In this week's reading on Paul I have again noticed the way many Paul scholars see the unfortunate caricature of "Jewish legalism" as that which generations of past ignorant scholars promulgated. This is then addressed by showing how "Jewish legalism" is a misportrayal because Judaism was not legalistic, but a religion of grace. That is, the second of the two terms is addressed.
In my opinion, resolution to the (largely appropriately diagnosed) caricature of "Jewish legalism" is not to tinker with the second term but the first. The problem is not "Jewish legalism." The problem is human legalism.
Judaism, simply because they were the one group given a law, wound up, for all their blessings, being the group most clearly manifesting the result of combining human sin with divine law. The problem is not racial. Any of us who had been born into Judaism would have been just as clear examples of what Paul critiqued.
It is humanity Paul critiqued, Judaism providing the clearest example of the problem. The solution to the caricature of Judaism as legalistic is not exonerating Judaism but co-indicting everyone. Instead of plucking Judaism out of the cooker, we should put the rest of us into it.