"The difficulty of interpreting GAlations fairly is compounded by Paul's own extreme views on Judaism, both before and after his messianic conversion: both as a Jew and as a Jewish Christian, Paul was far from typical of Jewish belief and practice. In what he calls his "earlier life in Judaism" he was fanatical, to the point of "trying to destroy" the Jewish movement, people he perceived as enemies to the Torah. Now, despite having renounced his former fanaticism, he continues to believe that as a fanatic he was a model Jew. Once assiduously Torah-observant, he now takes his own past as the measure of what law-observant Judaism has to offer. Never does he consider that a less-strict version of observance might be acceptable to God. On the contrary, "Cursed is everyone who does not observe and obey *all* the things written in the book of the law (Deut. 27:26 LXX). Any abrogation of any law brings God's curse. Ironically, the insistence on keeping "all" the laws appears only in the Greek tanslation of Deuteronomy; Paul's standard for legal observance actually exceeds that stated in the (Hebrew) Torah. Even leaders like James and Peter, who favored -- perhaps insisted on -- the full conversion of Gentiles, probably defined Jewishness in less rigid terms than Paul did. For Paul, the covenant was an all-or-nothing affair."
"The Reluctant Parting: How the New Testament's Jewish Writers Created a Christian Book," by Julie Galambush.
This paragraph seems to bring up a point I've only subconsciously considered. When most Christians picture Judaism, do they picture it in all the aspects in which it was taught? Or is taught? Or do they picture Paul's particular lens of Judaism only?
If it truly is an all or nothing affair for Paul, that would explain why I have a hard time meshing his viewpoint of the Torah with what I actually read in the Tanakh. I don't get the sense of the Torah provided to tell everyone how sinful they are, or that it's primary purpose is to show a need for a Savior. I don't get the sense that they dreaded being under it's power, or yearned to escape the burden of the Torah.
Perhaps if Paul held a less rigid view of the Torah and those who practice it ... would he still have proclaimed Jesus as the Messiah?