The very last word on Esav as Chazal saw him

A friend of mine who is smarter than the lot of you put together, said this:

The entire picture of Eisav as a whole, which emerges from the entire corpus of centuries' worth of rabbinic literature as a whole, is more nuanced and less black-and-white than our children are often taught in preschool, grade school, and even high school. That's point #1.

Point #2 is that when viewed through the lens of historical context, it is possible that some of the negativity we have come to associate, through Chazal's teachings, with the historical figure Eisav was indeed originally motivated not by traditions regarding the character in the Bible, but by the behavior of his descendants -- the Romans -- at a particular point in history. Did the formulators of those particular midrashim think the person Eisav shared these negative characteristics, or were they using his name solely as a metaphor to describe his descendants? Who knows. We can't ask them. All we have are the words they left us, and viewing those words in the context of the worldview of their formulators leaves open many possibilities. The possibility that Chazal intended for us to view the historical Eisav, son of Yitzchak, as a person of near-unambiguous evil is indeed one, but only one, of these possibilities.