What does "Yamim Rabim" comprise? What is the significance of that time period?
Rashi: It comprises the 22-year period that Yosef was separated from him, 1 corresponding to the 22 years that he stayed away from his parents - 20 years with Lavan, 2 plus two years on the journey home (eighteen months in Sukos, and six in Beis-El).
From when Yosef was age 17 'til 30 (when he stood before Pharaoh), plus the seven years of plenty and two years of famine, after which Yaakov went down to Egypt.
That is why Yaakov added the word "Li" when he said to Lavan, "Zeh Li Esrim Shanah b'Veisecha" (31:41) - 'The 20 years that I spent with you will rebound upon me' (in that he was destined to lose Yosef because of them).
Why does the Torah state that Yaakov rent "Simlosav," whereas in Pasuk 37:29, in connection with Reuven, it uses the word "Begadav"?
Oznayim la'Torah: 'Simlah' is, by definition, an important garment, one that Yaakov, the head of the family, would have worn, but not Reuven. Alternatively, Reuven wore sackcloth 1 because he was doing Teshuvah.
Ha'amek Davar: Yaakov tore Simlosav, i.e. all his important garments, even what he was not wearing at the time. We find that R. Yochanan tore 13 garments due to R. Chanina's death (Moed Katan 24a)! Reuven was in the field; he tore only the garments he was wearing then.
What exactly did Yaakov place on his loins, and why?
Seforno: A sort of woven belt made of hemp, the material from which, due to its thickness, one manufactures sacks. Malbim - He tore his clothes due to mourning, and wore sackcloth for Teshuvah. 1
Malbim: If one sent a Shali'ach in a dangerous place, and he was killed, he must repent (Maharil. Also others cite this in the name of Maharil, based on Teshuvas Chasam Sofer OC 177 or 184. The correct text should say Mahariyo (Mahari Veil, 125). - PF)
What is the symbolism behind Yaakov donning sackcloth?
Maharal (Ohr Chadash to Esther 4:1, p. 145): Sackcloth clings to the flesh, just as tragedies seemed to cling to Yaakov (more so than Avraham and Yitzchak).
What is the symbolism behind Yosef's unknown whereabouts?
Maharal (Netzach Yisrael Ch. 34): This would be a Siman for Yosef's descendants, as head of the ten tribes; they would be separated from their brethren to places unknown, until Hashem shall decide to reunite them amid much weeping. 1
Maharal: As the Navi describes in Yirmiyahu 31:8.
QUESTIONS ON RASHI
Rashi writes: "'Many days' - 22 years ... corresponding to the 22 years that Yaakov had not fulfilled Kibud Av v'Em." Why interpret this way?
Gur Aryeh: Why must the Torah describe the years as "many"? We can calculate them ourselves using the verses that Rashi cites! Rashi explains how they correspond to the years spent in Lavan's house, which Yaakov had originally perceived as [merely] "a few days" (Bereishis 29:20).
