What did Yaakov mean when he said about Yehudah (or Mashi'ach), "Chachlili Einayim mi'Yayin, u'Leven Shinayim me'Chalav"?
Rashi #1 and Rashbam: "Chachlili" means 'will turn red' - since the eyes of people who drink a lot of wine tend to turn red; and their teeth will turn white from the abundance of milk. 1
Rashi #2 (citing Targum Onkelos): His hills will turn red due to the many vineyards, and his winepresses will flow with wine. His valleys will turn white with grain and with the many flocks of sheep. 2
Ramban: He meant that due to the abundance of wine and milk, instead of painting their eyes with red paint and their teeth with cosmetics, 3 people will paint their eyes with wine and their teeth with milk.
Seforno: The fifth and final sign of Mashi'ach 4 is that the unnatural abundance that will occur with his arrival, 5 which is hinted here.
Kesuvos 111b: Keneses Yisrael asks Hashem, 'Please hint to me with Your eyes (i.e. view us favorably); this is more pleasing than wine! Please show (i.e. smile at) me with Your teeth; this is more pleasing than milk.' 6 To show one's friend the whiteness of one's teeth (to smile at him) is nicer than giving to him milk!
Da'as Zekenim: His face will turn red amidst drinking much wine. 'Einayim' means appearance. He will be healthy with white teeth from the abundance of milk.
Ohr ha'Chayim: Bamidbar Rabah (83:6) expounds "Motzi Asirim ba'Kosharos" (Tehilim 68:7) - as 'Bechi v'Shiros,' crying and singing. There was crying for the Egyptians, and singing for Yisrael. Chachlili (redness) hints to judgments - "v'Damim b'Damim Naga'u" (Hoshe'a 4:2). The source of judgment is mi'Yayin (from wine). Or, it hints to the reason for vengeance - [the nations] held back wine (i.e. they stopped Yisrael from learning Torah). "U'Leven" hints to Yisrael, whom Hashem calls 'Ben' - "Ha'Ven Yakir Li" (Yirmeyah 31:19). "Me'Chalav" hints to Chesed and mercy that our Father will arouse on us. "Ki'Yemei Tzeisecha..." (Michah 7:15) - just like there was crying and singing then, so will there be in the future!
Malbim: "Chachlili" is a kind of Kechol (mascara) used to paint the eyes - "Kachalt Einayich" (Yechezkel 23:40). "Shasisi Yeini Im Chalavi" (Shir ha'Shirim 5:1) - after drinking wine, which heats the body, one drinks milk, to pacify the sweltering due to the wine. Wine symbolizes the heat of war, in which he will paint his eyes with blood; after he will drink milk to soothe the heat, i.e. Shalom - "v'Diber Shalom la'Goyim" (Zecharyah 9:10), "v'Hayesah Menuchaso Kavod" (Yeshayah 11:10). The teeth of this lion ("Shinav Shinei Aryeh" - Yoel 1:6) will not be red from blood, rather, white from milk; he will have Shalom from all sides.
Ha'amek Davar: Just like he uses raw (undiluted) wine for laundering, so he will drink raw wine, 7 therefore his eyes will be red. If so, his teeth should be red, like his bones - one who drinks raw wine, his bones are burned (Nidah 24b)! The verse teaches that his teeth will be white, due to drinking milk from the abundant flock in his portion. They used to bring lambs to the Mikdash from Chevron, which is in Yehudah.
Due to the good grazing-grounds for the sheep.
See Rashi.
Ramban: Such activities were common in former times (See for example Kelim 13:2).
Seforno: As indicated in Tehilim 72:16. See also Shabbos 30b.
Maharal (Chidushei Agados Vol. 1, p. 166, to Kesuvos 111b): Maharal explains that wine and milk are physical enjoyment, whereas Hashem's love and favor surpass anything physical. (Compare to Shir Hashirim 1:2, and Rashi there.) (CS)
Chazal's wine was strong; normally, one diluted it with two or three measures of water for each measure of wine (Shabbos 77a).
QUESTIONS ON RASHI
Rashi writes: "According to Onkelos, 'eyes' (Enayim) alludes to mountain lookouts (covered with vines) ... or to springs (Ma'ayanos), [i.e.] the flow of the [wine] vats." Why does Onkelos veer from the literal meaning ("eyes reddened from wine")?
Gur Aryeh #1 (explaining Rashi): To literally have "reddened eyes" due to excessive wine consumption is a horrible trait, and is decried by Mishlei 23:29-30. Rather, this is a way of expressing the abundance that Yehudah's portion will produce. According to Rashi, the term "Enayim" is not literal, but a play on words to refer to mountains or vats.
Gur Aryeh #2: One may explain Onkelos unlike Rashi. The verse simply means that the wine will be abundant and red, in all the places it is normally found - while growing on the mountains, and when pressed in the vats. The overflowing vats will resemble the teary red eyes of one who has drunk.
Rashi writes: "According to Onkelos, 'teeth' allude to rocky cliffs (white with grain and flocks)." Why does Onkelos veer from the literal meaning ("whitened teeth from milk")?
Gur Aryeh: Teeth that are literally as white as milk are not so beautiful! Onkelos interprets the verse to mean that all the places milk is normally found, i.e. the valleys, will produce abundant flocks and grain. 1 They will be white, resembling teeth that have just consumed milk.
Gur Aryeh: When kernels of grain are pressed, they produce a milky substance; and grain fields in general are called 'Sedei Lavan' (white fields; e.g. Moed Katan 6b).
