The fundamental problem with boasting is only connected to the direct object in one sense. The one who boasts must boast in the Lord. A man who boasts in the Lord is guiltless because the object is right (2 Cor. 10:17). But if someone boasts in anything on this side of the Creator/creature divide, the problem cannot be fixed by changing the direct object. A man is an idolater whether the idol he worships is wood or stone, red or blue.
This is a basic point that I believe N.T. Wright repeatedly misses at some level. “‘Where then is boasting?’ asks Paul in 3:27. ‘It is excluded!’ This ‘boasting’ which is excluded is not the boasting of the successful moralist; it is the racial boast of the Jew, as in 2:17-24. If this is not so, 3:29 (‘Or is God the God of Jews only? Is he not of Gentiles also?’) is a non sequitur. Paul has no thought in this passage of warding off a proto-Pelagianism, of which in any case his contemporaries were not guilty. He is here, as in Galatians and Philippians, declaring that there is no road into covenant membership on the grounds of Jewish racial privilege” (What St. Paul Really Said, p. 129).
I have no problem with what Wright is affirming here, but I have a significant problem with what he is denying. Of course the Jews were boasting in their covenantal racial privileges. And of course, they were not followers of Pelagius, Norman Vincent Peale, or Tony Campolo). Paul’s Jewish adversaries were worshipers of the blue idol, and not the red one. So? The root of Pelagianism consists in the idolatry, not in the peculiar monastic techniques of Pelagius.
For the sake of the discussion, let’s grant that Caiphas was not a Pelagian. But what do we mean by this? In one sense, the point is as trivial as saying that he lived a few centuries early, ate different foods, and spoke a different language. And this is a point that everyone in this discussion can cheerfully grant. But there is another point that has to be made. What do we call the sin that can manifest itself in so many different cultural guises? What did Caiphas and Pelagius and the unconverted Saul all have in common? And was it wicked? Idolatrous? Self-righteous? Disobedient? At some place in our spiritual genus and species distinctions, we come down to two final categories — the seed of the woman and the seed of the serpent. Jesus expressly consigned the Pharisees to one of those two categories (brood of vipers), and there were only two possible categories. Pelagius, as it turned out, was also of that same brood. All spiritual and pastoral wisdom must know how to categorize in this way. So Caiphas was not Pelagian. And Pelagius was not a Pharisee. But they were both snakes.