One of the major advances in the 20th Cent was understanding the Jewish background of the NT. I would certainly never want to separate Jesus from that.I wonder if the teachings of Jesus can stand on their own or if they require the Jewish Law and the varying Jewish traditions that Jesus was challenging? Daniel Boyarin in "The Jewish Gospels" argued that modern readers have misunderstood Jesus. When Jesus appeared to be challenging the importance of the Jewish dietary laws and other traditions, He was actually only challenging certain details. For example, Boyarin believes that Jesus disagreed only with the Oral Torah and the Pharisees who were promoting it. This makes me think that the teachings of Jesus are merely an interpretation of the Torah. If a person thinks the Torah is a mess (as I do), then that person disagrees with the teachings of Jesus.
Both Jesus and Paul had problems with Jewish legalism. For Jesus it was people who put rules above the good of people. This wasn't a universal property of Jews, and probably not even of Pharisees. For Paul the issue was more specific, with Christian Jews. Paul approached it by saying that the Torah's role was temporary, as preparation for Christ. Hence in some sense (and the exact sense is debated) the Law no longer applied, at least to non-Jewish Christians.
Jesus got to the same result, but without rejecting the Torah. Rather, he interpreted it as expressing certain goals, so you should follow the intent of the Torah but not always the letter. You can see that particularly in Mat 5, but also other places, e.g. Luke 6:3. But Jesus was speaking to Jews, and Paul primarily to Gentiles.
Obviously applying this to our situation requires some analogy, since most Jews (both first century and today) don't think the Law applies to non-Jews. But it's still reasonable to see Jesus as challenging ethical approaches that focus on traditional rules (e.g. the oral law), in place of looking at the good of people and the quality of relationships. In my view this places Jesus in opposition to a lot of Christians, particularly in the area of sexual ethics.
In my opinion Jesus approach to the Torah provides a way to deal with the "mess" that you refer to. He looks at rules and asks what goal they were trying to achieve. Of course we don't know specifically how he would have dealt with other things, e.g. the genocides supposedly commanded by God. But I doubt he would affirm them. I doubt he would change his emphasis of looking at the impact on people and their relationships.
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