What is the connection between the development of Yaakov's family discussed here, and the development of Esav's family at the end of Vayishlach (Bereishis 36)?
Rashi #1: After glossing over Esav's family, which the Torah does not consider important, 1 it goes into great detail with regard to that of Yaakov, which it considers important. 2
Rashi #2: When Yaakov saw all the chiefs that emerged from Esav, he was concerned as to how he would be able to conquer all of them. The answer lies in the following Pasuk, "These are the generations of Yaakov, Yosef... " (37:2), who was the nemesis of Esav. 3
Ramban: To teach us that Esav's descendants moved to a land of their own, while Yaakov opted to live in a land where his father sojourned but that did not belong to him, in fulfillment of the decree that was issued to Avraham - that they would be "strangers in a land that was not theirs" (Bereishis 15:13). 4
Rashbam: To teach us that Esav moved away to make way for Yaakov, who lived with his father in the land of his fathers, because he would receive the birthright as the Bechor.
Oznayim la'Torah #1: As long as Yaakov was living in Padan Aram, Esav had the edge over him in two regards - 1. Kibud Av va'Em; 2. Yishuv Eretz Yisrael. Now that Esav had moved to Har Se'ir, giving up both advantages, Yaakov arrived in Cana'an and lived with his father, thereby fulfilling both Mitzvos and reversing the roles in his favor. 5
Oznayim la'Torah #2: The Torah is pointing out why Esav merited having a national heritage and a king, whereas it would be eight generations before Yisrael would be able to do so. This is because Esav's children, despite the fact that they descended from different mothers, lived in harmony. Thus, they were able to appoint a king over the entire tribe. But how could Yisrael, who could not get along with each other, possibly do the same? See how, the moment that one of them insinuated in a dream that he would become king, all the brothers turned against him! 6
In the same way as it did with the ten generations between Adam and Noach, and the ten generations between Noach and Avraham.
Rashi: This can be compared to a person who is searching for a jewel that he dropped in the sand. He quickly sifts through the sand until he finds the jewel, at which point he throws out the pebbles and takes the jewel.
Refer to 30:25:1:1 and notes. Rashi continues - This too, can be compared to a blacksmith, into whose shop entered a camel laden with flax. When he wondered as to where they would place all that flax, one smart fellow suggested that one spark from his bellows would quickly solve the problem.
See also Oznayim la'Torah DH "va'Yeshev Yaakov," 1, 2.
Oznayim la'Torah: And this will also explain why the Parshah begins with the episode of the sale of Yosef.
What are the implications of "va'Yeshev Yaakov, etc."?
Rashi (to 37:2) and Targum Yonasan: It implies that Yaakov intended to settle down tranquilly, 1 and it is because he did so that the incident with Yosef was sprung upon him. 2
Rosh: "[Va']Yeshev" is an acronym for the afflictions that befell him, i.e. [the temporary loss of] Yosef, Shimon, and Binyamin.
Sanhedrin 106b: Whenever the Torah uses the term "va'Yeshev," it is an expression of pain. 3
Moshav Zekenim: As opposed to his father Yitzchak, who lived there amidst fear (as the Torah hints in the word "b'Eretz Megurei Aviv"). Yaakov wanted to be 'Yoshev' (to settle), tranquilly, unlike the decree "Ger Yihyeh Zar'acha" (15:13). (But the Torah says "va'Yeshev" also regarding Avraham (13:18) and Yitzchak (25:11), and Chazal did not expound so about them! - PF)
Rashi (to 37:2): When Tzadikim seek tranquility, Hashem reminds them that their reward is reserved for them in Olam ha'Ba and that they should not be looking for it in this world as well. Hadar Zekenim (citing Midrash Tanchuma) - Hashem said, My Simchah (Chanukas ha'Mishkan) did not last long [before Nadav and Avihu died] - Do you want extended Simchah?!
Maharal (Derech Chayim to Avos 2:2, p. 71): When a person is toiling, he can reach his state of perfection; he will not revert to a state of deficiency. When he is at rest, however - as if he has already reached his goal - that is when he might fall short.
What is the direct connection between Yaakov's intention to settle down tranquilly (see Rashi), and the fact that the incident with Yosef was sprung upon him?
Oznayim la'Torah 1 : As long as the Avos sojourned in the Land, 2 their years of Geirus were included in the 400 years of Galus decreed upon Avraham's children. 3 The moment however, that Yaakov decided to settle in the Land, the time had come to go down to Egypt and suffer slavery 4 (Galus Mitzrayim). The sale of Yosef served as the prelude to Galus Mitzrayim, as well as ensuring that Yaakov would go down to Egypt honorably, and not in chains.
Refer to Bereishis 15:13:2:1.
Oznayim la'Torah: See for example Bereishis 21:34.
As Hashem said to Avraham, "Ki Ger Yihyeh Zar'acha..." (15:13).
As Hashem said to Avraham, "va'Avadum v'Inu Osam... " (ibid).
Why does the Torah insert both "b'Eretz Megurei Aviv" and "b'Eretz Kena'an"?
Riva, Moshav Zekenim: "B'Eretz Megurei Aviv" could refer to Avraham [who initially lived in Aram (Naharayim); as grandsons are like sons]. Had it said only "b'Eretz Kena'an," we would not know in which town.
Ohr ha'Chayim: Even though Esav took his inheritance, and even though Hashem promised the Land to Yaakov, Yaakov lived in it like a stranger, and treated it like Eretz Kena'an (not like his own land).
Ha'amek Davar: It explains why Yaakov was particular to live here, even though the Berachah of [receiving] the Land would not apply to until after exile. His fathers already implanted Kedushah in the Land, and there is a Mitzvah of dwelling in Eretz Kena'an, and it is most conducive to Taharas ha'Kodesh.
Why must the Torah say that he lived "b'Eretz Megurei Aviv, b'Eretz Kena'an"? It already said that he went to Chevron (35:27), and did not say that he left!
Refer to 37:1:151:2 and 37:1:151:3 .
Malbim: The Torah explains that without special Hashgachah (which brought about the famine), Yaakov would never have gone to Egypt, since it was the land where his father lived, and because Eretz Cana'an is conducive to Kedushah.
QUESTIONS ON RASHI
Rashi writes: "After the Torah wrote briefly about Esav's family and [place of] residence (Bereishis 36) ... it tells about Yaakov's residence and offspring at length." How does Rashi know to derive anything from the placement of this Parshah?
Gur Aryeh: Chronologically, "va'Yeshev Yaakov" should have immediately followed his return to Yitzchak (35:27). Instead, the Torah inserts Esav's offspring in the middle (Bereishis 36). Therefore, Rashi derives an interpretation from the adjacent sections.
Rashi writes: "Esav and his offspring were not deemed treasured or important (Sefunim va'Chashuvim)...." Why the doubled expression?
Gur Aryeh: They were not valued - so the Torah does not dwell on their settling [in Se'ir]. They were unimportant - so the Torah does not go into detail of their wars (they fought to conquer it).
Rashi writes: "... It is comparable to a pearl that fell into the sand; one feels and sifts through the sand until he finds the pearl. Upon finding it, he throws away the pebbles and keeps [only] the pearl." But in the previous two Parshiyos (Vayeitzei, Vayishlach), the Torah does tell the story of Yaakov - without telling us about Esav first?
Gur Aryeh #1: In the parable, the pearl became mixed with the sand. Brothers usually dwell together; it is only once Yaakov returns home (to Esav's proximity) that the Torah must tell about Esav first, in order to separate them by dismissing Esav.
Gur Aryeh #2: Had Esav remained with Yaakov, he would have inherited Eretz Yisrael along with him by default. The Torah is telling us that Esav took the Land of Se'ir instead, leaving Eretz Yisrael to Yaakov.
Rashi writes: "... This is comparable to a pearl that fell into the sand... he throws away the pebbles, and keeps [only] the pearl." The parable changes from sand to pebbles! What does each represent?
Gur Aryeh: A pearl cannot get lost among pebbles, only among sand. The sand represents Esav's dwellings while he was still in proximity to Yaakov (which the Torah sifts through briefly). The pebbles are the other events in Esav's life, which are worthless, and the Torah does not deal with at all. 1
Gur Aryeh seems to mean that regarding their settlement, Yaakov and Esav had something in common (i.e. they both had potential to inherit the Land). They are compared to the sand and the pearl; the Torah speaks briefly of Esav's settlement until reaching the topic of Yaakov. In other matters, Esav has nothing in common with Yaakov. They are compared to the pebbles and the pearl, and the Torah does not elaborate about Esav's life. (EK)
Rashi writes (to 37:2) that Yaakov intended to settle down tranquilly. Why did Yaakov want this specifically now?
Oznayim la'Torah: Because until now, many troubles had befallen him, either because he had failed to fulfill the vow that he made on his journey to Charan, or because of his failure to fulfill the Mitzvah of Kibud Av (and Yishuv Eretz Yisrael). 1 Now however, that he had made up for these deficiencies, he thought that it would be in order to settle down.
Rashi writes (to 37:2) that Yaakov intended to settle down tranquilly - Hashem said, is it not enough for them that their reward is reserved for them in Olam ha'Ba...?! Why is it sinful to live tranquilly in this world?
Oznayim la'Torah (citing his son, R. Elchanan): It is not sinful to live tranquilly in this world. 1 What is sinful is for Tzadikim to request to live tranquilly in this world; because by so doing, they are attaching undue importance to this passing world.
Oznayim la'Torah: Indeed, the Gemara in a number of places talks about inheriting this world and the next - See for example, Berachos 16b.