In NT scholarship, the Paul Within Judaism approach has gained considerable momentum. In this approach to Paul’s discourse on identity, a distinction is drawn between “Jewish” and gentile followers of Christ. “Jewish” followers, including Paul, are considered those that remain fully Torah-observant, whereas gentile followers are regarded as not fully Torah-observant, especially with respect to circumcision. In this contribution, Paul’s identity in relation to first-century “Judaism” and/or historical Israel is reconsidered. The main question that is asked in this regard is whether the Paul Within Judaism approach is a viable position in light of the hermeneutical difficulties surrounding first-century “Judaism”, as well as Paul’s own rhetoric around the Ἰουδαῖοι (“Jews”/“Judaeans”). Another question that is asked is whether Ἰσραήλ (“Israel”) and the Ἰουδαῖοι point to the exact same entity. Would it be more accurate to see Paul as being within Israel as one of God’s covenant people than as remaining a Ἰουδαῖος (“Jew”/“Judaean”)? Or did Paul leave his identity as a Ἰουδαῖος or as part of Israel behind for a new identity to be defined around Israel’s Messiah only? Lastly, it is considered whether Paul’s discourse on identity leaves room for an identity in Christ that is inclusive of an identity as a Ἰουδαῖος or as being part of Israel, or whether the identity in Christ excludes the latter.