I hadn't realized before one of the connections Jacob's wrestling with God has with the surrounding context: the word "face" and its importance.
In Gen 32 Jacob is approaching his probably enraged brother Esau and is terrified. To appease his brother (v. 20 uses the Hebrew word kipper, "atone") Jacob sends on ahead gifts (flocks, etc). Jacob thinks to himself, "I may appease his face with these gifts" (v. 20). Then he adds, "Then afterward I'll see his face" (v. 20). Jacob is terrified of meeting Esau face to face.
The immediately following passage then tells us of Jacob's wrestling with God. And in the wake of the struggle, Jacob gives the name of the place a certain name: Peniel (v. 30). "Peniel" in Hebrew means "face of God." His explanation? "For I have seen God face to face" (v. 30). The next verse then says it all: "The sun rose on Jacob as he passed, limping" (v. 31).
After Jacob and Esau meet and the reunion goes happily, Esau attempts to refuse Jacob's gifts, but Jacob insists that Esau keep the gifts. Why? "For I have seen your face which is like seeing the face of God, and you have accepted me" (33:10).
Jacob had to face Esau, yes. But that was only a mirage, an echo, of what Jacob really had to face. He had to confront Esau, but he more deeply had to confront God. He had to be reconciled to Esau, but more fundamentally to God. Jacob had been manipulating his circumstances his whole life in order to put himself in a position of strength--a fascinating study in itself. God finally had to manipulate Jacob himself in order to put him in a position of weakness. Jacob had to learn that it was not his circumstances but him that needed fixing. Only then could Jacob face Esau with the most important verdict behind him.