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כי עלה השחר FOR THE DAY BREAKETH, and I have to sing God’s praise at day (Chullin 91b; Genesis Rabbah 78:1).

כי עלה השחר, seeing that it is daylight already it is time for you to be on your way. (to the meeting with Esau).

לא אשלחך, this utterance by Yaakov confirms what the sages tell us that the righteous are greater than the ministering angels (Sanhedrin 92).

לא אשלחך, "I will not let you depart, etc." When the angel said to Jacob that he had struggled with a celestial being and had prevailed, he meant that he now could not depart without Jacob's permission. When Jacob said: "unless you bless me," he meant that he would assure him that the injury he caused to Jacob's hip-joint would not be permanent. It is also possible that the mere fact that Jacob now realised he had wrestled with an angel prompted him to ask for a blessing from that angel.

ויאמר שלחני, he meant that he had been sent by G’d to Yaakov to demonstrate to him by a factual illustration that he would not overcome him, and that a mere human being such as Esau would certainly not be able to harm him. Now that I have accomplished my mission, please let me go. In other words, “unless you have any other request from me, I am leaving.” Yaakov said that indeed he did want something else of him, and until that was granted he would not let him depart. He wanted to receive the angel’s blessing. The reason that the angel added the words

כי אם ברכתני, “unless you have first blessed me.” In accordance with the accepted principle that the person who inflicts injury is in a better position to heal same than anyone else by pronouncing a formula wishing his victim a speedy recovery. The angel wanted to know Yaakov’s name, as it is mandatory for the healer to know the victim’s name if his efforts are to be crowned with success. Another explanation of the meaning of כי אם ברכתני, has Yaakov asking for a blessing from the angel, as an acknowledgment that he had prevailed in the struggle. with celestial forces. This was the reason why Yaakov asked the angel for his name. He wanted to be able in the future to be able to tell whomever it concerned that he had battled an angel to a standstill. The angel protested that it would be embarrassing for him that Yaakov should boast to have overcome him. In lieu of revealing his name, he bestowed a blessing on Yaakov that incorporated an allusion to this nocturnal encounter every time he would be addressed by this name.

ויאמר שלחוני, “he (the angel) said: ‘let me go!’” The angel was afraid that if he were to leave without having obtained Yaakov’s permission they would punish him in heaven with having to endure the פולסי דנורא [some physical punishment administered by a fiery rod and mentioned in Chagigah 15 and elsewhere as an instrument for disciplining wayward angels. Ed.] We have another reference to this incident in (Hoseah 12,5) “He strove with an angel and prevailed; the other had to weep and implore him.”

Concede to me the blessings with which my father blessed me... You might ask: Perhaps Yaakov requested that he actually bless him? The answer is: The angel replied, “No longer will your name be spoken of as Yaakov.” How did this answer [Yaakov’s request]? Perforce, the angel’s answer means as Rashi explains: “It will no longer be said that the blessings came to you through deceit and trickery.” This implies that Yaakov had requested for a concession to the blessings, and the angel replied accordingly. (Re’m)

לא אשלחך כי אם־, wörtlich: ich entlasse dich nicht; denn (ich entlasse dich) wenn du mich gesegnet. So überall das לא־ כי אם־, das כי ist immer elliptisch: denn ich tue es, wenn — also ich tue es nur, wenn usw. — Jakobs Gegner kann also nur kämpfen, so lange es Nacht auf Erden ist, und zwar, so lange es Nacht ist, scheint er, wenn auch nicht der Sieger, doch der Mächtigere zu sein. Sobald es aber Tag zu werden beginnt, tritt das Gegenteil in die Erscheinung und Jakob wird der "Maßgebende" für die Beendigung des Kampfes. Und die Bedingung, die Jakob für das Ende des Kampfes setzt, somit das Ziel des Ganzen, ist: die Anerkennung, dass Jakob statt Anfeindung Segen und Förderung verdiene, indem nur in dieser Anerkennung die Völker sich selber segnen, und sich die Verheißung erfüllt: ונברכו בך כל משפחות האדמה ובזרעך. Die ganze Nacht hindurch, spricht daher Jakob, hast du mich angegriffen, mich also als ein Hindernis betrachtet, dessen Vernichtung in unablässigem Kampfe anzustreben wäre. Jetzt, da es tagt, gibst du den Kampf auf, ich aber nicht früher, als bis du mir die segnende Anerkennung gezollt. Das Ziel der Geschichte liegt nicht darin, dass Jakob gezwungen werde, in die Masse der Völker aufzugehen, sondern umgekehrt, dass die Völker zur Einsicht gelangen, gerade in dem, inmitten aller Kämpfe von Jakob vertretenen und emporgehaltenen Prinzip liege auch das Heil der Völker, dem sie sich huldigend anzuschließen, und das vielmehr sie selbst mit allen ihren geistigen und materiellen Mitteln zu fördern, ja als einziges Ziel anzustreben haben. —

שלחני כי עלה השחר, “give me permission to leave for dawn has arisen!” “Until now I held you up from proceeding according to plan; now you have permission to proceed on your way.” An alternate exegesis of this strange conversation: The angel told Yaakov that since it now was almost daylight, he no longer had anything to fear from him. It is not customary for destructive forces to do their jobs during the daylight hours.

ברכתני [EXCEPT] THOU BLESS ME — admit my right to the blessings which my father gave me and to which Esau lays claim.

כי אם ברכתני, as a sign that you have parted from me in peace, that I will not suffer harm or damage through having been in a struggle with you.. Now that it had become daylight Yaakov realised for the first time that his adversary had been an angel.

כי עלה השחר, that it is already becoming morning, was that Yaakov had no reason to be afraid, as the night, the time for fear, had already passed. Being alone, without escort during daylight is no reason for concern.

כי עלה השחר, “for dawn as risen.” When the angel asked to leave before daybreak Yaakov asked him: “are you a thief that you need to fear daylight?” He answered “I am an angel and ever since I have been created I have not yet had the opportunity to sing a song of praise to the Lord in the heavenly choir. Today is my opportunity.” There is a reference to this in Scripture (Job 38,7) ברן יחד כוכבי בוקר ויריעו כל בני אלוקים. “When the morning stars sang together and all the angels shouted for joy.” The time of dawn is the time when the קדושה is recited as mentioned by Isaiah 6,3 “and one would call to he other: Holy, Holy, Holy.” Hearing this, Yaakov replied:
לא אשלחך כי אם ברכתני, “I will not let you go unless you first bless me.” He wanted Esau’s angel to acknowledge that the blessing he had received from Yitzchak was acknowledged by Esau as being rightfully his. Thereupon the angel said:
לא יעקב יאמר עוד שמך כי אם ישראל, “your name will no longer be Yaakov but Israel.” He meant that from now on people will no longer say that you obtained the blessings by subterfuge, but they will admit that you are the rightful recipient of them. Alternatively, what the angel meant was that if anyone were to accuse Yaakov of having swindled Lavan they would be proven wrong as Yaakov had been accorded the attribute “Truth”, i.e. that he had acted truthfully in all his undertakings. This was confirmed in Michah 7,20 “You have given “truth” to Yaakov.”

כי אם ברכתני, “unless you first give me a blessing.” Yaakov meant that he would not accept the angel’s words until he had demonstrated that he meant it, by giving him a blessing. After that he would feel confident that he no longer had reason to fear him and would not seek revenge because he had failed to disable him. (Rash’bam)