A Portrait of Esav

Exegetical Approaches

Neutral

Esav was a mostly neutral character, with neither great attributes nor great faults.

In utero – These sources understand the movement of the twins ("וַיִּתְרֹצֲצוּ") to be the regular fetal exertions of babies,1 exacerbated due to the fact that there were two.  They do not suggest that it revealed anything about the character of the brothers themselves, despite the Torah's stating that it was symbolic of the future struggles between their two nations.
"אַדְמוֹנִי כֻּלּוֹ כְּאַדֶּרֶת שֵׂעָר" – According to these sources, this is just an external description of Esav which had no bearing on his inner qualities. Josephus, interestingly, makes no mention of Esav's redness, perhaps due to the negative connotations often associated with it in antiquity.2
"אִישׁ יֹדֵעַ צַיִד אִישׁ שָׂדֶה" – These sources do not read into these terms a description of Esav's character, apparently understanding them to simply be a statement of his occupation,3 carrying no negative connotation.4
Contrast between the brothers – Josephus omits the contrast entirely, perhaps to ensure that one not be drawn to make a negative evaluation of Esav based on the foil to Yaakov's innocence.5
Scorning the birthright – Most of these sources do not find Esav's scorning of the birthright problematic and view it neither as a foolhardy dismissal of a lofty status, nor as a rejection of Hashem:
  • Life over money – R"Y Bekhor Shor assumes that Esav was literally on the verge of death when he sold his birthright, and thus he does not fault him for his actions, pointing out that Esav rightfully recognized that all the money in the world is not worth one's life.6  Josephus goes even further, portraying Esav as the victim and Yaakov as taking advantage of his hunger to force him into the sale.7
  • Logical deal – Rashbam also assumes that Esav's actions were understandable, believing as he did that he might very well die before his father due to the dangers involved in hunting.  In addition, Rashbam asserts that Yaakov paid for the birthright not just with the stew but with actual money.  Thus, Esav was not throwing away the birthright for nothing.8 
Esav's marriage – This approach might suggest that though Esav erred in marrying Hittite wives,9 when he realized that this was against his parents' wishes, he took an additional wife from Avraham's family in order to please them.
Yaakov and Esav's reunion – According to Josephus and Rashbam, Esav was happy to see Yaakov and was bringing 400 men as an honor guard.  As evidence, Rashbam points to Esav's embrace of his brother in chapter 33.10
Yitzchak's preference for Esav – None of these sources elaborate on the reasons for Yitzchak's preference for Esav, perhaps because they do not find it surprising that he might do so.  If Esav is not a negative character, but provides for Yitzchak and is his first born, there would be no reason for Yitzchak not to love him or bless him.  R"Y Bekhor Shor even suggests that Yitzchak knew of the sale of the birthright and decided to bless Esav before his death so that he could evade paying the consequences of his action.
Esav's descendants – While the association of Esav and Rome might have motivated numerous Midrashic sources (see below) to paint a negative picture of Esav, the same connection had the opposite effect on Josephus, a Roman lackey.  He was loathe to denigrate his superiors, and thus paints a far more neutral portrait of the Biblical character.11

Negative

Esav was an unworthy character with several faults, but he was not wicked or implicated in terrible crimes.12

In utero – These commentators do not read into the fetal movement any significance for the character of Esav himself.  It only foreshadowed the future rivalry between the brothers and their future nations.
"אִישׁ יֹדֵעַ צַיִד אִישׁ שָׂדֶה" – Most of these sources suggest that this description sheds negative light on Esav's character:
  • Deceitful – Ibn Ezra, Ralbag, and Shadal13 see in Esav's chosen profession a sign of his devious nature, since the way of a hunter is to catch his prey by traps and cunning.
  • Power hungry – R. Avraham b. HaRambam compares this phrase to the similar one by Nimrod, "הוּא הָיָה גִבֹּר צַיִד", and asserts that it connotes one who chases power and wealth.14
  • Physical – Radak more simply asserts that Esav chose a worldly path rather than a spiritual one marked by wisdom, while Shadal suggests that "אִישׁ שָׂדֶה" refers to a toughened man of the wilderness.
Scorning the birthright – These commentators differ in their evaluation of Esav's actions during the sale:
  • Neutral –  Ibn Ezra and Shadal do not fault Esav for scorning the birthright, claiming that Esav thought it likely that he would die before his father.15 Ibn Ezra adds that the birthright was not worth much in any case, as Yitzchak was poor.16  Thus, Esav's willingness to sell it was very understandable.17 Shadal even points out that Esav, on his own, kept his side of the deal, moving to Seir and leaving Canaan to be inherited by his brother.
  • Negative –  Ramban asserts that Esav's action betrayed his need for immediate gratification, saying that he acted as a fool who thinks only of the moment and not the future.  Radak similarly points to his gluttony, while R. Avraham faults his disregard for the spiritual.
Esav's marriage – Radak and R. Avraham Maimonides suggest that, in marrying at forty, Esav was attempting to emulate his father.  Nonetheless, these sources fault him for not consulting with his parents or realizing on his own that the marriage was problematic.18 Ramban points out that even when Esav corrects his mistake by marrying into Yishmael's family, he does so only halfheartedly, for he neither divorces his first wives nor goes to his mother's family to find a new wife.
Yaakov and Esav's reunion – Most of these sources19 assume that Esav went to greet Yaakov with evil intent, but that he was appeased by the gifts and Yaakov's show of subservience.  Radak goes further to say that he forgave Yaakov and was filled with feelings of mercy towards him.20
Yitzchak's preference for Esav
  • No preference – Radak suggests that, in reality, Yitzchak loved Yaakov more than Esav; the verse is simply saying that the only reason he liked Esav was due to the food he brought him.  He similarly chose to bless him, not because he was deserving and more beloved, but precisely because he was not and thus needed the blessing more than Yaakov.21
  • Unaware of true nature - Ralbag asserts that Yitzchak was not aware of Esav's faults since Esav would deceive him.  When he discovered that Yaakov was more worthy, he switched his allegiance.22
  • First born and food supplier - Ibn Ezra, Ramban, and Shadal assert that Yitzchak's preference was related to the fact that he brought him delicacies, as the simple reading of the verse suggests.  Ramban further asserts that Yitzchak meant to give Esav the blessing of Avraham23 since he was the firstborn.24 As these commentators do not posit that Esav had any grievous faults, Yitzchak's thoughts were quite natural.
Esav's descendants

Wicked

Esav was a wicked and deceitful character who rejected Hashem, committed heinous crimes and was unworthy of being Yitzchak's spiritual heir.

Sources: Jubilees25:2-326:21-2335:10-4237:1-1538:1-15About Jubilees, PhiloQuestions and Answers on Genesis, IV:160-161Questions and Answers on Genesis, IV:165Questions and Answers on Genesis, IV:171-174Questions and Answers on Genesis, IV:198On the Birth of Abel and the Sacrifices 2 (4-6)About PhiloTargumimTargum Neofiti Bereshit 25:34Targum Pseudo-Jonathan Bereshit 25:27-34Targum Pseudo-Jonathan Bereshit 26:34-35Targum Pseudo-Jonathan Bereshit 27:31Targum Pseudo-Jonathan Bereshit 32:7Targum Pseudo-Jonathan Bereshit 33:1-4Targum Yerushalmi Bereshit 25:34Targum Yerushalmi Bereshit 32:7Targum Yerushalmi Bereshit 33:4About Targum NeofitiAbout Targum Pseudo-JonathanAbout Targum Yerushalmi, Bavli Bava Batra16bAbout the BavliBereshit Rabbah63:6-14About Bereshit Rabbah, Pesikta DeRav Kahana3:1 ("Zakhor")About Pesikta DeRav Kahana, TanchumaTanchuma Toledot 8Tanchuma Vayishlach 4Tanchuma Buber Toledot 2Tanchuma Buber Toledot 3About the Tanchuma, R. Saadia GaonCommentary Bereshit 25About R. Saadia Gaon, RashiBereshit 25:22Bereshit 25:27-28Bereshit 25:29Bereshit 25:32-34Bereshit 26:34-35Bereshit 27:5Bereshit 32:7Bereshit 32:12Bereshit 33:4About R. Shelomo YitzchakiMinchat YehudaBereshit 25:27About R. Yehuda b. Elazar, RanDerashot HaRan 2About R. Nissim Gerondi, AbarbanelBereshit 25 QuestionsBereshit 25:19Bereshit 25:24-34About R. Yitzchak Abarbanel, SefornoBereshit 25:27-34Bereshit 26:35Bereshit 27:1Bereshit 32:7About R. Ovadyah SefornoR. S"R HirschBereshit 25:27About R. Samson Raphael Hirsch, MalbimBereshit 27:1Bereshit 27:5About R. Meir Leibush Weiser
In utero – According to Bereshit Rabbah and Rashi, Esav displayed his wicked tendencies even while he was still in utero.  Whenever Rivka passed a house of idolatry, he would push forward in the womb,25 drawn to worship there.  R. Yochanan and Resh Lakish further suggest that the fetal movements were attempts on the part of the fetuses to kill or overpower one another, and that Esav's personal animosity towards Yaakov began even before they were born.26
"אַדְמוֹנִי כֻּלּוֹ כְּאַדֶּרֶת שֵׂעָר" – According to many, the description of Esav's external appearance is indicative of internal failings as well.  R. Abba b. Kahana in Bereshit Rabbah and Rashi maintain that the term "אַדְמוֹנִי" denotes one who spills blood.  Abarbanel explains similarly, and further suggests that hairiness, too, is associated with a nature of cruelty and anger.  Malbim, instead associates redness with cruelty and the hairiness with an intellectual and moral deficit.
"אִישׁ יֹדֵעַ צַיִד אִישׁ שָׂדֶה" – Many of these sources understand this phrase as describing Esav's character rather than his profession:27 
  • Trickster – Bereshit Rabbah, Tanchuma, Rashi, Abarbanel,28 and R. Hirsch assert that the words "אִישׁ יֹדֵעַ צַיִד" refer to one who is deceitful and traps (צד) people29 with his words.30
  • Murderer – Targum Pseudo-Jonathan makes Esav even more wicked, suggesting that the phrase teaches that Esav killed people as well as animals.31 Jubilees similarly suggests that he learned the art of war.
  • Asocial – Abarbanel asserts that the term "אִישׁ שָׂדֶה" refers to one who distances himself from society.32
Contrast between the brothers
  • Black and white – Many of these sources portray the twins as total opposites, making Esav the wicked counterpart of the righteous Yaakov.  Abarbanel goes as far as to suggest that all the negative traits inherited from Rivka's deceitful ancestors were passed to Esav, while all the positive traits from Avraham's side went to Yaakov.
  • Potentially equal – R. Hirsch asserts that the fact that the two brothers had such different natures in and of itself did not mean that one was to follow a path or righteousness while the other turned away from such a path.33 Esav's traits of energetic strength and courage, and even his cunning, could all have been harnessed for the good, had his parents recognized these and taught him according to his nature.  The fact that they did not is what led to his downfall.
"וַיָּבֹא עֵשָׂו מִן הַשָּׂדֶה וְהוּא עָיֵף" – Most of the Midrashic sources34 and Targum Pseudo-Jonathan find hints in this clause at two cardinal sins of Esav, both murder and illicit relations.35
"הִנֵּה אָנֹכִי הוֹלֵךְ לָמוּת" – Most of these sources36 read into these words, not just a personal assessment, but a theological denial of the principles of the Resurrection of the Dead or the World to Come.
Scorning the birthright – According to Rashi and Seforno, the birthright earned one the privilege to act as priest in serving Hashem.  Thus, in rejecting it, Esav was in effect scorning Hashem.37  R. Hirsch points out that this was Esav's general tendency, to always give up the spiritual for material gain.  Abarbanel goes further, depicting an Esav who did not believe that Hashem was going to fulfill His promise and give the Land of Israel to Avraham's descendants.38
Esav's marriage – Jubilees, Targum Pseudo-Jonathan, and Rashi all assert that Esav married idolaters, and this is why they were a source of distress to his parents.  Jubilees adds that they were full of fornication and debauchery, without any righteousness.
Yaakov and Esav's reunion
  • According to most of these sources, Esav went to greet Yaakov with an army of 400 men, intent to battle his brother.39  Many of the Midrashic sources and Targumim further suggest that Esav's kiss upon greeting Yaakov was insincere, and rather an attempt to bite his brother. 
  • Jubilees does not depict the reunion, but instead has Esav's clan convince him, after his parents' death, to actively attempt to eliminate Yaakov.40
Yitzchak's preference for Esav
  • Unaware of wickedness – According to many of these sources, Yitzchak was unaware of Esav's true nature, either because Esav tricked him into believing he was righteous,41 or because he had a natural love for his eldest son and was convinced of his bravery and strength by his tales of hunting.42 R. Hirsch adds that often people are attracted to their opposites, so Esav's active nature appealed to Yitzchak, and he did not see beyond to the negatives that lay beneath.
  • No preference for Esav – According to Seforno, the verse is not saying that Yitzchak preferred Esav, but rather that he loved him also43 (in contrast to Rivka who loved only Yaakov).44 
  • Split the blessing – Malbim suggests that Yitzchak was aware of his son's ways45 and had never intended to give him the blessing of Avraham, but only a material blessing.  He thought that both his children would be partners.  Yaakov would devote his life to service of Hashem, while Esav would provide for all his physical needs.46
Esav's descendants – Esav's descendants, Amalek and Edom (later associated with Rome and Christianity), have come to represent the arch-enemies of Israel throughout the ages.  It is not surprising, then, that many might have been inclined to view their ancestor, Esav, as  evil.  Moreover, Midrashic literature which consistently associated Esav with their contemporary enemy, Rome, was especially likely to adopt a harsh reading of Esav.
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