His eyes shall be red with wine
Signifying, not the intemperance of this tribe, and their immoderate use of wine, and the effect of it on them; but the goodness and generosity of their wine, that if drank plentifully of, and especially to excess, would have such an effect, see ( Proverbs 23:29 Proverbs 23:30 ) and, as applied to the Messiah, the antitype of Judah, and who was of this tribe, it may denote not so much the beauty of his eyes, as the Targums paraphrase it; as the joy and pleasure that sparkled in his eyes when he shed his blood on the cross, enduring that, and despising the shame of it, for the joy of the salvation of his people; or the clearness of his sight in beholding the actions of his enemies, and especially of the fierceness and fury of his wrath against them, whose eyes are said to be an flames of fire, ( Revelation 1:14 ) and his teeth white with milk;
denoting the fruitfulness of his land, producing fine pastures, on which flocks and herds fed, and gave abundance of milk; and so Onkelos paraphrases the whole verse,
``his mountains shall be red with his vineyards, and his hills shall drop wine, and his valleys shall be white with corn and flocks of sheep;''and much the same are the Targums of Jonathan and Jerusalem: the mystical sense may respect Christ and his people, and be expressive of the purity of his nature, life, and doctrine, and of the holiness of his members, their faith and conversation; or the clauses may be rendered, redder than wine, whiter than milk; but though whiteness recommends teeth, yet not redness the eyes; wherefore some F1 by transposing the first letters of the word for "red", make it to signify black, as it does with the Arabs, and that colour of the eye is reckoned beautiful.
F1 Danzius apud Stockium, p. 334.