Rashi (on 32:25) quotes R. Hama ben R. Hanina (Bereshit Rabbah 77:3) that the assailant was the guardian angel of Esav, and apparently he wanted to kill Yaakov. Rashi (on 32:27) quotes from the Talmud (Hullin 91b and Bereshit Rabbah 78:2) that the angel had to leave at daybreak since he had to sing G-d's praises at daytime. While I believe this is the most popular explanation for the identity of the assailant, it is a difficult approach. First, it is odd that Yaakov would be able to defeat an angel in battle. (A popular answer to this question is that the fight was really a dream, see Rambam, Moreh 2:42, but this answer is difficult since the Torah never states that the fight was a dream and 32:32 records that Yaakov was wounded from the fight.) Second, it is even odder that an angel had the free will to attack and wound Yaakov, but had to be singing the praises of G-d at daybreak. How do we know that all angels have to sing praises to G-d in the morning? It is very coincidental that the angel just happened to have to sing praises to G-d that morning. Thirdly, how do we know that guardian angels exist and that each person has one? Fourth, 32:25 specifically states that the assailant was a person, and the Torah never refers to the assailant as an angel.
A variation of the angel approach is that the assailant was not Esav’s guardian angel, but a different angel sent by G-d. There are several versions to this approach. The Rashbam (on 32:25, quoted by Hizkuni on 32:25) suggests that Yaakov was really trying to run away that night in order not to meet Esav, so the angel was to stop Yaakov from running away. N. Leibowitz (1976, p. 367) rejects this approach because it implies that Yaakov lost the struggle with the angel since he was unable to run away, but Yaakov was victorious in the battle. Radak (on 32:26), who is equivocal if the fight occurred or was a dream, suggests that in either event Yaakov's limping was because Yaakov was being punished for calling Esav his master, and for not showing enough trust in G-d. This also seems difficult since again according to this idea the angel was successful and Yaakov was being duly punished, while the text seems to indicate that Yaakov prevailed over the angel.
I believe that Yaakov fought with Esav. (I first made this argument in Schein, 1989, and afterwards, Jack Miles, 1995, made a similar argument.) In 32:25, the Torah records that the assailant was a man, and the most logical person was Esav. We know that Esav was in the area with Yaakov since he met Yaakov the following morning and that Esav wanted to kill Yaakov, 27:41. This fight at night was the conclusion of the fighting between the brothers that had begun in utero, 25:22. Kass (2003, p. 456) notes, “the struggle reminds us of the struggle in the darkness within Rivka’s womb (for example, the tenacious hold of Yaakov) and Yaakov’s renaming here appears to be a second birth.” Eric Sommers (personal correspondence) notes the parallelism between the fighting in the womb and here, as there Yaakov failed to hold back Esav, while here Yaakov succeeded in holding back Esav.
For Esav, this fight was personal and it had to be Esav, and Esav alone who fought with Yaakov. Esav attacked Yaakov at night because he thought he could surprise Yaakov, and if he succeeded, nobody would know that he was the murderer. (See our discussion on 27:41, "An alibi?") However, Yaakov was strong (see 29:10) and was able to hold off Esav's attacks. Thus, Esav hit Yaakov “below the belt,” but even that did not help him, 32:26. When Esav grasped that he could not overpower/ kill Yaakov, then he had a problem since Yaakov would recognize him in the daylight and he was supposed to officially meet Yaakov in the morning. (Yaakov did not recognize Esav because it was dark and it had been 20 years since he had been home.) Thus when the dawn was breaking, Esav asked Yaakov to release him, 32:27. However, Yaakov would not agree until Esav blessed him, 32:27. Possibly, Yaakov asked for a blessing to indicate that he had prevailed in the fight or maybe Yaakov wanted a blessing to portend to his success the following day with Esav. (Is this request for a blessing similar to Yaakov's request for Esav to swear by the selling of the soup for the birthright, 25:33?)
Esav responded by asking Yaakov his name and then giving him a new name, Yisrael, 32:28,29. Why did Esav give Yaakov a new name? Yaakov had asked for a blessing, which Esav gave in 32:30, but why did Esav feel a need to also give Yaakov a new name? The answer is that when Esav heard that Yaakov had stolen the blessings, he said, "This is why he was called Yaakov since he twice tricked me," 27:36. Esav had connected the name Yaakov with the theft of the blessings and he did not want to give a blessing to Yaakov. Hence, he changed Yaakov’s name to Yisrael, and his blessing was then to Yisrael and not to Yaakov. In addition, the name was meant as a lesson to Yaakov, see our discussion on 32:29 (and 30:8), "The name Yisrael."
Yaakov was amazed by this new name and he asked the assailant for his name, 32:30. Esav refused to tell Yaakov his name in order to keep his identity a secret, but then he blessed Yaakov, as Yaakov had demanded in 32:27, and apparently Yaakov let him go, 32:30.
With the change of name, Esav's explanation of the new name, "you strove with Elokim and people, and prevailed," 32:29, and the blessing, Esav was indicating that he agreed that Yaakov was the brother who was to be blessed. Rabbi Carmy, one of my professors in YU, noted that based on this approach there is parallelism between the giving of the blessings and Esav's agreement to the blessings. When Yitzhak gave the blessings, he did not know that Yaakov was receiving the blessings, while when Yaakov attained Esav's blessing, Yaakov did not know who was giving him the blessing.
Yaakov, who knew that the change of name had special meaning and that the end of the name Yisrael included G-d's name, "el", concluded that his assailant had been a divine being. Thus, he named the place of the encounter, Peniel, for “I have seen G-d, face to face, and survived," 32:31. Yaakov's assessment of the assailant accords with his previous experiences that G-d had appeared to him in the middle of the night, 28:13 and 31:11.
The following day, Yaakov met Esav officially, and he said "For I have seen your face, as one sees the face of G-d, and you have been gracious to me," 33:10. Sarna (1989, p. 230) notes that this verse seems to refer back to the incident in the previous night since Yaakov again refers to seeing G-d’s face as he claimed to have done the previous night, 32:31. What is the connection? Rashi, (on 33:10) based on Bereshit Rabbah 77:3, explains that Yaakov was saying that seeing Esav’s face was equivalent to seeing the face of Esav's guardian angel. Yet, how would Esav know that Yaakov was talking about his guardian angel? Did Esav know that his guardian angel fought with Yaakov? Do guardian angels look like the person they are guarding?
A simpler idea is that when Yaakov met Esav in the morning he realized that he had fought with Esav the previous night. Yaakov was saying I saw your face but I thought that I had seen the face of G-d. Yaakov continued and said "you were gracious to me" meaning that Yaakov was recalling how Esav had agreed to bless Yaakov. Furthermore, once Yaakov realized that the change of name had come from Esav, then while he still thought it was significant that Esav said it, see 33:20, he would naturally wonder if he should use a name from his brother, so G-d later would re-affirm the change of name, 35:10.
In conclusion, I believe that Yaakov fought with Esav. Yaakov thought that he was fighting with a divine being after he heard the change of name to Yisrael, but on the following day when he met Esav he realized that Esav had been his opponent.
Kass, Leon, 2003, The Beginning of wisdom, Chicago: University of Chicago Press.
Leibowitz, Nehama (1905-1997), 1976, Studies in Bereshit, translated by Aryeh Newman, Jerusalem: The World Zionist Organization.
Miles, Jack, 1995, God: A Biography, New York: Alfred A. Knopf Inc.
Sarna, Nahum (1923-2005), 1989, The JPS Torah Commentary: Genesis, Philadelphia: The Jewish Publication Society.
Schein, Andrew, 1989, Who fought with Yaakov? Rinat Yitzhak, pp. 89-92.
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