Parshat Vayishlach

Bereishit 32:25-30
Jacob was left alone. And a man wrestled with him until the break of dawn. When he saw that he had not prevailed against him, he wrenched Jacob’s hip at its socket, so that the socket of his hip was strained as he wrestled with him. Then he said, “Let me go, for dawn is breaking.” But he answered, “I will not let you go, unless you bless me.” Said the other, “What is your name?” He replied, “Jacob.” Said he, “Your name shall no longer be Jacob, but Israel, for you have striven with beings divine and human, and have prevailed.” Jacob asked, “Pray tell me your name.” But he said, “You must not ask my name!” And he took leave of him there.
And a man wrestled: … It denotes “intertwining,” for such is the manner of two people who make strong efforts to throw each other.
No longer Jacob: … It shall no longer be said that blessings came to you through supplanting and subtlety but through noble conduct and in an open manner.
Pirkei DeRabbi Eliezer 37:4
He answered him: I will not let you go until you tell me what your name is. And (the angel) called his name Israel like his own name, for his own name was called Israel.
Avivah Zornberg
The question of “wholeness” … is central and problematic in Jacob’s concept of himself and his destiny. … This is a problem in equilibrium, in the managing of contrary forms, in husbanding of divergent energies.
How does Jacob reconcile the experiences of his grandfather and his father — of lovingkindness and the brutal cruelty of the Akedah? His own simplicity and the deviousness he is capable of? His expansive experience outside of Canaan and returning home?
Characteristically, then, Jacob leads from behind: he is the thinker, the one who projects in images and words, the director behind the scenes.
It is the essential meaning of hokhma, wisdom–not to rush in where angels fear to tread, but to imagine and manipulate realities from the sidelines. The sophistication of one who lies in wait, who bides his time, who plans his strategies from the rear, is Jacob’s character and destiny.
There is, however, a darker aspect to lateness. Jacob–about to become Israel–lives the full ambiguity of being behind. In the midrash, his tragic flaw was defined as being related to lateness: “You delayed on the journey [back home].” There is a tendency in Jacob that can be called sophistication, subtlety, imagination, but that exposes him to less flattering epiphets
What are negative ways of framing this character?
Jacob seeks to avoid his father’s fate, of being a victim of capricious violence. He lacks trust, he does not have the openness of his grandfather.
To be obsessed with controlling the issues in a complex world is to risk losing all dynamic contact with that world. 
It is in this context that his confrontation with the man-angel becomes most significant. The mysterious “man” seems to come upon him unawares. Before he knows, before he can put himself on guard, he is embraced and held in the loving-hostile grip of the wrestler.
In [another midrash] the angel has come for no hostile purpose but “to save and rescue him.” This angel is called Israel, perhaps because that is the purpose of his mission, to show Jacob, in a therapeutic encounter, how to be become Isarel. Since angels are named for their mission, this may be the reason for the angel’s response to Jacob’s question … Jacob already knows in himself the purpose of the angel’s coming, for, essentially he is facing himself, the desired-feared necessity of a new name. He has summoned the angel to save him from the condition of being Jacob.
Ultimately, of course, Jacob and Israel both remain his names. … his two personae is never entirely resolved. This is true throughout the biblical and prophetic writings, where the passionate power of confrontation and the sophisticated “knowing from behind” both remain essential aspects of the man and the nation, undergoing mutations and reworkings throughout history.
Jacob-Israel is indeed an uneasy combination.
The answer offered in classic midrashic sources is that, in some sense, Jacob is to be the ideal “true” synthesis of the polar characteristics of Abraham and Isaac. But, in real terms, the problem of a Jacob is not capable of simple solutions.
This is Jacob’s dilemma. At the core, what “cripples” him is his sense of father’s crippling. Isaac, in the branding moment of his lief, was bound hand and foot; and Jacob, in spite of all his movements of hand and feet, spite of the freedom and energy he expresses in love and work … remains profoundly absorbed by his father’s trauma.
Jacob’s [life] … is a quest for equilibrium, for emet, truth on the psychological as well as the cognitive plane.
Jacob is trying to find the balance between love and fear (of God, of life). He does not fully find a solution to that problem, if one is even possible. How will this impact his children?