Why does the Old Testament prophesy both a coming King and Kingdom and a suffering Savior?
Because the Abrahamic covenant promised both a nation and land with God's government in a King, and also required a Redeemer to solve sin. Old Testament prophecy therefore runs parallel lines: a coming King and Kingdom, and a coming suffering Savior.
Les explains that this is covenant ground. The Abrahamic covenant was that out of Abraham would come a nation of people whom God would put in a geographical area of land, and then one day He would come and set up the government in the person of the King. But He would also have to be their Redeemer; there had to be a solution to the sin problem. So all the way up through the Old Testament there are these parallel lines of prophecy: the coming of a King and a Kingdom, but also the coming of a suffering Savior. The Jews of Jesus' day wanted the King and the Kingdom and wanted the Romans thrown out, but they did not want to deal with the sin problem because it got too close to home.