B'H
Parental Advisory warning on this one!
Also, these midrashim are super long - apologies if the translations seem disjointed, as I've tried to pull out the relevant bits. I'm fully aware that the sources are longer than the actual drasha.
Sources (all translations courtesy Sefaria.com, minor edits my own):
1) Devarim 25:17-19
זָכוֹר אֵת אֲשֶׁר־עָשָׂה לְךָ עֲמָלֵק בַּדֶּרֶךְ בְּצֵאתְכֶם מִמִּצְרָיִם׃
אֲשֶׁר קָרְךָ בַּדֶּרֶךְ וַיְזַנֵּב בְּךָ כׇּל־הַנֶּחֱשָׁלִים אַחֲרֶיךָ וְאַתָּה עָיֵף וְיָגֵעַ וְלֹא יָרֵא אֱלֹהִים׃
וְהָיָה בְּהָנִיחַ יְהֹוָה אֱלֹהֶיךָ לְךָ מִכׇּל־אֹיְבֶיךָ מִסָּבִיב בָּאָרֶץ אֲשֶׁר יְהֹוָה־אֱלֹהֶיךָ נֹתֵן לְךָ נַחֲלָה לְרִשְׁתָּהּ תִּמְחֶה אֶת־זֵכֶר עֲמָלֵק מִתַּחַת הַשָּׁמָיִם לֹא תִּשְׁכָּח׃
"Remember what Amalek did to you on your journey, after you left Egypt—how, undeterred by fear of God, he surprised you on the march, when you were famished and weary, and cut down all the stragglers in your rear. Therefore, when the LORD your God grants you safety from all your enemies around you, in the land that the LORD your God is giving you as a hereditary portion, you shall blot out the memory of Amalek from under heaven. Do not forget!"
2) Midrash Tanchuma Ki Tetze, Chapter 4 - Hebrew text (in full) here. Selections from English translation below:
"(Deut. 25:17:) “Remember what Amalek (Esau's grandson) did to you.” [...]
[(Ps. 109:14:) “And let not the sin of his mother be blotted out.”] But how had he sinned against his mother? R. Judah, R. Nehemiah, and [our] masters [differ]. R. Judah says, “When he left his mother's belly, he severed her uterus, with the result that she would not bear [any more children]. This is what is written (in Amos 1:11), ‘because he (i.e., Edom, which is Esau) pursued his brother with the sword and repressed his pity (rachamiv),’ as it is written, ‘his uterus (rechemo).’” Moreover, R. Berekhyah says, “You should not say [this] in reference to when he had left [his mother's uterus].Rather, as he was leaving his mother's uterus, his zerta' [i.e., fist] was stretched out against him (i.e., against his brother Jacob).” What is the reasoning? (Ps. 58:4:) “The wicked go astray (zoru) from the womb.”
R. Nehemiah says, “He was the cause of her not producing twelve tribes.” As Rav Huna has said, “Rebekah was worthy of producing twelve tribes, as stated (in Gen. 25:23), ‘And the Lord said to her, “Two nations are [in your womb].” Here are two. (Ibid., cont.:) “and two peoples.” Here are four. (Ibid., cont.:) “And one people shall be stronger than the other.” Here are six. (Ibid., cont.:) “And the elder shall serve the younger.”’ Here are eight. (Vs. 24:) ‘And behold there were twins in her womb.’ Here are ten. (Vs. 25:) ‘The first came out ruddy.’ That is eleven. (Vs. 26:) ‘And afterward his brother came out.’ Here are twelve.” And there are some who bring this [idea] from here (vs. 22); “and she said, ‘If so, why am I here (zh)?’” By gematria. z (=7) + h (=5) [for a total of] twelve. [...]"
3) Midrash Tanchuma Ki Tetze, Chapter 9 - Hebrew text (in full) here. Abridged English translation below:
"[...] R. Judan bar Gadya, R. Joshua ben Levi, and the masters [differ]. R. Judan bar Gadya said, “Remember what [our neighbor Amalek] did to us in the penis, which is attached to the lap (heq) [i.e., to the center] of a man.” And this agrees with what R. Hanina bar Shilqa, R. Joshua ben Levi and R. Jochanan said, “What did the House of Amalek do to Israel? They cut off their male organs and flung them heavenward, as they said, ‘This is what You have chosen, take for Yourself what You have chosen.’ This is related to the verse (in Ps. 9:6), ‘their taunt with which they have taunted You, O Lord.’” [...] When Samuel came, he repaid them, as stated (in I Sam. 15:33), “then Samuel hewed Agag.” What did he do to him?[...] Rabbi said, “He castrated him [...], as stated (in I Sam. 15:33), ‘But Samuel said, “As your sword has made women bereaved, so shall your mother be bereaved among women.”’” R. Levi said, “Moses also gave a hint to Israel in the Torah (about Agag's castration), since it is stated (in Deut. 25:11-12), ‘When two men get into a fight with each other, and the wife of one draws near [to save her husband from the hand of the one smiting him, if she puts out with her hand and grabs [the other man] by his male organs.] Then you shall cut off her hand….’ What is written after that (in vs. 17), ‘Remember what Amalek did to you. [...]’”
4) Midrash Tanchuma Ki Tetze, Chapter 10 - Hebrew text (in full) here. Abridged English translation below:
"(Deut. 25:18, cont.:) "And he cut off all who were lagging behind you". He smote them with a blow to the tail [alt. trans: 'male organ']. And this agrees with what R. Hanina bar Shilqa, said, “What did the House of Amalek do to Israel? They cut off their male organs and flung them heavenward, as they said, ‘This is what You have chosen, take for Yourself what You have chosen. [...]".
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The infamous curse against Amalek at the end of parshat Ki Tetze is the subject of many midrashim, especially in seeking to explain exactly what it was that Amalek is supposed to have done to B'nei Israel. Some of these midrashic explanations share a common theme - that of Amalek destroying B'nei Israel's reproductive capacity, and therefore preventing future generations from even being born.
The selections brought at source 2 above form part of a longer midrash which discusses the sins that Esav, Amalek's ancestor, committed against his righteous forefathers - thereby justifying him being cursed in this way. The midrash tries to deal with the problem of how Esav could be so cursed despite sharing exactly the same ancestry as Yaakov. As part of this, we find a dispute over exactly what it is that Esav is supposed to have done to his mother, Rivka.
One view is perhaps more well known - that Esav's evil reputation was such that when Rivka died, her funeral possession was conducted secretly at night to avoid any onlookers cursing her as Esav's mother. However, the conflicting views of Rabbi Yehuda and Rabbi Nechemya both argue that Esav's sin was hampering Rivka from giving birth, even to the point of destroying the source of life that was in her womb. Rabbi Yehuda states explicitly his version of events - that, as Esav was being born, he somehow destroyed Rivka's fallopian tubes and womb in such a way as to prevent her ever conceiving again. Rabbi Nechemya, meantime, does not explicitly state how Esav prevents Rivka giving birth again but does say that, had it not been for his actions, Rivka would have merited to give birth to all twelve tribes of Israel herself rather than leaving this to Yaakov's wives in the next generation.
The midrashim at sources 3 and 4 above introduce a different idea directly related to our source text in parshat Ki Tetze - that the act of 'cutting off' referred to here ('vay'zanev bekha') was in fact Amalek castrating the men of B'nei Israel when they were travelling from Egypt. This interpretation is cited in the name of several Sages including Rabbi Yochanan, Rabbi Yehoshua ben Levi and Rabbi Chama bar Shakla/Rabbi Chinena bar Shikla, but all are in agreement - after castration, Amalek threw up the severed male organs in the air as a taunt about circumcision and said 'This is what you have chosen? Go take what you have chosen!'.
As we can see, in both sets of midrashim Esav/Amalek is striking directly at the reproductive parts of B'nei Israel/Rivka Imeinu, and therefore at the source of human life itself. Esav/Amalek's intent appears to be literally genocidal - to prevent the birth of future generations of B'nei Israel.
Perhaps it is therefore appropriate that the mitzvah commanded here in parshat Ki Tetze is to wipe out 'zecher Amalek' from under the heavens. As 'zecher' means not only 'memory' but also 'seed', this therefore appears to be an act of retribution to remove Amalek's descendants from the earth - just as Amalek/Esav sought to do to us as the descendants of B'nei Israel.
RPT
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