This answer first appeared here, in a dialogue with Nate and others.
The Old Testament prophecies of Jesus’ crucifixion and resurrection do not show up in explicit form. That is, there is no verse that says, “The Messiah shall be crucified,” or “After his crucifixion, the Messiah shall be resurrected.” If it had, the Jewish Sanhedrin would never have given Jesus over to the Romans for crucifixion. They would have sought to dispose of him in some other way for they would not have wanted to play into the hands of those Jews who thought Jesus was the Messiah.
In order for the promises of God about Messiah to be fulfilled, they had to be given in veiled form – like a riddle. With riddle, the answer is inscrutable…until its given, and then it seems obvious. For example, what gets wetter and wetter the more it dries? A towel. Or consider this biblical riddle from Samson: “Out of the eater came something to eat, and out of the strong came something sweet” (Judges 14). What is it? The carcass of the lion Samson killed which housed a honeycomb. In somewhat similar fashion, the prophecies of Messiah were about his sufferings and his glories. Of course, sufferings and glories don’t naturally go together so it was puzzling…until it was revealed that his sufferings ended in death and his glories began with resurrection. For this reason, Paul talks about proclaiming “mysteries” that have been “revealed” (Romans 16:25-27 and elsewhere). Jesus also talks about things “hidden” that shall become “made known” (Matthew 10:26 and elsewhere). (For more on biblical riddles, see these posts.)
Therefore, prophecies of Jesus’ crucifixion include being “wounded for our transgressions” (Isaiah 53:5), “hung on a tree” (Deuteronomy 21:23), “looked upon as pierced” (Zechariah 12:10), and “the stone that was rejected” (Psalm 118:22). Prophecies of resurrection include “became the chief cornerstone” (the continuation of Psalm 118:22), “a prophet raised up” (Deuteronomy 18:15), “high and lifted up” (Isaiah 6:1), and “seated at God’s right hand” (Psalm 110:1). Of course, there are many, many more prophecies (promises) in both categories (suffering and glory).
This is why the first-century Jews we see described in the New Testament were focused on whether the reports they were hearing about Jesus’ resurrection were indeed consistent with the prophecies (see Acts 17:1-3, 10-11). Did this event solve the riddle of all riddles for the descendants of Abraham? That was the question. Certainly, Jesus’ lineage from David was critical because the Scriptures had made clear this requirement. Resurrection from the dead was indeed a big deal for these folks, as it would be for any folks, but it was the context of Israel’s Scriptures which invested the phenomenon with sufficient meaning for pious Jews to re-orient their lives around the One resurrected.
We can actually see Jesus presenting the messianic riddle to the Pharisees in Matthew 22:41-46. Essentially, he was asking them how David could be both superior to (i.e. an ancestor, and therefore a father, of David) and subordinate to (i.e. addressing as “Lord”) the Messiah. The Pharisees had no answer. It was a riddle that stumped them. Of course, in hindsight we are able to see the answer: David was Jesus’ superior (ancestor) according to the flesh, but his subordinate (follower) in the spirit by virtue of Jesus’ resurrection from the dead (a state which David had not been able to escape on his own).
The messianic prophecies of the Old Testament present a riddle to which the New Testament provides the only reasonable answer: that is, the crucifixion and resurrection of a descendant of David.