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Leah's Eyes: Vayetze 5785
(טז) וּלְלָבָ֖ן שְׁתֵּ֣י בָנ֑וֹת שֵׁ֤ם הַגְּדֹלָה֙ לֵאָ֔ה וְשֵׁ֥ם הַקְּטַנָּ֖ה רָחֵֽל׃ (יז) וְעֵינֵ֥י לֵאָ֖ה רַכּ֑וֹת וְרָחֵל֙ הָֽיְתָ֔ה יְפַת־תֹּ֖אַר וִיפַ֥ת מַרְאֶֽה׃ (יח) וַיֶּאֱהַ֥ב יַעֲקֹ֖ב אֶת־רָחֵ֑ל וַיֹּ֗אמֶר אֶֽעֱבׇדְךָ֙ שֶׁ֣בַע שָׁנִ֔ים בְּרָחֵ֥ל בִּתְּךָ֖ הַקְּטַנָּֽה׃
(16) Now Laban had two daughters; the name of the older one was Leah, and the name of the younger was Rachel. (17) Leah had weak eyes; Rachel was shapely and beautiful. (18) Jacob loved Rachel; so he answered, “I will serve you seven years for your younger daughter Rachel.”
מַאי ״קְדָמַתָּהּ לֵאָה בְּרַחֲמִים״? דִּכְתִיב: ״וְעֵינֵי לֵאָה רַכּוֹת״ – מַאי ״רַכּוֹת״? אִילֵּימָא רַכּוֹת מַמָּשׁ, אֶפְשָׁר בִּגְנוּת בְּהֵמָה טְמֵאָה לֹא דִּבֵּר הַכָּתוּב, דִּכְתִיב: ״מִן הַבְּהֵמָה הַטְּהוֹרָה וּמִן הַבְּהֵמָה אֲשֶׁר אֵינֶנָּה טְהֹרָה״; בִּגְנוּת צַדִּיקִים דִּבֵּר הַכָּתוּב?! אֶלָּא אָמַר רַבִּי אֶלְעָזָר: שֶׁמַּתְּנוֹתֶיהָ אֲרוּכּוֹת.

What does it mean that Leah advanced ahead of Rachel with mercy? As it is written: “And Leah’s eyes were weak [rakkot]” (Genesis 29:17). What is the meaning of “rakkot”? If we say that her eyes were literally weak, is it possible that the verse would say that? The verse there did not speak to the disparagement of even a non-kosher animal, as it is written: “From the pure animals and from the animals that are lacking purity” (Genesis 7:8). Did the verse speak here to the disparagement of the righteous? Rather, Rabbi Elazar says: The term alludes to the fact that her gifts were long-lasting [arukkot].

רַב אָמַר: לְעוֹלָם רַכּוֹת מַמָּשׁ, וְלֹא גְּנַאי הוּא לָהּ, אֶלָּא שֶׁבַח הוּא לָהּ. שֶׁהָיְתָה שׁוֹמַעַת עַל פָּרָשַׁת דְּרָכִים בְּנֵי אָדָם שֶׁהָיוּ אוֹמְרִים: שְׁנֵי בָנִים יֵשׁ לָהּ לְרִבְקָה, שְׁתֵּי בָנוֹת יֵשׁ לוֹ לְלָבָן, גְּדוֹלָה לַגָּדוֹל וּקְטַנָּה לַקָּטָן. וְהָיְתָה יוֹשֶׁבֶת עַל פָּרָשַׁת דְּרָכִים וּמְשָׁאֶלֶת: גָּדוֹל מָה מַעֲשָׂיו? אִישׁ רַע הוּא מְלַסְטֵם בְּרִיּוֹת. קָטָן מָה מַעֲשָׂיו? ״אִישׁ תָּם יֹשֵׁב אֹהָלִים״. וְהָיְתָה בּוֹכָה, עַד שֶׁנָּשְׁרוּ רִיסֵי עֵינֶיהָ.

Rav says: Actually, the verse means that her eyes were literally weak, and this is not a denigration of her but a praise of her. As she would hear people at the crossroads, who would say: "Rebecca has two sons, Laban has two daughters; the older will be married to the older, and the younger will be married to the younger." And she would sit at the crossroads and ask: What are the deeds of the older son? The passersby would answer: He is an evil man, and he robs people. She would ask: What are the deeds of the younger son? They would answer: He is “a quiet man, dwelling in tents” (Genesis 25:27). And she would cry until her eyelashes fell out.

Rabbi Dr. Julia Watts Belser
The Talmud tries to fashion Leah’s unconventional eyes into a mark of moral sensitivity, making her weak eyes a consequence of grief at being promised to a wicked man. But it feels like a thin attempt to salve the raw biblical story, to cover over the fact that Jacob doesn’t find her beautiful. While Rachel’s appearance catches Jacob’s eye and opens the door to his heart, Leah is unlovely. It is one of the first things we learn about her, this business about her eyes, this public judgment about her appearance. It is a powerful witness to the way of this world. Beauty gets positioned as a measure of a woman’s worth, the most crucial fact to understand about her personhood.
How do we undo this knot? One answer is to claim that beauty does not matter, that aesthetic judgments are only skin deep. It’s Leah’s heart that counts, the Talmud reassures us. Only a boor would judge on the basis of her beauty. But there’s something unsatisfying about this response, something that concedes to Jacob’s initial judgment. I don’t want a world where we look past her eyes. I want us to savor the shape of her—her skin, her face, her very particularity. I want her to savor that herself. I want her to own her own splendor, to know her own magnificence.
— Loving Our Own Bones: Disability Wisdom and the Spiritual Subversiveness of Knowing Ourselves Whole

רכות. כמשמעו ויש שואלים למה היה כן בעבור שחשבו שמחשבות השם כמחשבותיהם, וכל הנבראים ראויות צורתן להיות שוות ובן אפרים אמר שהוא חסר אל"ף וטעמו ארוכות והוא היה חסר אל"ף

WEAK. Rakkot is to be taken literally. Some ask, why were Leah’s eyes weak? They raise this question because they believe God’s thoughts are like their thoughts, and they think that all people have to be formed alike. Ben Efraim said that an alef is missing in the word rakkot (weak), its meaning being arukhot (long). However, Ben Efraim himself was missing an alef.