It can be confusing for people when they hear that 1) the Jews were expecting their Messiah to be a second King David, a glorious, nation-saving warrior, and so they looked for those things in Jesus, but also that 2) this captured-and-crucified Jesus is the Messiah, the long-promised savior, fulfilling all the Old Testament prophecies. These two ideas together seem to say that either the Jews didn't read their own books, or that the early Church had to fudge on what the Scriptures said and wrench the prophecies to fit Jesus' very-non-warlord career and the fact that he died.
And yes, there is tension between these two Old Testament images of a "savior messiah." And, yes, the Resurrection does serve as kind of God's final stamp that Jesus and the Church got the scriptural blueprint right. But really, the images of "great king who saves Israel and reigns gloriously" and of "suffering servant who saves us by bearing our punishments" are both in the texts and were ultimately true. The common perception in 1st century Judea seem to be simply that those were two separate personages: the hero-king and the exemplar-martyr. And frankly, that's not crazy, since the four Servant Songs of Isaiah never say the Servant is a king or the messiah. Many seem to have seen the Servant as "Israel, who has suffered so much," though that does leave the "suffered for us" part from Isaiah 53 unclear.
From the first days of the Church though, they read it the other way: Jesus came to live the Servant role the whole way—"not rebelling, not turning back"—as Israel never quite could. He suffered, and his sufferings made us whole. But, as those Servant Songs (and Psalms 16, 30, and 116) all assured, God would not abandon the Servant to the grave; He would uphold and rescue the him and the Servant would reign gloriously forever. It wasn't that the earliest Christians were stretching the prophecies, in fact they took them even more literally. It was just that no one before the Resurrection could conceive that "freed my soul from death" and "will not leave me in Sheol, nor let me see decay" could be read as more than a metaphor for "protected me and saved me." Nor could one imagine "will rule on high forever" meant more than "a long reign, with sons to carry on the dynasty for ages." Well, at least till Easter Sunday.
