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Why did Yehudah say in resignation "we will all be slaves" [Berashis 44:16], when Yosef's guy clearly said a few verses prior that only the person who has the Goblet will be a slave?

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They had offered to be slaves beforehand. 44:8. Yosef responded that would be the fitting punishment but he won't give it 44:9.

Rashi and other Rishonim say from the Medrash Rabbah that the reason they repeated the offer was because as they said immediately beforehand

מַה־נְּדַבֵּ֖ר 'וּמַה־נִּצְטַדָּ֑ק הָֽ מָצָא֙ אֶת־עֲוֹ֣ן עֲבָדֶ֔יךָ

They thought the false accusation and situation was just a punishment coming from Hashem. If it wouldn't be Yosef it would be someone else who would imprision them. (As above both Yosef and the brothers agreed that if the goblet was stolen they all should be imprisoned)

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    The Orach Chaim Hakadosh, adds that they assumed it was a punishment from Hashem and therefore all of them should be taken, however, if Yosef would insist on only Binyomin then they know it was not a punishment because Binyomin didn’t sell Yosef, and that’s why Yehuda faced off in the next parsha. Basically it was a test to see why it was happening and how to respond.
    – Chatzkel
    Dec 5, 2021 at 17:11
  • Why did they offer to all be slaves in 44:8 ? The same reason?
    – larry909
    Dec 10, 2021 at 2:12
  • The reason they offered to be slaves at first (according to at least meforshim) was because they were saying "as a group we are so far removed from theft that even if one of us stole we would all agree to be punished" Yosef responded that indeed that is what any very close knit group who has a member that steals deserves but he will be lenient and not not punish those who did not steal themselves
    – Schmerel
    Dec 10, 2021 at 16:28

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