In parashat vayishlach we see the moment where Jacob the trickster, the one focussed only on himself and his own needs and aspirations, is able to change. He is on his journey home, a wealthy and powerful man. However he must first encounter his estranged brother Esau whom he had dispossessed from his birthright and from whose terrible pain and murderous anger he had fled all those years ago.

In preparation for the encounter he sent out messengers in order to both impress Esau with his power and wealth, and in order to try to find out what was likely to be ahead of him. The messengers’ report on their return distressed him – they had met Esau on his way to meet Jacob, accompanied by four hundred men. His response – to try to save what he could of his family and possessions by dividing them into two groups, and then he prayed for help, invoking the merit of his ancestors and the promises God had made to him regarding his descendants. Following this, he began selecting groups of animals that he could send ahead as gifts to Esau, in order to appease him before their meeting. Then he says a particularly curious sentence, given what is about to happen:

וְאַֽחֲרֵי־כֵן֙ אֶרְאֶ֣ה פָנָ֔יו אוּלַ֖י יִשָּׂ֥א פָנָֽי”

And after this, I will see his face, perhaps he will raise my face/accept me”

Having taken his family, divided into two camps, across the ford of Jabok and over the stream, Jacob was left alone, yet in the same sentence that tells us  וַיִּוָּתֵ֥ר יַֽעֲקֹ֖ב לְבַדּ֑וֹ that he had been left behind and was completely and utterly alone, we are also told

     וַיֵּֽאָבֵ֥ק אִישׁ֙ עִמּ֔וֹ עַ֖ד עֲל֥וֹת הַשָּֽׁחַר:

And a man wrestled with him until the morning dawned.

He was alone, but he was not alone. He was in the dark of the night. He was wrestling. His struggles through the dark night of his soul changes him forever. He is in liminal transitional time after which he will be transformed and given a new name – though not so transformed that he would lose his old name forever….

Who is Jacob wrestling? The narrator of the text tells us it is “ish- a man.”

The wrestler himself is more complex telling Jacob that he has struggled with God and with men and has prevailed:

כִּֽי־שָׂרִ֧יתָ עִם־אֱלֹהִ֛ים וְעִם־אֲנָשִׁ֖ים וַתּוּכָֽל:

Later in the text Jacob seems to believe the fight was with God, as he names the place Peniel, the face of God:

וַיִּקְרָ֧א יַֽעֲקֹ֛ב שֵׁ֥ם הַמָּק֖וֹם פְּנִיאֵ֑ל כִּֽי־רָאִ֤יתִי אֱלֹהִים֙ פָּנִ֣ים אֶל־פָּנִ֔ים וַתִּנָּצֵ֖ל נַפְשִֽׁי:

And he continues “for I have seen God face to face and my soul is preserved”

Traditional explanations are that Jacob is fighting an angel, in particular the guardian angel of Esau who is attempting to weaken Jacob before the meeting, or that ‘the’man’ was Jacob himself, struggling with himself and his own feelings and needs, with the two inclinations all humanity possess – the yetzer ha’ra and the yetzer ha’tov, the inclination to be motivated primarily for one’s own self-interest versus the inclination to be motivated for the good of the community and of others, battling it out for charge of his soul.

There is, I think, a clue to this critical and iconic night of struggle in another part of the sidra. When Jacob meets Esau we find that Esau was coming with a welcoming party not a gang of ‘heavies’, and we are told that far from there being a clash between the brothers there is instead from Esau’s side real emotion and warmth at their reconciliation. We are told that he ran to Jacob and embraced him and fell upon his neck and kissed him:

 וַיָּ֨רָץ עֵשָׂ֤ו לִקְרָאתוֹ֙ וַֽיְחַבְּקֵ֔הוּ וַיִּפֹּ֥ל עַל־צַוָּארָ֖ו [צַוָּארָ֖יו] וַיִּשָּׁקֵ֑הוּ וַיִּבְכּֽוּ:

But written in the Masoretic text over the words “and he kissed him” וַיִּשָּׁקֵ֑הוּ are dots, and these are understood in the midrash to be there to draw attention to the word and to add to its meaning. Rashi quotes midrash (Sifrei) and comments that the dots are there to show that the kiss, while it seemed whole hearted, was actually insincere. But the weight of rabbinic tradition goes even further. In Midrash Genesis Rabbah (78:9) we are told that R.Yannai plays on the word ‘vayeshakei’hu’ and by changing just one letter in the word while keeping the sound, one can translate it as Esau biting Jacob. From this midrash comes the stream of Rabbinic traducing of the biblical Esau, to develop him into an enemy of the Jewish people, eventually becoming Edom, the code for the Roman oppression.

I do not like this interpretation, being in fact a big fan of the biblical Esau who just couldn’t somehow get it right, but who clearly loved his parents and who wanted to be the son they wanted. However, I would suggest that what was good enough for R.Yannai is good enough for us – so let us look at another word that could be available to the midrashic technique of creating a homophone with a meaning that can alter our understanding of what is happening. ‘Vayishlach’, the name of the sidra, comes from the root שָׁלַח ‘to send’

One homophone, a letter different, is the root סָלַח ‘to pardon or to forgive’

When Jacob then is sending out messengers, maybe we could see that he is in the beginning of the process of searching out for forgiveness, something he clearly needs to do as he has achieved so much of the material possessions he has desired but has not yet matched this achievement with the facing of what he did that had brought him to Laban as a young and frightened boy, alone in the world after having betrayed his father and brother, effectively excluded from his father’s house and inheritance.

So what happens if we bring this word play back into the text? When Jacob wrestles with a man while all alone, while he recognises that the man is in some way both God and human, he is indeed wrestling with himself and his own inclinations. But what he is wrestling with is not so much his two natures but his desire for pardon and his desire not to have to ask for it, not to have to climb down from his arrogance and his power and admit his wrong doing. In Jungian terms, Jacob is fighting with his Shadow side, the darker side of his own self, the irrational and instinctive and unknown aspect of his personality where a perceived personal inferiority is recognised as a perceived moral deficiency in someone else.

We all know the phrase that ‘sorry seems to be the hardest word’. For some people it is so hard that they will do almost anything not to have to say it. They will pass on the blame to others, project their feelings so that they see the reconciler as the attacker, reconstruct their narratives of the past so that they will appear the blameless ones, or even the victims of others. They will blacken the name of someone else in preference to owning up to their own mistakes. They will put obstacles in the way of meeting and encountering the other, so as not to have to face up to the humanity and reality of the person whom they have wronged. They will see the ‘admission’ of an apology as something that makes them vulnerable, lose power, or lose their status and become in some way the loser. Saying sorry might mean taking some responsibility for a problem, diminish them in some way, give others the right to judge…

We see this everywhere, from individual human interactions to workplace politics to the way that nations in conflict will absolve themselves from the problem and blame it all on the other side. The midrash that claims that Esau bites Jacob rather than kisses him is a manifestation of it. So the idea that Jacob is wrestling in order to say ‘selicha: I am sorry, please forgive me’, is a nice counterpoint.

It takes him the whole night and he is physically damaged in the encounter, leaving it with a permanent limp to remind him of both the struggle and the outcome. He is also changed – he can become Israel, the one who struggles with God- while sometimes reverting to Jacob, the heel and the trickster. Saying sorry isn’t a one-time thing – we can find it hard to repeat the word, or to say it in the next situation we should be saying it having made another mistake.

And yet apologising when we are at fault is the beginning of redemption. It is about recognising the effect of our actions and taking responsibility for them in order to change our selves and out behaviours. It is at the root of the idea of teshuva, of return to God, of return to the right behaviour that we would want and expect from ourselves.

It is the moment we can turn from Jacob to Israel, the moment when we stop focussing on our pride in our possessions and begin focussing with empathy on others and their needs.

Saying sorry is the pivotal moment when we change, when we notice our negative impact and begin to heal it. It is a lifetime process, a skill we need to practise again and again, the moment when we stop being obsessed with our own power and status and rightness and look around us with empathy and compassion and try to care more about others than about ourselves.

When Jacob wrestles and the dawn breaks, he realises that his struggle has meant that his soul is preserved, the sun comes up, the dark night of the soul is over. How did he preserve his soul? He learned of the importance of recognising his own responsibility in what he had done, he said ‘selicha’ he made his peace with the part of him that didn’t want to admit to any flaw or vulnerability. He took his place in the world and limped out, damaged by the encounter but also blessed by it, into the future.