Vayeishev

Rashi describes the similarities in life experiences between Yaakov and Yosef. Interestingly, there are also quite a few similarities between Yaakov and Yehudah: both left their brother(s) and lived apart from them for a long time; both played an integral role in fooling their father - Yaakov with the Bircos Yitzchak and Yehuda with the Ketoness of Yosef; both had a life altering event at a well/pit - Yaakov in his initial meeting with Rachel and Yehuda during the sale of Yosef; both began a crucial lineage in Jewish history - Yaakov with the Shevatim and Yehuda with Malchus Yisrael; both began that lineage by being duped by their respective wives - Yaakov with Leah and Yehuda with Tamar; and both struggled personally with the establishment of their respective legacies.
There is a key distinction between Yaakov and Yehuda. It is a lesson that Yaakov learned early but had to reinvigorate after some time, while Yehuda took more time to learn it initially.
The Gemara tells us that if it rains on Sukkos and we are forced to leave the Sukkah, we should exit with bowed heads for this is a Divine rebuke. The Gemara compares this to a servant serving his master wine and the master throws the water back in the servant's face. The example of the Gemara is puzzling. Why doesn''t the Gemara simply state that the master throws the WINE back at the servant? What is the water doing here?
We know that in the time of the Gemara wine could not be drunk raw. It was too strong. Therefore, it needed to be watered down. The water acted as a sweetener and softener of the harshness of the wine. The analogy of the Gemara is explained bearing this in mind. We have just finished the Yom Hadin of Yom Kippur. Sukkos introduces the Middas Harachamim that sweetens and softens the Middas Hadin of Yom Kippur. Sukkos symbolizes the Mercy of Hashem, His protection of us in everything we do. When we are forced to exit the Sukkah it is as if the sweetener, the softener, is being taken from us.
Yaakov and Yehuda both had life altering events at a pit/well. Yaakov, though, used the water - Vayashk es tzon Lavan achi imo. Yaakov performed acts of chesed - symbolized by the water. Chazal tell us that the brothers judged Yosef in a beis din. The beis din decided that Yosef was guilty so they threw him into the pit. Yehuda had the opportunity and authority to save Yosef but he chose not to. That is the meaning of v'habor reik, ein bo mayim. The Gemara asks: isn't it obvious that if the pit is empty that it has no water? The Gemara answers that its emptiness was of water but it contained snakes and scorpians. The Pasuk is emphasizing mayim ein bo. There was no water. There was nothing to sweeten the judgment. There was no tool utilized to deliver compassion, concern and sensitivity. Yaakov's actions at the well were those of kindness, concern, and compassion. Yehuda's actions were those of judgment, empty of compassion.
Yaakov and Yehuda created essential Jewish legacies. Yet, neither of these legacies could be fully established until the lesson of compassion and concern for every person was crystallized. Although Yaakov learned this lesson early, twenty years of association with Lavan dulled these ideals. Yaakov himself realized this after the birth of Yosef. Prior to the conception of Yosef, Yaakov acted with a lack of sensitivity. Rachel, pained by her barren existence, asks Yaakov to pray on her behalf. Yaakov answers with rebuke, explaining that her situation is beyond his control. After Yosef is born, Yaakov recognizes that his actions personified the dulling of his sensitivities. Lavan was, indeed, influencing him negatively. It was time to head home to envelop himself in the Kedusha of the home of Yitzchak and Rivka, to inhale the Kedusha of Eretz Yisrael. It is only upon his return to this atmosphere that his legacy can be completed with the birth of the twelfth tribe - Binyamin. Once compassion and sensitivity are restored, the lineage of the Jewish people can be established.
Yehuda took longer to learn the lesson. Eventually, he did. Yehuda's leadership ebbs and flows but does not get fully established until he accpets full responsibility for the safety of Binyamin. Once his compassion and concern for every individual is crystallized with this act, Yehuda can become the leader of his family and begin the line of Malchus Yisrael. Accepting responsibility, displaying compassion and sensitivity for every member of Klal Yisrael is essential for its establishment, its existence and, ultimately, its redemption.