People predicted I would marry my best friend (the one who was a girl, thank you very much), be a genius, eat spinach, and be a preacher. I'll eat spinach sometimes, but only when it's been covered with dough and cheese. The rest? Yeaaaaaaaaah. I predict my kids will have a weird dad, and that God will be with them.
1) Jesus, though innocent, was counted among the criminals.
2) Pilate may have been paying Jesus a complement. As in "This man was truly the greatest among you".
They wanted to avoid bringing the meteor of Rome down on their heads, for one I think. They may also have believed that God was their king (which is true).
Jesus was their rightful King, since not only was He God, but also a descendant of David.
3) Jesus was undoubtedly the real Messiah. The odds of one man fulfilling all those prophecies by random chance are astronomical.
4) He didn't just use his mom as a way for his entrance to the world, but truly loved her, and wanted her cared for in his physical absence.
5) They did as God had laid out beforehand, acting out of ignorance and doing what they did for various reasons. Jesus, however, took part in a story he had written already.
6) He had finished doing all the work God had planned for him to do.
7) Jesus was not forcibly murdered, or made to die. He planned it, and gave away his life of his own volition.

That he was actually human, and died the way a human would. Only a real death would work as a sacrifice, and Jesus needed to be fully human in order to truly live a sinless life, rather than just pretend to be tempted.
9) Jesus was our Passover lamb, and the Passover lamb could not have its bones broken.
It's comforting to me, since though I try to do what Jesus wants, I know I biff up a lourd of the time. And even then, God knows what He's doing and has a plan. I don't know that I would've been evaluating whether this man had achieved success or not, really. O_o Still, as a man who never hit it rich, but worked as a carpenter for a few years before becoming a traveling preacher, I 'spose by the worlds standards, by our logic, Jesus was not 'successful'. Which is crazy.
As another 'aside' I recently learned that the gall mixed into the vinegar or wine was actually a narcotic, and it was a 'tradition' of sorts for the women to offer it to those being crucified. So Jesus actually refused something which could have lessened his pain.