Vayechi: Judah's Wine-Dark Eyes

(21) Wine alludes only to Torah, as it is said: For thy love is better than wine (Song 1:2), and He hath brought me to the banqueting-house, and his hammer over me is love (Song 2:4).

(22) His eyes shall be red with wine (Gen. 49:12). You learn from this verse that he devoted himself to the study of the Torah. The word hakhlili (red) should be read as hekh li li (“it is tasty to me”), that is, the wine of the Torah is sweet to me. And His teeth white with milk (ibid.). That is, if they should sin, they shall be made as white as snow, because of the Torah (they study).

(1) חכלילי [HIS EYES] ARE RED — חכלילי denotes redness, as the Targum renders it: they shall become red. Similar is (Proverbs 23:29) “who hath redness (חכלילות) of eyes?” Redness of eyes is associated with wine because that is what usually happens to those who drink much wine — their eyes become red. (2) מחלב [AND THE WHITENESS OF HIS TEETH IS] FROM MILK— because of abundance of milk, for there will be in his land good pasture for herds of flock. The verse is therefore to be explained as follows: There will be redness of eyes because of abundance of wine and there will be whiteness of teeth because of abundance of milk.

"His eyes red from wine." His eyes, face, and complexion are red as if "covering the surface of the land" (Ex. 10:5), from the wine which he drinks. And his teeth are white from the milk which he consumes. Or it might be said: his complexion is redder than wine and his teeth whiter than milk, that is, he is good looking with a good physique and fit to be a king, as was written of David (1Sam 16:12): “He was ruddy-cheeked, bright-eyed, and handsome" (1 Sam. 16:12).

(1) חכלילי עינים מיין, “Red-eyed from wine,” This too is a hyperbole relating to the abundance of wine to be found in the tribal territory of Yehudah. Yaakov said that every person in the territory of Yehudah would have red-looking eyes due to the abundance of wine. The word חכלילי is really spelled backwards. Its meaning is as if it had been spelled כחלילי, as if the people would actually have blue eyes, i.e. כחול. Just as people throughout the rest of the country color their eyes blue [with eyeshadow] so the eyes of the women of Yehudah would be colored red from the abundance of wine. White teeth would be white by contrast due to the abundance of milk in the valley and the abundance of milk yielding flocks of sheep. (2) According to Bereshit Rabbah 99,8 the word חכלילי is a composition of the three words חיך לי לי, i.e. when the palate, חיך, has tasted the wine of the land of Yehudah its owners will request refills of this beverage by saying לי, לי “more for me, more for me.”

...This [haklili] is the same word as "who has redness [haklilut] of the eyes?" (Prov. 23:29). This is the same as kahlilut, meaning that his eyes are dark with wine and he cannot hide that he is drunk. Or "who has redness of the eyes," such that this person must color their eyes all the time? “Those whom wine keeps to the wee hours” (Prov. 23:30). For wine darkens their eyes, and they shed tears and their sockets rot (Zech 14:12), and so they need to use eyeshadow at all times. Scripture disparages wine due to the problems it causes, whether outside with quarrels or with injuries, or in the house where "oy" and "avoy" are heard. It mentions these damages [from wine] that occur to himself and to his body with the darkening of his eyes and many other ailments; and this is the correct interpretation and point.