We don't like these kinds of stories. They're an affront to what we believe, to our expectations, to our standards of conduct and principle. We like nice, neat, clean stories with a morally uplifting message.
Yet we've got these stories that challenge us gravely.
How can God allow the covenant blessing to be passed not to the entitled elder twin, but to the scheming weasel younger twin? It all hinges on primogeniture, the custom of the society. However, God doesn't seem to care too much about this human tradition. And it shows.
Jesus tells a story - a parable in particular - about a cheat who gets caught, and to deal with his exposed situation, cheats even more. For this, the master who got cheated (both times!) actually commends the cheater for being "shrewd." Really, Jesus?
Being a parable, we need to identify it and strip away all of the commentary that comes after it which is trying desperately to explain it and not doing a really good job. It seems like the confusion of today's Bible scholars is matched by the confusion of the Bible writers; they really didn't get it either. But there it is.
Want some answers? It is waaaay too involved to explain here, so you'll have to watch the sermon video below. Enjoy!