The Jews did expect Messiah to suffer but not not at all in the way in which he did. His suffering was only supposed to be a temporary set back as a King waging war against the Gentiles. He was expected to arrive and war with Gog and Magog. During that war against the Gentiles, both He and Israel would suffer, only to gain victory over the entire Gentile world. Then the Gentiles would confess the God of Israel only to later fall way and face the final judgment. His was at first supposed to come, disappear and then reappear to destroy the Gentiles once and for all. His appearance and reappearance was not supposed to be associated with the destructions of Jerusalem as Jesus had said (Mathew 23:39 – 24:2). This idea that Christ espoused would cause nothing but never ending confusion for the Jew. Neither would his suffering be from a rejection from his people, which would seem like defeat to the dream. His suffering would be in the fight with Gentiles for Israel resulting in total victory.
For anyone interested in the detail I have provided many below.
Alfred Edersheim a Jewish historian is, one of the, if not ‘the’ best resource for understanding Jewish expectations before Christ. In general Jewish writings designate a happy period that would succeed the ‘present dispensation’ or ‘world’ (Olam hazzeh). This happy period would begin with ‘the days of the Messiah’ (ימות המשיח). These would stretch into the ‘coming age’ (Aṯid laḇo), and end with ‘the world to come’ (Olam habba).
So the Jewish expectation of Messiah was under three progressive stages: ‘the days of the Messiah’, ‘coming age’ and ‘the world to come’.
The ‘days of the Messiah’:
Alfred Edresheim summarizes this from ancient Hebrew writings:
The Birth of the Messiah would be unknown to His contemporaries; that He would appear, carry on His work, then disappear – probably for forty-five days; then reappear again and destroy the hostile powers of the world, notably ‘Edom,’ ‘Armilos,’ the Roman Power – the fourth and last world-empire (sometimes it is said: through Ishmael). Ransomed Israel would now be miraculously gathered from the ends of the earth, and brought back to their own land, the ten tribes sharing in their restoration, but this only on condition of their having repented of their former sins. According to the Midrash, all circumcised Israel would then be released from Gehenna, and the dead be raised – according to some authorities, by the Messiah, to Whom God would give ‘the Key of the Resurrection of the Dead.’ This Resurrection would take place in the land of Israel, and those of Israel who had been buried elsewhere would have to roll under ground – not without suffering pain – till they reached the sacred soil. Probably the reason of this strange idea, which was supported by an appeal to the direction of Jacob and Joseph as to their last resting-place, was to induce the Jews, after the final desolation of their land, not to quit Palestine. This Resurrection, which is variously supposed to take place at the beginning or during the course of the Messianic manifestation, would be announced by the blowing of the great trumpet. It would be difficult to say how many of these strange and confused views prevailed at the time of Christ; which of them were universally entertained as real dogmas; or from what source they had been originally derived. Probably many of them were popularly entertained, and afterwards further developed – as we believe, with elements distorted from Christian teaching.
The ‘coming age’:
All the resistance to God would be concentrated in the great war of Gog and Magog, and with it the prevalence of all wickedness be conjoined. And terrible would be the straits of Israel. Three times would the enemy seek to storm, the Holy City. But each time would the assault be repelled – at the last with complete destruction of the enemy. The sacred City would now be wholly rebuilt and inhabited. But oh, how different from of old! Its Sabbath-boundaries would be strewed with pearls and precious gems. The City itself would be lifted to a height of some nine miles – nay, with realistic application of Isa_49:20, it would reach up to the throne of God, while it would extend from Joppa as far as the gates of Damascus! For, Jerusalem was to be the dwelling-place of Israel, and the, resort of all nations. But more glorious in Jerusalem would be the new Temple which the Messiah was to rear, and to which those five things were to be restored which had been wanting in the former Sanctuary; the Golden Candlestick, the Ark, the Heaven-lit fire on the Altar, the Holy Ghost and the Cherubim. And the land of Israel would then be as wide as it had been sketched in the promise which God had given to Abraham, and which had never before been fulfilled – since the largest extent of Israel’s rule had only been over seven nations, whereas the Divine promise extended it over ten, if not over the whole earth.
Interestingly, during this time some Rabbis thought that that the Law would be imposed onto the Gentiles but others thought that some things in the Law would cease and all would be brought under a new Law.
Jerusalem would be as large as, at present, all Palestine, and Palestine as all the world. Corresponding to this miraculous extension would be a miraculous elevation of Jerusalem into the air
The land would spontaneously produce the best dresses and the finest cakes; the wheat would grow as high as palm-trees, nay, as the mountains, while the wind would miraculously convert the grain into flour, cast it into the valleys. Every tree would become fruit-bearing; nay, they were to break forth, and to bear fruit every day; daily was every woman to bear child, so that ultimately every Israelitish family would number as many as all Israel at the time of the Exodus. All sickness and disease, and all that could hurt, would pass away. As regarded death, the promise of its final abolition was, with characteristic ingenuity, applied to Israel, while the statement that the child should die an hundred years old was understood as referring to the Gentiles, and as teaching that, although they would die, yet their age would be greatly prolonged, so that a centenarian would be regarded as only a child. Lastly, such physical and outward loss as Rabbinism regarded as the consequence of the Fall, would be again restored to man.
Jerusalem would, as the residence of the Messiah, become the capital of the world, and Israel take the place of the (fourth) world-monarchy, the Roman Empire. After the Roman Empire none other was to rise, for it was to be immediately followed by the reign of Messiah.
The end of the war with Gog and Magog would close the Messianic era. The nations, who had given tribute to Messiah, would then rebel against Him, when He would destroy them by the breath of His mouth. Israel alone would be left on the face of the earth. Then there would be only one Resurrection and that of Israel alone.
Then the final Judgment would then commence, to be held in the valley of Jehoshaphat by God, at the head of the Heavenly Sanhedrin, composed of the elders of Israel. At the time of Christ the punishment of the wicked was regarded as of ’eternal duration’. Although there was some belief that mere annihilation would await the ‘less guilty’, the ‘guiltiest’ were to be reserved for eternal punishment. After pleading for mercy the Gentiles would be punished.
The ‘world to come’:
After the final judgment, the renewal of heaven and earth would take place.
In the latter neither physical nor moral darkness would any longer prevail, since the yeṣer hara, or ‘Evil impulse,’ would be destroyed. And renewed earth would bring forth all without blemish and in Paradisiacal perfection, while alike physical and moral evil had ceased. Then began the ‘Olam haba,’ or ‘world to come.’ The question, whether any functions or enjoyments of the body would continue, is variously answered. The reply of the Lord to the question of the Sadducees about marriage in the other world seems to imply, that materialistic views on the subject were entertained at the time. Many Rabbinic passages, such as about the great feast upon Leviathan and Behemoth prepared for the righteous in the latter days, confirm only too painfully the impression of grossly materialistic expectations.
All quotes are from 'The Life and Times of Jesus the Messiah', by Alfred Edersheim.