What do we learn from Yehudah's undertaking, "Anochi E'ervenu, mi'Yadi Tevakshenu"?
Bava Basra 173b: We learn from "Anochi E'ervenu" that an Areiv Kablan - a guarantor who accepts full responsibility for a loan, is liable to repay the loan. 1
Ha'amek Davar: Returning Binyamin is not Arvus. It is like the borrower returning the loan! Arvus was accepting Binyamin's sins on himself, like I wrote above (42:37, that Reuven accepted so 2 ). "Mi'Yadi Tevakshenu" is a promise to guard him well from other people.
See Torah Temimah, note 9, who explains the differences between an Areiv Kablan and an Areiv S'tam.
Refer to 42:37:151:2*.
What did Yehudah mean when he said "Kol ha'Yamim"?
Midrash Tanchuma (Vayigash 4; cited by Rashi to 44:32): This alludes to two worlds - this world and the world to come. 3
Which explains why Yehudah's punishment (refer to 43:9:151) continued after his death (refer to Devarim 33:7:1:2; see Sotah 7b). See also Ba'al ha'Turim.
Gur Aryeh: Kol ha'Yamim" implies "Yom she'Kulo Aroch" (the day that is entirely long, i.e. eternal).
As for the contradiction between these two comments of Rashi, see 43:9:1.2:1.
Rashi (to Devarim 33:7) explains that Yehudah was punished due to this. Why is that so? He fulfilled his promise!
Moshav Zekenim #1: He did not double the Tenai (stipulation, and say 'if I will not bring him in front of you...'), so the Tenai is invalid (Kidushin 61a). 1
Makos 11b: Niduy on Tenai must be permitted (it takes effect even if he fulfilled the Tenai 2 ). Moshav Zekenim #2, citing Riva - This is in a case like Yehudah's, that he put himself in Safek, lest Binyamin die on the road. 3
Moshav Zekenim #3: We do not find that Binyamin returned with his brothers. Yosef sent 10 donkeys. Had Binyamin not stayed in Egypt, 4 there would be 11! R. Efrayim proves that Yehudah did not return Binyamin from Yaakov's disbelief. We do not find that he asked Binyamin about Yosef. However, he would have relied on Binyamin! 5
Moshav Zekenim #4, citing R. Chaim (from Makos 11a): A curse of a Chacham, even on Tenai, takes effect [in any case]. 6 Similarly, Rachel died due to "the one with whom you will find your gods will not live" (31:32). 7
Moshav Zekenim: Even Rabanan who disagree, agree about a Tenai "if...", like that of Bnei Gad and Bnei Reuven. Yehudah thought that it sufficed that he fulfilled his Tenai, so he did not permit his Niduy through a Chacham.
Makos 11b: This is why Yehudah's bones rolled in the coffin throughout the 40 years that Yisrael traveled in the desert, until Moshe prayed for him - Refer to Devarim 33:7:1:2. Mizrachi - How can the Gemara infer this? Perhaps Yehudah was punished because he did not double the Tenai! He and Yaakov would not have erred about this; we learn from Bnei Gad and Bnei Reuven. Ohr ha'Chayim - All Halachos were said on Sinai. If Yehudah knew about Tenai Kaful, he knew also about Niduy on Tenai! Rather, if he did not say 'and if not, there is no Niduy,' all agree that the Niduy takes effect (even R. Chanina ben Gamliel, who does not require Tenai Kaful).
Ohr ha'Chayim: The Gemara did not mention that it is because he put himself in Safek; it relies on the reader to learn only to similar cases. Likewise, we can say that this is only when he did not double the Tenai, and say 'and if... there is no Niduy.'
If his disbelief was only that Yosef remained a total Tzadik (refer to 45:26:151:2), perhaps he thought that Binyamin merely assumed so! Why would Yehudah agree to leave Binyamin in Egypt, and not fulfill his Tenai?! (PF)
Ohr ha'Chayim: If so, why did the Gemara learn from Eli, and not from Yehudah?
Moshav Zekenim: We find that Sha'ul cursed whoever will eat that day [in the war, and Yonasan ate and he lived]! Chachamim of the Gemara cursed on Tenai and it did not come! When the person can ensure fulfillment, it comes only if he does not fulfill.
How could Yehudah be a guarantor against the angel of death?
Moshav Zekenim: An "Ason" is not full (i.e. any) death, rather, death through fighting, e.g. "Ki Yinatzu Anashim... v'Lo Yihyeh Ason" (Shemos 21:22). Yaakov said that Binyamin lacks patience and he will quarrel on the way, and they will kill him. Yehudah was a guarantor about this, not to let him quarrel with anyone; Yaakov relied on this.
Ha'amek Davar: He was not a guarantor for this. Refer to 43:9:1:2.
QUESTIONS ON RASHI
Rashi writes: "'I will have sinned unto you' - in the world-to-come." But in Parshas Vayigash (when Yehudah re-tells this dialogue to the viceroy), Rashi (to 44:32) explains that Yehudah accepted excommunication in two worlds - this world and the next!
Gur Aryeh: In this verse, Rashi is explaining the term "Kol ha'Yamim;" it refers to Olam ha'Ba (and it goes without saying that he would be excommunicated in this world as well). In 44:32, Yehudah is explaining to the viceroy why he specifically is entering the fray to defend Binyamin, more so than his other brothers (Rashi loc. cit.); he therefore explains the full extent of the responsibility that he took upon himself.
