Biblical Personalities: Yehuda: The Alshich HaKodesh
“He will tie his donkey to the vine.” (Genesis 49:11) The Midrash states that if Israel deserves it the Messiah’s arrival will be hastened by God, if Israel does not merit it, the Messiah will nonetheless arrive at the predetermined date.
Similarly, we are told that if we are worthy we will see the Messiah arriving on a cloud of light in great pomp and ceremony, whereas if we will not be deserving the Messiah will arrive riding on a donkey. (Zohar)
Thus far Jacob had described the redemption as resulting from the merit of the Jewish people. Now, Jacob turns to the other method of the Messiah’s arrival, a situation in which Israel lacks the necessary merit.
In such an event there will still be some Torah scholars since the Jewish nation will never be completely without Torah scholars. Since Issachar represents the highest dedication to Torah study, he is described as the donkey that carries burdens. Jacob therefore employs the same hyperbole when describing the arrival of the Messiah at his appointed time, due to lack of merits on the part of Israel.
Israel is frequently referred to as a vine, or “choice vine.” When it is not united it is called “vine,” seeing that each branch grows apart, in disorder. It is called “Choice vine” when united, when it is clear to the naked eye that these plants have been carefully tended and nurtured.
“Osri,” means, “the detention,” delay of the arrival of the Messiah is due to its status as “Gefen,” vine. This will delay the donkey, or weak form of redemption. Minor merits of Israel will not hasten the coming of the Messiah until Edom’s measure of sin is full.
Only then will come the fulfillment of the verse, “he will launder his garment in wine, and his horse in the blood of grapes.”