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He Wrestled With Yeshua

By Rabbi Jay Ledbetter

Saturday, December 6, 2025,16 Kislev 5786

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12-06-25 Message to Roeh Israel – VaYishlach (and [Yacov] sent) Torah Portion; Genesis 32:3 – 36:43

Haftarah: Obadiah 1:1-21

Suggested Acheron K’tuvim: 2 Chron 7:12-15

He Wrestled with Yeshua

Central question of this message: Are you in fervent prayer when you are facing great challenges?

We are in parasha VaYishlach, which means “and he sent,” again referring to Yacov. Its name comes from the first three words in the English, and the first word in the Hebrew.

Gen 32:3-5

3 Then Jacob sent messengers before him to his brother Esau

in the land of Seir, the country of Edom. 4 He also

commanded them saying, "Thus you shall say to my lord

Esau: 'Thus says your servant Jacob," I have sojourned with

Laban, and stayed until now; 5 and I have oxen and donkeys

and flocks and male and female servants; and I have sent to

tell my lord, that I may find favor in your sight.

This parasha opens with Yacov sending his wives and possessions ahead of him as an offering to try to make peace with his brother Esav, who is approaching with a small army.

Twenty-two years have elapsed since Yacov saw his brother Esav. Only a few days short of twenty-two years also have elapsed since Yacov had the vision of the strong tower, the rock, the footstool of G-d from earth to heaven.

Yacov is now headed back to Canaan with two wives, eleven children, and many herds of animals. Benjamin had not been born at this time.

As an aside, why was the Temple eventually built upon the tribal land of Benjamin? The sages tell us that since Benjamin had not been born at this time, and since he was the only son who did not bow before Esav, he alone was found worthy.

The first thing we might see is that Yacov knows precisely where Esav has made his home. He’s been keeping track of his brother. He has known from the first that Esav threatened that once Yitzhak died, he would kill Yacov.

In our last parasha, we saw that G-d reaffirmed personally to Yacov that he would not die at the hand of Esav, but that the Abrahamic line of succession would indeed go through Yacov, and his descendants would be as the sand of the sea. Even with that assurance, does Yacov face the coming reunion with Esav with courage? With faith? No.

Yacov has clearly been pondering a worst-case-scenario, and has been working on a course of action as he rides southward towards the place where he will encounter his brother Esav.

Yacov begins with sending messengers, with a “white flag”. He hopes that the message they bring will soften Esav’s heart, and appeal to his desire for riches. And Yacov hopes to find out from the report Esav’s disposition toward him.

Gen 32:6

6 And the messengers returned to Jacob, saying, "We came to

your brother Esau, and furthermore he is coming to meet you, and four hundred men are with him."

The report of the messengers is, to say the least, disturbing. The Hebrew word translated here as “to meet you” is not at all as benign as it comes out in the English.

The root word is karah, and it can legitimately indicate a chance meeting, but in the context, it does seem that there is hostile intent.

And since we know that this encounter is not by chance – since Esav is setting out intentionally to encounter Yacov – then there seems to be a good chance that the message implied hostility. So, how does Yacov react to this report?

Gen 32:7-8

7 Then Jacob was greatly afraid and distressed; and he

divided the people who were with him, and the flocks and the herds and the camels, into two companies; 8 for he said, "If Esau comes to the one company and attacks it, then the

company which is left will escape."

It is clear that Yacov is in “damage control” mode. He is relying entirely upon his own cunning for his salvation. He figures that if he will offerup one of the groups as lost, then he might save the other.

Oh, and since he is in the rear of the battle, he will save himself. This is not what many of us would characterize as “courage.” On our best days, we fathers would send wives, children, servants, and flocks away, and go to face the antagonist alone. We would say, “Get out of here and live. He just wants me. I will give him me.”

In Yacov’s mind, he believes he has already lost the battle, and he just wants to get out with the smallest loss. This is because Yacov is consumed by fear. The Hebrew sentence structure describing the level of angst being experienced by Yacov is quite strong.

The word translated “distressed” is yitzer. It’s found at Strongs 3334.

It is used only ten times in all of Tanach. You can see the level of distress expressed here by looking at another passage that uses this same word to describe another hostile encounter.

In 1 Sam 30:1-6 the story is told of King David, at war with the Amalekites. The enemy raided the town of Ziklag, and burned it to the ground after taking all the people captive, including the families of the men who were with him. There was great agony in the camp.

1 Sam 30:5-6

5 Now David's two wives had been taken captive, Ahinoam

the Jezreelitess and Abigail the widow of Nabal the Carmelite.

6 Moreover David was greatly distressed because the people

spoke of stoning him, for all the people were embittered, each one because of his sons and his daughters. But David

strengthened himself in the Lord his God.

Looking back into the parasha for today, it is at this time in the unfolding story that Yacov finally, as what seems a last resort, seeks strength from G-d.

Yacov’s fear is based on ignorance. And that fear destroyed his faith.

Yacov doesn’t know what the remainder of the book containing the pages of his life holds. Yacov doesn’t know how many children he is supposed to have, for G-d plan to be fulfilled. He has some children already. Are those sufficient for G-d’s plan, and so G-d doesn’t need Yacov any longer? Yacov had lots of questions, and few answers.

Gen 32:9-12

9 Jacob said, "O God of my father Abraham and God of my

father Isaac, O Lord, who said to me, 'Return to your country and to your relatives, and I will prosper you,' 10 I am unworthy of all the lovingkindness and of all the faithfulness which You have shown to Your servant; for with my staff only I crossed this Jordan, and now I have become two companies. 11

"Deliver me, I pray, from the hand of my brother, from the

hand of Esau; for I fear him, that he will come and attack me and the mothers with the children. 12 "For You said, 'I will

surely prosper you and make your descendants as the sand of

the sea, which is too great to be numbered.'"

He doesn’t know that one of his children will rise in Egypt, and as he becomes the savior of the world in that day, he will become a type and figure of the Messiah. Only G-d knows.

Yacov needs not fear. But his ignorance of the future causes him to surrender to fear. He has insufficient faith in the One who holds his future.

From this passage, we can see that Yacov clearly remembers the promises, but he still thinks he needs a “plan B”. After the prayer, Yacov thinks up one more idea… he will give a lot of gifts to give to Esav.

Gen 32: 13-21

13 So he spent the night there. Then he selected from what he had with him a present for his brother Esau: 14 two hundred

female goats and twenty male goats, two hundred ewes and

twenty rams, 15 thirty milking camels and their colts, forty cows and ten bulls, twenty female donkeys and ten male

donkeys. 16 And he delivered them into the hand of his

servants, every drove by itself, and said to his servants, "Pass on before me, and put a space between droves." 17 And he

commanded the one in front, saying, "When my brother Esau

meets you and asks you, saying, 'To whom do you belong, and

where are you going, and to whom do these animals in front

of you belong?' 18 then you shall say,' These belong to your servant Jacob; it is a present sent to my lord Esau. And behold, he also is behind us.'" 19 Then he commanded also the second and the third, and all those who followed the droves, saying, "After this manner you shall speak to Esau when you find him;

20 and you shall say,' Behold, your servant Jacob also is

behind us.' "For he said," I will appease him with the present that goes before me. Then afterward I will see his face; perhaps he will accept me." 21 So the present passed on before him,

while he himself spent that night in the camp.

The troubled and timid Yacov spends the night in the camp. While he sends his servants, unarmed herders, out before him. Their lives were on the line. The news of the hostile army approaching was no secret. I am not so sure these who were sent ahead appreciated Yacov’s generous gestures all that much.

In his exhausted condition, Yacov isn’t thinking clearly. General Patton knew that rest is a combat force multiplier. He said, “Exhaustion makes cowards of us all.”

Let’s look at the animals. Yacov gives so many animals to his brother, some 550 animals, by my quick count. I think I have an idea why so many.

Yacov seems to have a plan, based on the fact that goats, sheep, donkeys, camels – especially with young – have a tendency to wonder off to be alone. They don’t like being together in a large group.

For Esav to accept and take control over all these animals, he will need to divide his army into smaller bands, each tasked to keep these animals in separate flocks, and under control. Thus diverting some of the soldiers to the task of herding.

Yacov sends them in the afternoon, so that they will arrive before nightfall. That means the next morning Esav will likely not break camp completely, but will cause some of his men to stay at that location to tend these huge flocks. More herders means fewer soldiers for the fight.

Let me assure you that all these choices by Yacov make sense in the world of earthly battle – with the exception of his cowardice of staying in the rear while sending forward his servants.

But with the advantage of knowing the end of this story, we know something Yacov does not: the best military tactics never can assure a good outcome, when the battle is the L-rd’s. The L-rd’s plans always succeed.

As the story continues, it is now dark, and camp is set. But I see Yacov pacing in the spaces between the tents, wracking his mind on what else he might do.

Suddenly, he breaks camp, and moves them out in the darkness to a new location. I am sure that the people who had to get out of bed, pack up all their belongings, take down the tents, pack the camels, and then get in line to move-out were absolutely…. delighted… with this turn of events.

On top of that, they had to ford the Yabbok river, and a lot of people and gear would be put up, and settled in for the night… wet.

Gen 32: 22-23

22 Now he arose that same night and took his two wives and

his two maids and his eleven children, and crossed the ford of the Yabbok. 23 And he took them and sent them across the

stream. And he sent across whatever he had.

Now Yacov is out of time, strength, and options. As what seems as his final act, he really begins to pray.

Gen 32: 24-30

24 Then Jacob was left alone, and a man wrestled with him

until daybreak. 25 And when he saw that he had not prevailed against him, he touched the socket of his thigh; so the socket of Jacob's thigh was dislocated while he wrestled with him. 26 Then he said, "Let me go, for the dawn is breaking." But he

said, "I will not let you go unless you bless me." 27 So he said to him, "What is your name?" And he said, "Jacob." 28 And

he said, "Your name shall no longer be Jacob, but Israel; for you have striven with God and with men and have prevailed."

29 Then Jacob asked him and said, "Please tell me your name." But he said, "Why is it that you ask my name?" And he blessed him there. 30 So Jacob named the place Peniel, for he said, "I have seen God face to face, yet my life has been preserved."

Who was this “man” who wrestled with Yacov? This question has provoked a number of speculations. Some sages say it was the angel of Esav, come to weaken Yacov before the coming battle. I disagree.

What was the “struggle?” The answer to that question provides the answer to the first question – who is the “man”?

The Hebrew depicting this “struggling with a man until dawn” is much more complex than its rendering in English. The English misses so many nuances that I believe have significant theological implications.

The Hebrew words translated “and he wrestled, a man” are v’ye’avech ish. It is legitimate to use the word “wrestled” as the translation.

But what does “wrestling” entail? Physical contact – grappling – with the other person. In English, it involves a degree of physical control by each

of the wrestlers over the other. And that is what most theologians impose upon this passage. But I want us to look deeper.

The root avech has a primary meaning – to float away, as a vapor.

The word translated as “man” is ish. That word means a mortal, human being. But this person is not ordinary.

It is equally legitimate to translate these words as, “a man whom one cannot grasp”. Or, “a mortal man whom one cannot control”.

But as we look at the passage closely, there seemed to be some sort of control by Yacov over this vaporous man, since Yacov demanded, and then received, a heavenly blessing and a changed name.

How is it possible that a mortal human being can be at once a vapor, uncontrollable, and then also solid enough – and powerful enough – to touch the hip of another human and throw it out of joint, causing a lifetime injury?

What kind of being is this who can also then confer G-d’s blessing? It can only be the one who men cannot control by force; one who can be a vapor, and immensely strong; with the very “face of G-d”. These attributes are combined in only one being - Yeshua.

Yeshua may well have become “a vapor” which no man can control at a later event we read about in Scripture. After He gave a particularly irritating message in the synagogue, this happened.

Luke 4:28-30

28 And all in the synagogue were filled with rage as they

heard these things; 29 and they rose up and cast Him out of the city, and led Him to the brow of the hill on which their city had been built, in order to throw Him down the cliff. 30 But passing through their midst, He went His way.

They wanted to wrestle with Yeshua – to throw Him off a cliff. It is clear that their purpose did not change at the top of the hill. But maybe Yeshua’s ability to be grasped did change. He might well have passed right through them…literally.

Back to discussing what Yacov did - what was this “wrestling”? Clearly, it was not a physical match of strength and endurance as we might see in an Olympic wrestling event. But there was some sort of control over Yeshua in this event.

How can one gain control over Yeshua? It is in the way that He permits control. In my opinion, there is only one way we can appropriate such control - if we are in supplication and prayer, Yeshua is compelled to attend to such prayers. He is compelled by His love for us.

How do I know that? It is set out in Scripture. That promise was affirmed in a passage that actually mirrors this event. Solomon has finished the Temple, and has intently prayed to the L-rd.

2 Chron 7:12-15

12 Then the Lord appeared to Solomon at night and said to

him, "I have heard your prayer, and have chosen this place for

Myself as a house of sacrifice. 13 If I shut up the heavens so that there is no rain, or if I command the locust to devour the land, or if I send pestilence among My people, 14 and My

people who are called by My name humble themselves and

pray, and seek My face and turn from their wicked ways,

then I will hear from heaven, will forgive their sin, and will heal their land.

This passage affirms that which was already so with Yacov on the banks of the Yabbok river. G-d not only listens to your prayers, He is compelled by His love to act upon them.

Is Yacov part of G-d’s people? Yes. Is Yacov called by His name? Yes.

Yacov actually received G-d’s name during this event. Isra-el. “El” is one of the names of G-d.

Yacov was humbling himself and praying. He was purposing to repent to Esav for what Esav considered Yacov’s wicked ways of deceit. Yacov did show humility and regret somewhat when he encountered Esav.

Back to the struggle with this heavenly being. This “wrestling match” is better characterized as a time of intense prayer. Now look at the phrase

that immediately precedes the event. I think it shows us a bit of how that prayer was answered.

Gen 32:22-23

22 Now he arose that same night and took his two wives and

his two maids and his eleven children, and crossed the ford of the Jabbok. 23 And he took them and sent them across the

stream. And he sent across whatever he had.

Look at the phrase translated, “he sent across whatever he had.” That is legitimate, but what is odd is that the passage had already listed what it was that he sent across. So, this addition seems to be unnecessary. This should alert us to look a bit deeper to see if there is something more.

The word v’yaaver which is translated “and sent over” can also be translated as “covered in an intimate way.”

The word asher can mean “that,” “which,” or “whom”.

The word lo is translated as “he had.” It can mean much more. It can mean “all that pertains to him.” In prebabylonian Hebrew, this word carries with it the concepts of “attached to authority.”

Coupling that with the aleph tav – which we now known can refer to Yeshua – we can maybe see a bit more there. Putting all these ideas together in a different translational choice would give us:

“Yeshua covered (protected) all that is within His authority.”

It can be inferred from this translation, together with the promises given Yacov by G-d, and also considering the rest of the story as it unfolds, that even before Yacov prayed, G-d had directed Yeshua to cover and protect all of Yacov’s assets, servants, wives, and children from harm. Yacov just hadn’t seen it yet in the physical realm.

Yacov will the next day be humble before his brother Esav, and even call him lord. Esav might have intended to destroy Yacov, but his heart was changed. The brothers will be reconciled. But their descendants will eventually remember the great divide that is between these two tribes.

The Jewish people today strive with the sons of Esav, and soon with all nations of the earth. The sons of Israel will, in the end, finally prevail.

Israel has, for two thousand years, wrestled with Yeshua, as if with a vapor that they cannot grasp, nor control. They carry with them a prominent spiritual crippling – because of their unbelief.

The blessing that Yeshua gave Yacov mirrors the blessings given to Abraham, Yitzhak and Yacov. That blessing remains. We today are the beneficiaries of this blessing.

None of us know what the remaining pages of the book of our life might hold. We don’t even know if there is another page after this one.

The world is full of hostility, and that hostility will increase. None of us knows the outcome of the various trials we face. But all of us know the One who is in control of the outcome at the end.

So… pray fervently. And wrestle with Yeshua if you must. But… pray.

Know that Yeshua still protects all that is within His authority for those who are truly His.

Torah portion
Vayishlach
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