Rosh Chodesh Bet
The Sar of Eisav is none other than Sam-Kel himself (Uncle 'Sam'). Therefore, here at the very end of his rule and his power, when he is the most dangerous, is no time to be under any illusions about his character.
On the matter of Eisav, the blog author follows these Torah sources as elucidated by the commentary on Parashat Toledot, The Stone Edition Chumash, ...
Each of the [three] Patriarchs maintained a yeshivah in which he taught about the existence of God and His will. Abraham's academy had hundreds if not thousands of students - Isaac had an academy of one. His lone student was Jacob, whom he trained and appointed to teach others (Rambam, Hil. Avodah Zarah 1:2-3). This provides a clue to the way in which Isaac's role diverged from that of Abraham. Abraham could accept everyone into his orbit; Isaac could not.
The Torah devotes much less space to Isaac's life than to the lives of Abraham and Jacob. On the one hand, Isaac seems to be but a bridge between his father and his son; on the other hand, he had the task of drawing the line between good and evil - as represented by Jacob and Esau - because the emerging nation of Israel could not be a mixture of good and evil. In contrast to Abraham whose primary characteristic was chessed, or kindness, Isaac's was gevurah, or strength. One requires strength to differentiate between good and evil - and then to purge the bad and nurture the good. Isaac and Rebecca produced two sons; one became the personification of righteousness and the other the personification of wickedness, and it was the lot of the parents to make the distinction so that the nation of Israel would be pure.
Lest one think that Isaac discarded Abraham's way in favor of his own, the Torah stresses at the very beginning of the Sidrah that Isaac was the son of Abraham - Abraham begot Isaac. In the Jewish scheme of life, kindness and strength must go together; either one without the other can be dangerous. Kindness not tempered by strength can lead to self-indulgence and hedonism; strength without kindness can lead to selfishness and cruelty.
...The children agitated. The Rabbis explain that [the word translated as agitated] is derived from the root...to run: When Rebecca passed the Torah academy of Shem and Eber, Jacob "ran" and struggled to come forth; and when she passed a temple of idol worship, Esau "ran" and struggled to come forth (Midrash). Gur Aryeh explains that this embryonic Jacob-Esau struggle was not influenced by their personal Good and Evil inclinations for they were not present before birth. Rather, Jacob and Esau represented cosmic forces in Creation, forces that transcended the normal course of personality development, and that existed even before birth.
She went to inquire. She went to the academy of shem (Rashi), a prophet, who could inquire of God on her behalf. She kept her predicament from Isaac and Abraham for fear that they might deem her suffering to be a sign of sinfulness on her part (Gur Aryeh).
As indicated by the next verse, Hashem conveyed the significance of her frightening symptoms only to her and not to Isaac. Since God did not reveal this prophecy to Isaac, Rebecca felt that she did not have the right to do so, even years later when she conspired to win Isaac's blessings for Jacob over Esau. Chizkuni explains that this is why Isaac could not imagine Esau to be a sinner.
...Hashem said to her. Through Shem, God conveyed to her that the unborn infants represented two nations and two conflicting ideologies - Israel and Edom - and that their struggle in the womb symbolized the future rivalries between them, which would end with the younger prevailing over the older (R' Hoffmann). Thus, the turmoil within her was due to the irreconcilable conflict between the two nations that was already taking shape (Mizrachi).
The Sages teach that the two of them will never be mighty simultaneously; when one falls, the other will rise (Megillah 6a). History has demonstrated this prophecy in practice. Two regimes, one espousing morality and justice and the other standing for license and barbarity, cannot long coexist. They must always be in conflict until one comes to dominate the other, whether through victory on the battlefield or in the contest for men's minds.
The birth of Jacob and Esau. From the moment they emerged from the womb, their eternal rivalry already showed itself, in their appearances and developing behavior.The Torah sources on Eisav as elucidated by the commentary on Parashat Vayishlach, The Stone Edition Chumash, ...
...The first one emerged red. His complexion was ruddy and he was as hairy as a woolen garment. The redness of his complexion portended his murderous nature (Rashi), since there was no other reason for the Torah to have mentioned it (Mizrachi).
The young King David, too, was ruddy, and Samuel feared that this might indicate a tendency toward bloodshed on his part. But, God reassured him, saying that David had beautiful eyes (I Samuel 16:12), meaning that he would kill only upon the ruling of the Sanhedrin, which acts as the eyes of the nation, whereas Esau would kill whenever the mood moved him (Midrash).
All character traits, even the basest, can be used for good. Man must harness his nature and not let his nature harness him. David and Esau had similar personalities, but David utilized it for good and became one of the greatest people who ever lived. Esau let his nature run rampant, and became the eternal symbol of evil and cruelty.
...After that, his brother emerged. The verse goes on to say that Jacob grasped Esau's heel, indicating that he was trying to prevent Esau from being born first. Rashi cites the Midrash that Jacob was justified in trying to be the firstborn because he had been conceived before Esau, so that Jacob should legitimately be born first.
Pachad Yitzchak expounds this seemingly strange comment. Briefly, he explains that the contention between Jacob and Esau was over who would assume the spiritual mission of Abraham and Isaac. Thus, the critical factor in their birth was the seed of the Patriarch that had been implanted in the mother's egg, for it contained the essence of the father. Consequently, since Jacob was conceived first, he was the spiritual firstborn and therefore entitled to the blessings. In the strictly legal sense, however - relating to shares in an inheritance and other legal privileges of the firstborn - the determining factor is birth, not conception. Thus, the later efforts of Jacob and Rebecca to secure the birthright for Jacob must be understood in the light of Jacob's spiritual superiority.
By grasping Esau's heel, the infant Jacob portended that Esau's period of dominion will barely be complete before Jacob wrests it from him (Rashi), so that Jacob's ascendancy will come on the heels of Esau's.
...The personalities emerge. Until they grew up - i.e., reached bar-mitzvah age - they were relatively similar to one another, and Esau's pranks were attributed to childishness (Sifsei Chachamim). From the age of thirteen, the essential differences became apparent, with Esau turning to idols and Jacob going to the study hall. Esau became a hunter, but not only in the literal sense. He became adept at trapping his father by asking questions that would make him appear to be unusually pious. He would ask, for example, how tithes should be taken from salt and straw [although he knew full well that they were not subject to tithes]. And he gained his father's love by serving him conscientiously; for example, by hunting game to put in his mouth, so that Isaac could eat fresh and tasty meat. Jacob, however, was morally wholesome, saying what he thought and never being duplicitous, and spending all his time in the study tents of Shem and Eber (Rashi).
Sale of the birthright. God's blessing to Abraham specified that only one of Isaac's children would be heir to the mission of Israel (see Rambam, Hil. Melachim 10:7), meaning that the Torah would go to Jacob or Esau, but not to both. This explains Jacob's intense desire to "purchase" the birthright. The episode seems more understandable in view of the circumstances in which Jacob was cooking the lentil stew. The Sages teach that Abraham died that day and Jacob was preparing the stew as the traditional mourner's meal for his father (Bava Basra 16b) - and on that very day, Esau's sinfulness became public knowledge. This made the birthright even more precious to Jacob, because the spiritual mission of Abraham's family was brought to mind and because Esau's unsuitability for it became so blatantly obvious.
The Midrash teaches that since the sacrificial service was performed by the firstborn in those days, Jacob said, "Shall this wicked man stand and bring the offerings!" Therefore, he strove mightily to obtain the birthright.
...Esau came in from the field. The great of all the nations stood in the mourner's row and lamented, "Woe to the world that has lost its leader; woe to the ship that has lost its pilot!" (Bava Basra 91b), but Esau went about his evil business as usual, uninvolved with his family's bereavement.
...Edom. The word Edom means red. Esau was ruddy and sold his birthright for the sake of red food. Thus, the name Edom is a term of contempt (Rashbam).
According to Sforno, onlookers gave Esau this name in a derogatory manner, as if to say, "You are so divorced from normal human values, so consumed with your hunting and plunder, that you look at food and refer to it only by its color - 'pour the red stuff down my throat!' A person like you should be red, like the stew you wish to swallow!"
...I am going to die. Esau thought he would very likely die as a result of performing the sacrificial service improperly, since some such breaches are punishable by death (Rashi); or, as a hunter, he was subject to constant danger and could not look forward to a long life (Ramban).
...And lentil stew. The food Jacob was cooking is not identified until after the sale, to emphasize Esau's grossness: For what did he give up his precious birthright? - for a pot of beans! (R' Bachya).
...Thus, Esau spurned the birthright. This sums up the transaction. Esau was neither duped nor defrauded. He sold the birthright because he held it in contempt. It had no value to him when he was famished and it remained meaningless after he was gorged.
As noted above, by Rashi...Esau feared the birthright because he knew that shortcomings in the performance of the service could be punishable by death. If so, he had good reason to spurn the birthright. This, however, was no justification. A sincere person must be ready to serve God even though it may require inconvenience, hardship, or even danger. He must be ready to subject himself to humiliation and attack if necessary. That Esau rejected the birthright because it involved difficulty, therefore, is held against him (R' Moshe Feinstein).
...Esau marries. Rashi cites the Midrash: Esau is compared to a swine that, when it lies down, stretches out its cloven hoof as if to say, "See, I am a kosher animal!" Similarly, the princes of Esau rob and extort while they pretend to be honorable....So it was with Esau. Until he was forty, he had been living immorally, enticing married women from their husbands, but when he became forty, he said hypocritically that he would follow the example of his father who married at that age.
Unlike his father, however, Esau married Hittite women; his passions were unbridled and he chose to marry into a nation that matched his evil nature. With these marriages, Esau set the seal on his complete unfitness to carry on the mission of Abraham. In a home ruled by two Hittite women, the Abrahamitic ideal lies buried (R' Hirsch).
This chapter  is one of the most crucial and mystifying in the Torah - crucial because the decision about which son was to receive the Patriarchal blessings would determine which would be God's Chosen People, so that the eternal destinies of Jacob and Esau and their offspring were in the balance. And mystifying because it is hard to fathom how the righteous Isaac could be so adamant in choosing Esau and why Rebecca would resort to such a blatant deception to secure the blessings for Jacob. The commentators offer many interpretations; our commentary will draw upon several of those themes.
Isaac's decision to bless Esau. As the firstborn, Esau had the presumptive right to the blessings, and Isaac would not have had the right to deny them to him unless there was compelling cause. Clearly, despite Esau's marriage to Hittite women, Isaac was unaware of the degree of Esau's sinfulness, and Rebecca had not been authorized to tell him about the prophecy given here at the beginning of the Sidrah. Also, Isaac felt that it was Esau who needed blessings to arm him in his struggle against an inborn nature that tended toward bloodshed and other cardinal sins, whereas Jacob had the inner strength to grow and be holy without the assistance of the blessings.
It seems also...that Isaac planned to bestow two sets of blessings, one for Esau and one for Jacob, each set suited to the needs and nature of its intended recipient. He also felt, according to some, that the two brothers should both be parts of God's nation: Jacob with the higher calling of Torah scholarship and spiritual ascendancy, and Esau with material success that he would use to support and assist Jacob. Had Esau been worthy, this could have happened, just as the tribe of Zevulun undertook to engage in commerce to support the Torah scholarship of Issachar, and in the time of the Mishnah, the wealthy Azariah supported his scholarly brother Shimon. Rebecca, however, guided by Divine inspiration, knew that Esau was not entitled even to this.
...The voice is Jacob's voice, but the hands are Esau's hands. Isaac could not have meant the sound of the voice, since the sages comment that Jacob and Esau sounded so alike that Isaac could not tell them apart. Rather, his statement that the voice is Jacob's voice refers to Jacob's manner of speaking, inasmuch as Jacob spoke gently and invoked the name of Heaven (Rashi).
Alternatively, Jacob's power is in the voice that prays; as the Sages teach (Gittin 57b), whenever a prayer is effective, a descendant of Jacob must have been among those who prayed. Esau's power is in his murderous hands - the hands of the Roman Empire, Esau's descendants, which destroyed the Second Temple and exiled us from our land. Whenever an army is victorious, Esau's descendants must have had a hand in it. (ibid.).
...Then Isaac trembled. Isaac perceived the Gehinnom open beneath Esau (Rashi), which was in sharp contrast to the fragrance of Eden that had accompanied Jacob into Isaac's chamber.
The presence of Gehinnom with Esau made Isaac realize that he had been deceived all along - Esau was truly evil. This made Isaac fear that the vision of Gehinnom proved that he, Isaac, would be punished for having allowed himself to be so grievously misled (Pesikta d'Rav Kahana).
...Esau's hatred of Jacob. The eternal rivalry between the brothers became intensified with Esau's determination to kill Jacob when the opportune time came. It was a resolve that his descendants would attempt to carry out time after time to this very day, but, as the Pesach Haggadah declares, the Holy One, Blessed is He, rescues us from their hands.
Esau marries the daughter of Ishmael. When Esau saw that in his second blessing to Jacob, Isaac conferred upon him the Abrahamitic gift of Eretz Yisrael, he assumed that he had been stripped of this blessing because he had wed Hittite women. Therefore, he now took a daughter of Ishmael in the hope that he would ingratiate himself with Isaac and regain the blessing of the Land (Rashbam).
...This passage justifies the portrait of Esau as a selfish person, oblivious to all but his own desires. For twenty-three years he had permitted the behavior of his Hittite wives to cause anguish to his parents, yet it seems to have dawned on him only now. Instead of divorcing them, however, he merely took another unsuitable wife in addition to them. Thus, he proved that he had no feeling for the House of Abraham, and Rebecca's assessment of his complete unfitness for the future leadership of the nation was fully justified (R' Hirsch).
Esau advances to attack Jacob. After he had received the Patriarchal blessings form Isaac, Jacob had been sent away from home to protect him against Esau's threatened vengeance. Now, thirty-four years later - including fourteen years of study in the academy of Shem and Eber and twenty years with Laban - Esau's hatred remained implacable and, as Jacob advanced toward Eretz Yisrael with his family and entourage, Esau advanced toward him with an imposing, frightening army, determined to carry out his old, but still-fresh threat.
...The struggle with the angel. The confrontation between Jacob and a "man" was one of the cosmic events in Jewish history. The Rabbis explained that this man was the guardian angel of Esau (Rashi) in the guise of a man. The Sages teach that every nation has a heavenly power, an angel that guides its destiny on earth, and acts as an "intermediary," between the nation and God. Two nations, however, are unique: Israel and Esau. Israel needs no go-between; it is God's own people. And Jacob, because his image is engraved upon God's Throne of Glory, symbolizes man's highest potential. Esau's guardian angel is different from all the others, for just as Esau epitomizes evil, so his angel is the prime spiritual force of evil - Satan himself.
At Seir. Jacob had no intention of going as far as Seir - indeed he did not go there... The Sages explain that Jacob was alluding to the End of Days, when, as Obadiah (Obadiah 1:21) prophesied, Jacob's descendants will come to Mount Seir to render judgment against Esau's descendants (Rashi).
Apparently there was a coolness between Jacob and Esau at the parting. It was not accompanied by kissing, as was Jacob's departure from Laban (Haamek Davar).
The chronicles of Esau. It is fundamental to a proper understanding of the Scripture narratives that the Torah is not a history book and that whatever it records must have a halachic or moral purpose. Many important principles of halachah are derived from a seemingly superfluous word or even letter, or from allusions suggested by syntax or construction. Consequently, it is obvious that the Torah would not have devoted an entire chapter to Esau's genealogy unless it contained vital teachings. Indeed, a section of the Zohar, Idra Rabbah, is devoted to the mystical exposition of this chapter.
In. the literal sense of the verses and from the parallel genealogies in Chronicles, it becomes clear that many of Esau's descendants were products of incest and illegitimacy. According to Mizrachi, this is reason enough for the chapter. There are other lessons, as well, some of them halachic, which are discussed by the commentators. Furthermore, the Torah teaches us the honor that came to Esau because he was the offspring of Abraham.
He is Edom. The name - and the fact that it was used throughout his life - gives an insight into Esau's base character. The name was given him as a reference to his gluttony when he sold the birthright for nothing more than red beans. That greed and depraved set of values characterized him all through his life (Sforno). ...In this genealogy lay the roots of Edom, which evolved into Rome, the perpetual enemy of Israel (Lekach Tov).
...He is Esau, father of Edom. This is Esau, who remained in his wickedness from beginning to end, for he never repented (Megillah 11a).