From the glossary:

Donkey as used by Jesus for His Triumphal Entry, recorded in Matthew 21:1-11, Mark 11:1-11, Luke 19:28-38, and John 12:12-19, is significant beyond the reference in Zechariah 9:9.  (See *** toward the end of this article) The first reference to this is in Genesis 49:10-12. "The scepter shall not depart from Judah nor a scholar from among his descendants until Shiloh arrives and his will be an assemblage of nations. He will tie his donkey to the vine; to the vine branch his donkey’s foal; he will launder his garments in wine and his robe in the blood of grapes. Red eyed from wine, and white toothed from milk." The Stone Edition Chumash, a volume with the Torah readings, the Haftorah, and Rabbinic commentary, is the source of the above translation and the following commentary. The italicized names are acknowledged Torah scholars.

"The scepter shall not depart from Judah. The privilege of providing Israel’s sovereign ruler - symbolized by the royal scepter - shall not pass from the House of Judah (Onkelos). This blessing did not take effect immediately, however, for the first Jewish king was Saul, a Benjamite. However, Jacob’s blessing applied uninterruptedly from the time that the monarchy went to David, and it continued even after the demise of the royalty, for after the destruction of the Second Temple, the Exhilarchs, or heads of the Babylonian exile, were appointed from the tribe of Judah (Rashi). As to present times and before the time of David, when kings did not come from Judah, Gur Aryeh explains as follows: Jacob’s blessings applied only when there would be a legally constituted king. The times of Saul and judges were temporary aberrations. Similarly, the current exile, too, will be followed by a return of the Davidic dynasty, proving that Jacob’s blessing remains in force.

"Nor a scholar, i.e., an allusion to Hillel’s descendants, the Nesi’im, or Princes in Eretz Yisrael, whose greatness in Torah was enhanced by their descent from the royal line of Judah (Talmud, Sanhedrin 5a).

"Until Shiloh arrives. Onkelos, followed by Rashi, (two great scholars, Onkelos 2nd century, Rashi 11th century) renders: until the Messiah comes, to whom the word Shiloh is a composite of the words Sh’ loh a gift to him, a reference to the King Messiah, to whom all nations will bring gifts. This verse is a primary Torah source for the belief that the Messiah will come, and the rabbis always referred to it in the Middle Ages, when they were forced to debate with clerics of other religions.

"The word until does not mean that Judah’s ascendancy will end with the coming of Messiah. To the contrary, the sense of the verse is that once Messiah begins to reign, Judah’s blessing of kingship will become fully realized and go to an even higher plateau (Sh’lah). At that time, all the nations will assemble to acknowledge his greatness and pay homage to him.

"11-12. Though Jacob could not reveal the "End" to his sons, he did provide them with tiny glimpses of the Messianic era (Abarbanel). Judah’s district will be productive and flow with wine like a fountain. So lush will his vineyards be that a farmer will tie his donkey to a single vine, for it will produce as many grapes as a donkey can carry (Rashi, Rashbam). The passage continues hyperbolically with more illustrations of the productivity of Judah’s land.

*** "Messiah is associated with a donkey rather than a horse ready for battle, because he is depicted not as a warrior but as a man of peace who represents prosperity; thus the simile of the vineyard. His wars will be won by God, not through force of arms (Sforno)."

The three verses from Genesis 49 are truly rich. Notice the reference in verse 11 to Messiah washing His garments in wine and His robe in the blood of grapes. Revelation 7:14 tells of the 144,000 who washed their robes and they made them white in the blood of the Lamb. It is obvious in reading the above that God blinded our Jewish brothers for a season. They see so much, but have been given a blind spot to hold the door open for the heathens. See Romans 11:8, 25-27, Deuteronomy 29:4, and Isaiah 29:10.