Why was Yaakov afraid that Binyamin would die on the way?
Rashi: Because the Satan prosecutes at a time of danger. 1
Refer to 44:29:151:1, refer to 42:36:151:3.
Malbim: Yosef was lost, even though he left in a way that does not arouse danger. Binyamin is in more danger, for (a) you will take him [forcibly; he does not go on his own]; (b) "Gam Es Zeh" (after his Mazal became bad); (c) he goes "me'Im Panai (far away)," whereas Yosef went "me'Iti (nearby)" (44:28); (d) this path (to Egypt) is prone to more dangers, not only beasts.
And traveling is always a source of danger (Yerushalmi Berachos, 4:4). Gur Aryeh - Tragedy might occur even at home, yet Yaakov was not afraid of that. That is because a journey is a time of danger - and Rachel, Binyamin's mother, had died while on the road.
How would an accident that would befall Binyamin, bring Yaakov down to the grave in grief?
Rashi: Binyamin was his consolation on the loss of his mother (Rachel) and his brother. If he were to die, it would be as if he lost all three in one day.
Ramban: If something were to happen to Binyamin as happened to his brother, he would die of a broken heart.
Seforno: Their father had only given permission to take Binyamin on account of the famine. Otherwise he made it clear, that if they fail to return him, he will drop dead.
Why did he say "me'Im Panai"?
Malbim: He goes far away - unlike Yosef, who went "me'Iti (nearby)" (44:28).
Ha'amek Davar: You remove him from my supervision and strong guarding over him. This obligates them to guard him extra, like when he was in front of his father. If not, "v'Karahu Ason!"
One should not 'open for the Satan (i.e. suggest tragedies).' Why did Yaakov and Yehudah suggest harm befalling Binyamin?
Moshav Zekenim: Since he already experienced loss through sending Yosef and Shimon, if he sends Binyamin, surely harm will befall him, for two occurrences make a Chazakah! 1
Refer to 42:36:151:3.
This is unlike he brought above from Chulin 95b! Refer to 42:36:151:1.
QUESTIONS ON RASHI
Rashi writes: "As long as Binyamin remains with me, I comfort myself over [the loss of [his mother and brother]. Why explain the verse this way?
Mizrachi: Yaakov said, "My wife (Ishti) bore me two [sons]" (44:27); rather than saying directly, 'Rachel bore me two sons.' He expressed how dear Rachel had been to him as a wife, and how Binyamin's presence comforted him over that loss.
Gur Aryeh #1: This verse concludes, "you would bring me down to the grave in bad [condition] (b'Ra'ah 1 )." Lack of a wife is called "Lo Tov" (Bereishis 2:18; Yevamos 62b) - which is equivalent to 'Ra.' Yaakov was expressing the void that he felt, and how Binyamin's presence comforted him over that loss.
Gur Aryeh #2: Yaakov said, "If you take [Binyamin away] ... you would bring me down to the grave in bad [condition]." Wasn't Yaakov already in a bad state, due to his many troubles? Rather, Binyamin's presence comforted him.
Gur Aryeh: As opposed to the term 'b'Yagon,' 'in sorrow;' as in 44:31.
