Bad Art, Good Torah: Vayishlach

(25) Jacob was left alone. And a figure wrestled with him until the break of dawn.(26) 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.(27) Then he said, “Let me go, for dawn is breaking.” But he answered, “I will not let you go, unless you bless me.”(28) Said the other, “What is your name?” He replied, “Jacob.”(29) Said he, “Your name shall no longer be Jacob, but Israel, for you have striven with beings divine and human, and have prevailed.”(30) Jacob asked, “Pray tell me your name.” But he said, “You must not ask my name!” And he took leave of him there.(31) So Jacob named the place Peniel, meaning, “I have seen a divine being face to face, yet my life has been preserved.”

ויאבק איש AND A MAN WRESTLED — Menachem (ben Seruk) explains: “a man covered himself with dust”, taking the verb as connected in sense with אבק “dust”. It would mean that they were raising the dust with their feet through their movements. I, however, am of opinion that is means “he fastened himself on”, and that it is an Aramaic word, as (Sanhedrin 63b) “after they have joined (אביקו) it", and (Menachot 42a) “and he twined (the “Fringes”) with loops”. It denotes “intertwining”, for such is the manner of two people who make strong efforts to throw each other — one clasps the other and twines himself round him with his arms. Our Rabbis of blessed memory explained that he was Esau’s guardian angel (Genesis Rabbah 77:3).

ויאבק איש עמו, “a man began to wrestle with him.” The “man,” was an angel who had assumed the form of a human being. The angel, Esau’s protective power, had come to prevent Yaakov from escaping from Esau. He realised soon that G-d’s assurances to Yaakov were strong enough to protect him against being harmed by Esau. (Rash’bam)

איש, the same type of איש as in Joshua 5,13, i.e. an angel. This was the angel Gavriel, described as איש par excellence in Daniel 9,21. The reason why these angels are called איש is because they appear to the people with whom they converse in human guise. The types of angels who speak with man are referred to as איש, as they appear either in a vision or while the person to whom they appear is fully awake. G’d had sent this angel to Yaakov to strengthen his courage, not to fear Esau. If Yaakov could prevail over an angel, surely he had no reason to be afraid of an encounter with someone like Esau! The fact that the struggle lasted until daybreak was an allusion to Yaakov that after a period of night, i.e. problems, adversity, there would come a period of light, peace and prosperity coupled with security..

פנים אל פנים, face to face. Jacob's amazement was not due to the fact that he had had an encounter with an angel; he had previously encountered angels. What amazed him was that he had been in a confrontation with an angel. The word פנים אל פנים is a term used in warfare as we know from Kings II 14,8.