Whatever conclusions you draw about Jacob’s character (or the lack of it), you have to grant that he had some help getting there. His grandfather and father struggled with telling the truth at times (Genesis 12:11ff, 20:1ff, 26:7ff), while his mother, Rebekah, instigated and served as his accomplice in the deception of his father, Isaac (27:5ff). And both Isaac and Rebekah were guilty of playing favorites in their parenting (25:27-28). Jacob’s family had issues and it’s not surprising that he became one of them!
His behavior in stealing his brother’s birthright was deplorable though Esau bore some responsibility (Hebrews 12:16-17). However, his deception of his infirmed father was cold-hearted. Nonetheless, there he was headed off to Haran to find a wife with the birthright and blessing secured and thinking for all of the world that he must be the shrewdest man on earth.
Perhaps in Canaan he could lay claim to the title, but not in the land of Harran, for that’s where Laban resided. He was an older, more experienced version of Jacob. He tutored Jacob in what it was like to be on the receiving end of exploitation and manipulation (i.e., Leah and Rachel). After twenty years of dealing with him, Jacob had enough and was desperate to return to Canaan. But it was not that easy. Returning home meant confronting the brother he had mistreated. That had him worried, but it appears that Jacob was weary of running and ready to face his past.
He was met by angels on his journey and perhaps inspired by their visit, he sent a deferential message to Esau. A response came back that Esau was on his way with four hundred men. Now Jacob was really nervous and he prayed like he never had before (v. 9-12).
He sent a procession of livestock (550 animals) ahead as a gift to Esau. He sent his entire family and all of his remaining possessions across the Jabbock into Canaan while he remained on the other side to spend the night and watch for Esau and his men.
Someone attacked him and the two men began fighting. Jacob refused to be defeated even though his hip was wrenched (temporarily dislocated?). They fought through the night and as dawn broke his assailant was ready to quit but Jacob refused to relinquish his hold until the man he seemed to recognize as an angel blessed him. The angel asked for his name and the son of Isaac and grandson of Abraham confessed who he was: Jacob (deceiver—see the footnote on 25:26).
Now he was ready to face Esau as well as return to Canaan. He had acknowledged the truth about the way he had lived and treated others as well as recognizing he was unworthy of all he had (Genesis 38:10). He was truly ready for a new name (v. 28) and a blessing (v. 29). He didn’t ride off into the sunset—he limped into the sunrise—changed forever!