Jacob vs. Esau



The Torah relates that Jacob and Esau, the twin sons of Isaac and Rebecca (Genesis 25:24), went on separate paths (Genesis 25:27), Esau the hunter and Jacob the man of tents. Later the Torah relates that Jacob disguised himself as his brother Esau to secure the blessings from his father Isaac (ibid. 27:14-27). As a result of this deception Esau felt that Jacob had cheated him (ibid. 27:36), hated Jacob, and planned to kill him (ibid. 27:41). A companion article on this web site “Jacob Takes the Blessings” analyzes this deception in detail with particular emphasis on the ethical dilemma of “The ends justify the means”. On the surface the narrative of Jacob vs. Esau appears as a simple case of sibling rivalry. However when delving into the oral Torah, this narrative has fear reaching implications. This article will examine the nature of this conflict and the underlying factors that determine its outcome through the pardes method of exposition (i.e. literal meaning, exegesis, allusions, and secrets of the Torah), drawn from scripture, Talmud, Midrash, and Zohar with associated commentaries. A companion article on this web site “History of Esau” will examine the role of Esau with respect to the Israelites starting from his birth, following through scripture, and ending with the messiah.    

Literal Meaning – פשט

This article will start by examining the following verses in Genesis to frame this conflict:

  1. The Struggle (Genesis 25:22).
  2. The Prophecy (ibid. 25:23).
  3. The Strengths of Jacob vs. Esau (ibid 27:22).
  4. Isaac’s Blessing to Jacob (ibid. 27:28-29).
  5. Isaac’s Blessings to Esau (Ibid. 27:39-40).
  6. Esau’s Hatred of Jacob (ibid. 27:41).
  7. Jacob’s Encounter with Esau (ibid. 33:3-16)

At a literal level, each of these verses relates to the personal lives of Jacob and Esau and appears to be a case of sibling rivalry. This section will quote these verses and raise questions which will be analyzed verse by verse in the following sections. To simplify the reading each verse will be analyzed in its entirety with quotes from the Talmud, Midrash and Zohar where applicable.

The Struggle

Verse 25:22 – “The children struggled within her.”

This verse relates that the unborn Esau and Jacob struggled in Rebecca’s womb indicating a difficult pregnancy leading to the following question:

Question – What is the significance of this struggle? 

The Prophecy

Following her difficulty in gestation Rebecca inquired of Hashem, “Is this just a personal matter or a portent of cosmic proportions?”

 Verse 25:23 – “Hashem spoke to her (Rebecca): Two nations are in your womb; two regimes from your insides shall be separated; dominion shall pass from one regime to the other, and the elder shall serve the younger. “

This verse contains several clauses which frame the struggle between Esau and Jacob through the ages. At a literal level it is clear that these predictions were not fulfilled in the lives of Esau and Jacob as follows:

  1. Two nations – During their lifetimes the major powers in the Middle East were Egypt and to a lesser extent Babylonia. In fact Jacob and his children were too small in number to even conquer Canaan (Genesis 34:30).
  2. Two regimes – Neither the families of Esau nor Jacob established regimes in their lifetimes but were considered as clans by the inhabitants of Canaan (Genesis 36:19 and 34:21, respectively).
  3. Dominion shall pass from one to the other – After Jacob returned from Haran, Esau left for Seir and they had little contact with each other (Genesis 36:6-7).  
  4. Elder shall serve the younger – On the contrary Jacob was subservient to Esau when they met (Genesis 33:3) and never attempted to rule over Esau.


  1. What is the meaning of this prophecy?
  2. When will these prophecies be fulfilled?

The Strengths of Jacob vs. Esau

Verse 27:22 – “Jacob drew near to Isaac, his father, who felt him and said: The voice is the voice of Jacob but the hands are the hands of Esau.”

At a literal level, this verse discusses Isaac’s reaction to his son seeking a blessing. Isaac is perplexed because this person has characteristics of both sons, the voice of Jacob and the hairy hands of Esau. Since Isaac was blind he could not see through the ruse.    

Question – What is the significance of this statement?

Isaac’s Blessings to Jacob

Verse 27:28 – “G-d shall give you of the dew of the heavens, richness of the earth, and abundant grain and wine.”

Verse 27:29 – “Nations will serve you. Major regimes will bow down to you, and be a leader to your brother.”

Although Isaac intended to give these blessings to Esau and thus may not be applicable to Jacob the Torah indicates that Isaac ratified these blessings to Jacob (Genesis 27:33). At a literal level these blessings were not fulfilled during Jacob’s lifetime because he did not take ownership of the land and was a shepherd and not a farmer. In addition Jacob and his sons did not rule over any nations. On the contrary after his sons attacked the inhabitants of Shechem, Jacob reprimanded his sons because he was few in number (ibid. 34:30). In addition Jacob feared Esau (ibid. 32:8) and was subservient to him (ibid. 33:3).


  1. When will these blessings be fulfilled?
  2. What is the meaning of nations, regimes, and your brother?

Isaac’s Blessings to Esau

Verse 27:39 – “Behold the richness of the earth shall be your dwelling and the dew of heavens above.”

Verse 27:40 – “By your sword you shall live, but your brother you shall serve (תעבד). However when you are aggrieved, you may cast off his yoke from your neck.”

At this point Isaac knew that Esau was unworthy of the blessings originally intended for him (i.e. Genesis 27:28-29) and therefore blessed him in a manner suitable for his character and destiny. 

The following questions arise:

  1. Where is Esau supposed to live, if Isaac granted the land of Israel to Jacob?
  2. Under which conditions will Esau serve Jacob?
  3. What are the consequences to Esau if he does not serve Jacob?

Esau’s Hatred of Jacob

Verse 27:41 – “Esau hated Jacob because of the blessing which his father had blessed him (i.e. Jacob). Esau thought: May the days of mourning for my father draw near, and then I will kill my brother Jacob.”

At a literal level this verse refers to Esau’s personal hatred of Jacob because of the blessings that Jacob obtained through a ruse.

Question – Did this hatred transfer to Esau’s descendants or was this a simple case of sibling rivalry?

The Encounter

Verse 33:4 – “Esau ran toward him, embraced him, fell upon his neck, and kissed him. Then they (both) wept.

The Torah records (Genesis 33:3-16) that Jacob encountered Esau and was subservient to him (ibid. 3). The next verse states that Esau ran to Jacob and hugged him and kissed him. Esau offered to escort Jacob to their father Isaac (ibid. 12) but Jacob politely declined (ibid. 13-15). Then Esau returned to his home in Seir (ibid.16). The Torah placed dots on all six letters of the word “kissed” (וישקהו) leading to the following questions: 

  1. What is the significance of the dots?
  2. What implications for the future does this verse teach?

Analysis – סוד רמז דרש

In previous articles, the author placed citations from the Talmud, Midrash, and Zohar in different sections. However in this article each verse will be expounded throughout the citations to facilitate reading of the article and to highlight critical themes in understanding the conflict between Jacob and Esau.

The Struggle


The Midrash (Genesis Rabbah 63:6) understands the struggle between Jacob and Esau, right from conception, in both planes:

  • Physical
  • Theological

The Midrash predicts that Esau will attempt to destroy Jacob and his descendants as indicated by the struggle in the womb. In addition they will conflict over theology with Jacob drawn to monotheism and Esau to paganism. The Midrash states that when Rebecca passed by a place of monotheistic worship or study Jacob wanted to emerge. By contrast when she passed by a place of idolatry Esau wanted to emerge.


The Midrash finds a hint to this theological conflict by splitting the Hebrew word they struggled (ויתרצצו) in two Hebrew words (צו ויתר) meaning he undid commandments. However this Midrash did not elaborate on this conflict (perhaps for fear of the censors). In addition to Midrash Rabbah, the author will quote from Midrash Lekach Tov (also called Pesikta Zutarta) compiled by Rabbi Tobiah ben Eliezer in the late 11th and early 12 centuries because this Midrash interprets these verses in a terse and profound manner. Here this Midrash on Genesis 25:22 identifies this theological conflict in terms of replacement theology (i.e. Church versus Judaism). For example the Israelites observe Saturday as the Sabbath but the Church observes Sunday. In addition the Israelites do not eat pork but the Church allows it. In addition to elaborating on this conflict this Midrash clearly identifies the Church with Esau. (Note: the author does not wish to disparage the Church and its teachings. Rather the author quotes this Midrash to emphasize the theological conflict between these two beliefs and the potentially violent manner of this dispute which led to deaths of many Israelites in the middle ages, especially during the Crusades and Spanish Inquisition.)       

The Maharal on Genesis 25:22 notes that the Talmud Sanhedrin 91b notes that the evil inclination becomes active after birth. Hence how could this struggle occur before birth (i.e. before the evil inclination is active)? The Maharal answers that this struggle is an exception to the rule indicating that this rivalry is of cosmic importance that will last until the messiah when good will triumph over evil. 


The Zohar (1:138a) similarly identifies this struggle between Esau and Jacob as a portent for the cosmic struggle between good and evil. In addition the Zohar notes that Jacob held the heel of Esau (Genesis 25:26) meaning that sometimes Jacob would not always prevail over Esau but could at least restrain him. The Hebrew word for heel is עקב which is similar to the root עקף (first two letters are the same) meaning subterfuge implying that Jacob must sometimes use cunning to outsmart Esau when he cannot overpower him.


Although the Torah mentions this struggle with reference to Esau and Jacob in their lifetimes the oral Torah extends this struggle throughout the ages in both physical and theological planes.

The Prophecy    

This prophecy (ibid. 25:23) establishes the roles of Jacob and Esau through the following statements which will be analyzed in depth:

“Two nations are in your womb; two regimes from your insides shall be separated; dominion shall pass from one regime to the other, and the elder shall serve the younger. “ (Genesis 25:23)

  • Two nations.
  • Two regimes.
  • Dominion shall pass from one regime to the other.
  • Elder Shall Serve the Younger

Two Nations


The Talmud notes that this verse (ibid. 25:23) uses the Hebrew word גיים which can be read as גאים indicating distinguished leaders in terms of wisdom and power (Avodah Zara 11a). The Talmud (ibid.) identifies these leaders as Antoninus of Rome (whom most commentators recognize as Marcus Aurelius) and Rabbi Yehudah HaNasi, the foremost leader of the Israelites after the second temple. These distinguished men were both contemporaries and great in their respective fields, (i.e. temporal and spiritual). In addition to his scholarship, as complier of the Mishna, Rabbi Yehudah HaNasi was very wealthy and greatly revered in Rome (ibid.). The Talmud (Gittin 59a) comments that from the days of Moses until the days of Rabbi Yehudah HaNasi we do not find unparalleled greatness in Torah knowledge and secular matters, including wealth and high political office, combined in a single individual. The Talmud recognizes that the descendants of Isaac and Rebecca (i.e. Esau and Jacob) have great potential each in their area of dominion, physical and spiritual respectively. It is interesting to ponder if this combination of leaders both great and contemporaries occurred at other times or will occur at the time of the messiah. 


In a similar vein the Midrash (Genesis Rabbah 63:7) understands that the word גיים can be read as גאים meaning proud ones, implying that Jacob and Esau and their descendants may be proud of their accomplishments each in their respective fields (viz. spiritual and temporal). In addition this Midrash identifies these two powerful leaders as Hadrian of Rome and King Solomon who in their respective times earned world recognition. Hadrian was the Caesar who ruled at the apex of the Roman Empire and subdued the Bar Kochva rebellion. Unlike the Talmud, the Midrash chose King Solomon instead of Rabbi Yehudah HaNasi, perhaps because the Midrash wanted to compare two actual kings even though they were not contemporaries. This Midrash also states that the nations of the world are jealous of the successes of Esau and Jacob by interpreting the word two (שני) as in two nations as שנאי meaning hated by the nations. The Midrash Yelammedenu (a version of Midrash Tanchuma) notes that Jacob and his descendants are hated by the nations (when they do not follow the Torah) and Esau and his descendants are hated by Hashem (when they do not follow the seven Noahide laws) as the verse states (Malachi 1:2-3),” Was not Esau a brother of Jacob … yet I (Hashem) loved Jacob and hated Esau.”    

The Midrash Lekach Tov on this verse states that because of their greatness the descendants of Jacob and Esau maintain a fierce sense of independence and do not readily accept subjugation.    

Two Regimes


The Torah alludes to two great regimes that will issue from the descendants of Esau and Jacob which represent world class physical and spiritual regimes respectively. The Midrash (Genesis Rabbah 63:7) comments that in the past, the 70 nations descended from Noah (Genesis 10:1-32) shared world power. However after the ascendancy of Rome the main powers in the world will be Esau and their allies. By contrast the descendants of Jacob will form the major religions of the Western world.  

Midrash Hachafetz, written in 15th century Yemen by Rabbi Zechariah the son of Solomon, identifies these two regimes as the House of David which will produce the messiah and the House of Esau which will rule the world. The author would like to point out that the word for regime in Hebrew (לאם) shares the same letters as מלא meaning full, implying that these regimes will impact the world spiritually and physically respectively. In a similar vein the MIdrash (Genesis Rabbah 63:7) notes that the greatness of the regimes of Jacob and Esau will be recognizable past  the days of the Pentateuch, House of David in the book of Samuel and Kings and House of Esau post scripture in the times of the Romans.          

Dominion one to the other


The verse predicts that power shall transfer from one kingdom (i.e. Esau) to the other (i.e. Jacob) or in the vernacular, “When one is up the other is down” because these two kingdoms represent different ideals, the former physical might and the latter spiritual guidance. The Talmud Megillah 6a comments on this clause, “The Sages said that the fortunes of Rome (literally Caesarea the seat of Roman government in Israel) and Jerusalem are diametric opposites. If, someone says to you that both cities are destroyed, do not believe him. Similarly, if he says to you that they are both settled in tranquility, do not believe him. If he says to you that Rome (literally Caesarea) is destroyed and Jerusalem is settled, or that Jerusalem is destroyed and Rome (literally Caesarea) is settled, believe him.” This concept of oscillating power follows the idea mentioned above that one of these regimes must fill the world.

This oscillation in power is dependent on the behaviour of the Israelites and controlled by Hashem. When the Israelites follow the ways of the Torah then Jerusalem prevails otherwise Rome prevails. For example, the Talmud (Sanhedrin 21b) explains that Rome emerged from failings of King Solomon. Rabbi Yitzchak says (ibid.), “When King Solomon married Pharaoh’s daughter (which is not permitted by Torah law – Deuteronomy 23:9), the angel Gabriel descended from heaven and implanted a pole in the sea. A sandbar gradually rose up, creating new land, and on it the great city of Rome was built.”

However one should not be tempted to make predictions of impending doom if one finds failings with the Israelites because Hashem is “slow to anger and abundant in kindness” (Exodus 34:6). Hence there may be a considerable time lag between the failings and subsequent corrective action. It is interesting to note that Talmud (Megillah 6a) focused on Jerusalem as a sign of the strength of the Israelites especially since Rome destroyed the Second Temple and exiled the Israelites from Jerusalem.


The Midrash Lekach Tov (on Genesis 25:23) comments on the nature of this oscillation. When Israel is great (i.e. in ascendancy) then Esau is subdued as in the days of King David (2 Samuel 8:14), “He (King David) placed governors in Edom and all of Edom became servants to David.” By contrast when Esau is great (i.e. in ascendancy) then the Israelites are subdued (Lamentations 1:5), “Her (referring to Israel) adversaries have become her master and her enemies are at ease” and (Deuteronomy 28:48), “You (Israel) will serve your enemies whom Hashem will send against you.” The former verse does not specifically refer to Esau but conveys the state of the Israelites when Esau is in ascendancy. However the latter verse refers to Rome because the following verse (ibid. 28:49), “Hashem will bring against you a nation from afar, from the end of the earth, as an eagle will swoop, a nation whose language you will not understand.”  Nachmanides identifies this nation as Rome because the following verses speak of destruction of the land (ibid. 51), hunger caused by siege (52-57), and captives sold into slavery (ibid. 68) all of which occurred during the Roman capture of Israel. The author would like to add that verse 49 alludes to Rome as “a nation from afar” (i.e. not from the Middle East) who speaks a language “you will not understand” (i.e. Latin). In addition the Roman legions prominently displayed the eagle on their military banners.  

Elder (Esau) Shall Serve the Younger (Jacob)

It is interesting to note that the Talmud does not comment directly on this clause, perhaps to discourage rebellion against Rome or fear of the censors during the middle Ages. The Targum, Yonatan ben Uziel on this verse, comments that Esau will serve Jacob whenever the descendants of Jacob follow the Torah (e.g. during the times of King David and Solomon and in the future during the messianic era).  


The Midrash (Genesis Rabbah 63:7) comments, “If the descendants of Jacob are worthy then Esau will serve Jacob, otherwise the reverse is true.” The Midrash notes that the word serve (יעבד) with different vowels can be read as subjugate, implying the duality of this prophecy. The Midrash Lekach Tov links this duality with Genesis 27:40, “However when you (Esau) are aggrieved, you may cast off his (Jacob’s) yoke from your neck.” The section “Isaac’s Blessing to Esau” in this article will elaborate on the dynamics of the Jacob vs. Esau struggle. 


The prophecy means that both Esau and Jacob will spawn world class regimes in their respective domains, physical and spiritual. Jacob prevailed in the times of King David and Solomon and will prevail in the time of the messiah. Between these two events Esau may prevail depend upon the relative strengths of Jacob vs. Esau as described in the next section.

The Strengths of Jacob vs. Esau

Verse 27:22 – “Jacob drew near to Isaac, his father, who felt him and said: The voice is the voice of Jacob but the hands are the hands of Esau.”


The Talmud Gittin 57b declares that the strength of Jacob is in his prayer, based upon Genesis 27:22, “The voice is the voice of Jacob”. By contrast the strength of Esau is in his hands to wage victorious wars based upon the same verse, “The hands are the hands of Esau.”The Talmud (ibid.) further comments that the “hands of Esau” correspond to “the wicked kingdom of Rome that destroyed our Temple, burned our Sanctuary, and exiled us from our land.” In addition the Talmud states that the voice of Jacob relates to the suffering of the Israelites inflicted by the hands of Esau (i.e. the Romans) at the destruction of the Second Temple in Jerusalem and the tragic losses as a result of the failed Bar Kochva rebellion. 


Similar to the Talmud, the Midrash (Genesis Rabbah 65:20) declares that the strength of Jacob is in his prayer and Torah study. By contrast the strength of Esau is in his hands, especially in waging war. This Midrash observes that if the voice of Jacob is strong in the synagogues and study halls then the hands of Esau cannot prevail. However if the voice of Jacob is weak then the hands of Esau may prevail with dire consequences. In the language of another Midrash (Lamentations Rabbah Introduction: 2), “When the Israelites cast off the yoke of Torah then the nations (especially Esau and his allies) enact decrees against the Israelites and are successful. During this mode of persecution it may appear that Hashem has abandoned his people. The Torah calls this mode (Deuteronomy 31:17-18),”Hiding of the countenance of Hashem” or in Hebrew,” פנים הסתרת”.

However as mentioned above Hashem will never abandon the Israelites and therefore they will always recover. Both of these sources from the Midrash find an allusion to this Jacob vs. Esau contention through the wording of Genesis 27:22, “The voice is the voice of Jacob and the hands are the hands of Esau”, implying that a weakness in the voice of Jacob will encourage and empower the hands of Esau. In addition the word the voice (הקל) is written without the usual letter vav (ו), implying a deficiency in the voice of Jacob. The Mechilta Beshalach 2 observes that the power of Esau is in his hands relates to Genesis 27:40, “By your sword you shall live.”  

In addition the Midrash (Genesis Rabbah 65:20) points out that if the Israelites complain to Hashem, instead of praying to Him then Hashem will allow the Amalek nation, direct descendants of the grandson of Esau and later the arch enemy of the Israelites, to prevail. The following verses from Exodus chapter 17 reflect this concept:

 Verse 3 -“The people thirsted for water and complained against Moses.”

Verse 8 – “Amalek came and waged war in Rephidim.”  


The Zohar (1:171a) and (2:58b) identifies the strengths of Jacob vs. Esau from a heavenly perspective. The latter source explains that the study and observance of Torah gives strength to the Israelites based upon Psalms 29:11, “Hashem will give strength to His people and bless them with peace.” The Talmud Zevachim 116a identifies this strength as study and observance of Torah. At a personal level this strength relates to spiritual fortitude to overcome hostile decrees, assimilation and intermarriage. However the Zohar (ibid.) understands this strength not from a personal perspective; rather as divine might and protection, thereby minimizing or entirely averting the harsh decrees of Esau during the long exile of the Israelites. In fact at a literal level the verse in Psalms indicates that this strength, which leads to peace, originates from Hashem.

The Zohar (1:171a) also notes that the strength of Jacob’s Torah does not reside with scholars alone but includes those that support Torah scholars with their wealth. The Zohar finds an allusion to this support in the verse (Genesis 32:26), “When he (i.e. the angel of Esau) saw that he could not overcome him (i.e. Jacob), he struck the socket of his hip.” The Zohar states that just as the hips support the body so do the supporters of Torah maintain Torah scholars. In addition the merit of supporting Torah scholars will lead to increased wealth as the sages say (Avot 3:17 in printed Mishna and 3:21 in prayer book), “If there is no flour (i.e. financial support then there is no Torah (study); If there is no Torah (study) then there is no flour (i.e. wealth).”  


The significance of verse 27:22 relating to the strengths and destinies of Jacob and Esau may be summarized as follows:

  • The power of Jacob is in his prayer and Torah study. The power of Esau is in his hands to wage war and inflict punishment.
  • If Jacob is weak in his voice (i.e. prayer and Torah study) then the hands of Esau prevail otherwise Jacob will prevail.
  • When Esau destroys with his hands then the descendants of Jacob cry in pain.

Isaac’s Blessings to Jacob

Isaac blessed Jacob with material wealth and political power as described in verses 27:28 and 29 respectively.

Verse 27:28 – “G-d will give you (לך) of the dew of the heavens, richness of the earth, and abundant grain and wine.”

Verse 27:29 – “Nations will serve you. Major regimes will bow down to you, and be a leader to your brother (and his descendants).”

Material Blessings

At a literal level the first verse (Genesis 27:28) refers to material blessings (viz. grain and wine) aided by dew. However by examining the precise wording of the verse one can find significant meaning to these blessings relating to the destiny of Jacob and his descendants as follows:

  • Divine conditions and merit
  • Resurrection
  • Direction – heaven to earth
  • Land of Israel

Divine conditions and merit

This verse indicates that G-d will bless Jacob with prosperity. The Midrash Lekach Tov (on this verse) and Midrash Tanchuma Yashan 14 on Toldot explain that this blessing is conditional upon following the ways of Hashem. In addition the Midrash (Genesis Rabbah 66:2) mentions that the Hebrew word לך (to you) meaning that the blessings are conditional upon the Israelites or in the vernacular “It’s up to you”.

The Zohar (1:143b) agrees that that the material blessings which Jacob received from Isaac are conditional upon adherence to the Torah. In addition Hashem confers upon the Israelites a spiritual blessing which cannot be revoked regardless of their material situation as the Torah attests (Deuteronomy 32:9), “For Hashem’s portion is His people; Jacob is the measure of His inheritance.”


The Zohar (2:83a) mentions, in addition to the literal meaning, that the dew of the heavens refers to the dew that Hashem will use in the resurrection of the dead based upon Isaiah 26:19, “May Your dead live; the corpses  shall rise;  … for a dew of lights is your dew.”

Direction – Heaven to Earth

The Zohar (1:143b) points out that blessing follows the direction from heaven to earth (i.e. dew of heavens and richness of the earth) reflecting Hashem’s expectations for Jacob and his descendants.

Land of Israel

The Midrash (Genesis Rabbah 66:3) emphasizes that these blessings apply in the land of Israel and abundance will be used for offerings to Hashem in the temple at Jerusalem thereby combining material blessings with service to Hashem. Specifically the Midrash relates the “dew of the heavens” of Genesis 27:28 to the dew on Mount Hermon in connection to verse (Psalms 133:3), “As the dew of Hermon which runs down on the mountains of Zion, for there Hashem commanded the blessing of life forever.”

Political Power

In the second verse (Genesis 27:29) Isaac blessed Jacob with political power to rule over nations, regimes, and even Esau. It is interesting to note that this verse does not indicate how dominance is achieved. Presumably the Israelites will wage war to achieve this position but the verse does not mention war because in the view of the Torah war is not an end in itself rather a means to achieve peace and security in Israel.


Similar to the Targum on Genesis 27:29, the Midrash (Genesis Rabbah 66:4) explains Isaac’s blessings in terms of political power and dominion by expounding each segment in the verse as follows:

  1. Nations will serve you – The seventy nations of the world who descended from Noah (Genesis 10:1-29)
  2. Major regimes will bow down to you – The descendants of Ishmael and Keturah (Genesis 25:12-16 and 1-4, respectively) who live in the Middle East.
  3. Leader to your brother (and his descendants) – This refers to Esau and his chieftains (Genesis 35:15-19). In the above verse the word for brother is spelled (with vowels) in the plural referring to Esau and his descendants.    

It would appear that this Midrash is advocating world domination by the Israelites reminiscent of totalitarian regimes of the past. However the Zohar provide a historical and religious perspective on this blessing without emphasizing war or oppression as follows.


The Zohar (1:143a) establishes the time of fulfillment of these blessings by comparing the text of Genesis 27:29 to other verses in scripture. In particular, the Zohar links the above verse to 2 Chronicles 9:23, “And all the kings of the earth sought Solomon’s presence to hear the wisdom with which G-d had endowed him”, illustrating the great respect for King Solomon and his wisdom without waging war. In addition these blessing will be fulfilled in the time of the messiah based upon Psalms 72:11, “All kings will bow (וישתחוו) to him; may all nations serve (יעבדוהו) him.” This verse speaks of a high level of respect because both verbs (i.e. serve and bow) are stated in this verse, indicating a worldwide respect for the messiah. In fact Psalm 72 speaks of the messianic era and emphasizes that the messiah will rule with righteousness and use force only when necessary as the verse (ibid. 72:4) says, “He will judge the poor of the people, save the children of the needy and crush the oppressor.” The Zohar (ibid.) recognizes that the expression “Be a leader to your brother” also applied during the reign of King David who waged wars to expand the borders of Israel and subdue the neighbouring peoples.      

The Zohar (1:143b) also links the service of the nations in Genesis 27:29 to the messianic prediction in Isaiah 61:5, “Strangers shall stand and pasture your sheep, and foreigners shall be your plowmen and your vinedressers.” The author would like to add the next verse (ibid. 61:6) as a continuation of this theme, “You shall be called the priests of Hashem and servants of our G-d. The possessions of the nations you shall eat and bask in glory.” Hence in the messianic era the nations will recognize the Israelites as the people of Hashem and honour them physically and spiritually without compulsion.   


These blessings were fulfilled in the time of King David and Solomon and will reach completion in the time of the messiah where the entire world will recognize Hashem and the Israelites as his chosen people.

Isaac’s Blessings to Esau

Verse 27:39 – “Behold the richness of the earth shall be your dwelling and the dew of heavens above.”

Verse 27:40 – “By your sword you shall live, but your brother you shall serve (תעבד). However when you are aggrieved, you may cast off his yoke from your neck.”

Similar to the blessings of Jacob, Isaac conferred both material (ibid. 39) and political blessings (ibid.40) to Esau.

Material Blessing

After realizing that Esau was unworthy of the blessings that Isaac conferred to Jacob, Isaac blessed Esau in a manner suitable to his temperament and destiny. The material blessing in Genesis 27:39 contrasts significantly with that of Jacob (ibid 27:28) in the following areas:

  • Divine conditions and merit
  • Resurrection
  • Direction
  • Land of Israel

Divine conditions and merit

In verse 39, Isaac blessed Esau with prosperity. However unlike the blessings given to Jacob, this verse mentions neither the name of G-d nor the Hebrew word לך (to you) meaning that these blessings are not conditional upon following the ways of Hashem. This does not imply that Esau is held unaccountable for his actions. Certainly Hashem will not tolerate evil indefinitely. Rather Hashem is patient (Exodus 34:6) and waits for the sinner to return to Hashem (Ezekiel 18:23 and 27-28). This blessing means that Esau is not held to the same standard as Jacob and will give Esau more latitude than Jacob.

The Zohar 1:143b states that if the Israelites do not follow the Torah then Esau may prevail and the material blessings of Jacob may not apply based upon Genesis 27:40. Nevertheless the Zohar concludes that in the messianic era Jacob will receive the material blessings and the wicked ones of Esau will be destroyed as the verse (Obadiah 1:18) predicts, “The house of Jacob will be a fire and the House  of Joseph a flame, and the House of (wicked) Esau like straw. They will kindle and consume them and there will be no survivors of the House of (wicked) Esau.”


In Jacob’s blessing the dew is both literal and refers to resurrection. By contrast the blessing of Esau refers to literal dew because the name of G-d is not mentioned in this verse. This does not imply that Esau’s descendants will not merit resurrection; rather they must seek out Hashem with greater effort than the observant descendants of Jacob who from early childhood, study and observe the laws of the Torah. 

On this point the author would like to nuance that there are many negative statements about Esau and his descendants which must be understood within the context of the brutality of Rome and its successors and the intense suffering of the Israelites from their hands. It is improper to generalize about a given people and certainly improper to generalize about all gentiles. In fact the Talmud (Avodah Zara 10b) records a number of discussions between Antoninus and Rabbi Yehudah HaNasi about the future of Rome and its successors with respect to the messianic era and the world to come. From a literal reading of the verses Antoninus concluded that there was no place for him and his fellow Romans in these domains. For example Obadiah (1:18) predicts, “None shall remain of the house of Esau.” Rabbi Yehudah HaNasi explained that this verse only refers to the evil ones of Rome who act like their ancestor Esau and not to moral individuals like Antoninus.     


The Zohar (1:143b) points out that Esau’s blessings follows the order from earth to heaven (i.e. richness of the earth and dew of heavens) which is the exact opposite of Jacob’s blessings. This direction reflects Hashem’s expectations for Esau which is primarily material but could reach the heavens when cooperating with Jacob and his descendants. 

Land of Israel

The Midrash (Genesis Rabbah 67:6) emphasizes that the blessings of Esau apply outside of Israel, initially in the area of Mount Seir which is in present day Jordan and then many centuries later in Rome. The Torah records that Esau left the land of Israel and settled near Mount Seir (Genesis 36:6-8) thereby acknowledging that the land of Israel was given to Jacob and his descendants. Even though Hashem did not grant Esau a portion of land in Israel Hashem did bequeath him the land of Seir (Deuteronomy 2:5). Although Esau was not destined to be heir to the land of Israel his descendants may play a role in developing the land. (The companion article on this web site “History of Esau” will examine this role especially with regard to the modern State of Israel.)

Political Blessing

This verse (ibid 27:40) refers to Esau’s position with respect to the world and his destiny with Jacob and his descendants. It contains multiple prophecies that have been fulfilled in the past and will be fulfilled in the messianic era as follows:

  • Military might – “Live by the sword”.
  • Serve Jacob – “Your brother you shall serve”.
  • Free from Jacob – “When aggrieved (תריד) you may cast off the yoke”

Military Might

This verse indicates that Esau shall live by the sword meaning that he will defend his land against invaders (Nachmanides ibid.). The Abarbanel (ibid.) explains that that Esau may extend his empire worldwide by conquest. Both of these explanations continue the theme of the previous verse of material prosperity. The Midrash (ibid. 67:7) limits the use of Esau’s sword to conquest but not to persecute Jacob. The verse reads in Hebrew תחיה חרבך ועל which literally means “upon the sword you shall live”. However the Midrash interprets the word ועל (upon), from an Aramaic perspective, which means enter (עול) the sword (in its scabbard) and live, advising against harming Jacob and his descendants.  

Esau serves Jacob

The Midrash (ibid. 67:7) points out that Esau shall serve (תעבד) when Jacob is worthy. The Midrash also notes that since the letters א and ע have a similar pronunciation they may be interchanged to seek hints and allusions in the Torah. Through this substitution the word serve (תעבד) becomes (תאבד) which means lost, implying that if Esau attacks Jacob when Jacob is worthy then Esau will be destroyed.   

Free from Jacob

Isaac told Esau that he must serve Jacob but only if Jacob follows the Torah. The Hebrew word תריד in Genesis 27:40 has two meanings:

  • Aggrieved – meaning that Esau can complain to Hashem because the blessings taken by Jacob are on the condition that the Israelites follow the Torah. If they do not then the Israelites lose their moral authority and Esau can rightly reclaim the blessings and as the verse says “You (Esau) may cast off the yoke from your neck.”
  • Falling – Israelites fall from their obligation to Torah (Targum Onkelos on Genesis 24:40) empowering Esau to prevail even without the complaints of Esau. The word תריד is related to the root ירד which means descent.

Midrash Rabbah (ibid. 67:7) and Lekech Tov (on this verse) similarly explain this relationship between Jacob and Esau following the principle of measure for measure (Sotah 8b). If Jacob or his descendants “cast off” the yoke of Torah (i.e. study and observance) then Esau can in turn “cast off” the yoke of Jacob. The Midrash continues and states that when Jacob is spiritually weakened then Esau may actually persecute the Israelites and be successful.         


It is interesting to note that the blessings given to Jacob and Esau parallel each other reflecting their different destinies and divine missions.  The first verse of each set describes blessings of prosperity with the second verse of each set relating to political power and dominion.

In summary Esau is destined to live outside of Israel and serve his brother when Jacob is worthy. Otherwise Esau is free of this obligation and may even rebel against Jacob. 

Esau’s Hatred of Jacob

Verse 27:41 – “Esau hated Jacob because of the blessing which his father had blessed him (i.e. Jacob). Esau thought: May the days of mourning for my father draw near, and then I will kill my brother Jacob.”

The Midrash (Genesis Rabbah 67:8) extends Esau’s hatred of Jacob to the Roman Empire by expounding on the following Roman themes:    

  • Senator
  • Saturn


The word senator when transliterated into Hebrew becomes סנטרוי. This word in turn becomes an acronym for the Hebrew words נוטר נוקם שונא which in English means enemy, seeker of revenge, and bearer of a grudge, respectively. The significant letters of these three words (ר,ט,נ,ש) spell the primary letters of  סנטרוי, with the letters ש,ס interchangeable because of their similar pronunciation. Admittedly this derivation uses several transformations and is therefore not straightforward. However it does illustrate these key points:

  • ·         Rome identified with Esau


The Jerusalem Talmud (Avodah Zara 1:2) points that the festival of Saturn, celebrated during the eight days before the winter solstice, when transliterated into Hebrew becomes הסטרנליי. This word in turn becomes an acronym for the Hebrew words נוטר נוקם שונא as explained above and similarly illustrates the hatred of Rome to the Israelites. In addition the Jerusalem Talmud (ibid.) notes that this word in Hebrew הסטרנליי alludes to hidden hatred (טמונה שנאה) by using the first two letters of this word as an acronym. This indicates that the Romans considered Jacob and his descendants as their enemies.      


Esau’s hatred of Jacob passed on to his descendants as a root cause of anti-Semitism.

The Encounter

Verse 33:4 – “Esau ran toward him, embraced him, fell upon his neck, and kissed him. Then they (both) wept.

Dots on Word

The rabbis of the Midrash (Genesis Rabbah 78:9) debate whether the embrace and kiss of Esau were sincere or sinister. The Midrash notes that the word “kissed” (וישקהו) is fully dotted in the Torah. The Torah does not provide dots for vowels and rarely places dots above letters of the Torah. However in this case each of the 6 letters of this word is dotted meaning that there is a special message. The Midrash states that in the case of dots above letters we follow the majority, meaning that if the majority of letters are dotted then we interpret the word as the primary message by using the dotted letters. Conversely if the majority of letters are without dots then we interpret the word, as the primary message, by using those letters. The Torah may be interpreted in many ways hence the secondary message is reflected in the actual letters whether dotted or not. In this case the Midrash is in a quandary because all of the letters are dotted meaning interpret the word with all of the letters. The Midrash then asks, “Why did the Torah dot the letters?”  

The Midrash then presents opposing views about this encounter. First the Midrash states that Esau’s motives were sincere and the dots allude to a change in attitude from hostile to friendly.  Then the Midrash records an opposing view that Esau intended to attack Jacob, literally to bite him on the neck because the root words of bite (נשך) and kiss (נשק) are similar in spelling and pronunciation. According to this opinion Esau cried because Hashem strengthened Jacob’s neck and as a result Esau hurt his teeth and Jacob cried due to Esau’s bite. By contrast according to the first opinion both cried from joy after being separated for over 20 years as Jacob lived in the in the house of Laban for 20 years (Genesis 31:38).   

In addition Rashi on Genesis 33:4 comments, like the Midrash, that there are conflicting opinions about the intention of Esau whether hostile or friendly. He quotes the view of Rabbi Shimon ben Yochai who says (Sifrei on Numbers 9:10), “It is a given fact that Esau hates Jacob but in this case his mercy was aroused and he kissed him with all his heart.”


Similarly the Zohar (1:171b-172a) takes both approaches to this embrace and kiss. At first the Zohar (1:171b) states that Esau’s intentions were hostile and he intended to bite Jacob when he kissed him and that is why he cried. The Zohar (ibid.) understands the word “neck” as an allusion to the temple (Megillah 16b) based on Songs of Songs 7:5, “Your neck is like an ivory tower”. The second temple was destroyed by the Romans, the descendants of Esau.

The Zohar records (1:172a) a dissenting opinion that Esau’s intention were sincere and the cry was one of intense emotion upon seeing his brother after a separation of more than 20 years. The Zohar adds (ibid.) that Esau was in a mood of reconciling with Jacob because he realized that Jacob overcame his ministering angel (Genesis 32:25-29) and this angel blessed Jacob. This indicated that Hashem would not allow Esau to harm Jacob at this point.

Other Encounters

The author would like to add that another Midrash (Genesis Rabbah 70:12) adds a scriptural perspective on kissing, when not used as an expression of passion, as follows:


In this verse, the prophet Samuel anointed King Saul and kissed him on his appointment. This connotation of kingship fits well with the encounter of Jacob and Esau. Esau should have acknowledged Jacob as his spiritual leader and king of the Israelites or at least equals like Moses and Aaron, as discussed in the next paragraph. Rather the embrace was just a family matter and led to separation like Ruth and Orpah, as discussed below.

Co- operation

The Torah, in Exodus 4:27, records that Aaron met his brother Moses at Mount Sinai and kissed him. This meeting led to a division of responsibilities with Moses receiving the word of Hashem as a prophet and Aaron the spokesman of the Israelites when negotiating with Pharaoh (ibid. 7:1). In this sense of division of responsibilities, ideally Esau should have assumed the role of defender of the Israelites through his might and cunning with Jacob the man of spirit dwelling in the tents of Torah based upon Genesis 25:27.     


The Torah, in Genesis 29:11, records that when Jacob met his cousin Rachel he kissed her as a form of affection within a family. Similarly when Esau met Jacob he kissed him, according to one opinion, as a form of affection but the meeting when no further than that. By contrast Jacob eventually married Rachel leading to the births of Joseph and Benjamin.  


After the death of the husbands of Ruth and Orpah, Naomi their mother in law, suggested that they return to their families in Moab (Ruth 1:8-13). Ruth remained loyal to Naomi and eventually converted to Judaism (Ruth 1:17), as the verse relates when Ruth speaks to Naomi, “Your people are my people and your G-d is my G-d”. By contrast Oprah returned to her people and their beliefs as the verses state (Ruth 1:14-15), “Oprah kissed her mother in law but Ruth clung to her. Naomi said to Ruth: Look, your sister in law (Orpah) returned to her people and god. Go follow your sister in law (but Ruth refused to leave Naomi).” In this case the kiss was of separation with Ruth converting to Judaism and spawning the Davidic line (Ruth 4:21-22). By contrast Orpah returned to her people and later became the mother (or ancestor) of Goliath (Sotah 42b) the enemy of the Israelites who was eventually killed by David. Hence this separation ends with an ironic twist, one descendant for life and the other for death. Similarly this kiss of separation led to Esau abandoning his ancestors and their beliefs and becoming an enemy of the Israelites.

Based upon the above themes, in the opinion of this author the dots above the expression “he kissed him” reflect the duality of this moment (i.e. potential vs. actual). Ideally Esau should have acknowledged Jacob as the leader of the Israelites (i.e. theme of kingship) or at least recognize him as an equal (i.e. theme of co-operation) in the divine mission to spread monotheism. Rather this encounter was a family reunion (i.e. theme of family) that led to separation of Jacob and Esau throughout history (i.e. theme of separation), meaning a missed opportunity. The dots indicate that the Torah considers the possibility of reconciliation at the end of days.     

Encounters of King Saul and David

The author would like to point out that the exact form of he kissed him (וישקהו) appears only two more times in all of scripture as follows:

Verse 1 (1 Samuel 10:1) – “Samuel took the vial of oil, poured it on his head, and kissed him (וישקהו). Then he said, “Indeed, the Hashem has anointed you to be a ruler over His inheritance.”

Verse 2 (1 Samuel 30:11) – “They found an Egyptian man in the field and brought him to David. They gave him bread to eat and water to drink (וישקהו).”

The first verse speaks of the coronation of King Saul by the prophet Samuel after the Israelites clamoured for a king. Samuel reluctantly agrees to their demand by anointing Saul but nevertheless and kissed him.

The second verse speaks of a battle between King David and the Amalekites, descendants of Esau. Initially the Amalekites destroyed the city of Ziklag (ibid. 1) and captured two wives of King David (ibid. 5). The people were disappointed with King David and threatened to stone him (ibid. 6). At this point, rather than being discouraged, King David placed his faith in Hashem (ibid. 6) and asked Hashem for permission to purse the Amalekites (ibid. 8). With Hashem’s blessings Kind David mobilized his men and prepared for battle (ibid. 9). On the way they found an Egyptian man (ibid. 11) who was a slave of an Amalekite master who abandoned him for three days (ibid. 13). The Israelites gave him bread to eat and water to drink (וישקהו), hence the link of this narrative to the encounter between Jacob and Esau. He promised to help them find the Amalekites if they agreed not to harm him or transfer him back to his master (ibid. 15). King David agreed to his request and the Egyptian led him to the Amalekites who were rejoicing over their booty (ibid. 16). With the help of Hashem King David was victorious and recovered all of the captives, his two wives, and the booty (ibid. 17-19).         

The reader may remark that the Hebrew word (וישקהו) in this verse means to drink and not to kiss. However the spelling of these words is the same suggesting a link between these this battle and the encounter of Jacob with Esau. In addition the Midrash Genesis Rabbah (78:15) links this battle of King David to the encounter of Esau and Jacob through numerology of 400. Esau approached Jacob with 400 men (Genesis 32:7) and they agreed not to attack Jacob after Esau decided to rerun to Seir (ibid. 32:16). As a reward for not harming Jacob, Hashem allowed 400 of their descendants to escape at the battle of King David (1 Samuel 30:17). Based upon this Midrash we see a link to themes of monarchy, alliances with gentiles, victory in battle which relates to the encounter between Jacob and Esau as discussed above in terms of kingship.


The dots on the word (וישקהו) indicate that Esau can express genuine love for Jacob or that he may attack Jacob in direct combat. These modes of Esau (i.e. love or hate) influence how the Israelites should deal with Esau through their existence in terms of kinship, co-operation, family, and possible separation, as explained above.   

Death of Esau

The reader may ask, “What happened to Esau since the Torah does not record his death?” The oral Torah states that Esau died at the burial of either:

Burial of Isaac

The Torah records that both Esau and Jacob were present at the burial of their father Isaac (Genesis 35:29) at the cave of Machpela (ibid. 49:31). The Yalkut Shemoni, a Midrash compiled between the 11th and 14th centuries, on Chapter 50 of Genesis relates that at the burial Esau planned Esau planned to ambush Jacob and kill him. Judah, Jacob’s son, was also in the cave and stealthily remained behind Esau and killed him from the back, as the verse states (Genesis 49:8), “Judah your hand was at your enemy’s (Esau) neck.” The verse may also be in reference to the future (e.g. King David) and thus reads, “Judah your hand will be at your enemies’ neck.”

Burial of Jacob

The Talmud (Sotah 13a) relates that when the sons of Jacob wanted to bury their father in the cave of Machpela, Esau insisted that he as the first born should be buried there instead of Jacob. The sons of Jacob claimed that Esau sold his burial plot when he sold the birthright to Jacob (Genesis 25:29-34). Then Esau asked for proof of this sale to which Jacob’s sons replied that the deed of sale was in Egypt. The sons of Jacob decided to send their brother Naphtali, a swift runner, back to Egypt to retrieve the deed of sale. In the mean time, Jacob’s grandson Chushim who was hard of hearing did not understand the reason for delaying the burial. Jacob’s sons explained that Esau contested the burial so they sent Naphtali to Egypt. Chushim protested and said, “My grandfather is lying in disgrace (and you are negotiating).” Chushim then took a staff and hit Esau on the head killing him.   


These two narratives show the negative side of Esau, stealth and intransigence, leading to his death which was avoidable. Instead of co-operating with Jacob’s sons he chose confrontation which led to his demise.         


This article analyzed the roles of Jacob vs. Esau through a number of different sources to obtain the following messages:

  • Struggle – Esau and Jacob will spawn world class regimes in their respective domains, physical and spiritual. The dominion shall pass from one to other but in the end Esau shall serve Jacob.
  • Strength of Jacob – The power of Jacob and his descendants is in his prayer and Torah study. If Jacob is weak in his voice (i.e. prayer and Torah study) then the hands of Esau will prevail.
  • Strength of Esau – The power of Esau and his descendants is in his hands to wage war and inflict punishment.
  • Blessings of Isaac – Isaac blessed both of his sons, Jacob and Esau, with material and political blessings. The blessings of Jacob are conditional upon serving Hashem. By contrast the blessings of Esau are not as conditional upon serving Hashem as long he does not abuse his position. 
  • Hatred of Esau towards Jacob – This hatred extends until today as one of the root causes of anti-Semitism.  
  • Jacob’s encounter with Esau – After this encounter Jacob and Esau went their separate ways, the former to the land of Israel and the latter to Mount Seir in modern day Jordan. This encounter is a portent for the future, indicated by the dots on the word (וישקהו), meaning that Esau’s descendants can express genuine love for Jacob’s descendants or that he may attack them in direct combat.
  • Death of Esau – Although the Torah does not disclose the death of Esau the oral law related that Esau was killed either by Jacob’s son or grandson, indicating a tragic end to Esau’s life. This is also a portent for the future indicating the end of Israel’s adversaries at the time of the messiah.    

The reader may ask, “Given this age old struggle between two regimes is at a national level, what can an individual do to change the outcome?” The Talmud (Kiddushin 40b) answers this question by stating that each mitzvah counts as follows, “Hashem judges the world according to the majority of its inhabitants and also judges an individual according to the majority of his deeds.” Rashi on this passage adds, “Therefore a person should consider himself as half-meritorious and half-guilty and the world as equally populated with righteous and wicked individuals.” The Talmud continues,” if an individual performs a single mitzvah he has tipped the scales for himself and the world at large to the side of merit. Conversely a single transgression tips the scales for him and the world to the side of guilt.”  In summary each mitzvah counts to defeat the evil forces, represented by some of Esau’s descendants.    

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