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There’s a famous Yalkut Shimoni (Nach 1056:18, referenced by Rashi in explaining Megillah 15a), which reads as follows:

א"ר חסדא זה בא בפרוזבולי וזה בא בפרוזבוטי, פעם אחת נתן המלך ממון ושגרם ב��אשי גייסות לכבוש את המדינה, נטל המן ממון שלו ואכלו ולא נשתייר לו ממון, כשבא להוציא על בעלי מלחמה לא היה בידו כלום, אבל מרדכי חצי של ממון היה בידו, בא המן אצל מרדכי אמר לו לויני ממון זה שבידך אמר לו אין אני מלוך אלא אם כן תמכור נפשך לעבד לי, קבל על נפשו והלוהו, וכתב לו הרי המן עבדו של מרדכי, זבין נפשיה למרדכי בטולמא דנהמא

Rav Chisda said: [Mordechai] came as a rich man, and [Haman] came as a poor man. Once, the king gave money, and when the heads of troops caused to conquer the country, Haman took his money, depleted it, and had nothing left. When he came to go out over the commanders of war, he didn’t have anything, but Mordechai had half of the money. Haman came to Mordechai and said to him, “Lend me this money that you have.” He said to him, “I will not lend to you unless you sell yourself as a slave to me.” He accepted it, and he lent him, and he wrote for him, “Behold, Haman is Mordechai’s slave; he sold himself to Mordechai for a loaf of bread.”

Compare this to Haman’s ancestor Esav selling the birthright to Mordechai’s ancestor Yaakov (Bereishis 25:29-34):

וַיָּ֥זֶד יַעֲקֹ֖ב נָזִ֑יד וַיָּבֹ֥א עֵשָׂ֛ו מִן־הַשָּׂדֶ֖ה וְה֥וּא עָיֵֽף׃ וַיֹּ֨אמֶר עֵשָׂ֜ו אֶֽל־יַעֲקֹ֗ב הַלְעִיטֵ֤נִי נָא֙ מִן־הָאָדֹ֤ם הָאָדֹם֙ הַזֶּ֔ה כִּ֥י עָיֵ֖ף אָנֹ֑כִי עַל־כֵּ֥ן קָרָֽא־שְׁמ֖וֹ אֱדֽוֹם׃ וַיֹּ֖אמֶר יַעֲקֹ֑ב מִכְרָ֥ה כַיּ֛וֹם אֶת־בְּכֹֽרָתְךָ֖ לִֽי׃ וַיֹּ֣אמֶר עֵשָׂ֔ו הִנֵּ֛ה אָנֹכִ֥י הוֹלֵ֖ךְ לָמ֑וּת וְלָמָּה־זֶּ֥ה לִ֖י בְּכֹרָֽה׃ וַיֹּ֣אמֶר יַעֲקֹ֗ב הִשָּׁ֤בְעָה לִּי֙ כַּיּ֔וֹם וַיִּשָּׁבַ֖ע ל֑וֹ וַיִּמְכֹּ֥ר אֶת־בְּכֹרָת֖וֹ לְיַעֲקֹֽב׃ וְיַעֲקֹ֞ב נָתַ֣ן לְעֵשָׂ֗ו לֶ֚חֶם וּנְזִ֣יד עֲדָשִׁ֔ים וַיֹּ֣אכַל וַיֵּ֔שְׁתְּ וַיָּ֖קָם וַיֵּלַ֑ךְ וַיִּ֥בֶז עֵשָׂ֖ו אֶת־הַבְּכֹרָֽה׃

Yaakov was cooking a stew. Esav came from the field, and he was tired. Esav said to Yaakov, “Please pour into me some of this red stuff, for I am tired.” (Therefore, his name was called Edom.) Yaakov said, “Sell me, as this day, your birthright.” Esav said, “Behold, I’m going to die, and what is this birthright to me?” Yaakov said, “Swear to me, as this day,” and he swore to him. He sold his birthright to Yaakov, and Yaakov gave to Esav bread and lentil stew. Esav ate, drank, got up, left, and despised the birthright.

In both instances, an Edomi wants food that a Jew has. The Jew is willing to give it to him, on condition that the Edomi sacrifice some significant freedoms, and that there be something legally binding enforcing the transaction. The Edomi agrees to the deal.

In both cases, it even comes back to bite them: Esav exclaims later about how he was swindled out of his birthright and his blessings (Bereishis 27:36), and Haman is forced to do menial work for Mordechai in preparation for parading him around the city (Megillah 16a).

Esther Rabbah 7:10 also highlights another comparison between them:

וַיִּבֶז בְּעֵינָיו לִשְׁלֹחַ יָד בְּמָרְדֳּכַי לְבַדּוֹ (אסתר ג, ו), בָּזוּי בֶּן בָּזוּי, לְהַלָּן כְּתִיב (בראשית כה, לד): וַיִּבֶז עֵשָׂו אֶת הַבְּכֹרָה, וְכָאן כְּתִיב: וַיִּבֶז בְּעֵינָיו.

"And it was despised in his eyes to send his hand against Mordechai alone." Despiser son of a despiser; there it is written, "And Esav despised the birthright," and here it is written, "And it was despised in his eyes."

Do any commentaries draw this connection between these two incidents?

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    I heard in a shiur from R' Eytan Feiner that the Arizal says Mordechai and Haman were gilgulim of Yaakov and Eisav. Fits in. Commented Mar 14, 2019 at 14:17

3 Answers 3

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Yes, the Manos Halevi brings what the actual Shtar said:

אני המן בן המדתא מזרע אגג, שלח אותי מלך אחשורוש במלחמה על עיר הינדקא, ומנה אותי המלך על ששה רבוא אנשי הצבא, ונתן לי המלך צידה לפרנס אותם, וכן עשה למרדכי בן שמעי בן קיש משבט בנימין, ואני בזבזתי נכסי המלך ויצאו מתחת ידי, ולא היה בידי ממון לפרנס חיילי צבא המלך, הלכתי ללוות מן מרדכי בריבית, ואמר דאסור לו להלוות בריבית משום דעשו ויעקב אחים היו, ולא יכולתי להוציא מתחת ידו עד עת שנמכרתי לו לעבד, ואם אני מעכב מלהיות לו לעבד, או שמא אין אני מודה שאני עבדו, או שמא אני מסרב לעבוד לו יום אחד בשבוע כל ימי חיי ובני ובני בני עד סוף כל הימים, או שמא אני נוטר שנאה על עסק המכירה שנמכרתי לו, כמו שנטר עשו ליעקב על עסק הבכורה שמכר לו, אז יתעקר עץ מביתי ויתלו אותי עליה, וקבלתי עלי אני המן בן המדתא מזרע אגג להיות עבד למרדכי היהודי ככל מה שכתוב באגרת הזאת, ברצוני ובחפץ נפשי

My Translation:

I am Haman the son of Hemdasa from the linage of Agag. I was sent by King Achashverosh to fight a war against the city of Hindahka. The king placed me in charge of 60,000 soldiers, and he gave me food to support them, and he did the same for Mordichai the son of Shmi the son of Kish from Shevet Binyamin. I wasted all the belongings of the king, and I did not have enough money to support the troops of the king. I went to borrow from Mordichai with interest, and he said to me that it is not permitted to lend to me with interest, since Esav and Yaakov were brothers. I was unable to do anything until I sold myself to him as a servant, and if I stopped being his servant, or even I don't admit to being his servant, or I don't show up for my work as a servant for one day of the week all the days of my life and my son and my sons son until the end of days, or have hatred because of the sale of selling myself to him, like Esav had towards Yaakov because of the selling of the bechorah, then you should uproot a piece of wood from my house and hang me upon it. I accept on myself, Haman the son of Hemdasa from the seed of Agag to be the servant of Mordichai the Jew like all that I have written in this letter, with my own will, and my wanting.

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  • Fascinating! Do you have an online link to this Manos HaLevi? This puts the Gemara in a different light that Haman prepared the gallows for himself.
    – DonielF
    Commented Mar 14, 2019 at 3:26
  • I see the beginning of this, which specifies that it was Achashveirosh who sent them, helps narrow down an answer to my other question on this Midrash.
    – DonielF
    Commented Mar 14, 2019 at 3:27
  • judaism.stackexchange.com/questions/36555/…
    – sam
    Commented Mar 14, 2019 at 3:33
  • The link is in that question that i asked a while back and answerd
    – sam
    Commented Mar 14, 2019 at 3:36
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I just stumbled across the Ba’al HaTurim on Bereishis 25:30:

הלעטיני נא מן - ראשי תיבות המן. לומר כשם שיעקב קנה מעשו בכורו בלחם ועדשים כך קנה מרדכי את המן לעבד בפת לחם

”Pour into me, please, from [this red stuff]” - This initials “Haman,” to say that just like Yaakov bought from Esav his birthright with bread and lentils, so did Mordschai buy Haman as a slave for a loaf of bread.

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The Toras Chaim on :חולין צז says the reason he put the slave deed on his leg was to remind Haman that this slave sale fight is an old fight, which began when the מלאך broke Yaakov’s leg, fighting over the בכורה sale of Esav.
And Mordechai and Haman’s sale fight was just a continuation of the old, old fight.

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  • I think it answers the question
    – user19400
    Commented Aug 2, 2019 at 18:41

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