A few points. I’m not sure you can look to the OT and find passages that foretell the Messiah would be crucified (I’m open to correction here). The OT does show that the Messiah would be a Suffering Servant. Read Isaiah 53:
“Who has believed what he has heard from us?
And to whom has the arm of the Lord been revealed?
For he grew up before him like a young plant,
and like a root out of dry ground;
he had no form or majesty that we should look at him,
and no beauty that we should desire him.
He was despised and rejected by men;
a man of sorrows, and acquainted with grief;
and as one from whom men hide their faces
he was despised, and we esteemed him not.
Surely he has borne our griefs
and carried our sorrows;
yet we esteemed him stricken,
smitten by God, and afflicted.
But he was wounded for our transgressions;
he was crushed for our iniquities;
upon him was the chastisement that brought us peace,
and with his stripes we are healed.
All we like sheep have gone astray;
we have turned—every one—to his own way;
and the Lord has laid on him
the iniquity of us all.
He was oppressed, and he was afflicted,
yet he opened not his mouth;
like a lamb that is led to the slaughter,
and like a sheep that before its shearers is silent,
so he opened not his mouth.
By oppression and judgment he was taken away;
and as for his generation, who considered
that he was cut off out of the land of the living,
stricken for the transgression of my people?
And they made his grave with the wicked
and with a rich man in his death,
although he had done no violence,
and there was no deceit in his mouth.
Yet it was the will of the Lord to crush him;
he has put him to grief;
when his soul makes an offering for guilt,
he shall see his offspring; he shall prolong his days;
the will of the Lord shall prosper in his hand.
Out of the anguish of his soul he shall see and be satisfied;
by his knowledge shall the righteous one, my servant,
make many to be accounted righteous,
and he shall bear their iniquities.
Therefore I will divide him a portion with the many,
and he shall divide the spoil with the strong,
because he poured out his soul to death
and was numbered with the transgressors;
yet he bore the sin of many,
and makes intercession for the transgressors.”
That is a beautiful passage. Why did the Jews miss the connection between Isaiah’s Suffering Servant and the Messiah? Well truthfully, not all did. Remember Simeon. He was a devout Jew full of the Spirit. When he saw the eight day old Jesus at the Temple this is what he said to Mary:
“Behold, this child is appointed for the fall and rising of many in Israel, and for a sign that is opposed (and a sword will pierce through your own soul also), so that thoughts
from many hearts may be revealed.” (Luke 2:34-35).
Simeon understood something – that though Jesus would bring salvation to the world, Jew and Gentile, he would be opposed and suffer. There weren’t many Simeons around though. Most Jews did not associate Isaiah’s Suffering Servant with the Christ (the Messiah). The Messiah would be a warrior king, like David, who would throw off the bonds of Roman tyranny. The Suffering Servant was a different figure, usually with the nation of Israel as a whole.
A couple other points need to be made. First, Jesus was not recognized as the Messiah because a veil remained over the OT. That’s what Paul says in 2 Corinthians 3:14-15, “But their minds were hardened. For to this day, when they read the old covenant, that same veil remains unlifted, because only through Christ is it taken away. Yes, to this day whenever Moses is read a veil lies over their hearts. But when one turns to the Lord, the veil is removed.” Remember, Jesus own disciples didn’t get that the Messiah would have to suffer. Look at the story on Mark 8. Peter has just confessed that Jesus is the Christ. Kuddo’s for Peter. But immediately Jesus begins to teach that he must be rejected, suffer, die and rise again. What’s Peter do? He rebukes Jesus! He didn’t get it. Even after the event the disciples didn’t get it – it took Jesus opening their eyes for them to see it: “Then he opened their minds to understand the Scriptures, and said to them, “Thus it is written, that the Christ should suffer and on the third day rise from the dead, and that repentance and forgiveness of sins should be proclaimed in his name to all nations, beginning from Jerusalem. You are witnesses of these things” (Luke 24: 45-48).
Second, this was to fulfill God’s purposes. The Jews didn’t receive Jesus as the Messiah because it was a part of God’s plan that they reject him. Remember from Isaiah, it was God’s will that his Son be crushed for our sin. Had he been embraced as the Messiah that would not have happened. The rejection and crucifixion were a part of God’s plan to redeem.
Lastly, it’s for us that Jesus was rejected, meaning us Gentiles. In Romans 11 we read Paul teaching the Gentile Christians that the Jewish branch was ‘broken off’ so the Gentile branch could be grafted in. This ingrafting of the Gentiles branch will make the Jewish branch jealous and they will in turn come back to the LORD and be regrafted in (“even they, if they do not continue in their unbelief, will be grafted in, for God has the power to graft them in again”, Romans 11:23). Does that mean all Israel will be saved? That is another post for another day!