Why did Moshe mention the names of the last five tribes (with the exception of Yisachar), twice?
Rashi #1 (citing Bava Kama 92a): He repeated the names of Zevulun, Gad, 1 Dan, Naftali and Asher in order to strengthen them, because they were naturally weaker than the other tribes. 2
Rashi #2 (Bereishis 47:2, citing Bereishis Rabah 95:4): He doubled their names, and also Yehudah, because they were the strongest.
We find that B'nei Gad were strong! Refer to 33:20:2:1, 20:20:3:1, and to Rashi on Pasuk 21, DH 'Roshei Am'. Perhaps this was due to Moshe's Brachah; it helped them more than the others, for they endeared Moshe more (refer to 33:21:2:1), and they were dedicated to fulfilling their stipulation to fight valiantly (they promised to go "Lifnei Bnei Yisrael", i.e. at the front of the troops (Bamidbar 32:17, Rashi).
Why did Moshe precede Zevulun's blessing to that of Yisachar?
Rashi: Because Zevulun and Yisachar entered into a partnership, whereby the former, who dwelt by the seashore, would travel to other lands in their ships where they would indulge in business. With half the proceeds they would sustain Yisachar, who would sit and study Torah. 1 Since the Torah of Yisachar was only possible through the efforts of Zevulun, Moshe gave Zevulun precedence.
The reward for which they would share with Zevulun.
What did Moshe mean when he said "S'mach Zevulun be'Tzeisecha"?
Rashi: He was blessing Zevulun that they should succeed in their business endeavors. 1
Targum Onkelos: 'Rejoice, Zevulun, when you go out to wage war against your enemies!'''
Alshich: Other merchants are not happy until they return, for they do not know if they will profit or lose. Zevulun are happy from the beginning because they enable Yisachar to learn.
Da'as Zekenim, Rosh: They went to Tzur, Tzidon and far places.
What did Moshe mean when he said "ve'Yisachar be'Ohalecha"?
Rashi #1: He was blessing the two hundred heads of Sanhedrin of Yisachar 1
Rashi: See Divrei Hayamim 1, 12:33.
QUESTIONS ON RASHI
Rashi writes that Moshe doubled the names of the weak Shevatim. In Bereishis (47:2), Rashi cites an opinion that he doubled the strong ones. In Bamidbar (32:17), he wrote that Reuven and Gad were both strong. This is unlike either opinion!
Perhaps Moshe repeated names of Shevatim prone to be weak because they come from a weaker son of Yakov, even if in Moshe's time, the men of the Shevet were strong. (PF)
