1) VaYeishev Yaakov (37:1) - Rashi notes that Yaakov wanted to sit B’Shalva – that’s why the trouble started with Yosef. Rav Moshe Feinstein ztl. noted that the Shalva he sought was from Chinuch – assuming that his children had all been brought up ok and now he was ready for a break. Hashem told him that there is no break from child rearing.
2) 2 dreams of Yosef – Maran HaRav Schachter Shlita quoted the great Rav Aharon Soloveitchik ztl who once noted that the brothers had been upset with Yosef’s second dream. Yaakov too, had dreamed but his dream was about spirituality. Yosef had had two dreams – one spiritual and the other physical. How could he have been so physically oriented? Rav Aharon answered that the dream of Yaakov was already broken into two – it was a ladder on the ground and its top reached the heavens. Yosef just focused it forward into two dreams. Maran HaRav Schachter shlita pointed out that the same is true about Halacha and Aggada. One focuses on how we act, the other on how we think. However, both come from the same source.
3) And they hated him (37:5-11) – The claims of Yosef’s brothers against Yosef are based on deep Halachic foundations. Still, the Torah seems to categorize the differences in simple terms of “hate” and “jealousy.” Why would the Torah imply that the tribes would alter Jewish destiny over a simple spat? Rav Shmuel Rozovsky ztl. explains that Hashem is the one who checks the insides and outsides of every person. He is able to inspect what is at the core of people’s choices in life. From the heavenly perspective, the emotions played a not-insignificant role in the decision making of the brothers. Therefore the emotions get top billing from Hashem in the Torah.
4) “And he said here I am (37:13) – Rashi notes that this highlights his humility and Zrizus. Harav Koppelman of Lucerne ztl. Pointed out that the recitation of Heneni prior to knowing the details of the mission is a display of Bittul and dedication to the mission of one’s friend or Hashem.
5) And the pit was empty, it had no water (37:24) – The midrash comments that the pit of Yaakov was empty since the children of Yaakov did not study Torah. Rav Chaim Yaakov Goldvicht ztl. pointed out that the Midrash is highlighting a critical idea. When someone does not study Torah sufficiently, that individual does not value the purpose of life. For if s/he did , s/he would be dedicated to furthering himself or herself. Accordingly, it is not wise to travel with such a person as it could be dangerous to travel with someone who does not value life himself. S/he is quick to choose death since s/he has already selected it insofar as his own life itself goes. Yosef’s brothers were quick to choose death, says Rav Goldvicht due to their lack of complete Torah study which would have strengthened the value of life in their eyes and minds.
6) Recognize to the one who owns these things am I bearing a child (38:25) – The commentaries abound as to why Tamar waited so long to identify her liaison with Yehuda. Why did she not tell him right away that she was pregnant and with HIS child? Rav Moshe Wolfson Shlita explains that when a person is given an initial moment, his first instinct is often guided by the Yetzer Hara which has a head start in developing into human instinct. Man’s first thought is to protect his own reputation right away. Having time for Yishuv HaDaas brings about better results as the person has a chance to consider his responsibilities – not only his reputation.
7) And it was on that day that he came to do his work (39:11) – The Yalkut Shimoni suggests that the day was Shabbos. If so, what was the work he was going to do? The Yalkut answers that he was going to study the laws of Shabbos that he learned with his father. In his final public address in 5754, Rav Shach ztl noted that the commitment to Halacha study and practice protected Yosef from outside forces as it provided a link to a past that he believed in . The same must be our mission as well if authentic Judaism is to survive.
8) Haftorah: For three transgressions of Israel but for 4 I will not pardon them. For selling a righteous man for money and a poor man for shoes (Amos 2:6) – The connection to the Parsha seems to be abundantly clearly related to the sale of Yosef which is described in Piyut as being for a pair of shoes. But Rav Soloveitchik ztl. noted a deeper theme that extended throughout the haftorah which goes on to deplore corruption and exploitation. Rav Soloveitchik explains that in the same way that Yosef’s brothers tried to stifle his dreams, Amos’s contemporaries tried to stifle his prophesy. Both point out that stifling is a dangerous process that cannot be easily stopped.