It's futile to have this discussion more than once with a Jew. The Old Testament is replete with prophecies of the Lord Jesus. They will look at the likes of Isaiah 53 or Psalms 22, and still just sit there, going, "Duh." You can't expect the revelation of God, that further unfolded in Jesus Christ, to be accepted by people who don't understand their own scripture when it even speaks of Him, who are blind to and refuse what are now known as fundamental things of God in their own book. The Scribes and Pharisees didn't know if they were coming or going, didn't know God when He was standing in front of them, but for perhaps Nicodemus. And in our time, how much worse can the blindness be, when we have hindsight of it all? Somebody can't add two and two, and you're going to try and explain Calculus to them? Lots of luck with that. This time is yet to come, as weird as it seems, given all the scripture, but spiritual blindness just that, weird: the Jews are going to require a heavy duty wake-up call.
Zechariah 12:10 And I will pour upon the house of David, and upon the inhabitants of Jerusalem, the spirit of grace and of supplications: and they shall look upon me whom they have pierced, and they shall mourn for him, as one mourneth for his only son, and shall be in bitterness for him, as one that is in bitterness for his firstborn.
Romans 11:25 For I would not, brethren, that ye should be ignorant of this mystery, lest ye should be wise in your own conceits; that blindness in part is happened to Israel, until the fulness of the Gentiles be come in.