Should we expect the rug to be pulled from under us?

This is something I've been thinking about a lot lately. A large portion of the gospel texts are trying to convince people why the Messiah was someone that needed to be killed. This ran contrary to all the messianic expectations Judaism had at the time, not to say that there was one vision of the messiah that all Jews shared, but usually messianic figures were powerful political people who helped out the Jewish people in big ways, we even have an example of this in the Old Testament with Cyrus the Great being hailed as a messianic figure. And we can't forget the Son of Man figure from Daniel 7 being given dominion to all of the nations. Regardless, whatever people's expectations of the Messiah were, surely none of them expected the Messiah to die in a very humiliating manner, and we know this because this is one of the main points in the gospels, that not even Jesus's disciples believed the Messiah had to die and would not be a political ruler in the way they thought.

Which leads me to my question: if the Messianic prophecies in the Old Testament could be subverted by God, how can we take Jesus at his word for what he says in the New Testament? Should we not expect the rug to be pulled from under us so to speak? If Jesus was the Messiah that nobody was expecting due to God subverting the prophecies in the OT and fulfilling them in liberal ways, why do we think that Jesus's messages will not be subverted similarly?