Paul’s writing reflects a variety of attitudes towards Jewish ritual precepts, among them a denial of those precepts’ helpfulness on the path to religious perfection. Paul indeed upholds the unshaken authority of the hard-core moral commandments of the biblical law; yet he is skeptical about the Torah’s ability to enable one to follow its ordinances. Paul’s attitude seems to have been partly conditioned by his projected gentile addressees, whom he saw – in agreement with Hellenistic Jewish tendencies – as those whose path to redemption is not defined by the Torah as the exclusive source of divine law. However, as the paper argues, Paul also had in mind an additional, implicit audience – the Jews within the Jesus movement; his letters therefore were to speak to that audience too. Keeping in mind that “hidden Jewish setting” of Paul’s arguments, the paper outlines broader trajectories in Jewish tradition that evolved in similar directions. Even when not questioning the Torah as the foundation of covenant, these trajectories highlighted problematic aspects of the revealed law formulated in a set of written decrees. Paul thus is shown to be a witness to a broader skeptical tendency, while the solution he offers clearly represents the apostle’s “sectarian” conviction.