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This article intends to verify which boasting is meant by Paul in Rom 2:17-3:27. First of all, three prophetic texts (Mic 3:11; Isa 48:1-2; Jer 7:4.8-10) which are, as it seems, in the background of Rom 2:17-23 are studied. The certainty of divine salvation is condemned by the three prophets, because of the transgression of the Mosaic Law. Second, this form of hypocrisy between faith and praxis is at best illustrated in the Gospels and especially in Matt 23:23-28, Mark 7:8-13 and Luke 18:9. These NT texts help to enlighten Paul’s parody against the Jew in Romans and, above all, the boast condemned, that is an attitude of arrogance before God. Third, the comparison between 1 Cor 1:29 and Rom 3:20 (and related contexts) confirms this evaluation of the boast meant, so that 1 Cor 1:29 and Rom 3:20 seem to be “interchangeable”: to glory before God = to be justified (by the deeds of the Law) before God. In sum, the “self meritorious legalism” is not to be excluded, but it needs to be integrated into a larger “crater”as the so-called Torah-centric legalism.