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Debating Judah's Long Speech: Rashi, Ramban, Rashbam, Ibn Ezra and Alter
The narrative of the Humash does not report the inner feelings of the parties, nor does it present their words when they were said. Important conversations are not reported in chronological sequence. Consistent with its methodology, the Midrash presents feelings, understandings or words which are not reflected in the text. What a complicated, dramatic and marvelous storyline!

(יט) אִם־כֵּנִ֣ים אַתֶּ֔ם אֲחִיכֶ֣ם אֶחָ֔ד יֵאָסֵ֖ר בְּבֵ֣ית מִשְׁמַרְכֶ֑ם וְאַתֶּם֙ לְכ֣וּ הָבִ֔יאוּ שֶׁ֖בֶר רַעֲב֥וֹן בָּתֵּיכֶֽם׃(כ) וְאֶת־אֲחִיכֶ֤ם הַקָּטֹן֙ תָּבִ֣יאוּ אֵלַ֔י וְיֵאָמְנ֥וּ דִבְרֵיכֶ֖ם וְלֹ֣א תָמ֑וּתוּ וַיַּעֲשׂוּ־כֵֽן׃

(כא) וַיֹּאמְר֞וּ אִ֣ישׁ אֶל־אָחִ֗יו אֲבָל֮ אֲשֵׁמִ֣ים ׀ אֲנַ֘חְנוּ֮ עַל־אָחִ֒ינוּ֒ אֲשֶׁ֨ר רָאִ֜ינוּ צָרַ֥ת נַפְשׁ֛וֹ בְּהִתְחַֽנְנ֥וֹ אֵלֵ֖ינוּ וְלֹ֣א שָׁמָ֑עְנוּ עַל־כֵּן֙ בָּ֣אָה אֵלֵ֔ינוּ הַצָּרָ֖ה הַזֹּֽאת׃

(כב) וַיַּ֩עַן֩ רְאוּבֵ֨ן אֹתָ֜ם לֵאמֹ֗ר הֲלוֹא֩ אָמַ֨רְתִּי אֲלֵיכֶ֧ם ׀ לֵאמֹ֛ר אַל־תֶּחֶטְא֥וּ בַיֶּ֖לֶד וְלֹ֣א שְׁמַעְתֶּ֑ם וְגַם־דָּמ֖וֹ הִנֵּ֥ה נִדְרָֽשׁ׃(כג) וְהֵם֙ לֹ֣א יָֽדְע֔וּ כִּ֥י שֹׁמֵ֖עַ יוֹסֵ֑ף כִּ֥י הַמֵּלִ֖יץ בֵּינֹתָֽם׃

(19) If you are being honest, let one of your brothers be held in your place of detention, while the rest of you go and take home rations for your starving households;(20) but you must bring me your youngest brother, that your words may be verified and that you may not die.” And they did accordingly.(21) They said to one another, “Alas, we are being punished on account of our brother, because we looked on at his anguish, yet paid no heed as he pleaded with us. That is why this distress has come upon us.”(22) Then Reuben spoke up and said to them, “Did I not tell you, ‘Do no wrong to the boy’? But you paid no heed. Now comes the reckoning for his blood.”(23) They did not know that Joseph understood, for there was an interpreter between him and them.

C.S.: The next midrash offers an interpretation which is totally unanticipated: that the brothers actually believed Joseph, the Egyptian, that their younger brother had stolen the goblet.

What a dysfunctional family!

(ב) וימצא הגביע. כיון שנמצא הגביע, אמרו לו אחיו, "גנב בר גנבתא, רחל אמך גנבה את התרפים, ואתה גנבת את הגביע!"

...

We now turn too Judah's speech, and a line which could be a lie, or variously understood. (Would a lawyer present a defense on behalf of his (accused) client that was unclear?)

(כב) וַנֹּ֙אמֶר֙ אֶל־אֲדֹנִ֔י לֹא־יוּכַ֥ל הַנַּ֖עַר לַעֲזֹ֣ב אֶת־אָבִ֑יו וְעָזַ֥ב אֶת־אָבִ֖יו וָמֵֽת׃

(כג) וַתֹּ֙אמֶר֙ אֶל־עֲבָדֶ֔יךָ אִם־לֹ֥א יֵרֵ֛ד אֲחִיכֶ֥ם הַקָּטֹ֖ן אִתְּכֶ֑ם לֹ֥א תֹסִפ֖וּן לִרְא֥וֹת פָּנָֽי׃

(22) We said to my lord, ‘The boy cannot leave his father; if he were to leave him, his father would die.’

[This translation adds an interpretation to the text. It literally states: "We said to our Master, "The lad cannot leave his father. If he left his father, he would die."]

[C.S.: Who would die? The antecedent is indefinite. The commentaries below debate the meaning of the pronoun.]

(23) But you said to your servants, ‘Unless your youngest brother comes down with you, do not let me see your faces.’

(א)ועזב את אביו ומת. ולמה לא הביא המזכיר החמשה שאין להם הכרע, כמו "וישלוף נעלו" (רות ד ח), וזה עמהם:

(1) FOR IF HE SHOULD LEAVE HIS FATHER, HIS FATHER WOULD DIE. Why didn’t the one who lists the five undecided verses not include our verse among them?

(The Talmudic sage Isi ben Judah (Yoma 92a,b) lists five verses wherein it is impossible to determine concerning what or of whom the verse speaks.)

(א)ועזב את אביו ומת. אִם יַעֲזֹב אֶת אָבִיו, דּוֹאֲגִים אָנוּ שֶׁמָּא יָמוּת בַּדֶּרֶךְ, שֶׁהֲרֵי אִמּוֹ בַּדֶּרֶךְ מֵתָה:

(1) ועזב את אביו ומת FOR IF HE SHOULD LEAVE HIS FATHER, HE WOULD DIE — If he leaves his father we shall be in anxiety lest he die on the journey, because indeed his mother died during a journey.

C.S.: Rashi invokes familial precedent: Like mother, like son.

(א)וְעָזַב אֶת אָבִיו וָמֵת פֵּרֵשׁ רַבִּי אַבְרָהָם, וּמֵת אָבִיו. וְאִם כֵּן הָיָה אוֹמֵר לֹא יוּכַל אָבִינוּ לַעֲזֹב אֶת בְּנוֹ, וְעָזַב אֶת בְּנוֹ וּמֵת. אוֹ לֹא נוּכַל שֶׁיַּעֲזֹב הַנַּעַר אֶת אָבִיו, כִּי לֹא יִתְלוּ הַחֶמְלָה עַל אֲבִיהֶם בַּנַּעַר, כִּי הֵם יַחְזִיקוּהוּ כְּיֶלֶד לֹא יֵדַע בֵּין טוֹב לָרַע. אֲבָל פֵּרוּשׁ "לֹא יוּכַל הַנַּעַר לַעֲזֹב אֶת אָבִיו" – מִפְּנֵי נַעֲרוּתוֹ וֶהֱיוֹתוֹ יֶלֶד שַׁעֲשׁוּעִים בְּחֵיק אָבִיו אֲשֶׁר אֲהֵבוֹ, וְאִם יַעַזְבֶנּוּ וְיָבֹא בַּדֶּרֶךְ, יָמוּת הַנַּעַר:

(1) AND WE SAID UNTO MY LORD: THE LAD CANNOT LEAVE HIS FATHER; FOR IF HE SHOULD LEAVE HIS FATHER, HE WOULD DIE. Rabbi Abraham ibn Ezra explained this to mean “and his father would die.” But if so, Judah would have said: “Our father cannot leave his son, for if he should leave his son, he [the father] would die.” Or he should have said, “We cannot bear that the lad leave the father,” for they would not make the plea for compassion for their father dependent upon the lad, [saying, as the verse has it. ‘The lad’ cannot leave his father for if he should leave his father, he would die], since they considered him as a child who did not know the difference between good and evil. [Therefore, if it be as Ibn Ezra says, i.e., that the concern in this verse is lest the father die, they would have said, “We cannot bear that the lad should leave his father,” or “Our father cannot leave his son.”]

Rather, the meaning is: The lad cannot leave his father on account of his youth and his being the darling son in the lap of his father who loves him, and if he should leave him and come on the journey, the lad would die.

(א) ועזב את אביו ומת - אביו ימות.

(1) ועזב את אביו ומת, his father will die as a result.

(א)לא יוכל הנער לעזוב את אביו. כי מאז שיעזוב את געגועי אביו והסברת פניו, יתעצב ונפל למשכב, ואז ימות:(ב)ועזב את אביו ומת. ועם זה, אביו ימות בלי ספק:

(1) לא יוכל הנער לעזוב את אביו, from the moment he will have left his father, he will pine for his father and become sick or die. Furthermore,(2) ועזב את אביו ומת, also his father will die without question if the lad leaves him.

Robert Alter, Commentary: "Should he leave his father, he would die." "The translation reflects the ambiguity of the Hebrew, and one may be skeptical of the often-made claim that the second "he" must refer to Jacob. It seems more likely that this is a studied ambiguity on Judah's part: he leaves it to Joseph to decide whether the old man would die if he were separated from Benjamin, or whether Benjamin could not survive without his father, or whether both dire possibilities might be probable (my emphasis)."