Following a Shiur this past week based upon one of Nechama Leibowitz’, Z”L, Gilayon for Parashat Toldot (see by In her essay for Parashat Toldot (see https://rayanotyaakov.wordpress.com/gilyanot-for-sefer-beraishit/ Toldot 5712; one can listen to the Shiur as well at the same site), we were discussing the personality of Eisav. One of the attendees mentioned that her father, R. Isaac Trainin, felt particular sympathy for Eisav, especially when he cried out upon realizing that his brother had taken the blessing that Yitzchak had intended for the son that he particularly loved:

Beraishit 27:34

When Eisav heard the words of his father (to the effect that Yaakov’s blessing, albeit illegally obtained, would stand), he cried with an exceeding great and bitter cry, and said unto his father: “Bless me, even me also, O my father.”

In “’Zeh Ratz LaHarog VeZeh Ratz LaHarog’: Midrasham Shel R. Yochanan V’R. Shimon b. Lakish” (in Hogim PaParasha: Parashat HaShavua KeHashra’a LeYetzira VeLahagut HaYehudit LeDoroteha, ed. Naftali Rotenberg), Dr. Irit Aminof (Oranim Educational Academy) notes at the outset of her essay the tension between how the biblical text depicts Eisav, an essentially sympathetic character, in contrast to his description by the Rabbis in the Midrash:

(With respect to the sale of the status of “first-born” [Beraishit 25:29-34]):

…The description of the sale, the story presents the seller as a simple man, lacking wisdom and insight, even foolish, who is at the mercy of his temporal impulses; the purchaser on the other hand is intelligent—even deceitful, who carefully plans his actions and achieves what he sets out to do…

(Regarding the depiction of Eisav by ChaZaL in general):

…Why did the Jewish people blacken (the reputation) of the biblical Eisav? And continually further “blackened” (“redden” [sic.] him [the Rabbis associate “red” with spilling blood; see Ibid. 25:25,30; 36:1]) throughout our history? What is the source of the paradox between the textual representation of Eisav—wholehearted, respectful, practically “a pure gentleman”…–and the Midrashic-Talmudic characterization of the evil-doer, murderer, sexual predator, idolater, liar, hypocrite, sybarite, homosexual and the like, possessor of other reprehensible attributes?…

To illustrate Aminof’s contention, consider the following chart, where I have quoted relevant sources and personally annotated them:

Eisav according to the Biblical text: Eisav according to the Rabbis:
Beraishit 25:27-28

27 And the boys grew; and Eisav was a cunning hunter, a man of the field; and Yaakov was a quiet man, dwelling in tents. 28 Now Yitzchak loved Eisav, because he did eat of his venison; and Rivka loved Yaakov.”

Eisav was an outdoors man. He also saw to making sure that his father would have food that he liked, and that Eisav took the trouble to obtain and prepare.

RaShI s.v. Yodeah Tzayid

To hunt and deceive his father with his mouth,

And he would ask his father, “How does one tithe salt and straw?”

This led his father to think that his son was being very precise in the performance of Comandments.

s.v. Ish Sadeh

As its implication, a person who is idle and hunts

animals with his bow.

Eisav was deceptive in his dealing with his father, leading him to conclude that he was more religious than he actually was. The profession of hunting is associated with someone who lacks direction or purpose in his life.

Ibid. 34

“And Yaakov gave Eisav bread and pottage of lentils; and he did eat and drink, and rose up, and went his way. So Eisav despised his birthright.

Eisav was hungry and when confronted with the need to give up his birthright in order to obtain food, he did so. His subsequent despising of the birthright could be a manifestation of the “sour grapes” phenomenon.

Beraishit 25:29 “And Yaakov sod pottage; and Eisav came in from the field, and he was faint.”

 

RaShI s.v. VeHuh Ayef

After murdering, as it is said, (Yirmiyahu 4:31) “Because my soul is weary after all of the murdered ones.”

 

Bava Batra 16b

Said R. Yochanan: Five sins did that evil one transgress that day—he was intimate with an engaged woman, killed someone, denied the belief in the resurrection of the dead, denied the Existance of God, and rejected the status of being the first-born… (with the exception of the last accusation which is based upon explicit verses, all of the other conclusions are reached via the hermeneutic principle of Gezeira Shava—a commonality of words in two different verses, suggesting a common topic.).

Eisav’s desparate hunger and forsaking the birthright are to be associated with extensive evil behavior.

Ibid. 26:34-5

34 And when Eisav was forty years old, he took to wife Yehudit the daughter of Be’eri the Chittite, and Basemat the daughter of Eilon the Chittite. 35 And they were a bitterness of spirit unto Yitzchak and to Rivka.”

Ibid. 28:8-9

8 and Eisav saw that the daughters of Canaan pleased not Yitzchak his father; 9 so Eisav went unto Yishmael, and took unto the wives that he had Machalat the daughter of Yishmael, Avraham’s son, the sister of Nevaiot, to be his wife.

If it had never been expressly stated to Eisav whom he should marry and who would be off-limits, can he be blamed for marrying local women? He did not extrapolate from his grandfather’s preference of a wife for Yitzchak that he was to do likewise. Although he did not divorce his first wives, perhaps it is because of compassion, or that he had come to love them. With respect to Yishmael, even the Rabbis assume that Eisav’s uncle repented at the end of his life. The same is never said regarding Lavan!

RaShi s.v. Forty years old

Eisav was comparable to a pig, as it is said,

(Tehillim 80:14) “The boar out of the wood doth ravage it…”

The pig, when it reclines, pushes forward its

hoofs, as if to say, “See, I am Kosher” (since it possesses split hoofs, one of the indicators that an animal can be eaten by a Jew.)

So too these (the generals descended from Eisav) steal and do violence, yet claim that they are “Kosher.”

For forty years, Eisav would “hunt” married women from their husbands and rape them.

And when he reached the age of forty, he said, “When father was forty, he got married. I will do the same.”

RaShI s.v. Al Nashav

He added evil to the evil that he had already perpetrated, because he did not divorce his first wives.

MaLBIM s.v. VaYar

And also because of this (Yaakov’s being sent away to Lavan’s family) he (Eisav) realized that the Canaanite women (that he had married) were inappropriate in the eyes of Yitzchak, his father.

It was evil that he failed to observe the negative Commandment by not divorcing the Canaanite wives, as well as the positive Commandment to marry into the family of Lavan, because instead of this, he went to Yishmael.

The fact that he went to Yishmael to marry the sister of Nevayot, who himself was an evil-doer, and children turn out like the brother of the mother (is another indication of Eisav’s evil)…

Eisav continues to mislead others regarding his personal values, and this tradition continued to be characteristic of his descendants. Not only did Eisav “hunt” his father, he also “hunted” married women. His marriages to inappropriate women were premeditated and indicative of his overall moral shortcomings and further efforts to mislead his parents.

Ibid. 27:3-4

3 Now therefore take, I pray thee, thy weapons, thy quiver and thy bow, and go out to the field, and take me venison; 4 and make me savory food, such as I love, and bring it to me, that I may eat; that my soul may bless thee before I die.”

Yitzchak turns to his son Eisav to request fresh meat and savory food in order to properly give him a final blessing.

RaShI s.v. Sa Na

A language of sharpening, as in (Beitza 38a) “One does not sharpen the knife, but rather cause it to be passed against another knife.”

“Sharpen your knife and slaughter the animal properly; don’t feed me improperly- slaughtered meat.”

s.v. Tzoden Li

From animals that are ownerless, rather than ones that are stolen.

Yitzchak didn’t entirely trust Eisav, and therefore had to remind him about the laws of ritual slaughter as well as thievery so that this would not be a case of “Mitzva HaBa’a BeAveira” (a Mitzva [respecting one’s parent] that would be perpetrated by means of transgression.)

Ibid. 36-41

36 And he said: “Is not he rightly named Yaakov? For he hath supplanted me these two times: he took away my birthright; and, behold, now he hath taken away my blessing” And he said: “Hast thou not reserved a blessing for me?” 37 And Yitzchak answered and said unto Eisav: “Behold, I have made him thy lord, and all his brethren have I given to him for servants; and with corn and wine have I sustained him; and what then shall I do for thee, my son?’ 38 And Eisav said unto his father: “Hast thou but one blessing, my father? bless me, even me also, O my father.” And Eisav lifted up his voice, and wept. 39 And Yitzchak his father answered and said unto him: “Behold, of the fat places of the earth shall be thy dwelling, and of the dew of heaven from above; 40 And by thy sword shalt thou live, and thou shalt serve thy brother; and it shall come to pass when thou shalt break loose, that thou shalt shake his yoke from off thy neck.” 41 And Eisav hated Yaakov because of the blessing wherewith his father blessed him. And Eisav said in his heart: “Let the days of mourning for my father be at hand; then will I slay my brother Yaakov.”

Eisav would seem to be justified in his indignity. Just because Yitzchak blesses him by saying that his son will live by his sword, does not inherently mean that he will be inordinantly violent—just that he would be a soldier. And even if his initial thought was that he would avenge himself from his brother at some future point, this might simply have been a statement in the heat of the moment, likely to pass with the passage of time. Rivka’s taking Eisav’s threat literally could have been a protective overreaction towards a son whom she did not particularly like.

These verses speak for themselves, without the need for Rabbinic interpretation. .
Ibid. 32:7 “

7 And the messengers returned to Yaakov, saying: “We came to thy brother Eisav, and moreover he cometh to meet thee, and four hundred men with him.”

Ibid. 33:4-15

4 And Eisav ran to meet him, and embraced him, and fell on his neck, and kissed him; and they wept. 5 And he lifted up his eyes, and saw the women and the children; and said: “Who are these with thee?” And he said: “The children whom God hath Graciously Given thy servant.” 6 Then the handmaids came near, they and their children, and they bowed down. 7 And Leah also and her children came near, and bowed down; and after came Yosef near and Rachel, and they bowed down. 8 And he said: “What meanest thou by all this camp which I met?” And he said: “To find favor in the sight of my lord.” 9 And Eisav said: “I have enough; my brother, let that which thou hast be thine.” 10 And Yaakov said: “Nay, I pray thee, if now I have found favor in thy sight, then receive my present at my hand; forasmuch as I have seen thy face, as one seeth the Face of God, and thou wast pleased with me. 11 Take, I pray thee, my gift that is brought to thee; because God hath Dealt Graciously with me, and because I have enough.” And he urged him, and he took it. 12 And he said: “Let us take our journey, and let us go, and I will go before thee.” 13 And he said unto him: “My lord knoweth that the children are tender, and that the flocks and herds giving suck are a care to me; and if they overdrive them one day, all the flocks will die. 14 Let my lord, I pray thee, pass over before his servant; and I will journey on gently, according to the pace of the cattle that are before me and according to the pace of the children, until I come unto my lord unto Seir.” 15 And Eisav said: “Let me now leave with thee some of the folk that are with me.” And he said: “What needeth it? let me find favor in the sight of my lord.”

What was implied by Eisav’s refusal to accept Yaakov’s gift? And  why was Eisav accompanied by 400 men? Can it be said with absolute certainty that his intentions were hostile? While Yaakov’s concerns are understandable, to what extent are his fears the product of his own guilty conscience?

RaShI s.v. VaYashkeihu

There are dots over it (the word as written in the Tora).

And there is a disagreement regarding the meaning of these dots in a Baraita in the Sifre (Parashat BeHa’aotcha

#69). There are those who interpret them to signify that he (Eisav) did not kiss him (Yaakov) wholeheartedly.

Said R. Shimon b. Yochai: It is a tradition that Eisav hated Yaakov, but at this point in time, he felt compassion for him, and he kissed him wholeheartedly.

Beraishit Rabba, Parashat VaYishlach 78:9

“And Eisav ran to greet him and kissed him.”

There are dots above the words.

Said R. Shimon b. Eleazar: Wherever you find more letters without dots than those with dots, then you interpret the non-dotted letters. If there are more dotted letters than ones without, then you interpret the dotted letters. In this case, the undotted letters do not outnumber the dotted ones, and the dotted letters do not outnumber the undotted ones. Therefore it is coming to teach that he (Eisav was overcome with kindness for him (Yaakov) and kissed him wholeheartedly.

Said to him R. Yanai: If that was the case, why are there dots over the letters at all? But rather you learn that he did not come to kiss him, but rather to bite him, and Yaakov’s neck was miraculously turned into marble and the teeth of that evil one were broken.

So what does it mean “they cried”? This one cried for his neck, and this one cried for his teeth”…

Eisav at best was only being polite upon being reunited with Yaakov. Another view was that he was quite hostile, and only “changed his tune” at the last minute, either because of a miracle protecting Yaakov, or because of a surprise emotional response to seeing his brother and his brother’s family.

It seems to me fairly obvious that the sources can be spun both positively and negatively.

Aminof argues that Jewish history plays a major role in the Rabbis viewing Eisav in a particularly negative manner. She points to several Midrashim involving the iconic figures, R. Yochana and Reish Lakish, whose relationship I find to be incredibly moving as encapsulated in the following Aggada:

Bava Metzia 84a

One day R. Yochanan was bathing in the Jordan, when Reish Lakish saw him and leapt into the Jordan after him. Said he (R. Yochanan) to him, “Your strength should be for the Torah.”  — “Your beauty,” he replied, “should be for women.” “If you will repent,” said he, “I will give you my sister (in marriage), who is more beautiful than I.” He undertook (to repent); then he wished to return and collect his weapons, but could not.  Subsequently, (R. Jochanan) taught him Bible and Mishna, and made him into a great man.

Now, one day there was a dispute in the schoolhouse (with respect to the following, viz., a sword, knife, dagger, spear, hand-saw and a scythe — at what stage (of their manufacture) can they become unclean? When their manufacture is finished.  And when is their manufacture finished? — R. Yochanan ruled: When they are tempered in a furnace. Reish Lakish maintained: When they have been furbished in water. Said he to him: “A robber understands his trade.”  Said he to him, “And wherewith have you benefited me: there (as a robber) I was called Master, and here I am called Master.”   “By bringing you under the wings of the Shechina,” he retorted. R. Yochanan therefore felt himself deeply hurt,  (as a result of which) Reish Lakish fell ill. His sister (sc. R. Yochanan’s, the wife of Reish Lakish) came and wept before him: “Forgive him  for the sake of my son,” she pleaded. He replied: “Leave thy children. I will preserve them alive.”   “For the sake of my widowhood then!”’ “And let thy widows trust in me,”  he assured her.

Reish Lakish died, and R. Yochanan was plunged into deep grief. Said the Rabbis, “Who shall go to ease his mind? Let R. Eleazar b. Pedat go, whose disquisitions are very subtle.” So he went and sat before him; and on every dictum uttered by R. Yochanan he observed: “There is a Baraitha which supports you.” “Are you as the son of Lakisha?”  he complained: “when I stated a law, the son of Lakisha used to raise twenty-four objections, to which I gave twenty-four answers, which consequently led to a fuller comprehension of the law; whilst you say, ‘A Baraitha has been taught which supports you:’ do I not know myself that my dicta are right?” Thus he went on rending his garments and weeping, “Where are you, O son of Lakisha, where are you, O son of Lakisha;” and he cried thus until his mind was turned. Thereupon the Rabbis prayed for him, and he died.

Here is one of the key sources that Aminof discusses in her article:

Beraishit 25:22

And the children struggled together within her…

Beraishit Rabba 63:6

R. Yochanan and Reish Lakish:

R. Yochanan said: This one ran to kill this one, and this one ran to kill that one.

Reish Lakish said: This one permitted his Commandments, and this one permitted his Commandments.

Whenever she would pass by the synagogues and houses of study, Yaakov would strive to get out, as it is said, (Yirmiyahu 1:5) “Before I Formed you in the womb, I have Known you.”

And whenever she would pass by the idolatrous temples, Eisav would strive to get out, as it is said, (Tehillim 58:4) “The evildoers are evil from the womb.”

Aminof posits that the Midrash reflects the struggles between Rabbinic Judaism and nascent Christianity which is associated with Eisav who is also cast as the progenitor of Rome. And what it comes down to is whether the enmity was a physical one to the point of one group wishing to destroy another, or was the point of contention the competing religious systems, with Christianity being viewed by some commentators as a form of Avoda Zora.

However, one chooses to view what spurred the Rabbis to approach Eisav as the embodiment of evil and corruption, it would appear that this is more of a homiletical approach than one that emphasizes the biblical text.