Parashas Vayishlach: Yaakov's Malachim, the Fight of the Yetzer Hara, and the Limits of Hishtadlus

Topics

• Parashas Vayishlach: Yaakov and Esav — Malachim, Independence, Bitachon, and the Yetzer Hara
• Why Actual Malachim?
• The Fight No One Can Fight for You
• "Vayivaser Yaakov Levado" — Independent of Influence
• Yaakov's Strength: "Am Levadad Yishkon"
• "Vayivaser Yaakov Levado" and the Importance of Self-Worth
• Why Was Yaakov So Afraid of Esav?
• "Katonti Mikol HaChasadim" — Asking Whether I Bear Responsibility
• "V'Lo Lamadti MiMa'asav HaRa'im" — Learning Enthusiasm from Esav
• Two Sisters, the Ramban, and Yaakov's Fear of Killing
• Yaakov's Fear of Harming Others — A Complex Halachic and Moral Question
• "I Don't Mind Being Wrong" — Ramban's Message for the Generations
• Why Did Yaakov and Esav Cry?
• "Vayehi Li Shor VaChamor" — How to Speak to Esav
• Giving a Person the Kavod of a Good Deed
• Who Was the "Ish" Who Wrestled with Yaakov?
• Did Yaakov Win the Wrestling Match?
• Chizkuni, Seforno, and the Baal HaTurim's Surprising Remez
• How Much Hishtadlus Is Too Much?
• Malbim and Abarbanel: Does Bitachon Remove Fear?
• Why Animals, Not Gold? And Each Person's Tefillah
• Fragmentary Post-Shiur Discussion: Dina
• Post-Shiur Fragment — Yaakov's Conduct Toward Esav
• Final Fragment — Avoiding Battle

Transcript

# Parashas Vayishlach: Yaakov and Esav — Malachim, Independence, Bitachon, and the Yetzer Hara

## Why Actual Malachim?
Rabosai, **"וישלח יעקב מלאכים לפניו אל עשו אחיו"** (Bereishis 32:4). Rashi explains **"מלאכים ממש"**—actual angels.

Why did Yaakov send angels rather than ordinary messengers? The mefarshim mention danger: Esav was an unpredictable and formidable man. My grandfather gives a deeper explanation: Esav had extraordinary powers of **influence**. His personality was capable of drawing people after him. Ordinary messengers might be affected, but malachim would not.

Don't imagine Esav as a cartoon villain carrying a bazooka. The Torah tells us Yitzchak Avinu took him very seriously. Esav must have had tremendous **potential and charisma**, even if he used his powers wrongly.

But there's a question that always bothered me. **Yaakov could send malachim; how could Esav see and receive them?** The Torah says Yaakov gave them an actual message, **"כה תאמרון לאדני לעשו"**. An angel's appearance to Yaakov does not mean he is accessible to Esav.

A talmid asks whether they actually spoke to Esav. In **Bereishis 32:7**, when the malachim return, they report only **"באנו אל אחיך אל עשו וגם הלך לקראתך וארבע מאות איש עמו."** The Torah doesn't tell us of a conversation.

That's a good **diyuk**. Perhaps Esav ignored them. It reminds me of an executive who tells his secretary to leave a visitor waiting: "I'm busy. I have a meeting!" But even if Esav ignored them, Yaakov must have thought they could make the mission.

Maybe the answer is that **because Yaakov sent them**, the malachim could appear in a form Esav would perceive. The power would be in **Yaakov's shlichus**, not Esav's spiritual level. That's a possible teretz; I haven't proven it.

And this brings me to a wonderful question once asked by **Rav Shmuel Berenbaum**.

## The Fight No One Can Fight for You
I was once driving **Rav Shmuel Berenbaum** to a melaveh malkah in Queens. He asked: Why does Yaakov use **malachim to approach Esav**, but when the struggle arrives, **"ויאבק איש עמו"**—he wrestles personally?

If he has heavenly messengers available, why not send them to fight?

I answered Rav Shmuel, and he was very pleased. When he liked an idea, he patted you vigorously. He was patting me while I drove, and I almost went off the road!

My answer is that the struggle with the **sar shel Esav** is the **war of the yetzer hara**. A person can ask someone else to deliver a peace offering, but **nobody else can fight the war inside him**.

The Midrash describes the dust of Yaakov's struggle as rising toward Heaven, expressing the enormous spiritual dimension of the confrontation. Some mefarshim understand **"עד עלות השחר"** as a hint to the dawn of the final geulah after the darkness of galus. I cite a thought from the Chofetz Chaim transmitted by **Rav Elchonon Wasserman** about Yaakov, the pillar of Torah, uniquely fighting this ongoing spiritual conflict. The precise source needs checking.

This brings us to **Rabbi Elazar ben Durdaya** in **Avodah Zarah 17a**. After grave sin, he begs the mountains and the heavens to plead for him. Finally he understands:

**"אין הדבר תלוי אלא בי."**

The matter depends on **me**.

There's a tremendous lesson here. Not that we don't need Hashem's help, but that a man cannot transfer **his responsibility for teshuvah** to anyone else.

So the malachim can negotiate. But the spiritual war is **Yaakov's war to fight**.

**"אין הדבר תלוי אלא בי."** Make up your mind and fight the good fight.

## "Vayivaser Yaakov Levado" — Independent of Influence
Now let's think about **"ויותר יעקב לבדו"** (Bereishis 32:25).

Why is the fact that Yaakov remained **alone** so important?

Chazal compare his *levado* to the expression **"ונשגב ה' לבדו"** (Yeshayahu 2:11). How can a created person be compared to Hashem, Who depends upon nobody?

I saw an explanation of **Rav Yerucham Levovitz**. There is a profound quality of being able to **stand alone** spiritually—to remain firm in one's identity without allowing the world to make one's decisions.

Klal Yisrael inherited that strength from Yaakov, as in **"הן עם לבדד ישכן ובגוים לא יתחשב"** (Bamidbar 23:9).

A discussion develops with talmidim about the experiences of Jews who lived in **Iran** and Jews in America. One student says that an enclosed community can protect people from secular influences, even if outside life involves danger. Another mentions real persecution, imprisonment for supporting Jewish causes, and hardships of practicing Jewish life in Iran. We must not pretend those experiences were all identical.

I remember growing up in America: Yankees, candy, yeshivah, everything a child could want. The environment encouraged learning, and it was easier for many of us to practice Jewish life openly. But the very ease of the larger society presents different spiritual challenges.

I understand both sides of the discussion. The point is that **"levado"** is the power not to be dictated to by one's surroundings.

And that leads us to another thought, brought by **Rav Wolbe** from the **Kuzari**, concerning **a person's inner self-worth**.

## Yaakov's Strength: "Am Levadad Yishkon"
Rabosai, the **"levado"** of Yaakov is a tremendous middah. Rav Yerucham explains that Yaakov was capable of standing on his own spiritually, not dependent upon what others thought of him.

**"הן עם לבדד ישכן ובגוים לא יתחשב"** (Bamidbar 23:9). Klal Yisrael can remain faithful to its identity even surrounded by other nations. The point isn't that a Jew must reject every conversation with another human being, but that his inner convictions must not be dictated by the outside world.

I saw Rav Wolbe bring an idea associated with the **Kuzari**. It has to do with recognizing **one's own spiritual identity and self-worth**.

A person often defines himself by the way he imagines other people see him. If they respect him, he feels valuable. If they dismiss him, he feels worthless. But that isn't the truth of a person.

The **sar shel Esav** attacks precisely that weakness. He says, "You're only as important as your possessions, your popularity, the enjoyment you can get, or the attention you can attract."

If you have no conception of the **pnimiyus** within you, the yetzer hara can move you in any direction.

Think about **shemiras einayim**. A forbidden visual pleasure may appeal to the eyes while failing to nourish the neshamah. It's like **empty calories**—a moment of taste without meaningful inner satisfaction.

Esav saw the red stew and cried, **"הלעיטני נא מן האדום האדום הזה"** (Bereishis 25:30). The appearance captured him. What is it? He isn't interested in the deeper significance. It's red, and he wants it.

And the **Eitz HaDaas** is described as **"וכי תאוה הוא לעינים"** (Bereishis 3:6), attractive to the eyes. I'm drawing a mussar lesson from that expression, not reducing the whole pasuk to a single detail.

You are not simply your eyes! **Who are you inside?**

That's the question of **"ויותר יעקב לבדו"**. Yaakov knew who he was before Hashem.

And when a Yid knows the value of the person within, the yetzer hara cannot so easily convince him that outside attractions and opinions are all that matter.

## "Vayivaser Yaakov Levado" and the Importance of Self-Worth
Rav Yerucham explains that Yaakov's strength was the ability to **stand alone**—not to let outsiders dictate his inner life. **"הן עם לבדד ישכן"** means Klal Yisrael need not be influenced by every pressure of the surrounding society.

I saw **Rav Wolbe** bring another explanation associated with the **Kuzari**: **self-worth**. If a person has no sense of who he is inside, the yetzer hara can use every desire and social pressure to define him.

I want you to hear this, rabosai. **Your eyes are not the whole you!** Your pleasures, purchases, and entertainment are not the **neshamah** inside.

An idea attributed to **Rav Avigdor Miller** is that modern people find it difficult to spend even a short time alone with themselves. They turn on television even when nobody is watching. The sound runs all day so they never have to sit with their own thoughts.

Why? Because **"there's no levado"**—they haven't made peace with the inner self.

Why do some people shop, watch shows, or seek other stimulation when they're miserable? Sometimes it's an attempt to distract themselves from what they feel within. This is a mussar observation, not a medical explanation that applies to every person.

I spoke about this in Lakewood, and people called me afterward to hear it again. The idea moved them because it's true to life: **the sar shel Esav attacks the person's individuality and self-respect**. He wants all of our value to be defined by externals.

And in our generation the struggle is intense. We possess technology, comforts, entertainment—yet people can still feel deeply unhappy. My grandfather remembered a Europe where people weren't constantly talking about therapy; some respond that people there may have **needed** help and simply did not receive it. That's a fair point. I'm not denigrating psychological care. I'm emphasizing that material comfort doesn't automatically produce inner wholeness.

The night of this struggle lasts **"עד עלות השחר"**, and some mefarshim read the approaching dawn as a hint to the final geulah. We are still facing the conflict between the **outside** and the **inside**.

That's the avodah of **"ויותר יעקב לבדו"**.

## Why Was Yaakov So Afraid of Esav?
We have reached **"ויירא יעקב מאד ויצר לו"** (Bereishis 32:8).

Why was Yaakov so afraid of Esav?

Chazal explain that he feared **being killed**, and he also feared **having to kill others**. And he turns to Hashem with the tefillah **"קטנתי מכל החסדים ומכל האמת"** (32:11).

Some Midrashic interpretations suggest that Esav possessed zechuyos, including **kibud av** and living in **Eretz Yisrael**, that Yaakov had not enjoyed to the same degree during the years in Lavan's house. The particular teaching I mention in the name of **Rashbam** needs its exact source checked.

A talmid wonders: what is the mitzvah of **yishuv Eretz Yisrael** worth if Esav committed sins? I find the question interesting. Perhaps the very presence in the land has significance, though many qualifications would be required before drawing modern halachic conclusions. I make a joking reference to controversies among **Satmar** Chassidim. That is a classroom aside, not a settled ruling on the contemporary mitzvah or politics.

But I want to tell you an extraordinarily beautiful thought from **Rav Shmuel Berenbaum**.

Yaakov was justified in receiving the brachos. So what was he frightened of? Why would Esav have a claim against him?

There is a halachic concept of **"אין לו עליו אלא תרעומת"**—sometimes a transaction cannot be enforced, but the other person retains a justified **complaint**. Rav Shmuel cited **Rav Yisrael Salanter** for the idea that even when a person has no legally enforceable remedy, the fact that he has a legitimate complaint is meaningful.

We should not dismiss him with, "You have no case, so I owe you nothing morally!"

Perhaps Yaakov said: Even if I was justified in taking the brachos, **Esav may still have some honest grievance**. After all, he was my older brother. I may need to recognize that even while standing by the truth.

That may explain the humility of **"אדני"**, my master, and the respectful bowing when the brothers meet.

It's a beautiful thought: **Yaakov, the man of emes, searches for the grain of truth even in the accusation of someone who wishes to harm him**.

## "Katonti Mikol HaChasadim" — Asking Whether I Bear Responsibility
Rav Shmuel Berenbaum's point moves me.

When another person is furious with you, it's easy to say, "He's completely wrong. What did I do?" But perhaps a person with the **middah of emes** asks himself a harder question:

**"Did I do something that contributed to this anger? Is there an aspect of his complaint that I ought to acknowledge?"**

Yaakov may have felt, "Esav is coming to kill me, and of course his violence is wrong. But am I certain I have no share in what led to this?"

That's not a justification for Esav's aggression. It's the inner honesty of Yaakov Avinu.

And the same *middah* appears in his tefillah:

**"קטנתי מכל החסדים ומכל האמת אשר עשית את עבדך"** (Bereishis 32:11).

Hashem has done so much for me. **Have I lived up to it?** Perhaps I could have done more.

A talmid asks: Chazal say **"שמא יגרום החטא"**—perhaps sin will cause a problem. If Yaakov knew of a particular sin, why not simply do teshuvah?

The point, according to the explanation I'm giving, is that Yaakov **didn't know**. His honesty made him examine the possibility of a deficiency in himself. Not everything that goes wrong is proof of a particular sin; I am explaining Yaakov's introspection, not instructing someone to blame himself for every hardship.

But this raises a tremendous kashya.

Yaakov tells Esav:

**"עם לבן גרתי"** (Bereishis 32:5), which Rashi explains through the remez **"ותרי"ג מצוות שמרתי ולא למדתי ממעשיו הרעים"**.

How can Yaakov say **"I kept the 613 mitzvos"** while also fearing that **"shema yigrom hachet"**?

Was he completely confident in his conduct or doubtful about it? You can't have it both ways!

Perhaps we need to be medayek in **"שמרתי"**, I guarded the mitzvos, rather than saying **"קיימתי"**, I fulfilled each one perfectly. Not violating a prohibition isn't the same as achieving the full positive potential of a mitzvah.

Like Shabbos: someone may avoid all prohibited melachos, but does that mean he has truly **made Shabbos** into the uplifting, Torah-filled day it should be?

Yaakov could truthfully say he **guarded** Torah while still worrying that he did not bring to its fulfillment all the energy and greatness he could have.

And that leads us to another remarkable interpretation of the end of Rashi's phrase.

## "V'Lo Lamadti MiMa'asav HaRa'im" — Learning Enthusiasm from Esav
Rashi's words are:

**"ותרי"ג מצוות שמרתי ולא למדתי ממעשיו הרעים."**

I guarded the mitzvos, and I did not learn from Lavan's evil ways.

But why must Yaakov tell Esav he didn't learn from the evil ways of Lavan? Isn't that obvious if he kept the mitzvos?

I saw a teaching attributed to the **Chofetz Chaim** that reads the phrase as Yaakov speaking **to himself**.

**"V'lo lamadti mima'asav hara'im"**: I did not learn even one thing from his wicked deeds—not the wickedness itself, chas v'shalom, but the **enthusiasm** with which people pursue their desires.

You know what it looks like when a fellow has to get to his favorite event, the ballgame, a dinner, or a simchah. **"I can't talk now! I'm in a rush!"** He drives as quickly as possible; he wants to arrive early, and his whole heart is there.

What about **davening**?

Wouldn't it be wonderful if a man said, **"I can't stop to chat; I'm going to speak to the Ribbono Shel Olam!"** If he ran to shul with the excitement he has when going to something he loves?

Or when he gets up to learn a daf Gemara, to do a mitzvah—what a privilege! Where is the **zerizus**, the enjoyment, the investment of all his kochos?

Yaakov may have said: I kept the mitzvos, but I could have learned something about **energy** from the way other people throw themselves into their chosen pursuits.

Now I have another question.

How could Yaakov say he kept **taryag mitzvos** while living in Lavan's house? He was far from Yitzchak and did not fulfill kibud av in the ordinary way. And what about **marrying two sisters**, Rachel and Leah? I bring a **Ramban** who discusses the observance of mitzvos by the Avos and the distinction between Eretz Yisrael and Chutz La'aretz.

The talmidim propose that the women had the status of **geros**, and that may affect the prohibition of sisters. There are interpretations associated with **Rav Yitzchak Hutner**. But the precise words of the Ramban and the other positions must be examined, and I have a substantial unanswered question.

**I don't have a clear answer yet.** Don't let an attractive teretz make us forget the actual language of the source.

## Two Sisters, the Ramban, and Yaakov's Fear of Killing
A talmid suggests that marrying Rachel and Leah could be understood in light of the halachos of **gerim**, but I keep asking: what does the **Ramban** actually say? He discusses the Avos' observance of mitzvos and the significance of **Eretz Yisrael**. He links Rachel's death to Yaakov's entering the Land, where he would not continue the marriage of two sisters. We can't simply substitute our preferred explanation without dealing with the Ramban's language.

We have to examine the argument attributed to **Rav Hutner** carefully. I hear the student's answer, but I'm not convinced it has resolved the source.

Now let's go back to **"ויירא יעקב מאד ויצר לו"** (Bereishis 32:8).

Rashi brings Chazal: Yaakov feared **being killed**, and he was distressed at **possibly killing others**.

Here's my kashya. If someone is coming to kill you, doesn't halachah recognize **self-defense**? So why should the possibility of killing Esav in self-defense cause such extraordinary distress?

The **Sifsei Chachamim** gives an approach involving **Yitzchak's reaction** to the death of his beloved son Esav. I could understand Yaakov's pain at causing his father anguish. But if we say Yitzchak would **curse Yaakov** for defending himself, that's a much harder assertion. Would Yitzchak want Yaakov to let himself be killed? I find that difficult.

I joke with the olam about what happens when one child hits another, and about biased reporting in the newspapers. But the underlying question is serious: **what exactly was Yaakov afraid of?**

Another explanation associated with **Mizrachi** is that perhaps one can stop an attacker without killing him, and Yaakov feared using more force than necessary. The distinction involving **"יכול להצילו באחד מאבריו"** is a recognized halachic question with qualifications.

But how does that apply **in war**, when conditions are altogether different? We need to distinguish self-defense against an individual from the halachos of soldiers and battlefield combat. This shiur raises the question; it does not settle modern rules of engagement.

## Yaakov's Fear of Harming Others — A Complex Halachic and Moral Question

Rabosai, Rashi interprets **"ויירא יעקב מאד ויצר לו"** as fear of being killed and distress about the possibility of **killing others**.

Some mefarshim discuss whether one who faces an attacker must use a less harmful way to stop him if that is reliably possible. The sugya of **"יכול להצילו באחד מאבריו"** requires careful attention to circumstances. I mention opinions attributed to **Mizrachi**, **Levush**, Rambam and **Rav Chaim Ozer**, and ask whether the halachos of an individual attacker apply in the same way during **war**. This is a complicated subject; no operational or practical ruling is established in the shiur.

A member of my shul, a former army serviceman and professional soccer player, related to me a very disturbing allegation from military service concerning an order involving a captive. I recount it as **his story**, not as an independently verified event or a justified act. I also make a dark joke using a childhood story attributed to Rav Chaim of Brisk, but a joke is not a halachic basis for using force.

The real question is why Yaakov was distressed.

**"שמא יהרוג אחרים"**—perhaps Yaakov feared he would kill **others**, people traveling with Esav who might not actually wish to fight, or who were under pressure from a formidable leader. The Midrash about the changing number of Esav's men needs textual checking; I am uncertain of the exact sequence.

Perhaps Yaakov was prepared to defend himself while still feeling **pain at any loss of human life**, even when an armed confrontation was unavoidable.

That is the moral point I want to make: **we must distinguish the necessity of an act from taking joy in harm**. Yaakov's compassion did not vanish because Esav threatened him.

These are proposals for understanding the pesukim, not definitive military law.

## "I Don't Mind Being Wrong" — Ramban's Message for the Generations
Someone finds a source concerning the four hundred men. We argue about whether they turned back while approaching Yaakov or later. I have an image of the Midrash in my mind, but maybe I remember it incorrectly.

**I don't mind being wrong.**

What is the difference? I'm a human being! Baruch Hashem I've learned a lot, but perhaps I made a mistake. **I want the emes.** Let's look it up.

The talmidim continue discussing soldiers who follow orders, including disturbing historical claims about wartime responsibility. Following orders is not, by itself, a general moral or legal excuse for atrocities. The historical and legal descriptions made in the shiur would require independent verification.

I come back to what I believe is a beautiful **middah of Yaakov**. Even if he was forced into a battle, he did not want to take pleasure in killing. **Necessary action and emotional cruelty are not the same thing.** He could be ready to defend himself while distressed over the possibility of taking human life.

Now look at the **Ramban on Bereishis 32:4**. The Ramban says the parashah teaches us that Hashem saved Yaakov from someone stronger than himself. It also teaches that Yaakov did not simply rely on his own righteousness. He made every possible responsible effort and prepared for **tefillah, gifts and the possibility of fighting or escaping**.

Most remarkably, the Ramban writes that this episode is **a sign for future generations**. What happened to Yaakov with Esav will have meaning for the struggles of Klal Yisrael in later history.

Think of **"והיה המחנה הנשאר לפליטה"** (Bereishis 32:9). Even if one camp were attacked, another might survive. The Ramban connects that to how Klal Yisrael may find rescue in one place while suffering danger in another.

I make a historical comparison to the **Nazi persecution** and the refuge many Jews found in other countries, especially America. This is an application to later history, not a statement the Ramban literally made about twentieth-century events.

My grandfather also used to cite an account, connected with the Chofetz Chaim, that **Eretz Yisrael** could be the place of survival in a future crisis. Again, the chain of transmission needs checking.

But listen to the Ramban's central lesson: **Yaakov's actions are not only a family story.** They teach us how to respond when a more powerful enemy threatens us.

## Why Did Yaakov and Esav Cry?
Now I want to raise another question I have always found difficult.

When Yaakov and Esav finally meet, it says:

**"וירץ עשו לקראתו ויחבקהו ויפל על צוארו וישקהו ויבכו"** (Bereishis 33:4).

They embraced, kissed, and **wept**.

Rashi records a reading that at this moment Esav's compassion was awakened and he kissed Yaakov wholeheartedly, alongside another tradition questioning the sincerity of the kiss.

But **Targum Pseudo-Jonathan**, as printed on Bereishis 33:4, is associated with a very different Midrashic account: Esav attempts to bite Yaakov's neck, his teeth are damaged, and their crying reflects their injuries.

I want to ask you something.

These were two strong men. Are we to understand that each one burst into tears simply because of a neck injury or pain in his teeth? I find that difficult. There must be something worth understanding about the **tzaar**, perhaps even something more than physical pain.

Of course I have a joke. If Esav received the **dentist's bill**, I could understand why he cried! My wife is a dentist, so I know the subject very well.

But seriously, why is the crying emphasized? Is it physical suffering, emotional pain, the moment of reunion, or some combination? The mefarshim offer different pictures of the moment.

Now I want to ask another question.

Chazal say **Yosef** was protected from the **ayin hara** partly because he stood before **Rachel** to conceal his mother from Esav's gaze.

But how old was Yosef? A little boy! How could a child successfully hide his mother, especially if Rachel was tall?

I remember a source attributed to **the Rosh** about Rachel's height, and a suggestion from the **Malbim** concerning how she might have carried Yosef. We must look at the actual words before settling the physical details.

Perhaps the point is that **Yosef wanted to protect her**. Even if a little child couldn't accomplish the whole task physically, the desire itself mattered.

This reminds me of Chazal's teaching about **Basya stretching her arm** toward baby Moshe. She reached even though he was beyond her normal reach, and the miracle followed.

Maybe Yosef's movement expresses the same kind of effort: **he tried** to do what he believed was right. But we should distinguish a meaningful mussar comparison from a verified literal explanation of the Midrash.

## "Vayehi Li Shor VaChamor" — How to Speak to Esav
We were discussing Yosef, who stood before Rachel to protect her from Esav's gaze. Could a small child really cover his mother? The Malbim and other mefarshim may address the physical circumstances. I suggested a mussar explanation: **the child wanted to protect her**, even if he could not fully accomplish it. Like **Basya** extending her arm to rescue Moshe, the willingness to do the right thing may precede knowing whether you can succeed.

Now Yaakov says to Esav:

**"ויהי לי שור וחמור צאן ועבד ושפחה"** (Bereishis 32:6).

Rashi explains that the **brachos** Yitzchak gave him were about the dew of Heaven and the fatness of the earth; Yaakov is telling Esav that the possessions he acquired are not a proof that he has taken the promised portion from Esav.

But one sefer, whose title is unclear in the transcription, gives what sounds like an extraordinary approach: Yaakov is saying, **"I have become wealthy, and I know you'll be happy for me!"**

What? Esav, the brother who hates him, is going to rejoice in Yaakov's prosperity? Imagine telling your greatest rival about your Rolls-Royce and million-dollar mansion because you are **sure** he'll be delighted. It's almost a comedy!

Then I saw an approach from the **Ksav Sofer** that explains something deeper.

Sometimes a businessman looks at a ben Torah and says, "You sit in yeshivah all day and expect me to support you!" The resentment comes from thinking the scholar has no resources of his own.

Yaakov tells Esav, **"I have cattle and donkeys and servants. I am not coming to take your possessions or demand a donation."** He wants to lower that resentment.

I suggested another angle. Wealthy people sometimes dismiss a poor person as insignificant. By saying he possessed wealth, Yaakov prevented Esav from looking upon him as a nothing.

But perhaps the first sefer has an even subtler point. To draw cooperation from a difficult person, give him the **kavod of the kind of person he ought to be**.

Don't say, "You're jealous and cruel." Say, **"Surely a man as important as you will rejoice in your brother's success."** Now Esav is being invited to act in accordance with that honorable picture of himself.

I have a family story from my grandfather that may illustrate this principle. Let's hear it.

## Giving a Person the Kavod of a Good Deed
My grandfather once explained a way to persuade people to participate in **hatzalah or communal chesed**.

A public campaign sought to help Jewish refugees, including children who needed assistance arriving from Europe after the war. In the family account, organizers approached **Mayor Dwyer** or another prominent official and invited him to participate publicly, so that his involvement would encourage others.

The name, precise initiative and historical details need verification. But the idea my grandfather drew from it was clear.

When you ask an important person simply for money, he can say, "I don't want to get involved."

But if you say, **"You're such an important leader; surely you will want to set an example of chesed for the entire community"**, you have given him a role in a positive picture of himself.

A politician may also think of the **photograph**, the publicity. The public image can encourage him to do the right thing.

Maybe that is how we should read Yaakov's message to Esav. **"Of course you'll be happy for me! I have no doubt you'll be happy!"** Instead of accusing Esav of jealousy, Yaakov appeals to the honorable response he wants Esav to give.

One talmid doesn't like that explanation. Why don't you like it? Perhaps you're too honest! You don't understand all these strategies and photo opportunities in the outside world. I'm joking.

But now we have another question.

### Who Was the "Ish" Who Wrestled with Yaakov?
Everyone knows Rashi on **"ויאבק איש עמו"** (Bereishis 32:25): it was **the sar shel Esav**.

But other Rishonim don't necessarily explain the episode that way.

The **Rashbam** interprets an angel as preventing Yaakov from fleeing the confrontation. According to this explanation Yaakov wanted to escape, and Hashem sent a malach to **hold him back**. The purpose of the encounter is very different from the idea that Esav's personal heavenly representative attacked Yaakov.

We examine the **Baal HaTurim** as well, who is cited in the shiur as naming **Michoel**. I also compare Rashi elsewhere, on the **"ish"** who encountered Yosef in Bereishis 37:15, identified there with **Gavriel**, and a statement attributed to **the Rosh** that links *ish* with **Refael** through gematria.

Which malach was it? Are those identifications meant as a universal rule for every appearance of **"ish"**? We have to look at the sources.

That's a beautiful kashya, rabosai. I have pages of questions like this from learning Chumash and the Rishonim over many years.

## Did Yaakov Win the Wrestling Match?
Let's examine the different explanations of **"ויאבק איש עמו"**.

Rashi brings the **sar shel Esav**. The Rashbam speaks of an angel stopping Yaakov from running. Other mefarshim identify the angel differently. We should not collapse their individual explanations into one as if they agree.

Now I want to ask you a different question. **Who won the fight?**

Was it a **knockout**? Or was it a **draw**?

The angel injured Yaakov's thigh, and Yaakov continued holding him. Then the angel says **"שלחני כי עלה השחר"**—let me go, because dawn has come (Bereishis 32:27). Some talmidim say, "Of course Yaakov won! The angel asked to be released."

But does asking to be released necessarily mean he was **defeated**? Or did neither overcome the other in a simple way?

We're going to learn the **Seforno** and **Chizkuni**. Some language in the mefarshim emphasizes Yaakov **overcoming** the angel; another passage describes his becoming **equal** to the malachim rather than superior to them. I want to be medayek whether the distinction reflects a victory or a stalemate. The exact words and which commentary uses each expression need verification before settling this as their intended disagreement.

I joke about the rules of professional boxing. If a boxer asks to stop, is that a loss by forfeiture or a draw? What would the newspaper headline say?

I'm trying to get the olam to look again at words everybody assumes they already understands.

Then I turn to a talmid I appreciate greatly, **Mr. Kaikov**. Every Sunday he comes early and remains for the whole learning, asking and working through everything. I tell him how much I value that dedication.

**"Ashrecha!"** You could have done so many other things with your Sunday morning, but you come to learn. I grew up in a house of rabbanim and marbitzei Torah; this is the life I knew. A person who chooses to devote his time to learning amid many alternatives deserves extraordinary respect.

Learn to appreciate a good Yid, rabosai. **Appreciate mesiras nefesh for Torah.**

Now, let's read the Seforno and Chizkuni carefully.

## Chizkuni, Seforno, and the Baal HaTurim's Surprising Remez
We're looking at the different meanings of **"כי שרית עם אלקים ועם אנשים ותוכל"** (Bereishis 32:29).

What does **"ותוכל"** mean here? Did Yaakov conquer the malach, or simply survive and stand on equal footing? The olam argues about the words of the **Seforno** and **Chizkuni**. I suggest one emphasizes **Yaakov's superiority** and another the idea of being **equal** to a malach. It is an interesting reading, but the precise text must decide.

Whatever the outcome, the battle teaches about the ongoing struggle with the yetzer. It attacks the **shoresh** of Yaakov's strength. Rather than telling a man directly to stop learning, it looks for a weakness that will make Torah and spiritual life collapse.

Now I want to show you two remazim in **Baal HaTurim**.

First, on the tefillah:

**"הצילני נא מיד אחי מיד עשו"** (Bereishis 32:12).

The initial letters of **"הצילני נא מיד"** form **המן**—Haman. In the shiur I connect this with the Purim words **"שושנת יעקב צהלה ושמחה"**, citing **Taamei HaMinhagim**. The published wording and exact initial-letter computation should be checked, but it's a beautiful traditional association: Yaakov prays for deliverance from enemies in later generations.

A talmid says he's heard this on a recording already. Excellent! Then you can take your credit back.

Now another Baal HaTurim puzzles me more deeply.

He is cited as analyzing the numbers of animals Yaakov sent in his gift to Esav and making a connection with **korbanos in the Beis HaMikdash** and a possible deficiency in Yaakov's **bitachon**.

What? Are you telling me that our later avodah of korbanos relates to something Yaakov did wrong when preparing gifts and making hishtadlus?

That is a tremendous chiddush! We need the exact text before stating that **the entire system of korbanos** was created because Yaakov sinned; such a sweeping interpretation would be stronger than what we have verified.

But the possibility that Yaakov's extensive preparations could be critiqued as a lack of **bitachon** raises an important question that will carry us into the next part of the shiur.

**Was Yaakov right to prepare for the confrontation with so many gifts, messengers, and strategies?**

## How Much Hishtadlus Is Too Much?
The **Baal HaTurim** on Yaakov's gifts and preparations seems, in a passage we are reading aloud, to suggest a **chisaron in bitachon**, even drawing a remarkable connection to korbanos and kaparah. I am astonished, and I want to understand exactly what he means.

But the **Ramban**, on Bereishis 32:4, teaches a very different emphasis: Yaakov **"השתדל בהצלה בכל יכלתו"**—he exerted himself in every possible way for his rescue. The Ramban presents his preparation for **tefillah, gift-giving, and defense** as a model for future generations.

Is there a fundamental **machlokes**? Was Yaakov doing exactly the right thing, or **too much**? First we need to inspect the precise Baal HaTurim before turning the apparent implication into a sweeping charge against Yaakov Avinu.

Now, another question: **"ויירא יעקב מאד"**—why was Yaakov afraid if he had bitachon?

The **Abarbanel** is quoted as distinguishing natural temperament from spiritual commitment. A person can feel **fear** by nature but respond with complete trust in Hashem. The **Malbim** will offer another approach to **"ויירא ... ויצר לו"**, possibly understanding the distress as concern over the fear itself.

I tell stories about the **Brisker Rav** and his descendants being exceedingly careful, including repeated checking and extra readings. There's an anecdote about a talmid asked by Rav Dovid Soloveitchik to name an example, who cautiously asks how often his rebbe returns to check a door is locked. The answer: a few times! These are oral recollections, not verified personal characterizations.

But they make the conceptual point: **bitachon does not necessarily erase someone's natural temperament**. We have to learn whether perfect bitachon requires not feeling fear, or whether it means mastering fear through reliance on Hashem.

That's the next issue in the sugya.

## Malbim and Abarbanel: Does Bitachon Remove Fear?
There is a fascinating distinction between two approaches as I understand them.

According to the **Abarbanel** as we discussed, Yaakov's fear could be a matter of **teva**, his natural emotional tendency. His bitachon lay in how he acted in spite of that feeling.

But the **Malbim** reads **"ויירא יעקב מאד ויצר לו"** as showing that Yaakov was distressed **because he was afraid**—perhaps he felt the fear revealed a deficiency in his complete bitachon.

Do you hear the difference?

Does real **bitachon** mean that a person is simply **not afraid**?

Or can someone be afraid and still possess bitachon by reminding himself of the Ribbono Shel Olam and refusing to let the fear control his decisions?

That's a tremendous question in avodas Hashem.

I bring an oral story of the Brisker Rav during the Second World War, when he reportedly resisted going to an air-raid shelter and was eventually persuaded by his son. He later interpreted damage to a building in an extraordinary way through his bitachon. **The particulars and historical accuracy need verification**, and this anecdote does not establish a general permission to ignore safety measures.

What I'm trying to understand is whether trust is measured by the **absence of fear** or by the **ability to work through fear**.

Now I want to move to another question about the gifts Yaakov sent Esav.

In the shiur we look at a passage cited as **Darkei Moshe, Yoreh Deah 35**, quoting **Tashbatz**, concerning a traditional diagnostic sign in an animal and how it responds when pressed down. The exact text, its reliability and its contemporary practical use require a careful primary-source check. **This is not a recommended method for determining whether an animal is kosher.**

I joke about whether modern animals have enough **anavah** to pass such a test! But the question of the animal's response is raised because of a further Midrashic suggestion about what kinds of animals Yaakov might have sent to Esav.

Some propose he gave **treifos** or animals unsuitable for his own kosher use. Why would that be the purpose of a gift? And what about animals fit for **korbanos** offered by a ben Noach?

I don't yet have a satisfactory answer. Let's continue reading the mefarshim.

## Why Animals, Not Gold? And Each Person's Tefillah
The suggestion that Yaakov sent animals of a certain condition raises questions about the status of animals offered by **bnei Noach** and whether a **baal mum** is subject to the same rules in their korbanos as in ours. Those are separate halachos; the classroom suggestion needs exact sources.

And then I have an apparently simpler question.

**Why did Yaakov send Esav all those animals?**

He gave flocks and herds. But Esav was a hunter and a powerful man. Wouldn't a rich man appreciate **gold and silver** more than being presented with a goat or a donkey?

I joke that perhaps in the old days an animal was the kind of gift people brought to a simchah. Imagine going home and saying, "Here's a lamb for Chanukah!" But of course livestock was a significant store of wealth and trade in that society.

The **Ramban** discusses the animals Yaakov selected; another teaching quoted as **Baal HaTurim** suggests costly valuables such as jewelry or precious stones. We need to locate the exact passages before deciding whether they truly disagree.

Perhaps the difference reflects **two levels of hishtadlus**. One view emphasizes showing friendship with a respectful present, another giving something impressive enough to change Esav's thinking. It's an interesting *svara*, but I don't want to force the sources into my theory.

Before we end, I want to give the olam one more **kashya**.

The pasuk describes Yaakov's arrangements in **separate groups**, and I bring a reading attributed to **Baal HaTurim** saying that each person should **daven individually**—**"כל אחד יתפלל לבדו."**

What? Don't we know the value of **tefillah b'tzibbur**? Why emphasize that each should pray alone?

Maybe there's a beautiful lesson here.

In a **sha'as tzarah**, a person must learn how to turn to the Ribbono Shel Olam **personally**. It's wonderful that everybody says Tehillim together, but each person needs his own heartfelt tefillah, his own conversation with Hashem.

It doesn't mean to reject communal tefillah. It means not to lose your **personal relationship with Hashem** inside a communal crisis.

All right, rabosai, I see the olam is getting tired! We've learned for a long time, and there's still much more here.

**We'll continue next week**, b'ezras Hashem.

[The main recorded shiur ends here. Several subsequent chunks consist of fragmentary, off-microphone discussion after the shiur, including later questions about Dina. Those fragments cannot be treated as a complete independent lesson.]

## Fragmentary Post-Shiur Discussion: Dina

*[The formal shiur has ended. This audio includes informal conversation, multiple voices and substantial gaps in the transcription.]*

The speakers first discuss an unrelated donation and counting money, followed by an unclear comparison with remembering **Sefiras HaOmer**.

They then turn to Yaakov's daughter **Dina**, Yaakov's efforts to keep her away from Esav, and differing interpretations of the episode of **Shechem**.

One explanation attributed generally to the **Baalei Mussar** distinguishes the physical decision to conceal Dina from the **attitude** accompanying that decision. Another speaker asks whether there may have been some possibility of influencing Esav positively. A reference to **Rav Hirsch** is too fragmentary to establish a precise source.

The conversation then raises questions about Dina's own conduct and how some people unfairly blame victims when others have wronged them. **The unresolved question concerns whether such blame can be justified.** There is no complete source or concluded ruling in this fragment.

*[The remaining speech is incomplete and cannot be reliably assigned to specific speakers. Further editing requires review against the recording.]*

*[Post-shiur audio fragment — unclear. The source transcribes roughly: "But really ... [unclear] ... should have been that ... Why mix it back? ... You know that. No." There is insufficient context to identify a Torah source or create a faithful prose rewrite. The original transcription is retained unchanged.]*

## Post-Shiur Fragment — Yaakov's Conduct Toward Esav

*[Multiple speakers, substantial missing words.]*

The conversation returns to Yaakov and Esav. A speaker challenges the idea that Yaakov should have approached Esav with **bitachon** but without sending malachim, bowing, or making preparations.

**"Not true, not like that,"** he responds, referring to the **Ramban**. His point appears to be that Yaakov's preparations did not necessarily show a deficiency in bitachon.

The discussion is interrupted by informal farewells and incomplete sentences. We cannot reliably determine the entire argument from this chunk alone.

## Final Fragment — Avoiding Battle

*[Very short, incomplete source ending.]*

Someone asks what would have happened if Yaakov had not made his preparations, and whether he was simply supposed to fight.

The response invokes the **Ramban** and appears to defend Yaakov's initial attempts to **avoid a confrontation**, rather than rush into combat: first try to resolve the danger without fighting.

The speaker's last sentence breaks off before the reasoning is complete. **No final conclusion can be reconstructed from the available audio transcription.**