In trying to build on what was said in part 1, I would like to begin this post by stating the Lord cannot fully bless a man until He has first conquered him. The degree of blessing that can be experienced by an individual corresponds exactly with the amount of completeness God has had victory over them. And it is in the illustration of Jacob wrestling with God this is no more apparent.
Little did Jacob know, while standing on the ford of Jabbok, when the sun began to set and darkness commenced to cover the land that his victory would be found in defeat. All night long he resisted God, until (in the kindness that only God can have) his hip was touched and put out of place. God had now gained His victory and it was through this humiliating defeat that I believe Jacob began to feel “the joy of the release” from his own strength. It was the delight of Gods conquest over him that caused this subtle, yet joyous emotion to rise from inside. Only then was it that he cried out for a blessing. He had become another man, the stubborn rebel was turned into a meek and dignified friend of God. He had prevailed, but it was through weakness, not strength. The valuable truth brought forth here is that only the conquered can know true blessedness.
It is the strength of our flesh that is an ever present danger to our souls. Deliverance from this so called “thorn” can come only through the defeat of our old life (Rom. 6:3-6; Phil. 3:13). God is the great lifeguard that saves us from the ever dangerous life destroying torrent, known as ourselves. He does this by breaking us, shattering our strength and wiping out our resistance. And it is then, in which He invades our natures with that oh so ancient eternal life that has been since the genesis of time. God confronted Jacob in order to save him from a deceptive hope. To save him from self-trust, it was necesary for God to conquer him, to wrench control away from him and to take His great power and rule with a rod of love.
The great hymn writer Charles Wesley penned what he contemplated the prayer of Jacob would be that night as he wrestled on the ford of Jabbok:
My strength is gone, my nature dies;
I sink beneath thy weighty hand;
Faint to revive, and fall to rise:
I fall and yet by faith I stand.
I stand, and will not let Thee go,
Till I Thy Name, Thy Nature know.
Lame as I am, I take the prey;
Hell, earth, and sin, with ease o’ercome;
I leap for joy, pursue my way,
And as a bounding hart fly home,
Through all eternity to prove,
Thy nature and thy name is love.
They are strangers and pilgrims on the earth 
Another solid post, Brandon, which I see to be the norm for you.
This touches on a topic I have been putting off analyzing: to what extent does God want to “break” us?
I am hesitant to embrace this concept, because I know that our expectations often become our reality. I’ve seen too many Christians embrace misfortune and/or poverty, wearing it as a badge of honor as though it were proof of God’s favor.
It goes something like “I’m nobody special, I’m just a and I just drive a and I’m just barely getting by, and enduring this horrible world, etc. etc.” And I think to myself, ” ‘God’ might not put you in such humble circumstances if you upgraded your skills, furthered your education, took personal responsibility for your life, stopped watching 3 hours of television nightly, etc. etc.”
You know what I’m saying? I’m by no means saying God wants fame, riches, and success for everyone, but it seems to me a lot of people are just lazy and not willing to take responsibility for their crappy life, so they tell themselves fairy tales about how God has ordained their circumstances.
However, these people that I speak of are probably not the people you are addressing here on your blog. So, before I go off on another tangent, I’d be interested in hearing some more Scriptural reasoning for your stance on brokenness. (I know that it’s not the exact topic of your post and not the term you use, but hey, humor your fellow name-bearer).
You call the outcome a “humiliating defeat.” I think lasting all night in a wrestling match with God is a pretty acceptable outcome for us mortals! :) That’s not to say your overall point is lost on me, as I fully acknowledge that God definitely showed him what was up.
However, if God would have, say, broken every bone in his body and left him nubs for limbs then I think it would go further to support the position that God wants to completely and utterly break us.
Anyway, just to reiterate: I don’t really know what I believe on this topic, and I’d love to get more reasoning on your position.
Thanks!