Jacob mentions a season in Genesis 49:10, which he refers to as the last days (cp. Genesis 49:1). He says that the rod of rulership, vis-à-vis the scepter of a king or the baton of a general, would not be taken from Judah, nor a lawgiver from his descendants, until **he** comes who is the true Lawgiver and King, vis-à-vis the Messiah. While it is true that both Israel (the northern kingdom) and Judah (the southern kingdom) went into captivity, Daniel was a descendant of David (Daniel 1:3), and he had great influence over the kings of Babylon, until Cyrus released the Jews under Joshua the high priest, and Zerubbabel, the governor and son of David (Ezra 1:1-5; 2:1-2). Afterwards, Judah’s self-governance continued, until just after Jesus was born (cir. BC 3), and self-rule was taken away from Herod Archelaus a few years later, when he was exiled and Judea was made a province of Rome (cir. AD 6).
Except during the time of David, who was a type of Messiah, when did all of the people gather themselves together under Judah’s banner?[1] In effect, therefore, the phrase: “…unto him will the gathering of the people be” cannot refer to Judah, as the nation, especially because Jacob is speaking of the last days, not the days of David. Instead, the gathering of the people (Genesis 49:10) must refer to the Messiah, unto whom not only Israel gathers, but the whole world flows (John 12:32; cp. 11:52; Haggai 2:7).
Finally, Jacob describes Judah mysteriously, as one who ties his ass’s colt to a choice vine, while he presses out the juice of the grapes dying his garments red in the process. Afterward, his eyes are red with wine and his teeth are white with milk (Genesis 49:11-12). What can we say of this? Consider that Jesus told a parable about his Father planting a vineyard, which is a metaphor for the Kingdom of Israel. It was the Lord who planted it and pruned it etc. He then let it out to husbandmen, vis-à-vis the authorities that governed Israel. However, when he sent for its fruits, the husbandmen persecuted the king’s servants and finally slew his son in an effort to keep the vine for themselves (Luke 20:9-16; cp. Matthew 21:33-46). This points to Jesus being sent by the Father, but condemned to be crucified by the Jewish authorities. Nevertheless, the parable also points to the culmination of the last days with the total destruction of Judah as a nation, leaving both its capital and its Temple in ruins.
According to the text’s fulfillment in the last days, it was the Messiah, whose eyes were red with fire, and whose garments were dyed red with blood, as he threaded out the wine-press of the wrath of God in AD 70 (Revelation 19:11-16). Moreover, in the Book of Isaiah, the prophet, says: “Let everyone who thirsts come and buy and eat. Buy wine and milk without money and without price” (Isaiah 55:1), which is, clearly, a prophecy of the time of the Messiah (cp. John 2:3-10; 7:37-38).
The point is not in the drinking of wine but in drinking in the Spirit of God, which gives eternal life. Wine causes behavioral change without any effort on the part of man. Similarly, the Spirit of God does the same. The Holy Spirit changes men, changes our behavior and causes us to resort to God’s original command to imitate him (Genesis 1:26-27). Yet, none of this is done through the works of the flesh. Jacob’s prophecy about Judah was a prophecy through Judah to point to the Messiah. Just as his three brothers before him, as a nation lost the prize, so did Judah, when, as a nation he rejected the Messiah, while at the same time he embraced another king (John 19:15).
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[1] Although Solomon reigned over all Israel too, David reigned over a willing kingdom, but Solomon reigned over an oppressed kingdom. In fact, due to his oppression of heavy taxation, the kingdom was divided (1Kings 12:1-4, 13-14, 16-17).