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Is there any Torah commentary that addresses how Yaakov’s ten sons could have been so cold, heartless and cruel, to cause Yaakov’s intense, 22-year, unconsolable grief over Yosef’s death? What child puts a parent through such hell?

Bereishis / VaYeshev 37:35: All his sons "and all his daughters" tried to console him, but he refused to be comforted. He said, "I will go down to the grave mourning for my son." Rashi says that each of Yaakov’s sons had twin sisters. Yaakov actually had 14 daughters: one daughter was born with each of his sons – except for Binyamin – making 11 and then there was Dinah, and Binyamin’s two twin sisters. They subsequently died by the time Yaakov entered Egypt, as evidenced by the fact that they were not counted in VaYigash as part of the 70 who came to Egypt. Yaakov was therefore a bereaved parent 14 times over for the deaths of his 14 daughters. This makes the brothers' causing their (bereaved) father Yaakov to grieve even worse. What child puts a bereaved parent through such hell - again?

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The Midrash says it was God’s plan:

[The brothers] decided: “Let us make a vow to excommunicate any one of us who tells our father, Jacob, that Joseph is alive.” Judah said: “Reuben is not here, and a vow of excommunication cannot be executed unless ten witnesses are present.” So what did they do? They included the Holy One, blessed be He, in their pact of excommunication [and God agreed]. [Midrash Tanchuma, Vayeshev 2:5]

So God agreed that Jacob must not be told, because it suited His plan.

Another Midrash tells us that Jacob’s father Isaac knew prophetically that Joseph was alive, but said nothing. The Torah says:

And all of Jacob's sons and all his daughters rose up to comfort him [for the loss of Joseph]. But he refused to be comforted and said: “No, I will go down to the grave mourning for my son.” And his father wept for him. [Gen. 37:35]

This does not refer to Jacob weeping for Joseph, but Isaac weeping because of Jacob's deep pain... And why did Isaac not reveal to Jacob that Joseph was alive? Because Isaac thought: If the Holy One, blessed be He, has not revealed it to him, who am I to reveal it to him? [Genesis Rabbah 84:21]

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The entire story is one of extreme action. How could they put Yaakov through such grief? Well, how could they plot to kill Yosef, and then carry out a plan to sell him into slavery? This is part of the extreme action that they took, and from the perspective of the story itself, one is not more surprising then the other. They wouldn't sell him only to immediately get caught.

In terms of the premise of the question, that Yaakov had many daughters who died. Yes, this is one of the two positions in the Rashi you cite, from Rabbi Yehuda (the other position, of Rabbi Nechemiah, being that these were daughters-in-law). And you could bolster your follow-up deduction that they died by pointing to the explicit Rashi in Vagiyash, counting the 66 souls. There, Rashi explains according to each position. If like Rabbi Yehuda, then since we are counting women (Serach and Yocheved), then these twin sisters must have died. And if these were daughters-in-law before, then they didn't die, but were simply not counted here since we aren't counting wives. (We don't know that Rabbi Yehuda himself would have agreed with this particular assumption that this is why the twin sisters weren't listed; for instance, it could be because they were also wives.)

With this assumption firmly established, you write:

This makes the brothers' causing their (bereaved) father Yaakov to grieve even worse. What child puts a bereaved parent through such hell - again?

However, the lie to Yaakov was earlier, before the death of these twin sisters. Otherwise, how could the daughters have tried to console Yaakov at the time?! Your question might instead be how they could have continued to remain silent about it...

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