Why did the angel plead with Yaakov to let him go, specifically at dawn-break?
Rashi and Targum Yonasan: Because that was when he was due to sing Shirah before Hashem (for the first time since the creation - Targum Yonasan). 1
Rashbam: The angel simply meant that, since day had arrived, it was time for Yaakov to be on his way.
Malbim: This hints that man's war [with is Yetzer ha'Ra] is only at night (in this world), but when man returns to the world of light, and his Ru'ach return to Hashem, his Nefesh will separate from his body, and receive a Berachah also from the physicality that opposed him his entire life. Since it was connected to physicality and overcame it, it is greater than [angels] that were never clothed in physical garments.
Ha'amek Davar (to 32:25): Din (strict justice) overpowers only at night. From dawn, Kedushah becomes stronger.
Why was this so? Refer to 32:27:1.03.
What was Yaakov's initial reaction to the angel's request to leave because dawn had broken?
Chulin 91a: He asked the angel whether he was a thief or a gambler (or a kidnapper) who was afraid of dawn-break, lest he be discovered.
How can a human-being manipulate an angel?
Seforno: Because Tzadikim are greater than angels.
Ohr ha'Chayim: This is indeed what the angel said, "Ki Sarisa Im Elohim... va'Tuchal" (32:29).
What Berachah did Yaakov want?
Rashi: He was asking the angel to corroborate the Berachos that he had received from Yitzchak 1 (not for new ones). 2
Rashbam: Yaakov simply asked for a Berachah that the angel should send him away in peace, and unharmed.
Ohr ha'Chayim #1: Yaakov should not be damaged through the uprooting of his thigh.
Ohr ha'Chayim #2: Since Yaakov recognized that he is an angel, he strove to get a Berachah from him.
Malbim: At the end of days, dawn and the Ge'ulah will come, and Esav's Sar will ask to be sent, for then Ru'ach ha'Tum'ah will depart and all will return to true Emunah. Yaakov wanted a Berachah for then, since the Yetzer ha'Ra will be Batel and there is no more Avodah.
Malbim: Since you were not able to make me sin, agree that you are my slave!
Bartenura: This is why he said "Berachtani" (in the past), and not 'Tevarecheni' (in the future). See also Ba'al ha'Turim. Gur Aryeh - The Mal'ach responded, "'It will no longer be said that your name is Yaakov; but rather Yisrael' (32:29); 'at the end, Hashem will appear to you in Beis El... and I will concede the blessings to you there' (Rashi loc. cit).
QUESTIONS ON RASHI
Rashi writes: "'For the dawn has risen' - and I must sing praises by day." How do we know that this is what the Mal'ach meant?
Maharal (Chidushei Agados Vol. 4, p. 108, to Chulin 91b): The Mal'ach's argument was that he should be released for Hashem's honor - for it was his time to recite Shirah.
Rashi writes: "'For the dawn has risen' - and I must sing praises by day." Why is dawn the time for Shirah?
Maharal (Chidushei Agados Vol. 4, p. 109, to Chulin 91b): The Gemara establishes that Shirah is recited by the Mal'achim every day; it should take place at the beginning of the day; i.e. at dawn.
Rashi writes: "'For the dawn has risen' - and I must sing praises by day." Why did this angel's time to sing Shirah arrive specifically now, after he fought with Yaakov?
Maharal (Chidushei Agados Vol. 4, p. 109, to Chulin 91b): "The Mal'ach said, 'From the day I was created, my turn to sing has not come until now!' ... Yisrael sings Shirah constantly" (Chulin 91b). The angel was striving to overcome Yaakov at his level; as such, the angel had to recite Shirah. 1
Michtav me'Eliyahu (Vol. 5, p. 469) - The purpose of the Yetzer ha'Ra is that good conquer it. Yaakov was the first Shalem ("va'Yavo Yaakov Shalem" - 33:18) to conquer it to the point that it had no connection to him.
According to the approach that this Mal'ach was the Sar of Esav, we may explain that Yaakov and Esav are diametric opposites; when one rises the other falls; therefore, to overcome Yaakov, the Mal'ach had to emulate him. Alternatively, perhaps Yaakov's victory over Esav's Mal'ach was in itself the rectification the Mal'ach needed. (EK)
