According to Jacob, the last days pertained to his children (Genesis 49:1), and the last days would arrive and culminate in the arrival of Shiloh, i.e. the Messiah (Genesis 49:10). Centuries after Jacob’s blessing of his sons, Ezekiel prophesied that Judah’s kings would cease from ruling over the land, and the Lord would wait until the coming of the Messiah and give the crown of authority to him (Ezekiel 21:26-27). Whatever we may think of the time before David, in the context of the lawgiver and the scepter, or after the Jews were exiled to Babylon, or during the reigns of Herod the Great and his son, Archelaus, or during the time of the Roman governors, the Jewish scholars didn’t seem to be troubled over Jacob’s prophecy failing. Controversy over that prophecy, at least from a Christian perspective, didn’t develop among Jewish scholarship until forty years prior to the destruction of the Temple in 70 AD:
“Forty years before the destruction of the Temple, the Sanhedrin were exiled and took up residence in Hanuth. Whereon R. Isaac b. Abudimi said: This is to teach that they did not try cases of Kenas. ‘Cases of Kenas!’ Can you really think so! Say rather, They did not try capitol charges.” [Babylonians Talmud: Sanhedrin 24a; emphasis mine]
Interestingly, forty years prior to the destruction of the Temple would have been 30 AD or the time of the crucifixion of Jesus. The Sanhedrin met in the Hall of Hewn Stones, which was within the Temple precincts along the southern wall. It was in this building that Jesus was judged and found guilty of blasphemy, a capital crime (Matthew 26:65-66; Luke 22:66-71), for which he was condemned to die. After Jesus was crucified and died, there was a great earthquake (Matthew 27:51), which broke the lintel atop of the doors into the Holy Place of the Temple. The veil of the Temple hung from the lintel, which weighed about thirty tons. As one piece broke off and fell to the Temple floor, it tore the veil from top to bottom. At the same time, the quake damaged the Hall of Hewn Stones, rendering it unusable. Thus, the Sanhedrin was exiled, as the Jewish scholars noted in the excerpt above.
Personally, I don’t believe Jacob’s prophecy has anything to do with man, i.e. whether or not one of Jacob’s descendants was reigning at any particular time, or whether the Jews were in exile or ruled by Rome or even scattered throughout the world in the dispersion that resulted from the destruction of Jerusalem in 70 AD. Isaiah 33:22 identifies the Lord as Israel’s Lawgiver, so in this context, the Father would not depart from the descendants of Jacob, as their covenantal Lawgiver, until Messiah came. During that time, i.e. the last days (Genesis 49:1), the Father turned the reins of government of the Kingdom over to Jesus in a new covenantal relationship between God and mankind (cp. 1Corinthians 15:25-27).
Nevertheless, it does seem significant to the Jewish scholars, as is recorded in the Talmud, quoted above. They seem to be disturbed over the possibility of Jacob’s prophecy failing, because Messiah, according to them, had not come.[1] Since earthquakes are often viewed in the Bible as an act of God, the court was exiled by God out of his immediate presence, causing the judgment they had made against his Son to be the last judgment made by that court in the Hall of Hewn Stones, within the Temple compound, and therefore, in the presence of God. The earthquake that occurred in 30 AD destroyed the meeting place of the Sanhedrin, broke the lintel over the gate of the Temple, and in doing so symbolically prophesied of the destruction of the whole Temple in 70 AD. That last judgment of God ended the Old Covenant.
Remember Jacob’s prophecy was for the last days (Genesis 49:1), and those last days pertained to his descendents. At that time, Shiloh would take the reins of government, and to him the gathering of the people would be (Genesis 49:10). The gathering points to the establishment of the New Covenant (2Thessalonians 2:1; Hebrews 10:25; cp. Matthew 23:37; 24:30-31), and, of course, all these things occurred in the first century AD, just as Jesus said (Matthew 24:34), and we should not believe Jesus for his words sake, but for his works sake (John 10:36-38; cp. Matthew 26:64-65).
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[1] Another excerpt from the Talmud: “Rab said: The world was created only on David’s account. Samuel said: On Moses account; R. Johanan said: For the sake of the Messiah. What is his [the Messiah’s] name? — The School of R. Shila said: His name is Shiloh, for it is written, until Shiloh come. [Babylonians Talmud: Sanhedrin 98b; emphasis mine]