When you look at the characters in the gospels, none of them get who Jesus is on the basis of the OT. That's a pretty strong statement, but I advance it as a hypothesis - can anyone contradict it? Think of Nathanael in John's gospel - he needs a miracle before he believes; Peter in the synoptics has Jesus' identity revealed to him by the Father; the people who are really well trained in the Scriptures actually cite them to show that Jesus cannot be the Christ (a prophet from Nazareth?!) The big one for me is the beloved disciple, looking into the empty tomb. He 'saw and believed' but 'as yet they did not understand the Scripture, that he must rise from the dead' (John 20:8,9). The miracle came first, and only then did they go back to the Scriptures and understand them.
Outside the gospels, I think Paul is a test case. His conversion is related by Luke three times, and I can't help thinking that is because Luke wants us to see this as a paradigm of someone coming to Christian faith. Paul knows his OT, no doubt about it. But it takes a personal intervention from Christ before he understands that those Scriptures speak of Christ.
For all these people, despite centuries of careful preparation and witness to Christ in the OT, revelation came out of nowhere and bowled them over.
I think that's important for our understanding of how revelation works. Revelation is always grace - if anyone sees Christ, it is because he freely reveals himself to them. That means revelation is never something that I can get hold of, possess, tame, and call my own. It is always something that can jump out at me, as something new and quite possibly alarming. In that sense, the relation between the OT and Christ is a chronological representation of the relationship that always exists between the Scriptural witness as a whole and Christ.
But when they have seen Christ - and in particular, when they have seen the risen Christ - all these witnesses understand the OT to be all about Christ. They don't think they are significantly reinterpreting it. They are not reading Christ into the OT. But their understanding has changed. They see now, in the light of the resurrection, that Jesus is Lord. Specifically, that means Jesus is, and always has been, Lord over and in Israel's history. The resurrection vindicates Christ, shows that he is the Messiah and the culmination of Israel's hopes and dreams, and in the process shows what those hopes and dreams really were. It always was about him.
That means that when I approach Scripture - Old or New Testament - I approach it as something that genuinely is about Jesus. I do that even for the bits which don't immediately seem to be about him, and the bits which I just don't understand. I study it, wrestle with the content, try to work out what it is saying about Jesus. But I do all that on the understanding that my study and work is not able to produce a view of Jesus which will prompt me to faith and adoration. That would require a work of grace. Jesus is Lord, even over the Bible.
So as a Christian - as someone who has encountered the risen Christ through the Biblical witness applied by the Spirit - I have to read the OT this way. And yet every time I do, there is the possibility (in God's grace) that I will be bowled over again.