That night, he lay down to sleep.
(25) Jacob was left alone. And a man wrestled with him until the break of dawn.
If he was alone how could Rashi say that his struggle is with an angel? Or was it because he was alone that a Divine being came to wrestle with him? But does the text say "angel" or that an ISH, a man, strove with him? Was this a private meeting between two brothers? Did Esau startle him leaping out of the darkness of the night pinning him to the ground injuring his thigh? Did he make him beg for mercy?
Or, was the struggle internal due to the turmoil? This "man" could have been Jacob himself! He was called as much in chapter 30:43 of Genesis before our verse in chapter 32. "The man was exceedingly successful...." was the description used for Ya'akov. Was he worried that his success would be seen as degrading and insulting to his brother? Did he worry about being "the man he had become" despite the time away. Was he putting his entirely family in danger just because he needed to make up with his brother, say he was sorry, hope for an acceptance of his apology?
What is the true meaning of the "ish" in the verse? the verb we translate as wrestle - "v'yeavek?" It is the only occurrence of the word in the entire Tanakh.
In the Medieval era, Rashi asserted the Midrashic text was right. It was an angel. And most understood the term v'yeiavek as wrestled or struggled with. But let's examine art that presents insights into the text. What new understandings arise from contemplating the creative work of the masters below?
ויאבק איש. מְנַחֵם פֵּי' וַיִּתְעַפֵּר אִישׁ, לְשׁוֹן אָבָק, שֶׁהָיוּ מַעֲלִים עָפָר בְּרַגְלֵיהֶם עַ"י נִעְנוּעָם. וְלִי נִרְאֶה שֶׁהוּא לְשׁוֹן וַיִּתְקַשֵּׁר, וְלָשׁוֹן אֲרַמִּי הוּא, בָּתַר דַּאֲבִיקוּ בֵיהּ, וַאֲבֵיק לֵיהּ מֵיבַק – לְשׁוֹן עֲנִיבָה, שֶׁכֵּן דֶּרֶךְ שְׁנַיִם שֶׁמִּתְעַצְּמִים לְהַפִּיל אִישׁ אֶת רֵעֵהוּ, שֶׁחוֹבְקוֹ וְאוֹבְקוֹ בִּזְרוֹעוֹתָיו. וּפֵרְשׁוּ רַזִ"לִ שֶׁהוּא שָׂרוֹ שֶׁל עֵשָׂו (בראשית רבה):
RASHI ON "A MAN WRESTLED WITH HIM"
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).

Note that Rembrandt uses strikingly different colors for Jacob and the angel. What was the red symbolic of in this case? The white? It seems the angel's expression is one of tenderness. Of course, located above Jacob, we get the sense of Divine Presence. The right hand of God or right side is known as the side of mercy. The "man" or "angel" in the biblical text wants to know Jacob's name. Or have Jacob consider who he is and what he has become. Is that the look on Jacob's face - inner contemplation and questioning?
Contrast the Jacob of Gustave Dore, French, 1832 - 1883 to Rembrandt's Jacob (1606 - 1669). Was Jacob crushed by the ultimate defeat or strengthened? How does Dore's work give us insight into Jacob's character?

Is the light and Divine radiance transcendent or nearer the earthly man and terrain? Gustave Moreau's work shines light on a more imminent God, an earthly spirituality, a godliness that works within that churns the soul and prepares a person for a new day. Examine his composition below - still with an angel, note where light is coming from, how close it is to Jacob in the scene.

And what of the glance of the angelic figure in Moreau's work? Do we get a sense that the Divine both pays particular attention to those in need and yet stares off to a future that only God knows? Or is there another way to interpret the eyes and hand upon the head?
Ya'akov's inner struggle is given voice if the text is interpreted as him wrestling with himself or even a Divine angel. In the end Jacob could not defeat, or dismiss, the angel, the history, the reality he faced.
We will all have nights that we twist and turn facing our struggles, repenting for dishonesty and worrying about the encounters we orchestrate to repair relationships.
In the end, Jacob overcomes his fears. He meets his brother. Decisively, he determines to forge his own path forward despite his brother's invitation to "travel and walk together."
