What does the Torah mean when it writes that "Leah's eyes were Rakos"?
Rashi: When Leah overheard people saying that Rivka's older son would marry Lavan's older daughter, and Rivka's younger son, Lavan's younger daughter, she would weep uncontrollably. 1 And it was the constant weeping that affected her eyes and made them soft. 2
Targum Onkelos and Rashbam: It means that she had beautiful eyes. 3 Ha'amek Davar - however, the sun would harm them, so she could not tend the flock.
Moshav Zekenim: It teaches why Yaakov chose Rachel. Leah was no less beautiful, just her eyes were tender, and wind would harm them.
Tosfos ha'Shalem (6, citing R. Yosef Karo): They were b'Simchah and beautiful.
Tosfos ha'Shalem (6): This is an expression of royalty. 4
Tosfos ha'Shalem (10, citing Chatzi Menasheh citing Ben Efrayim brought by the Ibn Ezra): It means that they were Aruchos (long); it is written lacking the Aleph. 5
She would pray that she not fall to the lot of Esav (Targum Yonasan). Maharal (Nesivos Olam, Nesiv ha'Tzenius Ch. 1, p. 105) - Although Leah did not know this for a fact, 'her Mazal knew,' and she would beg Hashem for a more proper mate.
Maharsha (to Bava Basra 123a) - Due to Leah's pain and tears (the gates of tears are never closed - Berachos 32b), Leah merited to marry Yaakov.
And Chazal have said (Ta'anis 24a) that a Kalah whose eyes are beautiful, the entire body does not require examination. Da'as Zekenim - Rachel's eyes hurt [after she married Yaakov (PF)], for she was barren; she cried lest Yaakov divorce her, and she fall to Esav.
Surely, this is because Yehudah would come from her (PF).
What is the difference between "Yefas To'ar" and "Yefas Mar'eh"?
Tosfos ha'Shalem (2): The former refers to the face. The latter is grace in the eyes of those who saw her.
Tosfos ha'Shalem (3): The former is beauty of stature and limbs.
Ohr ha'Chayim: Yefas To'ar is each detail by itself - the eyes, nose, neck... like it says in Shir ha'Shirim. Yefas Mar'eh refers to the face and body as a whole, or grace in the eyes of those who saw her, that they desire her.
Why does the Torah mention that the Imahos were beautiful? "Sheker ha'Chen v'Hevel ha'Yofi" (Mishlei 31:30)!
Kol Eliyahu: This is without Yir'as Shamayim, but if she fears Shamayim, "Hi Sis'halal" also for grace and beauty. 1 Similarly, Chochmah, Gevurah and wealth are attributes only if the bearer knows (fears) Hashem (Yirmeyahu 9:22-23).
QUESTIONS ON RASHI
Rashi writes: "Leah's eyes were tender (Eineha Rakos) - She thought that she would end up given to Esav, and she would weep...." The Gemara (Bava Basra 123a) cites an additional interpretation - 'her gifts would be long-standing (Matenoseha Arukos).' How does each approach interpret the Pasuk?
Maharal (Chidushei Agados Vol. 3, p. 125, to Bava Basra 123a): 'Long standing gifts" are lofty, spiritual gifts - namely, Leah was the mother of three dynasties - Kohanim, Leviyim, and Davidic kings. On a deeper level, tender eyes means her Guf was imperfect, therefore she merited completeness in her spiritual gifts. According to the opinion that her eyes were tender from crying, although she was the 'Gedolah,' and fit for Esav in terms of age, she was more fitting for Yaakov who was 'great' in terms of deeds. She cried due to her strong opposition to Esav, and her distress over their association, and she overcame it. 1
Either way, the Torah tells us this detail in praise of Leah. (EK)