Taking a look at the passage in context:-
I am quite curious as to why a wrestling match was nestled in the passage about Jacob meeting Esau. Jacob remembers his encounted with Esau 20 years ago when he had tricked his elder brother of his birthright. Esau had been so incensed that he willed to kill Jacob after the passing and the mourning of their father. Now that Jacob is moving out from Laban's he will be passing close to where Esau was. He had to meet his brother. He was worried. He made preparations and proceeded to meet him, but before that happened, Jacob wrestled with God. Why?
I do not have any commentaries (at least not yet) on Genesis and I have to resort to the next best: http://www.bible.org/. Deffinbaugh said, "As biblical scholars have observed over the centuries, there is much in this episode that is cloaked in mystery." It is certainly good to know many have wrestled with this passage and now I can draw on their discoveries.
Notice some very interesting points to the event:
The man wrestled with him. Jacob did not initiate it, instead God initiated the conflict. Jacob is standing between his past struggles with Laban and the impending one with Esau. God wanted to show him that his real struggle is with God and not with men. If he had struggled with God and still held onto him, he will be able to face anyone.
The man can overpower him anytime but he did not do it till daybreak, they wrestled for hours in the night. And by just a touch, he dislocated Jacob's hip. God wanted to show Jacob who is he up against.
The man asked to be released at daybreak after dislocating Jacob's hip. This indicates that Jacob must have held on to him and not letting him go. Jacob wrestled with God and did not let go of God even at the last stage when he knew he has lost. He did not give up, but gave in to him and asked to be blessed.
The man asked for Jacob's name when Jacob asked for a blessing. Take note that 20 years ago, when asked the same question. Ravi Zacharias in Can Man Live Without God commented, "The last time Jacob was asked for his name, the question had come from his earthly father. Jacob had lied on that occasion and said, 'I am Esau,' and stole the blessing. Now he found himself, after many wasted years of running through life looking over his shoulder, before an all-knowing, all-seeing heavenly Father, once more seeking a blessing, Jacob fully understood the reason and the indictment behind God's question and he answered, 'My name is Jacob.' 'You have spoken the truth,' God said, 'and you know very well what your name signifies. You have been a duplicitous man, deceiving everyone everywhere you went. But now that you acknowledge the real you, I can change you, and I will make a great nation out of you.'
Greatness in the eyes of God is always preceded by humility before Him. There is no way for you or me or anyone else to attain greatness until we have come to Him.
The man dislocated Jacob's hipbone. This happens to be the strongest joint in the body. At the time when Jacob thought he was the strongest, God brought him back to reality.
We need to know that at times when we are sailing high thinking we are the best in the world, God will wrestle with us and he will not give up until we give in to him. As long as we do not surrender to God, he will wrestle with us till daybreak, till we realise who is in charge, who is God. The encouragement we can draw upon though is that God does not give up on us. He still chose us in our weaknesses and idiosyncracies. He can zap us in our weakness and even in our strength but instead he chose us.
I realise that God indeed is the one who starts wrestling with us. I may feel that I started the debate but I believe now how I would have started to debate and wrestle with God in any issues in my life must have been his nudging in the first place. He would be whispering to me, "this is not right" or "I think you better go talk to him" or "you need to work this out".
Prayerfully prevailing with God assures us of prevailing with men. If God is on our side, we cannot be overcome. This is what verse 28 was intended to convey to Jacob. In learning how to prevail with God, Jacob had also found God’s means of prevailing with men (Deffinbaugh).