the Lukan Paul, in the Messiah Jesus; thsoe who violently oppose Paul and/or reject his message of the resurrectioned Messiah find themselves excludes from their own covenantal blessings (13:46; 18:26; 28:25-28).
Otherwise, check out Josh Jipp on the TEDS podcast Foreword and his new book The Messianic Theology of the New Testament (Grand Rapids, MI: Eerdmans, 2020).