Although Yaakov and Eisav were twins, they had little in common. Their goals and values couldn’t have been farther apart. The Alter of Kelm explains that the tremendous gap between them lies in one fundamental difference. In contrast to other animals which are born already capable of sustaining themselves, human babies are born needing a great deal of care. The Alter explains that God made it this way is so that they will be prepared to learn from their parents and elders.
The name Eisav (עשו) is related to the word עשוי – made. Rashi writes that Eisav was born with hair, much like an older child. Eisav was born viewing himself as a completed package, and he had no interest in learning from others. This stands in stark contrast to Yaakov. The name Yaakov is associated with the word Ekev – heel. Yaakov viewed himself as being at the bottom of his life’s work. Additionally, Yaakov’s name is expressed in the future tense, as he understood that he wasn’t a finished product. He constantly had to work to maximize his potential.
In his dream in next week’s parsha (28:12), he sees a ladder which reaches all the way to Heaven. This is the potential of a person who constantly seeks to improve himself. At the age of 63, Yaakov opted to spend an additional 14 years studying in yeshiva before seeking a wife (Rashi 28:9). Later, as he traveled with his family to Egypt to be reunited with Yosef at the advanced age of 130, his first priority was to send Yehudah ahead to establish a yeshiva so that he wouldn’t miss out on even one day of his studies (Rashi 46:28).
The verse in Hoshea states (11:1) כי נער ישראל ואהבהו – God declares His love for the Jewish people because no matter how old and wise we grow, we still view themselves as a נער – an adolescent who has much to learn. The greatest level a yeshiva student strives to attain is that of תלמיד חכם – Torah scholar. Even a sage who reaches such a level is still referred to as a תלמיד, a student with much still to learn.
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If Eisav hated Yaakov for taking the blessings from their father Yitzhak and wanted to kill him to get revenge, why did he plan to wait to do so until after Yitzhak would die (27:41) instead of attempting to do so immediately?
The Targum Yonason ben Uziel writes that Eisav was afraid that if he killed Yaakov while Yitzhak was still alive, Yitzhak may have another child with whom he would have to share his inheritance, just as Adam had another child after Kayin killed Hevel.
Alternatively, the Kli Yakar explains that Eisav recognized that Yaakov’s Torah study would protect him from being killed. Yitzhak had blessed Eisav (27:40) that he would only rise above Yaakov whenever Yaakov declined spiritually by not studying Torah. Since a mourner is forbidden to study Torah, Eisav reasoned that this would be the ideal time to kill Yaakov. In fact, the Talmud (Brachos 44b) teaches that a mourner needs extra guarding because he is lacking the traditional protection offered by Torah study.
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When Eisav returned from hunting in the field, he asked Yaakov to give him some of the red lentil stew that he was cooking (25:30). Why did Yaakov give him bread and stew to eat (25:34) when Eisav had requested only the stew?
Maharam Schiff (end of Bava Kama) answers that Yaakov wanted to purchase the birthright from Eisav with the food that he gave him, but he was concerned that they monetary value of the stew may have been less than one perutah, which is the minimum amount required to legally effect a monetary transaction, so he added the bread to ensure that the food items would be worth more than one perutah.
Alternatively, Rav Yehoshua Leib Diskin cites the ruling of the Talmud (Shavuos 26a) that an oath made under duress is not legally binding. He explains that when Yaakov was planning to have Eisav swear to uphold the sale of the birthright, but when Eisav remarked (25:32) that he was so exhausted and sick that he thought he may die, Yaakov was concerned that such an oath would be considered to have been made under duress and would not be binding, so he first gave Eisav bread to eat to restore his health so that the oath that he would make when selling the birthright for the lentil stew would be legally binding.
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Rashi writes (27:33) that when Eisav entered the room to receive his father’s blessings, Yitzhak began to tremble in fear because he saw Gehinnom (purgatory) open beneath Eisav, and this stood in sharp contrast to the fragrant aroma of Gan Eden which accompanied Yaakov when he entered the room (Rashi 27:27). As Eisav’s wickedness had been concealed from his father until now, what suddenly changed which caused Yitzhak to recognize the truth and see Gehinnom open underneath him?
Rav Meir Shapiro (Imrei Daas) writes that each mitzvah that a person does creates a spiritual light, and each of the 613 mitzvot has its own unique light. Although Yaakov was certainly much more righteous than Eisav, there was one mitzvah that Eisav performed with more dedication than Yaakov: honoring his parents. As a result, whenever Yitzhak interacted with his sons, he noticed that Yaakov had many more spiritual lights than Eisav due to the fact that he excelled in his performance of 612 of the mitzvot, but he was also aware that Eisav possessed one unique light that Yaakov was missing. This caused Yitzhak to conclude that although Yaakov may have been more righteous, there was also at least one mitzvah in which Eisav was superior to him, and this blinded Yitzhak to recognizing Eisav’s true colors.
This all changed when Yaakov risked being cursed by his father in order to fulfill his mother’s instructions. This self-sacrifice for the mitzvah of honoring his mother created a spiritual light equal to that which had always accompanied Eisav. When Eisav entered the room, Yitzhak noticed that he no longer had any unique spiritual light, which enabled him to finally recognize the truth and see Gehinnom open beneath him.