What did Yehudah mean when he told Yosef that the brothers "would be bringing Yaakov's old age down to the grave"?
Ramban #1 (to 44:19): This was a diplomatic way of saying that Yosef will have caused Yaakov's death, 1 since he only sent him on account of the famine, and if they would return without him, he would die of a broken heart.
Ramban #2 (to 44:32): He meant literally, that, since I had guaranteed Binyamin's return, we would be held responsible for our father's death, if we return without him.
Seforno (to 44:30): Since Yaakov warned them not to return without Binyamin, if Yehudah were to return without him, he would ascribe it, not to some natural occurrence, but to the work of their hands.
Why does it say "Ki Ein ha'Na'ar"? The preceding verse already said, "veha'Na'ar Einenu Itanu" (44:30)!
Malbim: "Veha'Na'ar Einenu Itanu, v'Nafsho Keshurah b'Nafsho" (44:30) is a Ma'amar Musgar (parenthetical comment). Even when the youth is not with us, rather, with his father, his soul is tied to him. All the more so the love will increase when he is separated from him!
Ha'amek Davar: "Va'Mes" refers to Binyamin. When Yaakov sees that Binyamin is not with us, Yaakov will assume that Binyamin has died. 1
But refer to 44:31:152:1*.
Will Yaakov die immediately when he sees that Binyamin is not with them?
Malbim: Yes. We will not have time to explain that Binyamin is with the ruler in Egypt 1 !
Some say that Binyamin did not return with the brothers to Eretz Kena'an (refer to 43:9:151:3; 45:26:151:1*; 46:26:1:5); and Yaakov was fine! And in any case, if they sent one brother in front, he could explain that Binyamin is alive! (PF)
Does the possibility lest Yaakov die change Binyamin's final verdict?
Malbim (to 44:19, citing Akeidah): Yes. We do not punish a sinner if this will cause harm to others. 1
Beis Din executes without concern for harm to others! A Shogeg murderer is exiled, and his Rebbi is exiled with him (Makos 10a)! Perhaps Yehudah discusses a king, who can override Torah law due to such concerns, e.g. David's ruling to exempt the man who [the Ishah Chachamah said] killed his brother (Shmuel II 14:11). (PF)
Why does it say "b'Yagon, She'olah"? Verse 44:29 said "b'Ra'ah, She'olah"!
Ha'amek Davar (to 44:29 and 44:31): It says "Ra'ah" (44:29), for if one dies amidst crying, it is a bad sign (Kesuvos 103b). It says "Yagon," for his sons will be sad that he did not have Ru'ach ha'Kodesh before his death to bless them.
QUESTIONS ON RASHI
Rashi writes: "Va'Mes - [I.e.] his father [Yaakov, will die] of pain." How else might I have understood it?
Gur Aryeh: I might have interpreted this word as part of what Yaakov will assume - 'If Yaakov sees that the youth is not here, and [presume that the youth has] died.' 1 But why would he assume so, if told that he was alive in Mitzrayim? 2 Rather, it means that Yaakov would die.
Ha'amek Davar in fact interprets this way; refer to 44:31:151:2.
Refer to 44:31:152:1 and the note there.
