Eight times the Torah tells us that Yosef cried (Bereishis 42:24 and 43:30 and 45:2, 14-15 [there Binyamin cried too] and 46:29 and 50:1,17). Why, of all the shevatim, is it Yosef who cried?
Previously, only Yaakov among the Avos is recorded as crying (Bereishis 29:11). It happened when he met Rochel and realized that they wouldn’t be buried together. And of the Imahos, Rochel famously cried for her children (Yirmiyahu 31:14). What is behind the tears of this unit of the family?
Rashi says that Yaakov, meeting Rochel for the first time, cried over his and Rochel’s future separation (after death). According to a Pesikta, though, Yaakov cried not “merely” because he and Rochel would not be buried together, but because of the reason for it: he was prophetically given a glimpse of the suffering of their future progeny, who on their road to galus would cry at Rochel’s kever — so purposefully placed there.
People generally cry when overwhelmed by their own difficulties, but the tears of Yaakov and Rochel were other-oriented. While both of them suffered in their lives — Yaakov from Esav and Lavan, and from the troubles of Dina and Yosef; Rochel from her father’s treachery, her childlessness and her shortened life — yet when they cried, what they cried over was the pain of their descendants.
And their children learned from them to cry for others. Yosef and Binyamin each suffered much travail, but when they were reunited at last, what they cried over were the churbanos of Mishkan Shiloh and
the Beis Hamikdash. Wherever Yosef’s tears are recorded, they are always a reaction of sensitivity to the plight of other people, not his own.
When Yosef was born, Yaakov could finally feel safe enough to return home, because “The House of Yaakov will be fire and the House of Yosef a flame and Esav as straw” (Ovadiah 1:18). Yaakov foresaw that it was Yosef who would overcome Esav. Why was Yosef specifically the nemesis of Esav?
Esav’s strength was kibbud av. The pesharah (compromise) between the twin brothers was that Yaakov would get Olam Haba and Esav would get Olam Hazeh. Therefore, since Esav belonged in and to olam hazeh, he honored his father, because one’s father gives a person a connection to Olam Hazeh (Maharal). (One’s rebbi gives him a connection to Olam Haba.)
Yosef was a paradigm of this same mitzvah of kibbud av. Knowing that his brothers hated him, he was still willing to go to them in Shechem, honoring his father Yaakov’s request even at the risk of his life; in addition, for the burial of Yaakov, Yosef occupied himself more than his brothers did with honoring his father. So, due to his kibbud av, Yosef also has a claim to Olam Hazeh; thus he will be the one to conquer Esav.
(Note: “Only Esther, who was orphaned of both her father and mother and therefore was never guilty of transgressing the mitzvah of kibbud av va’eim, was to fight Amalek, the grandson of Esav” (Rabbeinu Yonasan 3:7).
Returning to our question of why Yosef is recorded as crying, and not any of his brothers, Rabbi Elazar answered: When the wicked Esav lost the brachos to Yaakov, he shed three tears. Since Yosef was destined to be the one to defeat Esav, he was also the one to shed tears — in order to nullify those of Esav (Midrash Tanchuma).
Malbim quotes the Chavos Yair: It is well known that we are in galus because of the three tears Esav shed when he lost the brachos; we will be redeemed only when “those tears become batel (are nullified)” (Zohar). But rivers of tears have already been shed by Am Yisrael! How can those three tears not be nullified yet?
The answer is that tears cannot nullify tears unless they are different tears. When Jewish tears will be different from Esav’s, then they will finally cancel out Esav’s tears.
Why did Esav cry? Esav cried because he lost his father’s brachah of Olam Hazeh.
And why did Yosef cry? Yosef cried because he foresaw the churban of the Beis Hamikdash!
The problem is that we ourselves are crying over Olam Hazeh and our hardships in it. If we would cry, like Yosef, for what is really wrong — that the Shechinah is in galus and we cannot have atonement through korbanos — then Esav’s tears will finally be nullified. Our tears, if they will be shed for purely spiritual goals like Yosef’s, can nullify Esav’s olam haze’dige tears.
This is the meaning of the passuk “With crying they will come and with pleading I will lead them…because I [Hashem] will be a father to Yisrael, and Efraim [all of Israel] is my first-born son” (Yirmiyahu 31:8).